Metabolomic Profiling, In Vitro Antioxidant and Cytotoxicity Properties of Caulerpa racemosa : Functional Food of the Future from Algae

Metabolomic Profiling, In Vitro Antioxidant and Cytotoxicity Properties of Caulerpa racemosa : Functional Food of the Future from Algae | Research Square window.SnipcartSettings = { analytics: { enabled: false } }; (function() { var accessVector = localStorage.getItem('access_vector') || ''; window.dataLayer = window.dataLayer || []; if (accessVector) { window.dataLayer.push({ user: { profile: { profileInfo: { snid: accessVector } } } }); } })(); (function(w,d,s,l,i){w[l]=w[l]||[];w[l].push({'gtm.start':new Date().getTime(),event:'gtm.js'});var f=d.getElementsByTagName(s)[0],j=d.createElement(s),dl=l!='dataLayer'?'&l='+l:'';j.async=true;j.src='https://www.googletagmanager.com/gtm.js?id='+i+dl;f.parentNode.insertBefore(j,f);})(window,document,'script','dataLayer','GTM-K279D39R'); Browse Preprints In Review Journals COVID-19 Preprints AJE Video Bytes Research Tools Research Promotion AJE Professional Editing AJE Rubriq About Preprint Platform In Review Editorial Policies Our Team Advisory Board Help Center Sign In Submit a Preprint Cite Share Download PDF Research Article Metabolomic Profiling, In Vitro Antioxidant and Cytotoxicity Properties of Caulerpa racemosa : Functional Food of the Future from Algae Fahrul Nurkolis, Nurpudji Astuti Taslim, Hardinsyah, Son Radu, and 6 more This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-2158307/v2 This work is licensed under a CC BY 4.0 License Status: Posted Version 2 posted You are reading this latest preprint version Show more versions Abstract Marine macroalgae are nutraceuticals rich in nutritional profile and secondary bioactive metabolites. However, they have varied nutritional and biochemical qualities due to a variety of reasons. This study aimed to determine the phytochemical profile and biological activities of Caulerpa racemosa , edible green algae also known as Sea grapes. The study successfully identified secondary metabolites through metabolomic profiling untargeted by LC-HRMS as well as a bioactive peptide. In addition, antioxidant activity and cytotoxicity of extracts and compounds were determined. A total of 103 metabolites were identified in C. racemosa extract obtained by the maceration, while 48 were detected in the soxhlet extract. A peptide with the sequence ELWKTF (Glu-Leu-Trp-Lys-Thr-Phe; C 41 H 58 N 8 O) and its abundance was identified in the α-chymotrypsin hydrolysate of C. racemosa . In the antioxidant activity test, Soxhletated-extract (ES) and purified fraction 1 (PF1) had half-maximal effective concentration (EC 50 ) < EC 50 of control/GSH (DPPH inhibition) and PF1 had EC 50 < EC 50 of control/Trolox (ABTS inhibition). The cytotoxicity results showed that macerated-extract (EM), ES, and PF1 as antioxidant agents in the observed EC 50 were safe. In general, C. racemosa contains antioxidant nutrients, metabolites, and bioactive peptides, a factor that makes it a promising functional food and pharmaceutical. Food Chemistry Food Science & Technology Marine and Freshwater Biology Molecular Biology Drug Discovery, Design, & Development Caulerpa racemosa metabolites nutraceuticals antioxidants green algae Figures Figure 1 Figure 2 Figure 3 Figure 4 Figure 5 Figure 6 Figure 7 Figure 8 Figure 9 Figure 10 1 Introduction Marine life is a rich natural source of numerous bioactive compounds. Marine organisms exist in various complex habitats with extreme circumstances, and these biochemically and ecologically significant differences provide a wide variety of specific, potent, and novel compounds that are not yet extensively explored 1,2 . Among these organisms, marine macroalgae are currently recognized as 'superfoods' because of their superior nutritional profile and abundance of bioactive secondary metabolites. They are rich in carbohydrates, proteins, unsaturated fatty acids, a complete set of vitamins, and estimated minerals 10 – 100 higher than terrestrial vegetables due to their bioabsorption and bioaccumulative properties 2,3 . The global harvest of macroalgae in 2013 was estimated at $ 6.7 billion, with more than 95% produced in mariculture countries, making Indonesia one of the top producers 4 . Indonesia has around ⅔ of its territory as sea and is well known as one of the mega-diversity areas in the world, with more than 555 macroalgal species reported from its waters 5 . Furthermore, most of the islands of Indonesia are located within the Coral Triangle, which has been identified as an area with a high diversity of Caulerpa , a genus of green algae 4 . Caulerpa racemosa or Sea grapes is one of the green seaweeds that grow naturally in the waters of Indonesia, found in coral reef areas or sand-rubble substrates. It is traditionally used as a fresh vegetable; however, its consumption range is still limited to fishermen or communities in the coastal region 6 . C. racemosa is famous for its high nutritional content, which includes minerals, dietary fibers, rich polyunsaturated fatty acids, secondary metabolites such as phenolics, alkaloids, polysaccharides, flavonoids that act as bioactive compounds, and many more 7,8 . Studies have shown that these bioactive molecules are behind a diverse range of health benefits, including antioxidant, anticancer, antibacterial, antiobesity, and antidyslipidemic properties 9,10 . In addition, C. racemosa is also rich in macro and micro minerals, including Mg, Ca, K, Na, Fe, Cu, and Zn, which are needed to sustain metabolic processes. Due to these beneficial findings, C. racemosa has been considered a potentially valuable functional food, with tremendous development prospects due to its distinctive taste and color 11 . To further incorporate these bioactive molecules into ideal formulations with enormous health and economic potential, these compounds must first be separated by extraction, analysis, and identification 12 . Classical maceration and Soxhlet extraction are the most popular techniques among conventional extraction methods. Maceration is an easy and low-cost method of extracting bioactive compounds because it uses non-complicated utensils with barely any operator skills 13–15 . The plant source is ground to increase the surface area and then mixed with chosen solvents, followed by periodic shaking to increase diffusion. This method is suitable for thermolabile plant materials, water as a solvent, extended exposure to the menstruum, and the need for large final volume products 12,16 . Meanwhile, Soxhlet extraction, known as continuous hot extraction, is carried out by repeatedly washing the matrix with a warm solvent, allowing higher possible solubilization of the compounds 17,18 . Advantages of Soxhlet extraction include that large amounts of drugs can be extracted with a lower amount of solvent than maceration, no filtration is required, and a high amount of heat can be applied. However, this method is labor-intensive and unsuitable for thermolabile sources 19 . Furthermore, hydrolysis extraction methods use protease enzymes (such as the enzyme α-chymotrypsin) which are usually used to extract a bioactive peptide content in foodstuffs 20 . However, it should also be noted that natural populations of C. racemosa tend to have varying nutritional and biochemical properties due to several environmental factors such as sedimentation, salinity, temperature, pollution, and nutrients; therefore, different geographical growing fields can contribute to varying levels of nutrients and secondary metabolites 9 . Despite its abundance, the exploration, identification, and isolation of Indonesia’s C. racemosa- specific bioactive molecules profiling, bioactive peptides, and their direct activities are still minimal. A compelling approach to conduct this metabolomics identification is liquid chromatography coupled with high-resolution mass spectrometry (HPLC-ESI-HRMS/MS), which is increasingly used in metabolomics, allowing comprehensive analysis of phytochemicals and semiautomatic collection of study samples 21 . Therefore, this research aims to identify bioactive molecules of C. racemosa by metabolomic profiling, bioactive peptides by proteomics, and examine its antioxidant potentials and cytotoxicity in vitro MTT assays on normal cell lines to ensure its safety. This research is part of foodomics (a comprehensive study involving genomics, proteomics, metabolomics, nutrigenomics, and chemogenomics of food) and their interactions with humans, which is currently a trend in food and health research 22,23 . 2 Materials And Methods The sample collection has been approved by the local authorities and the owner of the Sea grapes pond. Fresh Sea grapes ( Caulerpa racemosa ) were collected from the Sea grapes cultivation pond in Jepara Regency, Central Java Province, Indonesia (6°35'12.5"S latitude 110°38'36.0"E longitude). Botanical identification and authentication were confirmed in the Integrated Laboratory of the Faculty of Sciences and Technology (Herbarium Laboratory), UIN Sunan Kalijaga, Yogyakarta-55281, Indonesia, conducted by Dian Aruni Kumalawati, M.Sc and then followed by confirmation by biologist Prof. Dr. Trina Ekawati Tallei (Expert and Professor of Biology), and has complied with National Center for Biotechnology Information (NCBI) Taxonomy ID 76317 (Eukaryota/Viridiplantae/Chlorophyta/Ulvophyceae/Bryopsidales/Caulerpaceae/Caulerpa). Specimens were collected for future reference. Researchers (authors) state and confirm that all methods carried out in this study are in line or in accordance with relevant guidelines and regulations of in vitro and algae study. 2.1. Sea Grapes Extract Preparations Sea grapes (C. racemosa) were thoroughly washed so that the dirt attached to the sea grapes becomes lost and clean. Washed Sea grapes were then twisted and dried in an oven (Memmert Incubator IN55) at a temperature of 60 °C for 3 x 24 hours. Sea grapes (whole-body) were dried, cut into small pieces, and then mashed with a blender to obtain Sea grapes simplicia powder ( C. racemosa ). Dried simplicia was mashed and then extracted using two methods: the hot and cold ways. Maceration represents the cold way, while Soxhlet extraction represents the way of heat. 2.1.1. Maceration Extraction Method A total of 1,000 g of simplicia powder Sea grapes (C. racemosa) were put in a dark bottle, then 96% ethanol solvent (C₂H₅OH; Merck) as much as 2 L with a ratio of 1:2 between simplicia and solvent were mixed and soaked for 3 x 24 hours. Every 1 x 24 hours, the acquired filtrate was occasionally stirred, then filtered with Whatman 41 paper, and the residue was re-macerated with a new 96% ethanol solvent. The extracted sample was concentrated using a rotary evaporator (RV 8 IKA) under low pressure (100 millibars) for 90 minutes and re-evaporated in the oven (Memmert Incubator IN55) at a temperature of 40 °C so that a thick extract of Sea grapes were obtained. The extract was stored in the refrigerator at a temperature of 10 °C until used in research. 2.1.2. Soxhlet Extraction Method Fifty grams of Sea grapes simplicia powder (C. racemosa) was wrapped in filter paper and inserted into a Soxhlet tube (thimble) on installed Soxhlet tools (PYREX® Soxhlet extractor). 96% ethanol solvent (C 2 H 5 OH; Merck) along with 250 ml of the solution were divided into two parts; 150 ml was inserted into the Soxhlet gourd (pumpkin round base), and 100 ml was inserted into the Soxhlet tube to moisten the simplicia. The ratio between simplicia and solvent was 1:5. The Soxhlet extraction process was carried out at a temperature of 70 – 80 °C, and the extraction was carried out for up to 3 repeat cycles. The extract was stored in the refrigerator at a temperature of 10 °C until used in research. 2.1.3. Hydrolysis Extraction Method by α-Chymotrypsin for Bioactive Peptide Measurements C. racemosa simplicia was dissolved in a 1.0 mM phosphate buffer and then hydrolyzed with the α-chymotrypsin enzyme under its optimal conditions, referring to 20 , which utilizes 1,200 U/mg enzyme activity, 37 °C temperature, at 8.0 pH with digestion time of 2 hours, substrate concentration of 20 mg/mL, 4.0 E/S (w/w) (%). The reaction was stopped by heating at 95 °C for 15 minutes, and the hydrolysate protein was centrifuged at 16,000 rpm for 10 minutes at 4 °C. The supernatant protein (PS) was lyophilized and stored at a temperature of -20 °C for further use in the analysis of the bioactive profiling of peptides. 2.2. Metabolomic Profiling Extract from Maceration and Soxhlet Methods The untargeted metabolomics profiling test on Sea grapes extract samples (Maceration; Soxhlet Method) was carried out using the Liquid Chromatography High-Resolution Mass Spectrometry (LC-HRMS) method at the Laboratorium Sentral Ilmu Hayati (LSIH; ISO 9001:2008 and ISO 17025:2005; Central Laboratory of Life Sciences; Brawijaya University, Malang-65145, Indonesia) testing services, with the test number 041/LSIH-UB/LK/II/2022. 2.2.1. Analysis of the Maceration and Soxhlet samples by HPLC-ESI-HRMS/MS Fifty (50) μl of extract samples (Maceration; Soxhlet Method) were diluted using 96% ethanol up to a final volume of 1,500 μl. The solutions were vortexed at 2,000 rpm for 2 minutes and then span-down at 6,000 rpm for 2 minutes. The supernatant was taken and then filtered using a 0.22μm syringe filter and injected into the vial. The sample in the vial was ready to be inserted into an autosampler and then injected into LC-HRMS (Liquid Chromatography High-Resolution Mass Spectrometry). LC-HRMS uses High-Performance Liquid Chromatography (HPLC) Thermo Scientific Dionex Ultimate 3000 RSLC nano with microflow meter. Solvents A and B consist of 0.1% formic acid in water and 0.1% formic acid in acetonitrile. The analytical column uses Hypersil GOLD aQ 50 x 1 mm x 1.9 μ particle size with a flow rate of 40 uL/min, a flow gradient run time of 30 minutes, and a column oven with a temperature of 30 °C. High-Resolution Mass Spectrometer using Thermo Scientific Q Exactive with a full scan at 70,000 resolution, data-dependent MS/MS at 17,500 resolution, and run time of 30 minutes, with both positive and negative mode. 2.2.2. Processing Data Software Annotated or detected compounds were automatically identified via mzCloud MS/MS Library (Thermo Scientific Q Exactive Software), which were performed by Midia Lestari Wahyu Handayani, S.TP, M.Sc., MP., Ph.D., a certified laboratory technician at the Sentral Ilmu Hayati Laboratorium (LSIH; ISO 9001:2008 and ISO 17025:2005; Central Laboratory of Life Sciences; Brawijaya University, Malang-65145, Indonesia). 2.3. Proteomics Assay of Sequence and Molecular Weight of Amino Acids 2.3.1. Ultrafiltration and Reversed-Phase HPLC (RP-HPLC) The hydrolyzed protein (PS) of C. racemosa was divided into 3 peptide fractions based on molecular weight ((F1; 10 kDa)) using ultrafiltration membrane of 10 kDa and 3 kDa. This approach referred to 20 , which showed that peptide fraction of F1 (MW 3 kDa). Peptides with lower molecular weight are more active than those with a high molecular weight 20 . 2.3.2. Separation of fraction F1 by RP-HPLC Fraction 1 (F1; < 3 kDa) was purified using RP-HPLC. 40 mg of peptide fraction was dissolved into 1 mL 0.05% TFA (v/v) and then was filtered using micropores membrane (0.22 m) before being inserted into Agilent ZORBAX SB-C18 (5 m, 9.4 × 150 mm). A binary moving phase system was used in this study along with eluent A (0,1% TFA (v/v)) and moving phase B (ACN, 0.05% (v/v) TFA). The solution was eluted with a linear gradient of 0 – 40% moving phase B from 0 – 40 minutes dan 40% moving phase B from 40 – 55 minutes. All fractions were collected and lyophilized for further activity assays. The purification level of fractions with the highest activity was further analyzed using the Sunfire C18 column (5 m, 4,6 mm × 150 mm; Waters, USA). The column was eluted using a linear gradient of 0 – 20% moving phase B from 0 – 20 minutes and 20% moving phase B from 20 – 25 minutes, resulting in a purified fraction 1 (PF1). 2.3.3. Analysis of Amino Acid Sequence and MW The ELWKTF (Glu-Leu-Trp-Lys-Thr-Phe) peptide was synthesized in the Laboratory of Biochemistry and Biomolecular Medicine, Faculty of Medicine, Universitas Brawijaya, Malang, Indonesia. A protein sequencer from Applied Biosystems 494 (ProciseTM 494 N-terminal sequencer; Applied Biosystems Inc, Foster City, CA, USA) was used to examine the amino acid sequence of the purified fraction (PF1) based on time-of-flight quadrupole mass spectrometer (MS/MS) paired with electrospray ionization (ESI) source to determines the molecular weight of the ELWKTF (Glu-Leu-Trp-Lys-Thr-Phe). Analysis of the sequence and molecular weight of ELWKTF was performed according to the method described by Zhang et al . (2019) 24 . The results of research by Xiaoqian Zhang et al. 2019 showed good activity of ELWKTF (Glu-Leu-Trp-Lys-Thr-Phe) against radical scavenging activity (DPPH and ABTS) 20 . 2.4. DPPH Antioxidant Radical Scavenging Activity Assay The percentage (%) of the inhibition of 2,2-diphenyl-1-picrylhydrazyl (DPPH) was measured using a method referring to Kaur et al ., (2021) 25 and Permatasari et al ., (2022) 26 , on all samples which include a macerated extract (EM), soxhlet extract (ES), and purified fraction 1 (PF1), while glutathione (GSH; 354102, Sigma-Aldrich) was used as a positive control. In the testing vial (at a concentration of 1, 2, 3, 4, 5 μg, an aliquot (100 μL) of samples and control was added, followed by a DPPH reagent addition (3 mL). The DPPH-extract combination that resulted was then left undisturbed (30 min; dark cycle). The samples were read at 517 nm absorbance with a UV-Vis Shimadzu 80 spectrophotometer. To ensure the validity of the data results, each sample was checked three times (n = 3). Inhibition of DPPH was expressed as a percentage and is determined according to the formula below: A0 = Absorbance of blank; A1 = Absorbance of standard or sample. The half-elimination ratio (EC 50 ) was used to express the radical scavenging capacity of EM, ES, PF1, and GSH and defined as the concentration of a sample that caused a 50% decrease in the initial radical concentration. 2.5. ABTS Radical Scavenging Activity assay For testing the 2,2’-Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) or diammonium salt radical cation (ABTS+; Sigma-Aldrich), the procedure follows the method introduced by Arnao et al. (2010) with some modifications 27 . The stock solution includes 7 mM ABTS solution and 2.4 mM potassium persulfate solution. The working solution was prepared by mixing two stock solutions in equal quantities and letting them react for 14 hours at room temperature under dark conditions. The solution was then diluted by mixing 1 mL of ABTS solution with 60 mL of ethanol to set absorbance to 0.706 ± 0.01 units at 734 nm using a spectrophotometer (Thermo Scientific™ GENESYS™) is obtained. A fresh or new ABTS fresh/new solution was prepared for each test. Samples (at a concentration of 1, 2, 3, 4, and 5 μg) were allowed to react with 1 ml of ABTS solution, and the absorbance was taken at 734 nm after 7 minutes using a spectrophotometer. Treatment was carried out in the same way for all samples, including extract maceration (EM), extract-soxhletation (ES), purified fraction 1 (PF1), and Trolox (6-Hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid; Sigma-Aldrich) was used as a positive control. All determinations were performed in three replication (n = 3). A0 = Absorbance of blank; A1 = Absorbance of standard or sample. The half-elimination ratio (EC 50 ) was used to express the radical scavenging capacity of EM, ES, PF1, and GSH and defined as the concentration of a sample that caused a 50% decrease in the initial radical concentration. 2.6. Cytotoxicity Evaluation using MTT Assay Cell viability was assessed on the Human Caucasian skin fibroblast cell line (Normal cell; Bud-8) 28 . The proliferation rate of the Bud-8 cell line after sample treatment was determined by a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) test. A mitochondrial dehydrogenase reduces MTT to a purple compound formazan that is insoluble in water, depending on the viability of the cell. Cells were preserved in Dulbecco's Modified Essential Medium (DMEM), which was supplemented with 10% fetal bovine serum (FBS) and 1x Penicillin-Streptomycin-Neomycin (PSN). One hundred microliters of cells (4 × 10 4 cells/mL) were seeded in a 96-well plate and incubated at 37°C, 5% carbon dioxide for 24 hours. After 24 hours of incubation, the cells were treated with 100 μL of 100, 200, 300, 400, and 500 μg/mL of samples (EM, ES, PF1). The plate was incubated at 37°C, with 5% CO 2 for 24 and 48 hours. After incubation, the morphology of the cells was examined under a microscope. Twenty microliters of MTT (5 mg/mL) (Sigma) solution was added to each well plate. The plate was further incubated for 2 to 4 hours, and the medium was removed. Formazan crystals dissolved with 100 μL dimethyl sulfoxide (DMSO; Sigma). Absorbance was measured at 560 nm, and the percentage of cell viability and LC 50 cells is calculated by: Where A0 is absorbance control in cells given 1%, DMSO and A1 are cells' absorbance samples given the test sample. Lethal concentration (LC 50 ) is the lowest concentration of samples that inhibits 50% of cells. In general, a low LC 50 value indicates high toxicity. Extracts with high LC 50 are preferred for use due to their low toxicity effect on host cells 28 . 2.7. Data Management and Analysis Data from in vitro tests (DPPH antioxidants, ABTS antioxidants, and Cytotoxicity) were analyzed for significance or not between groups (EM, ES, PF1, or control) using two-way ANOVA CI 95% (0.05) with the MacBook version of GraphPad Prism 9.0.0 premium software. All data were presented in the form of average ± SEM. Graphic visualizations were presented using the MacBook version of GraphPad Prism 9.0.0 premium software. The graphical abstract was designed using the author's licensed BioRender Premium (Fahrul Nurkolis). 3 Results 3.1 Caulerpa racemosa metabolite profiles by non-targeted metabolomic profile Figure 1 indicated the LC-MS/MS total ion chromatogram and mass spectrum of the macerated Sea grapes ( C. racemosa ) extract used to determine the peaks representing the number of annotated ions, the retention time, and the relative abundance of the ions. Annotated compounds were automatically identified via mzCloud MS/MS Library (Thermo Scientific Q Exactive Software). Based on non-targeted metabolomic profiling results with Liquid Chromatography-High Resolution Mass Spectrometry (LC-HRMS), within a retention time of 40 minutes, macerated Sea grapes ( C. racemosa ) Extract (which represents cold extraction) contained a total of 103 compounds that were eluted between 0.00-30.0 minutes (Figure 1A). One hundred and three metabolite derivatives were successfully identified in Sea grapes ( C. racemosa ) from macerated extracts and were presented in Table 1. Figure 1B FTMS + p ESI Full ms. [50.0000-750.0000] is a spectrum with a base peak intensity of 2.90 x 10 6 counts (combination of electrospray ionization (ESI) with Fourier transform mass spectrometry (FTMS)). This FTMS was in positive mode and with electrospray ionization (ESI) continuous measurements from m/z 50 to m/z 600 (NL = normalization rate). The data shown in Table 1 were based on matches with libraries or mzCloud Best Match (>90%) and in order according to their abundance. This was what causes the difference between the calculated exact mass (*) observed in the LC-HRMS results and the predicted-calculated molecular mass (**) in both PubChem and ChemDraw databases. Therefore, we presented molecular mass data by juxtaposing Calculated Exact Mass (*) with Predicted-calculated molecular mass (**) from ChemDraw in Table 1. Table 1. 103 Compounds Observed from HPLC-ESI-HRMS/MS Analysis of Macerated Sea grapes ( C. racemosa ) Extract. No. RT (min) Abundance (Area Max.) Observed HR-ESIMS m/z* Calculated HR-ESIMS m/z ** Molecular Formula Tentatively Identified Compound Category 1. 15.508 2,607,709,506.66 366.0987 344.1100 C 15 H 20 O 9 3-[3-(beta-D-Glucopyranosyloxy)-2-hydroxyphenyl]propanoic acid Carboxylic Acids 2. 0.948 1,702,868,432.32 103.0996 104.1100 C 5 H 13 NO Choline Amines (Quartenary Ammonium Compounds) 3. 0.952 815,230,823.19 117.0787 117.0800 C 5 H 11 NO 2 Betaine Amines (Quartenary Ammonium Compounds) 4. 18.019 530,234,031.11 278.1504 278.1500 C 16 H 22 O 4 Dibutyl phthalate Carboxylic Acids (Phthalic Acids) 5. 10.763 484,746,646.13 312.0885 312.0900 C 18 H 11 F 3 N 2 2-(1H-indol-3-yl)-3-[4-(trifluoromethyl)phenyl]acrylonitrile Organofluorine compounds 6. 0.931 464,700,110.40 189.0429 167.0600 C 8 H 9 NO 3 2-(3,4-dihydroxyphenyl)acetamide Organonitrogen compound (carboxamide) 7. 12.259 312,358,366.23 157.146 156.1400 C 9 H 19 NO 2,2,6,6-Tetramethyl-1-piperidinol (TEMPO) Heterocyclic compounds (piperidines) 8. 21.93 275,377,138.03 255.2549 255.2600 C 16 H 33 NO Hexadecanamide Fatty Acids (Palmitic Acids) 9. 17.905 273,288,427.76 278.1504 276.1400 C 16 H 22 O 4 Diisobutylphthalate Carboxylic Acids 10. 0.927 209,833,574.73 205.0169 205.0200 C 10 H 7 NO 2 S 5-(2-Thienyl)nicotinic acid Carboxylic acid (aromatic carboxylic acid) 11. 0.916 204,192,224.93 87.10487 87.1000 C 5 H 13 N Isoamylamine Amines 12. 18.231 188,856,575.32 296.2341 Cannot be generated C 18 H 34 O 4 NP-008993 unknown 13. 15.894 188,602,459.59 276.2077 254.2200 C 16 H 30 O 2 Palmitoleic Acid Fatty Acids 14. 17.615 128,180,581.48 294.2184 294.2200 C 18 H 30 O 3 9-Oxo-10(E),12(E)-octadecadienoic acid Fatty Acids 15. 17.427 123,110,274.85 294.2183 312.2300 C 18 H 32 O 4 (±)13-hydroperoxy-9Z,11E-octadecadienoic acid Fatty Acids 16. 13.158 120,142,739.65 294.1819 294.1800 C 17 H 26 O 4 6-Gingerol Alcohol (Fatty Alcohols) 17. 1.001 115,965,792.41 270.108 135.0500 C 5 H 5 N 5 Adenine Heterocyclic compounds (purines) 18. 21.564 113,705,808.63 281.2706 281.2700 C 18 H 35 NO Oleamide Fatty Amides 19. 16.815 101,832,983.44 278.2234 278.2200 C 18 H 30 O 2 α-Eleostearic acid Fatty Acids 20. 16.451 95,661,314.03 268.2027 Cannot be generated C 16 H 30 O 4 NP-001596 unknown 21. 11.582 85,055,308.35 326.1044 326.1000 C 16 H 14 N 4 O 4 4-{[(4,6-Dimethoxypyrimidin-2-yl)amino]methylidene}-2-phenyl-4,5-dihydro-1,3-oxazol-5-one Organofluorine compounds 22. 14.177 82,274,117.71 148.0883 148.0900 C 10 H 12 O Cuminaldehyde Hydrocarbons (Terpenes) 23. 15.669 79,749,057.14 326.2445 326.2500 C 19 H 34 O 4 1,2-dihydroxyheptadec-16-yn-4-yl acetate Organic Hydroxy compound (alcohol) 24. 1.024 79,366,759.62 267.0956 267.1000 C 10 H 13 N 5 O 4 Adenosine Carbohydrates (Purine Nucleosides) 25. 20.046 75,757,786.32 278.2234 278.4400 C 18 H 30 O 2 α-Linolenic acid Essential fatty acid 26. 17.351 73,810,505.50 342.0991 320.1200 C 19 H 16 N 2 O 3 ethyl 3-oxo-5,6-diphenyl-2,3- dihydropyridazine-4-carboxylate Fatty acid transporters 27. 16.633 70,444,302.73 292.2026 322.2500 C 18 H 28 O 3 12-Oxo phytodienoic acid Fatty Acids (Octadecanoids) 28. 1.044 70,264,037.81 122.0476 122.0500 C 6 H 6 N 2 O Nicotinamide Heterocyclic compounds (Pyridinecarboxylic acids) 29. 23.794 66,634,752.38 283.2858 283.2900 C 18 H 37 NO Stearamide Amides 30. 21.936 62,781,318.81 307.2861 325.3000 C 20 H 39 NO 2 Oleoyl ethanolamide Amines (Amino alcohols) 31. 13.43 61,670,246.92 276.1714 Cannot be generated C 15 H 26 O 3 NP-020014 unknown 32. 17.56 58,853,299.74 302.2233 320.2400 C 20 H 32 O 3 11,12-epoxy-5,8,14-eicosatrienoic acid Eicosanoids 33. 20.518 57,317,714.92 622.2406 584.6600 C 29 H 44 O 12 Ouabain Autacoids (Eicosanoids) 34. 12.847 56,359,590.26 164.0831 182.0900 C 10 H 14 O 3 1-(4-methoxyphenyl)propane-1,2-diol Hydrocarbon (cyclic hydrocarbon) 35. 0.873 53,487,771.60 235.1412 235.1400 C 14 H 18 FNO 4-Fluoro-α-pyrrolidinobutiophenone Butyrophenones 36. 1.305 53,461,055.41 167.0611 167.1600 C 8 H 9 NO 3 Pyridoxal Heterocyclic compounds (Pyridine carboxaldehydes) 37. 14.862 53,396,851.21 214.135 232.1500 C 15 H 20 O 2 (4aR,5R,6R)-6-hydroxy-4a,5-dimethyl-3- (prop-1-en-2-yl)-2,4a,5,6,7,8- hexahydronaphthalen-2-one Terpenoid 38. 14.874 51,133,618.50 356.1586 334.1800 C 19 H 26 O 5 (3S,3aR,4S,4aR,7aR,8R,9aR)-3,4a,8- trimethyl-2,5-dioxo- 2H,3H,3aH,4H,4aH,5H,7aH,8H,9H,9aHazuleno[ 6,5-b]furan-4-yl 2-methylpropanoate Heterocyclic Compounds 39. 15.089 47,187,926.45 328.0835 328.0800 C 18 H 17 ClN 2 S 1-(4-chlorobenzyl)-2-{[(4- methylphenyl)thio]methyl}-1H-imidazole Protein Enzyme 40. 16.835 44,926,299.27 328.2602 328.2600 C 19 H 36 O 4 1,4-dihydroxyheptadec-16-en-2-yl acetate Organic Hydroxy compound (alcohol) 41. 22.189 43,991,117.28 500.2191 250.1100 C 16 H 14 N 2 O Methaqualone Heterocyclic compounds (Quinazolines) 42. 16.48 41,454,327.51 250.1923 426.3000 C 16 H 26 O 2 Octylphenol Ethoxylates (OPEO) alkylphenols 43. 14.714 38,806,980.21 273.2655 256.2400 C 16 H 32 O 2 Palmitic Acid Fatty acids 44. 16.334 37,032,281.51 300.2076 318.4600 C 20 H 30 O 3 8-Hydroxyeicosapentaenoic acid ((±)8-HEPE) Hydroxy fatty acid 45. 20.987 35,975,153.82 282.2548 282.2600 C 18 H 34 O 2 Ethyl palmitoleate Fatty acid ester (Fatty acid ethyl ester) 46. 21.041 34,105,859.15 280.239 Cannot be generated C 18 H 34 O 3 NP-011548 unknown 47. 11.577 33,493,328.71 164.0831 164.0800 C 10 H 12 O 2 4-Phenylbutyric acid Carboxylic Acids (Phenylbutyrates) 48. 14.077 32,107,702.51 248.1766 266.1900 C 16 H 26 O 3 Tetranor-12R-HETE Organy Hydroxy compound (Hydroxy carboxylic acid) 49. 16.588 31,279,593.58 314.1846 292.2000 C 18 H 28 O 3 4-hydroxy-6-[2-(2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)ethyl]oxan-2-one Heterocyclic compound (oxacycle) 50. 17.366 31,243,191.82 354.2756 354.2800 C 21 H 38 O 4 1-Linoleoyl glycerol Glycerides 51. 18.021 31,197,110.75 323.2083 306.1800 C 18 H 26 O 4 n-Pentyl isopentyl phthalate Phthalates 52. 16.258 30,927,401.68 268.2028 Cannot be generated C 16 H 30 O 4 NP-001596 unknown 53. 7.466 30,636,932.36 197.1198 197.1200 C 14 H 15 N Dibenzylamine Amines 54. 18.515 30,124,986.19 318.216 Cannot be generated C 18 H 32 O 3 NP-014287 unknown 55. 12.819 29,968,764.20 232.1455 Cannot be generated C 15 H 22 O 3 (1aR,1bR,2R,3R,7R,7aS)-1b,2-dimethyl-7a-(prop-1-en-2-yl)-1aH,1bH,2H,3H,4H,5H,7H,7aH-naphtho[1,2-b]oxirene-3,7-diol unknown 56. 15.64 28,287,214.04 196.0881 196.0900 C 14 H 12 O 4-Methylbenzophenone Ketones (Benzophenones) 57. 14.449 27,409,945.13 214.135 232.1500 C 15 H 20 O 2 (4aR,5R,6R)-6-hydroxy-4a,5-dimethyl-3-(prop-1-en-2-yl)-2,4a,5,6,7,8-hexahydronaphthalen-2-one Terpenoid 58. 16.302 27,286,206.71 302.2444 302.2500 C 17 H 34 O 4 2,3-dihydroxypropyl 12-methyltridecanoate Glyceride 59. 15.864 25,328,627.10 316.2003 316.2000 C 20 H 28 O 3 Cafestol Hydrocarbons (Terpenes) 60. 14.695 24,803,082.67 508.263 526.2700 C 27 H 37 F 3 N 2 O 5 [6-Hydroxy-1-(hydroxymethyl)-1,4a-dimethyl-5-(2-oxo-2-pyrrolidin-1-ylethyl)-2,3,4,5,6,7,8,8a-octahydronaphthalen-2-yl] N-[3-(trifluoromethyl)phenyl]carbamate Organofluorine compounds 61. 20.606 24,591,569.01 308.2339 302.2200 C 20 H 30 O 2 Eicosapentaenoic acid Fatty Acids 62. 21.592 23,630,078.82 313.2967 313.3000 C 19 H 39 NO 2 R-Palmitoyl-(2-methyl) ethanolamide Lipid (Fatty Amide) 63. 12.163 23,533,439.36 370.094 Cannot be generated C 21 H 20 Cl 2 N 2 2-(2,4-dichlorophenyl)-4,4,7,9-tetramethyl-4,5-dihydro-3H-naphtho[1,2-d]imidazole unknown 64. 12.76 23,504,570.02 234.1611 252.1700 C 15 H 24 O 3 Ageratriol Terpenoids 65. 14.233 23,426,676.24 244.1091 262.1200 C 15 H 18 O 4 (3aR,4aS,5R,8S,9aR)-5-hydroxy-4a,8-dimethyl-3-methylidene-2H,3H,3aH,4H,4aH,5H,6H,8H,9H,9aH-azuleno[6,5-b]furan-2,6-dione Terpenes 66. 13.406 23,234,665.52 232.1455 Cannot be generated C 15 H 22 O 3 (1aR,1bR,2R,3R,7R,7aS)-1b,2-dimethyl-7a-(prop-1-en-2-yl)-1aH,1bH,2H,3H,4H,5H,7H,7aH-naphtho[1,2-b]oxirene-3,7-diol Nuclear receptor 67. 12.099 22,988,983.05 384.1096 Cannot be generated C 18 H 19 F 3 N 2 O 2 S ethyl 2-(methylthio)-4-tetrahydro-1H-pyrrol-1-yl-8-(trifluoromethyl)quinoline-3-carboxylate unknown 68. 18.446 22,839,809.05 218.1662 Cannot be generated C 15 H 24 O 2 NP-004713 unknown 69. 20.376 22,099,138.42 330.2546 330.2600 C 22 H 34 O 2 Eicosapentaenoic acid ethyl ester Fatty Acids 70. 17.161 21,808,214.15 270.2183 Cannot be generated C 16 H 32 O 4 NP-020214 unknown 71. 13.431 20,606,367.65 261.1354 239.1500 C 13 H 21 NO 3 Levalbuterol Amines (Phenethylamines) 72. 20.074 20,450,089.14 306.2545 306.2600 C 20 H 34 O 2 Linolenic acid ethyl ester Fatty Acids 73. 21.707 19,935,241.14 310.2857 310.2900 C 20 H 38 O 2 Ethyl oleate Fatty Acids 74. 14.41 19,870,753.40 182.0725 182.0700 C 13 H 10 O Benzophenone Ketones (Benzophenones) 75. 17.367 18,964,856.34 262.2285 280.4500 C 18 H 32 O 2 Octadec-9-ynoic acid Hydrocarbons (Alkynes) 76. 15.997 18,954,242.24 228.1141 246.1300 C 15 H 18 O 3 (3aS,5aS,9bR)-5a,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,5aH,6H,7H,8H,9bH-naphtho[1,2-b]furan-2,5-dione Terpenes 77. 19.433 18,184,819.14 328.2388 328.2400 C 22 H 32 O 2 Docosahexaenoic acid Fatty Acids 78. 26.392 18,033,386.90 283.3227 284.3300 C 19 H 41 N Cetrimonium Amines (Quartenary Ammonium Compounds) 79. 17.063 17,943,409.82 398.169 398.1700 C 22 H 26 N 2 O 3 S 3-(3,4-dimethoxyphenethyl)-2-[(4-isopropylphenyl)imino]-1,3-thiazolan-4-one Organic Chemicals 80. 9.957 17,802,168.49 236.1402 254.1500 C 14 H 22 O 4 (±)-C75 Organic heterocyclic compound 81. 16.951 17,509,512.15 234.1611 234.1600 C 15 H 22 O 2 3,5-di-tert-Butyl-4-hydroxybenzaldehyde Aldehydes (Benzaldehydes) 82. 20.317 17,492,831.93 299.2812 299.2800 C 18 H 37 NO 2 Palmitoyl ethanolamide Amines (Amino Alcohols) 83. 15.118 16,405,749.44 467.3231 467.3100 C 28 H 41 N 3 O 3 Oxethazaine Amines (Amino Alcohols) 84. 19.858 16,337,402.48 305.2705 Cannot be generated C 20 H 35 NO NP-016582 unknown 85. 20.015 16,138,319.09 321.2654 299.5000 C 18 H 37 NO 2 Sphingosine (d18:1) Amines 86. 16.742 15,941,236.73 692.3268 Cannot be generated C 22 H 22 N 2 O 2 4-(3-methoxy-5,6-dihydrobenzo[c]acridin-7-yl)morpholine unknown 87. 13.152 15,540,877.24 334.1743 334.1700 C 21 H 22 N 2 O 2 (-)-Strychnine Alkaloids (Indole Alkaloids) 88. 20.726 15,378,473.45 304.2391 304.2400 C 20 H 32 O 2 Arachidonic acid Autacoids (Eicosanoids) 89. 16.279 15,308,423.13 356.0783 356.0700 C 20 H 12 N 4 OS 3,4-Diphenylpyrimido[4',5':4,5]thieno[2,3-c]pyridazin-8(7H)-one Thienopyridazine derivatives 90. 17.305 14,960,482.55 378.2755 378.2800 C 23 H 38 O 4 2-Arachidonoyl glycerol Glycerolipid 91. 19.83 14,601,900.81 442.3432 442.3400 C 29 H 46 O 3 Testosterone decanoate Gonadal Steroid Hormones (Testosterone congeners) 92. 14.886 14,357,946.57 274.1558 252.1700 C 15 H 24 O 3 (5E)-7-methylidene-10-oxo-4-(propan-2-yl)undec-5-enoic acid Terpenes 93. 17.72 13,897,675.48 312.2651 306.2600 C 20 H 34 O 2 γ-Linolenic acid ethyl ester Fatty acid derivative 94. 15.669 12,500,838.24 510.2786 Cannot be generated C 27 H 40 N 2 O 6 6-Hydroxy-1-(hydroxymethyl)-5-{2-[2-(hydroxymethyl)-1-pyrrolidinyl]-2-oxoethyl}-1,4a-dimethyldecahydro-2-naphthalenyl phenylcarbamate unknown 95. 19.475 12,426,002.76 344.195 344.2000 C 21 H 28 O 4 Nor-9-carboxy-δ9- tetrahydrocannabinol Terpenes 96. 26.449 12,331,286.20 131.0942 131.0900 C 6 H 13 NO 2 6-Aminocaproic acid Carboxyclic Acid (Caproates) 97. 17.805 9,806,912.19 340.1637 340.1600 C 20 H 24 N 2 OS Propionylpromazine Sulfur compounds (Phenothiazines) 98. 23.138 9,589,300.00 390.2753 390.2800 C 24 H 38 O 4 Di(2-ethylhexyl) phthalate Carboxylic acid (Phthalic acid) 99. 20.548 9,339,555.94 176.1194 194.1300 C 12 H 18 O 2 Sedanolide Heterocyclic Compound (Benzofurans) 100. 19.703 9,113,695.23 303.2549 303.2600 C 20 H 33 NO Arachidonoyl amide Fatty acid derivative (fatty amide) 101. 16.962 8,865,034.10 248.1766 266.1900 C 16 H 26 O 3 Tetranor-12(S)-HETE Organic Hydroxy compound (hydroxy carboxylic acid) 102. 18.548 8,618,378.15 306.2545 306.2600 C 20 H 34 O 2 8Z,11Z,14Z-Eicosatrienoic acid Autacoids (Eicosanoids) 103. 21.448 8,239,070.91 363.3121 357.3000 C 24 H 39 NO Oleyl anilide Amines (Anilides) RT = Retention time (minutes); * = Calculated exact mass observed from LC-HRMS; Predicted-calculated molecular mass from ChemDraw. Figure 2 indicated the LC-MS/MS total ion chromatogram and mass spectrum of the soxhlet extraction of Sea grapes ( C. racemosa ) used to determine the peaks representing the number of annotated ions, the retention time, and the relative abundance of the ions. Just like in the maceration extract, Annotated compounds were automatically identified via mzCloud MS/MS Library (Thermo Scientific Q Exactive Software). Based on non-targeted metabolomic profiling results with Liquid Chromatography-High Resolution Mass Spectrometry (LC-HRMS), within a retention time of 40 minutes, soxhlet of Sea grapes ( C. racemosa ) extract (which represents heat extraction) contained a total of 48 compounds that were diluted between 0.00-30.0 minutes (Figure 2A). Forty-eight (48) metabolite derivatives were successfully identified in Sea grapes ( C. racemosa ) from soxhlet extraction extracts then presented in Table 2. Figure 2B FTMS + p ESI Full ms. [50.0000-750.0000] was a spectrum with a base peak intensity of 2.52 x 10 6 counts (combination of electrospray ionization (ESI) with Fourier transform mass spectrometry (FTMS)). This FTMS was in positive mode and by electrospray ionization (ESI) continuous measurements from m/z 50 to m/z 670 (NL = normalization rate). Table 2. Forty-eight Compounds Observed from HPLC-ESI-HRMS/MS Analysis of Soxhlet Extraction of Sea grapes ( C. racemosa ). No RT (min) Abundance (Area Max.) Observed HR-ESIMS m/z* Calculated HR-ESIMS m/z** Molecular Formula Tentatively Identified Compound Category 1. 0.902 615,708,699.02 117.0787 117.0800 C 5 H 11 NO 2 Betaine Amines (Quartenary Ammonium Compounds) 2. 21.916 353,793,967.91 255.25505 255.2600 C 16 H 33 NO Hexadecanamide Fatty Acids (Palmitic Acids) 3. 17.877 344,623,223.38 278.15076 276.1400 C 16 H 22 O 4 Diisobutylphthalate Carboxylic Acids 4. 12.294 274,478,961.83 157.14607 156.1400 C 9 H 19 NO 2,2,6,6-Tetramethyl-1-piperidinol (TEMPO) Heterocyclic compounds (piperidines) 5. 18.209 195,885,637.15 296.23405 Cannot be generated C 18 H 34 O 4 NP-008993 unknown 6. 16.424 119,602,748.90 268.20276 Cannot be generated C 16 H 30 O 4 NP-001596 unknown 7. 21.547 104,636,468.21 281.27056 281.2700 C 18 H 35 NO Oleamide Fatty Amides 8. 0.901 104,452,391.68 131.09424 131.0900 C 6 H 13 NO 2 DL-β-Leucine Amino Acids 9. 16.928 82,954,091.16 278.22365 278.2200 C 18 H 30 O 2 α-Eleostearic acid Fatty Acids 10. 23.776 82,837,237.90 283.28606 283.2900 C 18 H 37 NO Stearamide Amides 11. 13.397 79,829,227.71 276.17153 Cannot be generated C 15 H 26 O 3 NP-020014 unknown 12. 18.681 75,543,295.89 282.25472 282.2600 C 18 H 34 O 2 Ethyl palmitoleate Fatty acid ester (Fatty acid ethyl ester) 13. 17.587 75,423,822.44 294.21851 312.2300 C 18 H 32 O 4 (±)13-HpODE Fatty acid 14. 0.911 70,567,131.89 87.10485 87.1000 C 5 H 13 N Isoamylamine Amines 15. 21.92 67,501,000.61 307.2863 325.3000 C 20 H 39 NO 2 Oleoyl ethanolamide Amines (Amino alcohols) 16. 0.906 62,987,796.05 103.0996 104.1100 C 5 H 13 NO Choline Amines (Quartenary Ammonium Compounds) 17. 0.835 60,193,728.47 228.97644 228.9800 C 9 H 5 ClFNOS 2-(3-Chloro-2-fluorophenyl)-2,3-dihydroisothiazol-3-one Enzyme 18. 18.938 42,693,613.10 308.19524 Cannot be generated C 16 H 30 O 4 NP-001596 unknown 19. 17.881 42,504,568.52 323.20854 306.1800 C 18 H 26 O 4 n-Pentyl isopentyl phthalate Phthalates 20. 16.455 39,764,527.54 250.19238 426.3000 C 16 H 26 O 2 Octylphenol Ethoxylates (OPEO) alkylphenols 21. 17.434 39,577,349.70 316.20043 316.2000 C 20 H 28 O 3 Cafestol Hydrocarbons (Terpenes) 22. 16.654 37,079,182.87 254.22351 254.2200 C 16 H 30 O 2 Palmitoleic acid Fatty Acids 23. 22.8 33,398,733.18 309.30147 C 20 H 41 NO 2 Stearoyl Ethanolamide Fatty Acids 24. 20.591 32,595,365.73 308.23406 302.2200 C 20 H 30 O 2 Eicosapentaenoic acid Fatty Acids 25. 17.87 31,871,173.23 294.21853 294.2200 C 18 H 30 O 3 9-Oxo-10(E),12(E)-octadecadienoic acid Fatty Acids 26. 14.577 31,454,460.53 273.26564 256.2400 C 16 H 32 O 2 Palmitic Acid Fatty acids 27. 7.411 31,100,701.46 197.11981 197.1200 C 14 H 15 N Dibenzylamine Amines 28. 17.367 30,483,737.39 280.2392 Cannot be generated C 18 H 34 O 3 NP-011548 unknown 29. 26.447 29,296,796.45 131.09427 131.0900 C 6 H 13 NO 2 6-Aminocaproic acid Carboxyclic Acid (Caproates) 30. 19.991 29,136,008.89 278.22365 278.4400 C 18 H 30 O 2 α-Linolenic acid Essential fatty acid 31. 13.398 25,493,790.28 261.13552 239.1500 C 13 H 21 NO 3 Levalbuterol Amines (Phenethylamines) 32. 22.054 19,542,351.23 361.2968 361.3000 C 23 H 39 NO 2 Methanandamide Fatty acid derivative 33. 16.914 17,243,572.51 234.16117 234.1600 C 15 H 22 O 2 3,5-di-tert-Butyl-4-hydroxybenzaldehyde Aldehydes (Benzaldehydes) 34. 13.132 16,983,601.06 276.17153 276.1700 C 17 H 24 O 3 Shogaol Phenols 35. 20.295 16,462,133.15 299.28127 299.2800 C 18 H 37 NO 2 Palmitoyl ethanolamide Amines (Amino Alcohols) 36. 14.576 14,874,891.90 414.20268 414.2000 C 24 H 30 O 6 Bis(4-ethylbenzylidene)sorbitol Sugar alcohol 37. 19.986 14,176,669.67 321.26558 299.5000 C 18 H 37 NO 2 Sphingosine (d18:1) Amines 38. 19.715 13,852,334.54 336.20778 336.2100 C 20 H 29 FO 3 Fluoxymesterone Hormones 39. 17.688 13,159,097.66 350.24193 328.2600 C 19 H 36 O 4 2,4-dihydroxyheptadec-16-en-1-yl acetate Unsaturated Fatty Acids 40. 26.392 12,768,022.53 283.32268 284.3300 C 19 H 41 N Cetrimonium Amines (Quartenary Ammonium Compounds) 41. 23.12 12,428,205.36 390.2755 390.2800 C 24 H 38 O 4 Bis(2-ethylhexyl) phthalate Carboxylic Acids 42. 16.474 11,621,213.91 266.16368 266.1600 C 12 H 27 O 4 P Tributyl phosphate Organophosphorus Compounds 43. 16.926 10,593,568.28 248.17679 266.1900 C 16 H 26 O 3 Tetranor-12(S)-HETE Organic Hydroxy compound (hydroxy carboxylic acid) 44. 20.537 9,753,652.00 176.11943 194.1300 C 12 H 18 O 2 Sedanolide Heterocyclic Compound (Benzofurans) 45. 21.427 8,882,476.13 363.31224 357.3000 C 24 H 39 NO Oleyl anilide Amines (Anilides) 46. 11.188 8,843,434.72 294.21855 294.2200 C 18 H 30 O 3 13(S)-HOTrE Unsaturated Fatty Acids 47. 11.662 8,423,640.09 191.13033 191.11300 C 12 H 17 NO Diethyltoluamide or DEET Carboxylic Acids 48. 21.688 7,026,193.73 310.28584 310.2900 C 20 H 38 O 2 Ethyl oleate Fatty Acids RT = Retention time (minutes); * = Calculated exact mass observed from LC-HRMS; Predicted-calculated molecular mass from ChemDraw. 3.2. Identification of the peptide in purified fraction 1 of C. racemosa PF1 of C. racemosa found a bioactive peptide named (2S,5S,8S,11S,14S,17S)-11-((1H-indol-3-yl)methyl)-17-amino-8-(4-aminobutyl)-2-benzyl-5-((R)-1-hydroxyethyl)-14-isobutyl-4,7,10,13,16-pentaoxo-3,6,9,12,15-pentaazaicosanedioic acid or ELWKTF (Glu-Leu-Trp-Lys-Thr-Phe) which was eluted at a retention time of 30.9 minutes with a peak area of 815,602,581.03 (Table 3). The structural visualization of ELWKTF is shown in Figure 3. Table 3. Amino Acids (ELWKTF) Analysis . Peptide Sequence Average Local Confidence (ALC, %) Length* m/ z Retention Time (RT) Theoretical Mass/Observed Mass (Da) Peak Area (max) ELWKTF 97 6 412.2320 30.9 822.43/822.428 815,602,581.03 Chemical Formula : C41H58N8O10. Exact Mass : 822.43. Molecular Weight : 822.96. m/z : 822.43 (100.0%), 823.43 (45.4%), 824.43 (13.0%), 823.42 (3.0%), 825.44 (2.4%). Elemental Analysis : C, 59.84; H, 7.10; N, 13.62; O, 19.44. *, The number of amino acids on the peptide. 3.3. The DPPH Radical Scavenging Activity of C. racemosa Figure 4 showed the results of an in vitro study inhibiting DPPH radical scavenging activity. The inhibitory activity of DPPH was compared among C. racemosa macerated extract (EM), Soxhlet extract (ES), purified fraction 1 (PF1), and glutathione (GSH). The results showed lesser DPPH inhibition activities than GSH or control at 1 μg/mL, 2 μg/mL, 3 μg/mL, and 4 μg/mL of EM; and 1 μg/mL, 2 μg/mL, 3 μg/mL, 4 μg/mL, 5 μg/mL of ES and PF1(p < 0.0001). The DPPH inhibition of EM was to close with GSH at a dose of 5 μg/mL with a percentage of 87.43 ± 0.67% and 86.73 ± 0.61%, respectively (Figure 4). As shown in Figure 5, the EC 50 yields of EM, ES, PF1, and GSH were 2.945 μg/mL, 2.297 μg/mL, 2.302 μg/mL, and 2.691 μg/mL, respectively. ES and PF1 show good potential effectiveness in DPPH radical elimination activity because the EC 50 values are lower than the control or GSH. 3.4. ABTS Radical Scavenging Activity of C. racemosa Figure 6 showed the results of an in vitro study inhibiting the radical scavenging activity of ABTS. The inhibitory activity of ABTS was compared among the macerated extract of C. rasemosa (EM), the soxhletated extract (ES), the purified fraction 1 (PF1), and the Trolox or control. The results showed lesser of ABTS inhibition activities at doses 1 μg/mL, 2 μg/mL, 3 μg/mL, 4 μg/mL and 5 μg/mL for ES and PF1, compared to Trolox or control (p < 0.0001). As shown in Figure 7, the EM, ES, PF1, and Trolox yield was EC 50 of 3.306 μg/mL, 3.244 μg/mL, 2.508 μg/mL, and 2.547 μg/mL, respectively. PF1 showed good potential effectiveness in the radical elimination activity of ABTS because it has a lower EC 50 value than the control or Trolox. 3.5. Cytotoxicity Evaluation of C. racemosa using MTT Assay Figure 8 showed the difference in the viability percentage of normal cells or fibroblasts from the human Caucasian cell line. There was a significant difference (p<0.05) between each concentration between the groups during 24 hours of incubation and 48 hours. The sequence of LC 50 samples that are lowest or show the highest cytotoxicity to the lowest cytotoxicity is EM 914.78 μg/mL, PF1 2069.21 μg/mL, and ES 2227.85 μg/mL at 24 hours; and, ES 1816.17 μg/mL, PF1 2173.02 μg/mL, and EM 2971.15 μg/mL at 48 hours (Table 4). This result suggested EM, ES, and PF1 as antioxidant agents in the observed EC 50 were safe. Furthermore, in terms of cytotoxicity, it was observed that C. racemosa was safe to be potentially developed into various products. In addition, the value of LC 50 is presented in Table 4. Table 4 . LC 50 Value of C. racemosa on Cytotoxicity Test in BUD-8 Cell Lines Hours of incubation LC 50 (μg/ml) EM ES PF1 24 hours 914.78 2227.85 2069.21 48 hours 2971.15 1816.17 2173.02 4 Discussions Seaweed is traditionally used as a sea vegetable in Asian countries, especially Indonesia, but its consumption is still minimal. C. racemosa is one of the green seaweeds whose metabolite profiles, health properties, and potential use as functional ingredients in food, supplements, and pharmaceuticals should be further explored. This will be a new opportunity to introduce C. racemosa indirectly into the human food chain in western countries, especially in Europe. Foodomics is a discipline that studies the domain of food and nutrition through the application and integration of advanced technology "-omics" to improve the well-being, health, and knowledge of consumers 22,23 . One part of Foodomics is the metabolomic study 29 which was applied in this study and successfully profiled the secondary metabolites of C. racemosa with different extraction methods. On the other hand, the bioactive peptides were also successfully identified using proteomics approaches. Secondary metabolites and bioactive peptides are expected to be a data challenge for other researchers or follow-up research to find their continued effects on health and product development based on C. racemosa . This untargeted metabolomic profiling study that we conducted has succeeded in profiling secondary metabolites of C. racemosa , which was previously a challenge from the research of Pangestuti et al . (2021) 30 . Study by Pangestuti et al . (2021) only observed at phytochemicals of C. racemosa in terms of total phenolic, saponins, and flavonoid contents without the metabolite compounds 30 . There was a difference in the number of compounds identified in the maceration (cold) and soxhletation (heat) methods of extraction of sea grapes Sea grapes ( C. racemosa ) extract through the extraction-maceration method had higher bioactive compound than the Sea grapes extracted using a Soxhlet. The soxhlet extraction method integrates the advantages of reflux and percolation extraction, which utilizes the principle of reflux and siphon to continuously extract the herb with fresh solvent 13 . Extraction using the soxhlet method has the advantage of an automatic continuous extraction method with less extraction time and less solvent use than maceration or percolation 13 . However, high temperatures and long extraction times in soxhlet extraction will increase the likelihood of thermal degradation. This is what is strongly suspected to cause differences in the results of compounds from the two extracts in this C. racemosa study. In line with the results of our study, other studies showed that the degradation of catechins in tea was also observed in soxhlet extraction due to the high extraction temperature 31 . The total polyphenol and total alkaloid concentrations of the soxhlet extraction method decreased compared to the maceration method 31,32 . The bioactive compounds found in this study showed both health benefits and toxic effects based on other literature (see Supplementary). However, not all bioactive compounds will have a significant effect since the dose of each metabolite should be considered. For example, an in vivo intervention study using 450 mg/kgBW of sea grapes extract on rats showed no adverse effects 10 . Proteins in foods sourced from marine resources and their by-products have high structural diversity and are a considerable resource for exploring bioactive peptides 33 . Previous literature suggests that the types of amino acids in Bioactive Peptides (BPs) are considered a critical factor in their activity 34 . Residual hydrophobic groups from hydrophobic amino acids such as Pro, Met, Ala, Leu, and Ile, can strongly react with hydrophobic polyunsaturated fatty acids (PUFAs) to inhibit lipid peroxidation in lipid-rich foods 35,36 . The EC 50 of PF1 which was allegedly derived from ELWKTF activity in this study was more potential than Trolox (in ABTS inhibition assay) and GSH (DPPH inhibition Assay) as a control based on the EC 50 value. Carboxyl and amino groups in polar amino acid residues are essential to capture hydroxyl radicals and the metal-ion chelating capacity of BPs 36,37 . In addition, Glu and Leu residues can maintain the high flexibility of the polypeptide skeleton, and its single hydrogen atom can be donated to neutralize Reactive Oxygen Species (ROS) 34,38 . Therefore, polar amino acids, including -Glu and -Leu residues in ELWKTF, may have played an essential role in hydroxyl radical capture activities. C. racemosa, which has an abundance of ELWKTF, can be a source of free radical inhibition activity through the mechanism presented in the previous sentence. Recent scientific evidence suggested that dietary proteins may have function as nutrients and can also modulate the body's physiological functions 39 . This physiological function is mainly regulated by several encrypted peptides in the original protein sequence. This bioactive peptide can provide beneficial properties for health and is therefore considered a significant compound for developing nutraceuticals or functional foods to fight metabolic syndrome, obesity, cancer, diabetes, and aging, which are associated with cardiovascular disease. This study that we conducted showed novelty on the measurement of bioactive peptides and their antioxidant activity, which in previous studies had never been reported or carried out 30,40 . Lethal concentration (LC 50 ) is the lowest concentration of samples that inhibits 50% of cells. In general, a low LC 50 value indicates high toxicity. Extracts with high LC 50 are preferred for use due to their lower toxicity effect on host cells 28 . The interpretation of the LC 50 value was based on the National Cancer Institute 41 , LC 50 value of 20 μg/mL indicates strong cytotoxic properties, 21-200 μg/mL indicates moderate cytotoxicity, 201-500 μg/mL exhibits weak cytotoxicity, and > 500 μg/mL indicates no cytotoxic properties. C. racemosa has a potential antioxidant activity of EC 50 value accompanied by an LC 50 value which was in a safe category. This is in line with similar studies that observed at the cytotoxicity of C. racemosa in subcritical water extraction, which did not show significant cytotoxicity activity 30 . Furthermore, a review study by Aroyehun et al . (2020) stated that in addition to minimal toxicity, C. racemosa has bioprospecting as a promising nutraceutical due to its nutritional values 9 . 4.1 The Potential and Prospects of Caulerpa racemosa as Nutraceuticals and Pharmaceuticals in Terms of Cultivation and Use in Commercial Industrial Production Applications. Fewer incidences of diet-related diseases, especially non-communicable diseases and including cancer and cardiovascular disease have been observed in countries that consume high amounts of seaweed as a supplement or food 42,43 . Seaweed consumption has been shown to reduce the prevalence of different non-communicable diseases due to the metabolites and other bioactive compounds working as a defense mechanism 43 . Studies carried out with seaweed extracts or their specific metabolites proved that they have cytotoxins, which prevent the proliferation of cancer cells 44 . In this study, the results showed that. ES and PF1 show good potential effectiveness in DPPH radical elimination activity because the EC 50 values are lower than the control or GSH. This was in line with a review study by Collins et al., 2016, which focused on the potential use of bioactive seaweed derivatives, including polysaccharides, antioxidants, and fatty acids, among others, to treat chronic non-communicable diseases 42 . Furthermore, the main compounds resulting from the identification of C. racemosa metabolomic profiling , such as choline 45 , betaine 45 , oleamide 46 , hexadecanamide 47 , palmitoleic acid 48 , and α-eleostearic acid 49 may become therapeutic drugs for non-communicable diseases. Furthermore, we also explored the antioxidant activity of each secondary metabolite of metabolomic profiling results by a review approach, which can be seen in Supplementary Table 1 . The therapeutic activity of food-derived bioactive proteins and peptides – such as from medicinal plants – is attracting increasing attention in the research community 39 . Bioactive peptides offer promising potential as antiviral drugs, and therapeutic peptides are an exciting alternative to be developed into anti-Dengue virus drugs due to their safety and diverse biological and chemical properties 50 . In addition, many potential compounds were identified from C. racemosa metabolites profiles , such as choline 51 , betaine 52 , oleamide 53 , hexadecanamide 54 , palmitoleic acid 55 , and α-eleostearic acid 56 . More research is needed to examine the clinical effects of C. racemosa as a nutraceutical. 4.2 Potential for Future Research. Many strategies are needed to further develop C. racemosa products to explore their secondary metabolites and health benefits. In addition, environmental factors play an essential role in influencing the composition of secondary metabolites in C. racemosa 57 , 58 , which is important to be considered. To ensure the validity and safety of Sea grapes research development, the drug discovery process should be carried out through various steps as recommended by the Food and Drug Administration (FDA, US), which can be seen in Figure 10. The process initiated by metabolomic profiling identifies what processes/pathways can be targeted to affect the disease/condition. Compound screening can also be done to identify compounds that can be promising candidates for further development. Next, an in silico study is needed for target validation, determining whether the drug can provide therapeutic benefit to the target, and lead discovery to identify the lead compound to be observed for further studies. Subsequently, preclinical trials are needed to evaluate therapeutic index and dose using in vitro and in vivo approaches and evaluate the aspects of pharmacokinetics and pharmacodynamics in experimental animals (Figure 10). Finally, to ensure efficacy and safety, three phases of clinical trials need to be conducted, first on healthy patients and then on obese or patients with other cardiovascular diseases. 4.3 Strengths and Limitations of Study The results of this study complemented the published data related to secondary metabolites from Caulerpa racemosa found and grown in Asia, especially in Indonesia waters. Furthermore, this study succeeded in profiling the bioactive peptide and their bioactivity properties from the purified fraction 1 of Caulerpa racemosa (Graphical Abstract). In addition, the synthesis and purification of their respective compounds (metabolites and bioactive peptides) for the development of food and drug products and the exploration of bioactive carbohydrates and other bioactive peptides is a limitation of this research. It is hoped that more research will be carried out in the future. Seeing the metabolomic results which show indications of several compounds that are thought to be anti-nutrients, further studies are needed to confirm whether they are naturally present in Sea grapes or as contaminants. References indicating the activity of the health benefits of each metabolite that have been successfully identified are still very few and limited, so computational molecular docking or in silico studies are needed for various disease-causing receptors. 5 Conclusions The abundance of secondary metabolites and bioactive compounds in Sea grapes (Caulerpa racemosa) was obtained from the maceration method's extraction process. The bioactive peptide purified fraction 1 (PF1), as shown in ELWKTF, was also analyzed for its antioxidant and cytotoxicity activity. These metabolites were responsible for high biochemical activity (antioxidants, scavenging, and reducing) and have good prospects of cytotoxicity. The study revealed that C . racemosa contained antioxidant nutrients, metabolites, and bioactive peptides (Graphical Abstract); these factors make it a promising functional food and pharmaceutical. From a future perspective, C. racemosa is a potential candidate for development as a functional food and other nutraceutical applications, including pharmaceuticals. 6 Patents Patent Number S00202107179 (Fahrul Nurkolis is a patent holder, https://pdki-indonesia.dgip.go.id/detail/S00202107179?type=patent&keyword=Formula+Anggur+Laut). Abbreviations ABTS = 2,2'-Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid); BPs = Bioactive Peptides; DENV = Dengue virus; DMEM = Dulbecco's Modified Essential Medium; DMSO = Dimethyl sulfoxide; DPPH = 2,2-diphenyl-1-picrylhydrazyl; ELWKTF : Glu-Leu-Trp-Lys-Thr-Phe; EM = Macerated Extract (Extract Maceration); ES = Soxhletated Extract (Extract-Soxhletation); ESI = Electrospray ionization; FBS = Fetal bovine serum; GSH = Glutathione; HPLC = High Performance Liquid Chromatography; HRMS = High Resolution Mass Spectrometry; IUPAC = International Union of Pure and Applied Chemistry; MTT = 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide; PS = Protein Supernatant; PSN = Penicillin-Streptomycin-Neomycin; PUFAs = Polyunsaturated fatty acids; ROS = Reactive Oxygen Species. Declarations Author Contributions or Authors CRediT (Contributor Roles Taxonomy) : FN and HH: conduct experiments, analyzed data, write the manuscript, design research, and conceptualize ideas; while HH, VMY, MY, RJK: contribute to data analysis, critiquing manuscript, interpret manuscript results, assisting in the processing of data, as well as helping to revise and graphical abstract editing. IWH, WBG, SR, NAT, NM, NS, AT, RK: critiquing, writing – review & editing manuscript. TET, RK, SR, EI, and CFT reviewed and edited the final manuscript text. All authors have read and also approved this final manuscript. Funding: This research received no external funding. Data Availability Statement: The data presented in this study are available on request from the corresponding author and/or the original contributions presented in the study are publicly available. The datasets generated and/or analysed during the current study are available in the [Figshare] repository, [https://doi.org/10.6084/m9.figshare.20518485.v1]. Acknowledgments: The authors thank all of the contributors for their outstanding help in research and also in formatting the paper. I also want to express my gratitude to my two special people, who have provided suggestions and comments on the research and writing of this manuscript, as well as the motivation that has led the authors to keep the passion for research during the pandemic: 1. Professor Hardinsyah, MS, Ph.D . (the President of the Federations of Asian Nutrition Societies; President of the Food and Nutrition Society of Indonesia; and Member of the Southeast Asian Probiotic Scientific and Regulatory Experts Network), and 2. Professor Dr. Nurpudji A Taslim, MD., MPH, Sp.GK (K) (Chair of the Indonesian Clinical Nutrition Physician Association). Also to Julia M. L. 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PLoS One 17 , e0265954 (2022). Additional Declarations The authors declare no competing interests. Supplementary Files TableSupplementary1.AntioxidantReviewofMetabolitesCaulerparacemosa.docx Table Supplementary 1. Antioxidant Review of Metabolites Caulerpa racemosa GraphicalAbstractMetabProfiling2.png Graphical Abstract. Schematic of Metabolomic Profiling, In Vitro Antioxidant, and Cytotoxicity Properties of Caulerpa racemosa Cite Share Download PDF Status: Posted Version 2 posted You are reading this latest preprint version Show more versions Research Square lets you share your work early, gain feedback from the community, and start making changes to your manuscript prior to peer review in a journal. As a division of Research Square Company, we’re committed to making research communication faster, fairer, and more useful. We do this by developing innovative software and high quality services for the global research community. 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Maksum","email":"","orcid":"","institution":"Department of Chemistry, Faculty of Mathematics and Natural Science, Universitas Padjadjaran, Sumedang 45363, Indonesia","correspondingAuthor":false,"prefix":"","firstName":"Iman","middleName":"Permana","lastName":"Maksum","suffix":""}],"badges":[],"createdAt":"2022-10-12 11:01:27","currentVersionCode":2,"declarations":{"humanSubjects":false,"vertebrateSubjects":false,"conflictsOfInterestStatement":false,"humanSubjectEthicalGuidelines":false,"humanSubjectConsent":false,"humanSubjectClinicalTrial":false,"humanSubjectCaseReport":false,"vertebrateSubjectEthicalGuidelines":false},"doi":"10.21203/rs.3.rs-2158307/v2","doiUrl":"https://doi.org/10.21203/rs.3.rs-2158307/v2","draftVersion":[],"editorialEvents":[],"editorialNote":"","failedWorkflow":false,"files":[{"id":62550947,"identity":"fef6356f-cc82-4ca4-9522-777c0485c630","added_by":"auto","created_at":"2024-08-15 17:21:55","extension":"jpg","order_by":1,"title":"Figure 1","display":"","copyAsset":false,"role":"figure","size":232032,"visible":true,"origin":"","legend":"\u003cp\u003e\u003cstrong\u003e1A. \u003c/strong\u003eTotal Ion Chromatogram (TIC) of Macerated Sea grapes (\u003cem\u003eC. racemosa\u003c/em\u003e) Extract by HPLC; \u003cstrong\u003e1B. \u003c/strong\u003eMass spectrum\u003cstrong\u003e \u003c/strong\u003eof Macerated Sea grapes (\u003cem\u003eC. racemosa\u003c/em\u003e) Extract by MS/MS. S#: Scan number; RT: Retention time; AV: Averaged (followed by the number of averaged scans); SB: Subtracted (followed by subtraction information); NL: Neutral loss; T: Scan type; F: Scan filter.\u003c/p\u003e","description":"","filename":"Fig1.jpg","url":"https://assets-eu.researchsquare.com/files/rs-2158307/v2/4157af7205d15ef18d891ad2.jpg"},{"id":62550517,"identity":"4b0b783a-9b54-45a8-9cdf-ee7f4756c61c","added_by":"auto","created_at":"2024-08-15 17:13:55","extension":"jpg","order_by":2,"title":"Figure 2","display":"","copyAsset":false,"role":"figure","size":282321,"visible":true,"origin":"","legend":"\u003cp\u003e\u003cstrong\u003e2A. \u003c/strong\u003eTotal Ion Chromatogram (TIC) of Soxhlet Extraction of Sea grapes (\u003cem\u003eC. racemosa\u003c/em\u003e) Extract by HPLC;\u003cstrong\u003e 2B. \u003c/strong\u003eMass spectrum of Soxhlet Extraction of Sea grapes (\u003cem\u003eC. racemosa\u003c/em\u003e) Extract by MS/MS . S#: Scan number; RT: Retention time; AV: Averaged (followed by the number of averaged scans); SB: Subtracted (followed by subtraction information); NL: Neutral loss; T: Scan type; F: Scan filter.\u003c/p\u003e","description":"","filename":"Fig2.jpg","url":"https://assets-eu.researchsquare.com/files/rs-2158307/v2/093489b2cab7c5be44ab087c.jpg"},{"id":62550943,"identity":"235e3071-2827-49c2-b61e-a39a983d7832","added_by":"auto","created_at":"2024-08-15 17:21:55","extension":"jpg","order_by":3,"title":"Figure 3","display":"","copyAsset":false,"role":"figure","size":132724,"visible":true,"origin":"","legend":"\u003cp\u003eELWKTF Analysis and Visualization Results Using ChemDraw 21.0.0 Macbook Version.\u003c/p\u003e","description":"","filename":"Fig3.jpg","url":"https://assets-eu.researchsquare.com/files/rs-2158307/v2/aca60d548ddcffccaa8b8d26.jpg"},{"id":62551632,"identity":"0826bb8d-d071-4980-9a09-717d2b770f98","added_by":"auto","created_at":"2024-08-15 17:29:55","extension":"jpg","order_by":4,"title":"Figure 4","display":"","copyAsset":false,"role":"figure","size":271206,"visible":true,"origin":"","legend":"\u003cp\u003eComparison of DPPH Radical Scavenging Activity. * = p 0.0374; *** = p 0.0002; **** = p \u0026lt; 0.0001; ns = Not significant (p \u0026gt; 0.05).\u003c/p\u003e","description":"","filename":"Fig4.jpg","url":"https://assets-eu.researchsquare.com/files/rs-2158307/v2/4ec350fcb7c39878a9f863f7.jpg"},{"id":62550519,"identity":"9bd0c515-8040-4c23-9b70-94827fee948c","added_by":"auto","created_at":"2024-08-15 17:13:55","extension":"jpg","order_by":5,"title":"Figure 5","display":"","copyAsset":false,"role":"figure","size":213589,"visible":true,"origin":"","legend":"\u003cp\u003eDose-response Curve of EM, ES, PF1, and GSH Regarding DPPH Radical Scavenging Activity. EC\u003csub\u003e50 \u003c/sub\u003e= Half-maximal effective concentration. EM = Macerated extract (Extract maceration); ES = Soxhletated extract (Extract-soxhletation); PF1= Purified fraction 1.\u003c/p\u003e","description":"","filename":"Fig5.jpg","url":"https://assets-eu.researchsquare.com/files/rs-2158307/v2/ad113c79edabe27778cfedf5.jpg"},{"id":62550525,"identity":"b748f042-9f38-4668-93e0-393264b09f5a","added_by":"auto","created_at":"2024-08-15 17:13:55","extension":"jpg","order_by":6,"title":"Figure 6","display":"","copyAsset":false,"role":"figure","size":269684,"visible":true,"origin":"","legend":"\u003cp\u003eComparison of ABTS Radical Scavenging Activity. *** = p 0.0004; **** = p \u0026lt; 0.0001; ns = Not significant (p \u0026gt; 0.05).\u003c/p\u003e","description":"","filename":"Fig6.jpg","url":"https://assets-eu.researchsquare.com/files/rs-2158307/v2/c55a5bc2eff82f447ca8fa6a.jpg"},{"id":62550524,"identity":"fbc3da2e-399e-4346-bb7c-9753d09f249d","added_by":"auto","created_at":"2024-08-15 17:13:55","extension":"jpg","order_by":7,"title":"Figure 7","display":"","copyAsset":false,"role":"figure","size":251441,"visible":true,"origin":"","legend":"\u003cp\u003eDose-response Curve of EM, ES, PF1, and Trolox Regarding ABTS Radical Scavenging Activity. EC\u003csub\u003e50 \u003c/sub\u003e= Half-maximal effective concentration. EM = Macerated extract (Extract maceration); ES = Soxhletated extract (Extract-soxhletation); PF1= Purified fraction 1.\u003c/p\u003e","description":"","filename":"Fig7.jpg","url":"https://assets-eu.researchsquare.com/files/rs-2158307/v2/dcadab5faf33e7c2a233841d.jpg"},{"id":62550946,"identity":"f47c1d5a-64bb-47a8-948d-0b650137c2cb","added_by":"auto","created_at":"2024-08-15 17:21:55","extension":"jpg","order_by":8,"title":"Figure 8","display":"","copyAsset":false,"role":"figure","size":471279,"visible":true,"origin":"","legend":"\u003cp\u003ePercentage of cell viability evaluation of \u003cem\u003eC. racemosa\u003c/em\u003e cytotoxicity using MTT assay on the human Caucasian skin fibroblast cell line. \u003cstrong\u003eA= \u003c/strong\u003eCytotoxicity Evaluation using MTT Assay at 24 Hours. \u003cstrong\u003eB\u003c/strong\u003e= Cytotoxicity Evaluation using MTT Assay at 48 Hours. ** = p 0.0096; *** = p 0.0002; **** = p \u0026lt;0.0001 ; ns = not significant (p = 0.2745). EM = Macerated extract (Extract maceration); ES = Soxhletated extract (Extract-soxhletation); PF1= Purified fraction 1.\u003c/p\u003e","description":"","filename":"Fig8.jpg","url":"https://assets-eu.researchsquare.com/files/rs-2158307/v2/922376d8cb9cc5e19950e961.jpg"},{"id":62550522,"identity":"3fbb1751-4b74-44df-914e-2740d30c6104","added_by":"auto","created_at":"2024-08-15 17:13:55","extension":"jpg","order_by":9,"title":"Figure 9","display":"","copyAsset":false,"role":"figure","size":278438,"visible":true,"origin":"","legend":"\u003cp\u003eLog Concentrations of \u003cem\u003eC. racemosa \u003c/em\u003eCytotoxicity Assay. Macerated Extract (EM), Soxhletated Extract (ES), Purified Fraction 1 (PF1). LC\u003csub\u003e50 \u003c/sub\u003e= half-maximal lethal concentration (lowest concentration of samples that inhibit 50% of cells).\u003c/p\u003e","description":"","filename":"Fig9.jpg","url":"https://assets-eu.researchsquare.com/files/rs-2158307/v2/acd3a3aee0d741400d489c62.jpg"},{"id":62550527,"identity":"2aa9071d-d3f5-4d00-99bc-9f7afbd81805","added_by":"auto","created_at":"2024-08-15 17:13:55","extension":"png","order_by":10,"title":"Figure 10","display":"","copyAsset":false,"role":"figure","size":2995217,"visible":true,"origin":"","legend":"\u003cp\u003eThe Flow of Research and Product Development of \u003cem\u003eC. racemosa\u003c/em\u003e in the Future.\u003c/p\u003e","description":"","filename":"Figure10.TheFlowofResearchandProductDevelopmentofC.racemosaintheFuture.png","url":"https://assets-eu.researchsquare.com/files/rs-2158307/v2/6843c882e1572b98de088dcb.png"},{"id":62552052,"identity":"b4e4ff87-0f50-4242-be2f-de05f04f4050","added_by":"auto","created_at":"2024-08-15 17:38:00","extension":"pdf","order_by":0,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":6645038,"visible":true,"origin":"","legend":"","description":"","filename":"manuscript.pdf","url":"https://assets-eu.researchsquare.com/files/rs-2158307/v2/826276c0-c9e9-45f9-ad5a-f4a07d58576e.pdf"},{"id":62550516,"identity":"95457c9d-34cf-42b1-aa1f-eb0a9cf224e3","added_by":"auto","created_at":"2024-08-15 17:13:55","extension":"docx","order_by":1,"title":"","display":"","copyAsset":false,"role":"supplement","size":69367,"visible":true,"origin":"","legend":"\u003cp\u003e\u003cstrong\u003eTable Supplementary 1. \u003c/strong\u003eAntioxidant Review of Metabolites \u003cem\u003eCaulerpa racemosa\u003c/em\u003e\u003c/p\u003e","description":"","filename":"TableSupplementary1.AntioxidantReviewofMetabolitesCaulerparacemosa.docx","url":"https://assets-eu.researchsquare.com/files/rs-2158307/v2/5813db121af32728a38397d1.docx"},{"id":62550944,"identity":"4a058b5c-ded0-4a29-acb2-bd6be630907d","added_by":"auto","created_at":"2024-08-15 17:21:55","extension":"png","order_by":2,"title":"","display":"","copyAsset":false,"role":"supplement","size":2217225,"visible":true,"origin":"","legend":"\u003cp\u003e\u003cstrong\u003eGraphical Abstract\u003c/strong\u003e. Schematic of Metabolomic Profiling, In Vitro Antioxidant, and Cytotoxicity Properties of \u003cem\u003eCaulerpa racemosa\u003c/em\u003e\u003c/p\u003e","description":"","filename":"GraphicalAbstractMetabProfiling2.png","url":"https://assets-eu.researchsquare.com/files/rs-2158307/v2/a51c1d222c95e15b577a279e.png"}],"financialInterests":"The authors declare no competing interests.","formattedTitle":"\u003cp\u003eMetabolomic Profiling, \u003cem\u003eIn Vitro\u003c/em\u003e Antioxidant and Cytotoxicity Properties of \u003cem\u003eCaulerpa racemosa\u003c/em\u003e : Functional Food of the Future from Algae\u003c/p\u003e","fulltext":[{"header":"1 Introduction","content":"\u003cp\u003eMarine life is a rich natural source of numerous bioactive compounds. Marine organisms exist in various complex habitats with extreme circumstances, and these biochemically and ecologically significant differences provide a wide variety of specific, potent, and novel compounds that are not yet extensively explored \u003csup\u003e1,2\u003c/sup\u003e. Among these organisms, marine macroalgae are currently recognized as \u0026apos;superfoods\u0026apos; because of their superior nutritional profile and abundance of bioactive secondary metabolites. They are rich in carbohydrates, proteins, unsaturated fatty acids, a complete set of vitamins, and estimated minerals 10 \u0026ndash; 100 higher than terrestrial vegetables due to their bioabsorption and bioaccumulative properties \u003csup\u003e2,3\u003c/sup\u003e. The global harvest of macroalgae in 2013 was estimated at $ 6.7 billion, with more than 95% produced in mariculture countries, making Indonesia one of the top producers \u003csup\u003e4\u003c/sup\u003e. Indonesia has around ⅔ of its territory as sea and is well known as one of the mega-diversity areas in the world, with more than 555 macroalgal species reported from its waters \u003csup\u003e5\u003c/sup\u003e. Furthermore, most of the islands of Indonesia are located within the Coral Triangle, which has been identified as an area with a high diversity of \u003cem\u003eCaulerpa\u003c/em\u003e, a genus of green algae \u003csup\u003e4\u003c/sup\u003e.\u003c/p\u003e\n\u003cp\u003e\u003cem\u003eCaulerpa racemosa\u0026nbsp;\u003c/em\u003eor Sea grapes is one of the green seaweeds that grow naturally in the waters of Indonesia, found in coral reef areas or sand-rubble substrates. It is traditionally used as a fresh vegetable; however, its consumption range is still limited to fishermen or communities in the coastal region \u003csup\u003e6\u003c/sup\u003e. \u003cem\u003eC. racemosa\u003c/em\u003e is famous for its high nutritional content, which includes minerals, dietary fibers, rich polyunsaturated fatty acids, secondary metabolites such as phenolics, alkaloids, polysaccharides, flavonoids that act as bioactive compounds, and many more \u003csup\u003e7,8\u003c/sup\u003e. Studies have shown that these bioactive molecules are behind a diverse range of health benefits, including antioxidant, anticancer, antibacterial, antiobesity, and antidyslipidemic properties \u003csup\u003e9,10\u003c/sup\u003e. In addition, \u003cem\u003eC. racemosa\u003c/em\u003e is also rich in macro and micro minerals, including Mg, Ca, K, Na, Fe, Cu, and Zn, which are needed to sustain metabolic processes. Due to these beneficial findings, \u003cem\u003eC. racemosa\u003c/em\u003e has been considered a potentially valuable functional food, with tremendous development prospects due to its distinctive taste and color \u003csup\u003e11\u003c/sup\u003e.\u003c/p\u003e\n\u003cp\u003eTo further incorporate these bioactive molecules into ideal formulations with enormous health and economic potential, these compounds must first be separated by extraction, analysis, and identification \u003csup\u003e12\u003c/sup\u003e. Classical maceration and Soxhlet extraction are the most popular techniques among conventional extraction methods. Maceration is an easy and low-cost method of extracting bioactive compounds because it uses non-complicated utensils with barely any operator skills \u003csup\u003e13\u0026ndash;15\u003c/sup\u003e. The plant source is ground to increase the surface area and then mixed with chosen solvents, followed by periodic shaking to increase diffusion. This method is suitable for thermolabile plant materials, water as a solvent, extended exposure to the menstruum, and the need for large final volume products \u003csup\u003e12,16\u003c/sup\u003e. Meanwhile, Soxhlet extraction, known as continuous hot extraction, is carried out by repeatedly washing the matrix with a warm solvent, allowing higher possible solubilization of the compounds \u003csup\u003e17,18\u003c/sup\u003e. Advantages of Soxhlet extraction include that large amounts of drugs can be extracted with a lower amount of solvent than maceration, no filtration is required, and a high amount of heat can be applied. However, this method is labor-intensive and unsuitable for thermolabile sources \u003csup\u003e19\u003c/sup\u003e. Furthermore, hydrolysis extraction methods use protease enzymes (such as the enzyme \u0026alpha;-chymotrypsin) which are usually used to extract a bioactive peptide content in foodstuffs \u003csup\u003e20\u003c/sup\u003e.\u003c/p\u003e\n\u003cp\u003eHowever, it should also be noted that natural populations of \u003cem\u003eC. racemosa\u003c/em\u003e tend to have varying nutritional and biochemical properties due to several environmental factors such as sedimentation, salinity, temperature, pollution, and nutrients; therefore, different geographical growing fields can contribute to varying levels of nutrients and secondary metabolites \u003csup\u003e9\u003c/sup\u003e. Despite its abundance, the exploration, identification, and isolation of Indonesia\u0026rsquo;s \u003cem\u003eC. racemosa-\u003c/em\u003especific bioactive molecules profiling, bioactive peptides, and their direct activities are still minimal. A compelling approach to conduct this metabolomics identification is liquid chromatography coupled with high-resolution mass spectrometry (HPLC-ESI-HRMS/MS), which is increasingly used in metabolomics, allowing comprehensive analysis of phytochemicals and semiautomatic collection of study samples \u003csup\u003e21\u003c/sup\u003e. Therefore, this research aims to identify bioactive molecules of \u003cem\u003eC. racemosa\u0026nbsp;\u003c/em\u003eby metabolomic profiling, bioactive peptides by proteomics, and examine its antioxidant potentials and cytotoxicity \u003cem\u003ein vitro\u0026nbsp;\u003c/em\u003eMTT assays on normal cell lines to ensure its safety. This research is part of foodomics (a comprehensive study involving genomics, proteomics, metabolomics, nutrigenomics, and chemogenomics of food) and their interactions with humans, which is currently a trend in food and health research \u003csup\u003e22,23\u003c/sup\u003e.\u003c/p\u003e"},{"header":"2 Materials And Methods","content":"\u003cp\u003eThe sample collection has been approved by the local authorities and the owner of the Sea grapes pond. Fresh Sea grapes (\u003cem\u003eCaulerpa racemosa\u003c/em\u003e) were collected from the Sea grapes cultivation pond in Jepara Regency, Central Java Province, Indonesia (6°35'12.5\"S latitude 110°38'36.0\"E longitude). Botanical identification and authentication were confirmed in the Integrated Laboratory of the Faculty of Sciences and Technology (Herbarium Laboratory), UIN Sunan Kalijaga, Yogyakarta-55281, Indonesia, conducted by Dian Aruni Kumalawati, M.Sc and then followed by confirmation by biologist Prof. Dr. Trina Ekawati Tallei (Expert and Professor of Biology), and has complied with National Center for Biotechnology Information (NCBI) Taxonomy ID 76317 (Eukaryota/Viridiplantae/Chlorophyta/Ulvophyceae/Bryopsidales/Caulerpaceae/Caulerpa). Specimens were collected for future reference. Researchers (authors) state and confirm that all methods carried out in this study are in line or in accordance with relevant guidelines and regulations of \u003cem\u003ein vitro\u003c/em\u003e and algae study.\u003c/p\u003e\n\u003cp\u003e\u003cem\u003e2.1. Sea Grapes Extract Preparations\u003c/em\u003e\u003c/p\u003e\n\u003cp\u003eSea grapes \u003cem\u003e(C. racemosa)\u003c/em\u003e were thoroughly washed so that the dirt attached to the sea grapes becomes lost and clean. Washed Sea grapes were then twisted and dried in an oven (Memmert Incubator IN55) at a temperature of 60 °C for 3 x 24 hours. Sea grapes (whole-body) were dried, cut into small pieces, and then mashed with a blender to obtain Sea grapes simplicia powder (\u003cem\u003eC. racemosa\u003c/em\u003e). Dried simplicia was mashed and then extracted using two methods: the hot and cold ways. Maceration represents the cold way, while Soxhlet extraction represents the way of heat.\u003c/p\u003e\n\u003cp\u003e2.1.1. Maceration Extraction Method\u003c/p\u003e\n\u003cp\u003eA total of 1,000 g of simplicia powder Sea grapes \u003cem\u003e(C. racemosa)\u003c/em\u003e were put in a dark bottle, then 96% ethanol solvent (C₂H₅OH; Merck) as much as 2 L with a ratio of 1:2 between simplicia and solvent were mixed and soaked for 3 x 24 hours. Every 1 x 24 hours, the acquired filtrate was occasionally stirred, then filtered with Whatman 41 paper, and the residue was re-macerated with a new 96% ethanol solvent. The extracted sample was concentrated using a rotary evaporator (RV 8 IKA) under low pressure (100 millibars) for 90 minutes and re-evaporated in the oven (Memmert Incubator IN55) at a temperature of 40 °C so that a thick extract of Sea grapes were obtained. The extract was stored in the refrigerator at a temperature of 10 °C until used in research.\u003c/p\u003e\n\u003cp\u003e2.1.2. Soxhlet Extraction Method\u003c/p\u003e\n\u003cp\u003eFifty grams of Sea grapes simplicia powder \u003cem\u003e(C. racemosa)\u003c/em\u003e was wrapped in filter paper and inserted into a Soxhlet tube (thimble) on installed Soxhlet tools (PYREX® Soxhlet extractor). 96% ethanol solvent (C\u003csub\u003e2\u003c/sub\u003eH\u003csub\u003e5\u003c/sub\u003eOH; Merck) along with 250 ml of the solution were divided into two parts; 150 ml was inserted into the Soxhlet gourd (pumpkin round base), and 100 ml was inserted into the Soxhlet tube to moisten the simplicia. The ratio between simplicia and solvent was 1:5. The Soxhlet extraction process was carried out at a temperature of 70 – 80 °C, and the extraction was carried out for up to 3 repeat cycles. The extract was stored in the refrigerator at a temperature of 10 °C until used in research.\u003c/p\u003e\n\u003cp\u003e2.1.3. Hydrolysis Extraction Method by α-Chymotrypsin for Bioactive Peptide Measurements\u003c/p\u003e\n\u003cp\u003e\u003cem\u003eC. racemosa\u0026nbsp;\u003c/em\u003esimplicia was dissolved in a 1.0 mM phosphate buffer and then hydrolyzed with the α-chymotrypsin enzyme under its optimal conditions, referring to \u003csup\u003e20\u003c/sup\u003e, which utilizes 1,200 U/mg enzyme activity, 37 °C temperature, at 8.0 pH with digestion time of 2 hours, substrate concentration of 20 mg/mL, 4.0 E/S (w/w) (%). The reaction was stopped by heating at 95 °C for 15 minutes, and the hydrolysate protein was centrifuged at 16,000 rpm for 10 minutes at 4 °C. The supernatant protein (PS) was lyophilized and stored at a temperature of -20 °C for further use in the analysis of the bioactive profiling of peptides.\u003c/p\u003e\n\u003cp\u003e2.2. Metabolomic Profiling Extract from Maceration and Soxhlet Methods\u003c/p\u003e\n\u003cp\u003eThe untargeted metabolomics profiling test on Sea grapes extract samples (Maceration; Soxhlet Method) was carried out using the Liquid Chromatography High-Resolution Mass Spectrometry (LC-HRMS) method at the Laboratorium Sentral Ilmu Hayati (LSIH; ISO 9001:2008 and ISO 17025:2005; Central Laboratory of Life Sciences; Brawijaya University, Malang-65145, Indonesia) testing services, with the test number 041/LSIH-UB/LK/II/2022.\u003c/p\u003e\n\u003cp\u003e2.2.1. Analysis of the Maceration and Soxhlet samples by HPLC-ESI-HRMS/MS\u003c/p\u003e\n\u003cp\u003eFifty (50) μl of extract samples (Maceration; Soxhlet Method) were diluted using 96% ethanol up to a final volume of 1,500 μl. The solutions were vortexed at 2,000 rpm for 2 minutes and then span-down at 6,000 rpm for 2 minutes. The supernatant was taken and then filtered using a 0.22μm syringe filter and injected into the vial. The sample in the vial was ready to be inserted into an autosampler and then injected into LC-HRMS (Liquid Chromatography High-Resolution Mass Spectrometry). LC-HRMS uses High-Performance Liquid Chromatography (HPLC) Thermo Scientific Dionex Ultimate 3000 RSLC nano with microflow meter. Solvents A and B consist of 0.1% formic acid in water and 0.1% formic acid in acetonitrile. The analytical column uses Hypersil GOLD aQ 50 x 1 mm x 1.9 μ particle size with a flow rate of 40 uL/min, a flow gradient run time of 30 minutes, and a column oven with a temperature of 30 °C. High-Resolution Mass Spectrometer using Thermo Scientific Q Exactive with a full scan at 70,000 resolution, data-dependent MS/MS at 17,500 resolution, and run time of 30 minutes, with both positive and negative mode.\u003c/p\u003e\n\u003cp\u003e2.2.2. Processing Data Software\u003c/p\u003e\n\u003cp\u003eAnnotated or detected compounds were automatically identified via mzCloud MS/MS Library (Thermo Scientific Q Exactive Software), which were performed by Midia Lestari Wahyu Handayani, S.TP, M.Sc., MP., Ph.D., a certified laboratory technician at the Sentral Ilmu Hayati Laboratorium (LSIH; ISO 9001:2008 and ISO 17025:2005; Central Laboratory of Life Sciences; Brawijaya University, Malang-65145, Indonesia).\u003c/p\u003e\n\u003cp\u003e2.3. Proteomics Assay of Sequence and Molecular Weight of Amino Acids\u003c/p\u003e\n\u003cp\u003e2.3.1. Ultrafiltration and Reversed-Phase HPLC (RP-HPLC)\u003c/p\u003e\n\u003cp\u003eThe hydrolyzed protein (PS) of \u003cem\u003eC. racemosa\u0026nbsp;\u003c/em\u003ewas divided into 3 peptide fractions based on molecular weight ((F1; \u0026lt; 3 kDa), (F2; 3–10 kDa), and (F3; \u0026gt; 10 kDa)) using ultrafiltration membrane of 10 kDa and 3 kDa. This approach referred to \u003csup\u003e20\u003c/sup\u003e, which showed that peptide fraction of F1 (MW \u0026lt; 3 kDa) at 4 mg/mL had better antioxidant activity than F2 (3 – 10 kDa) dan F3 (MW \u0026gt; 3 kDa). Peptides with lower molecular weight are more active than those with a high molecular weight \u003csup\u003e20\u003c/sup\u003e.\u003c/p\u003e\n\u003cp\u003e2.3.2. Separation of fraction F1 by RP-HPLC\u003c/p\u003e\n\u003cp\u003eFraction 1 (F1; \u0026lt; 3 kDa) was purified using RP-HPLC. 40 mg of peptide fraction was dissolved into 1 mL 0.05% TFA (v/v) and then was filtered using micropores membrane (0.22 m) before being inserted into Agilent ZORBAX SB-C18 (5 m, 9.4 × 150 mm). A binary moving phase system was used in this study along with eluent A (0,1% TFA (v/v)) and moving phase B (ACN, 0.05% (v/v) TFA). The solution was eluted with a linear gradient of 0 – 40% moving phase B from 0 – 40 minutes dan 40% moving phase B from 40 – 55 minutes. All fractions were collected and lyophilized for further activity assays. The purification level of fractions with the highest activity was further analyzed using the Sunfire C18 column (5 m, 4,6 mm × 150 mm; Waters, USA). The column was eluted using a linear gradient of 0 – 20% moving phase B from 0 – 20 minutes and 20% moving phase B from 20 – 25 minutes, resulting in a purified fraction 1 (PF1).\u003c/p\u003e\n\u003cp\u003e2.3.3. Analysis of Amino Acid Sequence and MW\u003c/p\u003e\n\u003cp\u003eThe ELWKTF (Glu-Leu-Trp-Lys-Thr-Phe) peptide was synthesized in the Laboratory of Biochemistry and Biomolecular Medicine, Faculty of Medicine, Universitas Brawijaya, Malang, Indonesia. A protein sequencer from Applied Biosystems 494 (ProciseTM 494 N-terminal sequencer; Applied Biosystems Inc, Foster City, CA, USA) was used to examine the amino acid sequence of the purified fraction (PF1) based on time-of-flight quadrupole mass spectrometer (MS/MS) paired with electrospray ionization (ESI) source to determines the molecular weight of the ELWKTF (Glu-Leu-Trp-Lys-Thr-Phe). Analysis of the sequence and molecular weight of ELWKTF was performed according to the method described by Zhang \u003cem\u003eet al\u003c/em\u003e. (2019)\u003csup\u003e\u0026nbsp;\u003c/sup\u003e\u003csup\u003e24\u003c/sup\u003e. The results of research by Xiaoqian Zhang et al. 2019 showed good activity of ELWKTF (Glu-Leu-Trp-Lys-Thr-Phe) against radical scavenging activity (DPPH and ABTS) \u003csup\u003e20\u003c/sup\u003e.\u003c/p\u003e\n\u003cp\u003e2.4. DPPH Antioxidant Radical Scavenging Activity Assay\u003c/p\u003e\n\u003cp\u003eThe percentage (%) of the inhibition of 2,2-diphenyl-1-picrylhydrazyl (DPPH) was measured using a method referring to Kaur\u003cem\u003e\u0026nbsp;et al\u003c/em\u003e., (2021) \u003csup\u003e25\u003c/sup\u003e and Permatasari \u003cem\u003eet al\u003c/em\u003e., (2022) \u003csup\u003e26\u003c/sup\u003e, on all samples which include a macerated extract (EM), soxhlet extract (ES), and purified fraction 1 (PF1), while glutathione (GSH; 354102, Sigma-Aldrich) was used as a positive control. In the testing vial (at a concentration of 1, 2, 3, 4, 5 μg, an aliquot (100 μL) of samples and control was added, followed by a DPPH reagent addition (3 mL). The DPPH-extract combination that resulted was then left undisturbed (30 min; dark cycle). The samples were read at 517 nm absorbance with a UV-Vis Shimadzu 80 spectrophotometer. To ensure the validity of the data results, each sample was checked three times (n = 3). Inhibition of DPPH was expressed as a percentage and is determined according to the formula below:\u003c/p\u003e\n\u003cp\u003e\u003cimg src=\"data:image/png;base64,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\" width=\"278\" height=\"40\"\u003e\u003c/p\u003e\n\u003cp\u003eA0 = Absorbance of blank; A1 = Absorbance of standard or sample.\u003c/p\u003e\n\u003cp\u003eThe half-elimination ratio (EC\u003csub\u003e50\u003c/sub\u003e) was used to express the radical scavenging capacity of EM, ES, PF1, and GSH and defined as the concentration of a sample that caused a 50% decrease in the initial radical concentration.\u003c/p\u003e\n\u003cp\u003e2.5. ABTS Radical Scavenging Activity assay\u003c/p\u003e\n\u003cp\u003eFor testing the 2,2’-Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) or diammonium salt radical cation (ABTS+; Sigma-Aldrich), the procedure follows the method introduced by Arnao et al. (2010) with some modifications \u003csup\u003e27\u003c/sup\u003e. The stock solution includes 7 mM ABTS solution and 2.4 mM potassium persulfate solution. The working solution was prepared by mixing two stock solutions in equal quantities and letting them react for 14 hours at room temperature under dark conditions. The solution was then diluted by mixing 1 mL of ABTS solution with 60 mL of ethanol to set absorbance to 0.706 ± 0.01 units at 734 nm using a spectrophotometer (Thermo Scientific™ GENESYS™) is obtained. A fresh or new ABTS fresh/new solution was prepared for each test. Samples (at a concentration of 1, 2, 3, 4, and 5 μg) were allowed to react with 1 ml of ABTS solution, and the absorbance was taken at 734 nm after 7 minutes using a spectrophotometer. Treatment was carried out in the same way for all samples, including extract maceration (EM), extract-soxhletation (ES), purified fraction 1 (PF1), and Trolox (6-Hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid; Sigma-Aldrich) was used as a positive control. All determinations were performed in three replication (n = 3).\u003c/p\u003e\n\u003cp\u003e\u003cimg src=\"data:image/png;base64,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\" width=\"394\" height=\"47\"\u003e\u003c/p\u003e\n\u003cp\u003eA0 = Absorbance of blank; A1 = Absorbance of standard or sample.\u003c/p\u003e\n\u003cp\u003eThe half-elimination ratio (EC\u003csub\u003e50\u003c/sub\u003e) was used to express the radical scavenging capacity of EM, ES, PF1, and GSH and defined as the concentration of a sample that caused a 50% decrease in the initial radical concentration.\u003c/p\u003e\n\u003cp\u003e2.6. Cytotoxicity Evaluation using MTT Assay\u003c/p\u003e\n\u003cp\u003eCell viability was assessed on the Human Caucasian skin fibroblast cell line (Normal cell; Bud-8) \u003csup\u003e28\u003c/sup\u003e. The proliferation rate of the Bud-8 cell line after sample treatment was determined by a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) test. A mitochondrial dehydrogenase reduces MTT to a purple compound formazan that is insoluble in water, depending on the viability of the cell. Cells were preserved in Dulbecco's Modified Essential Medium (DMEM), which was supplemented with 10% fetal bovine serum (FBS) and 1x Penicillin-Streptomycin-Neomycin (PSN). One hundred microliters of cells (4 × 10\u003csup\u003e4\u003c/sup\u003e cells/mL) were seeded in a 96-well plate and incubated at 37°C, 5% carbon dioxide for 24 hours. After 24 hours of incubation, the cells were treated with 100 μL of 100, 200, 300, 400, and 500 μg/mL of samples (EM, ES, PF1). The plate was incubated at 37°C, with 5% CO\u003csub\u003e2\u003c/sub\u003e for 24 and 48 hours. After incubation, the morphology of the cells was examined under a microscope. Twenty microliters of MTT (5 mg/mL) (Sigma) solution was added to each well plate. The plate was further incubated for 2 to 4 hours, and the medium was removed. Formazan crystals dissolved with 100 μL dimethyl sulfoxide (DMSO; Sigma). Absorbance was measured at 560 nm, and the percentage of cell viability and LC\u003csub\u003e50\u003c/sub\u003e cells is calculated by:\u003c/p\u003e\n\u003cp\u003e\u003cimg src=\"data:image/png;base64,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\"\u003e\u003cbr\u003e\u003c/p\u003e\n\u003cp\u003eWhere A0 is absorbance control in cells given 1%, DMSO and A1 are cells' absorbance samples given the test sample.\u003c/p\u003e\n\u003cp\u003eLethal concentration (LC\u003csub\u003e50\u003c/sub\u003e) is the lowest concentration of samples that inhibits 50% of cells. In general, a low LC\u003csub\u003e50\u003c/sub\u003e value indicates high toxicity. Extracts with high LC\u003csub\u003e50\u003c/sub\u003e are preferred for use due to their low toxicity effect on host cells \u003csup\u003e28\u003c/sup\u003e.\u003c/p\u003e\n\u003cp\u003e2.7. Data Management and Analysis\u003c/p\u003e\n\u003cp\u003eData from \u003cem\u003ein vitro\u003c/em\u003e tests (DPPH antioxidants, ABTS antioxidants, and Cytotoxicity) were analyzed for significance or not between groups (EM, ES, PF1, or control) using two-way ANOVA CI 95% (0.05) with the MacBook version of GraphPad Prism 9.0.0 premium software. All data were presented in the form of average ± SEM. Graphic visualizations were presented using the MacBook version of GraphPad Prism 9.0.0 premium software. The graphical abstract was designed using the author's licensed BioRender Premium (Fahrul Nurkolis).\u003c/p\u003e"},{"header":"3 Results","content":"\u003cp\u003e\u003cem\u003e3.1 Caulerpa racemosa metabolite profiles by non-targeted metabolomic profile\u003c/em\u003e\u003c/p\u003e\n\u003cp\u003eFigure 1 indicated the LC-MS/MS total ion chromatogram and mass spectrum of the macerated Sea grapes (\u003cem\u003eC. racemosa\u003c/em\u003e) extract used to determine the peaks representing the number of annotated ions, the retention time, and the relative abundance of the ions. Annotated compounds were automatically identified via mzCloud MS/MS Library (Thermo Scientific Q Exactive Software). Based on non-targeted metabolomic profiling results with Liquid Chromatography-High Resolution Mass Spectrometry (LC-HRMS), within a retention time of 40 minutes, macerated Sea grapes (\u003cem\u003eC. racemosa\u003c/em\u003e) Extract (which represents cold extraction) contained a total of 103 compounds that were eluted between 0.00-30.0 minutes (Figure 1A). One hundred and three metabolite derivatives were successfully identified in Sea grapes (\u003cem\u003eC. racemosa\u003c/em\u003e) from macerated extracts and were presented in Table 1. Figure 1B FTMS + p ESI Full ms. [50.0000-750.0000] is a spectrum with a base peak intensity of 2.90 x 10\u003csup\u003e6\u003c/sup\u003e counts (combination of electrospray ionization (ESI) with Fourier transform mass spectrometry (FTMS)). This FTMS was in positive mode and with electrospray ionization (ESI) continuous measurements from m/z 50 to m/z 600 (NL = normalization rate).\u003c/p\u003e\n\u003cp\u003eThe data shown in Table 1 were based on matches with libraries or mzCloud Best Match (\u0026gt;90%) and in order according to their abundance. This was what causes the difference between the calculated exact mass (*) observed in the LC-HRMS results and the predicted-calculated molecular mass (**) in both PubChem and ChemDraw databases. Therefore, we presented molecular mass data by juxtaposing Calculated Exact Mass (*) with Predicted-calculated molecular mass (**) from ChemDraw in Table 1.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eTable 1.\u0026nbsp;\u003c/strong\u003e103 Compounds Observed from HPLC-ESI-HRMS/MS Analysis of Macerated Sea grapes (\u003cem\u003eC. racemosa\u003c/em\u003e) Extract.\u003c/p\u003e\n\u003ctable border=\"1\" width=\"708\"\u003e\n \u003cthead\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e\u003cstrong\u003eNo.\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e\u003cstrong\u003eRT (min)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e\u003cstrong\u003eAbundance (Area Max.)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e\u003cstrong\u003eObserved HR-ESIMS m/z*\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e\u003cstrong\u003eCalculated HR-ESIMS m/z\u003c/strong\u003e\u003cstrong\u003e**\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e\u003cstrong\u003eMolecular Formula\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e\u003cstrong\u003eTentatively Identified Compound\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e\u003cstrong\u003eCategory\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/thead\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e1. \u0026nbsp; \u0026nbsp; \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e15.508\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e2,607,709,506.66\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e366.0987\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e344.1100\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e20\u003c/sub\u003eO\u003csub\u003e9\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e3-[3-(beta-D-Glucopyranosyloxy)-2-hydroxyphenyl]propanoic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eCarboxylic Acids\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e2. \u0026nbsp; \u0026nbsp; \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e0.948\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e1,702,868,432.32\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e103.0996\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e104.1100\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e5\u003c/sub\u003eH\u003csub\u003e13\u003c/sub\u003eNO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eCholine\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eAmines (Quartenary Ammonium Compounds)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e3. \u0026nbsp; \u0026nbsp; \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e0.952\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e815,230,823.19\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e117.0787\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e117.0800\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e5\u003c/sub\u003eH\u003csub\u003e11\u003c/sub\u003eNO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eBetaine\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eAmines (Quartenary Ammonium Compounds)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e4. \u0026nbsp; \u0026nbsp; \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e18.019\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e530,234,031.11\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e278.1504\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e278.1500\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e22\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eDibutyl phthalate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eCarboxylic Acids (Phthalic Acids)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e5. \u0026nbsp; \u0026nbsp; \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e10.763\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e484,746,646.13\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e312.0885\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e312.0900\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e11\u003c/sub\u003eF\u003csub\u003e3\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e2-(1H-indol-3-yl)-3-[4-(trifluoromethyl)phenyl]acrylonitrile\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eOrganofluorine compounds\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e6. \u0026nbsp; \u0026nbsp; \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e0.931\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e464,700,110.40\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e189.0429\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e167.0600\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e8\u003c/sub\u003eH\u003csub\u003e9\u003c/sub\u003eNO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e2-(3,4-dihydroxyphenyl)acetamide\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eOrganonitrogen compound (carboxamide)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e7. \u0026nbsp; \u0026nbsp; \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e12.259\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e312,358,366.23\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e157.146\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e156.1400\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e9\u003c/sub\u003eH\u003csub\u003e19\u003c/sub\u003eNO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e2,2,6,6-Tetramethyl-1-piperidinol (TEMPO)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eHeterocyclic compounds (piperidines)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e8. \u0026nbsp; \u0026nbsp; \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e21.93\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e275,377,138.03\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e255.2549\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e255.2600\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e33\u003c/sub\u003eNO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eHexadecanamide\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eFatty Acids (Palmitic Acids)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e9. \u0026nbsp; \u0026nbsp; \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e17.905\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e273,288,427.76\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e278.1504\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e276.1400\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e22\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eDiisobutylphthalate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eCarboxylic Acids\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e10. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e0.927\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e209,833,574.73\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e205.0169\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e205.0200\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e10\u003c/sub\u003eH\u003csub\u003e7\u003c/sub\u003eNO\u003csub\u003e2\u003c/sub\u003eS\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e5-(2-Thienyl)nicotinic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eCarboxylic acid (aromatic carboxylic acid)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e11. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e0.916\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e204,192,224.93\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e87.10487\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e87.1000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e5\u003c/sub\u003eH\u003csub\u003e13\u003c/sub\u003eN\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eIsoamylamine\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eAmines\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e12. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e18.231\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e188,856,575.32\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e296.2341\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eCannot be generated\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e34\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eNP-008993\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eunknown\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e13. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e15.894\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e188,602,459.59\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e276.2077\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e254.2200\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003ePalmitoleic Acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eFatty Acids\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e14. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e17.615\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e128,180,581.48\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e294.2184\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e294.2200\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e9-Oxo-10(E),12(E)-octadecadienoic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eFatty Acids\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e15. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e17.427\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e123,110,274.85\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e294.2183\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e312.2300\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e32\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e(\u0026plusmn;)13-hydroperoxy-9Z,11E-octadecadienoic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eFatty Acids\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e16. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e13.158\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e120,142,739.65\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e294.1819\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e294.1800\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e17\u003c/sub\u003eH\u003csub\u003e26\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e6-Gingerol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eAlcohol (Fatty Alcohols)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e17. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e1.001\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e115,965,792.41\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e270.108\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e135.0500\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e5\u003c/sub\u003eH\u003csub\u003e5\u003c/sub\u003eN\u003csub\u003e5\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eAdenine\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eHeterocyclic compounds (purines)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e18. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e21.564\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e113,705,808.63\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e281.2706\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e281.2700\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e35\u003c/sub\u003eNO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eOleamide\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eFatty Amides\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e19. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e16.815\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e101,832,983.44\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e278.2234\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e278.2200\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e\u0026alpha;-Eleostearic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eFatty Acids\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e20. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e16.451\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e95,661,314.03\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e268.2027\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eCannot be generated\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eNP-001596\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eunknown\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e21. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e11.582\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e85,055,308.35\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e326.1044\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e326.1000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eN\u003csub\u003e4\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e4-{[(4,6-Dimethoxypyrimidin-2-yl)amino]methylidene}-2-phenyl-4,5-dihydro-1,3-oxazol-5-one\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eOrganofluorine compounds\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e22. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e14.177\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e82,274,117.71\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e148.0883\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e148.0900\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e10\u003c/sub\u003eH\u003csub\u003e12\u003c/sub\u003eO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eCuminaldehyde\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eHydrocarbons (Terpenes)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e23. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e15.669\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e79,749,057.14\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e326.2445\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e326.2500\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e19\u003c/sub\u003eH\u003csub\u003e34\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e1,2-dihydroxyheptadec-16-yn-4-yl acetate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eOrganic Hydroxy compound (alcohol)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e24. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e1.024\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e79,366,759.62\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e267.0956\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e267.1000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e10\u003c/sub\u003eH\u003csub\u003e13\u003c/sub\u003eN\u003csub\u003e5\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eAdenosine\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eCarbohydrates (Purine Nucleosides)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e25. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e20.046\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e75,757,786.32\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e278.2234\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e278.4400\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e\u0026alpha;-Linolenic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eEssential fatty acid\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e26. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e17.351\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e73,810,505.50\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e342.0991\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e320.1200\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e19\u003c/sub\u003eH\u003csub\u003e16\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eethyl 3-oxo-5,6-diphenyl-2,3- dihydropyridazine-4-carboxylate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eFatty acid transporters\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e27. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e16.633\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e70,444,302.73\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e292.2026\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e322.2500\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e28\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e12-Oxo phytodienoic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eFatty Acids (Octadecanoids)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e28. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e1.044\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e70,264,037.81\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e122.0476\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e122.0500\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eNicotinamide\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eHeterocyclic compounds (Pyridinecarboxylic acids)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e29. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e23.794\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e66,634,752.38\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e283.2858\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e283.2900\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e37\u003c/sub\u003eNO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eStearamide\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eAmides\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e30. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e21.936\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e62,781,318.81\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e307.2861\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e325.3000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e39\u003c/sub\u003eNO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eOleoyl ethanolamide\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eAmines (Amino alcohols)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e31. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e13.43\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e61,670,246.92\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e276.1714\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eCannot be generated\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e26\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eNP-020014\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eunknown\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e32. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e17.56\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e58,853,299.74\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e302.2233\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e320.2400\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e32\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e11,12-epoxy-5,8,14-eicosatrienoic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eEicosanoids\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e33. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e20.518\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e57,317,714.92\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e622.2406\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e584.6600\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e29\u003c/sub\u003eH\u003csub\u003e44\u003c/sub\u003eO\u003csub\u003e12\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eOuabain\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eAutacoids (Eicosanoids)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e34. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e12.847\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e56,359,590.26\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e164.0831\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e182.0900\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e10\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e1-(4-methoxyphenyl)propane-1,2-diol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eHydrocarbon (cyclic hydrocarbon)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e35. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e0.873\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e53,487,771.60\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e235.1412\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e235.1400\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e14\u003c/sub\u003eH\u003csub\u003e18\u003c/sub\u003eFNO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e4-Fluoro-\u0026alpha;-pyrrolidinobutiophenone\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eButyrophenones\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e36. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e1.305\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e53,461,055.41\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e167.0611\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e167.1600\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e8\u003c/sub\u003eH\u003csub\u003e9\u003c/sub\u003eNO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003ePyridoxal\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eHeterocyclic compounds (Pyridine carboxaldehydes)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e37. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e14.862\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e53,396,851.21\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e214.135\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e232.1500\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e20\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e(4aR,5R,6R)-6-hydroxy-4a,5-dimethyl-3-\u003c/p\u003e\n \u003cp\u003e(prop-1-en-2-yl)-2,4a,5,6,7,8-\u003c/p\u003e\n \u003cp\u003ehexahydronaphthalen-2-one\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eTerpenoid\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e38. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e14.874\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e51,133,618.50\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e356.1586\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e334.1800\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e19\u003c/sub\u003eH\u003csub\u003e26\u003c/sub\u003eO\u003csub\u003e5\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e(3S,3aR,4S,4aR,7aR,8R,9aR)-3,4a,8-\u003c/p\u003e\n \u003cp\u003etrimethyl-2,5-dioxo-\u003c/p\u003e\n \u003cp\u003e2H,3H,3aH,4H,4aH,5H,7aH,8H,9H,9aHazuleno[\u003c/p\u003e\n \u003cp\u003e6,5-b]furan-4-yl 2-methylpropanoate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eHeterocyclic Compounds\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e39. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e15.089\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e47,187,926.45\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e328.0835\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e328.0800\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e17\u003c/sub\u003eClN\u003csub\u003e2\u003c/sub\u003eS\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e1-(4-chlorobenzyl)-2-{[(4-\u003c/p\u003e\n \u003cp\u003emethylphenyl)thio]methyl}-1H-imidazole\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eProtein Enzyme\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e40. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e16.835\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e44,926,299.27\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e328.2602\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e328.2600\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e19\u003c/sub\u003eH\u003csub\u003e36\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e1,4-dihydroxyheptadec-16-en-2-yl acetate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eOrganic Hydroxy compound (alcohol)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e41. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e22.189\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e43,991,117.28\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e500.2191\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e250.1100\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eMethaqualone\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eHeterocyclic compounds (Quinazolines)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e42. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e16.48\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e41,454,327.51\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e250.1923\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e426.3000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e26\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eOctylphenol Ethoxylates (OPEO)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003ealkylphenols\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e43. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e14.714\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e38,806,980.21\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e273.2655\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e256.2400\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e32\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003ePalmitic Acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eFatty acids\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e44. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e16.334\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e37,032,281.51\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e300.2076\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e318.4600\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e8-Hydroxyeicosapentaenoic acid \u0026nbsp;((\u0026plusmn;)8-HEPE)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eHydroxy fatty acid\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e45. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e20.987\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e35,975,153.82\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e282.2548\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e282.2600\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e34\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eEthyl palmitoleate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eFatty acid ester (Fatty acid ethyl ester)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e46. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e21.041\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e34,105,859.15\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e280.239\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eCannot be generated\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e34\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eNP-011548\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eunknown\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e47. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e11.577\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e33,493,328.71\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e164.0831\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e164.0800\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e10\u003c/sub\u003eH\u003csub\u003e12\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e4-Phenylbutyric acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eCarboxylic Acids (Phenylbutyrates)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e48. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e14.077\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e32,107,702.51\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e248.1766\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e266.1900\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e26\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eTetranor-12R-HETE\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eOrgany Hydroxy compound (Hydroxy carboxylic acid)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e49. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e16.588\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e31,279,593.58\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e314.1846\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e292.2000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e28\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e4-hydroxy-6-[2-(2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)ethyl]oxan-2-one\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eHeterocyclic compound (oxacycle)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e50. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e17.366\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e31,243,191.82\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e354.2756\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e354.2800\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e21\u003c/sub\u003eH\u003csub\u003e38\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e1-Linoleoyl glycerol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eGlycerides\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e51. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e18.021\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e31,197,110.75\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e323.2083\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e306.1800\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e26\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003en-Pentyl isopentyl phthalate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003ePhthalates\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e52. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e16.258\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e30,927,401.68\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e268.2028\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eCannot be generated\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eNP-001596\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eunknown\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e53. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e7.466\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e30,636,932.36\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e197.1198\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e197.1200\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e14\u003c/sub\u003eH\u003csub\u003e15\u003c/sub\u003eN\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eDibenzylamine\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eAmines\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e54. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e18.515\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e30,124,986.19\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e318.216\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eCannot be generated\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e32\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eNP-014287\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eunknown\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e55. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e12.819\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e29,968,764.20\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e232.1455\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eCannot be generated\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e22\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e(1aR,1bR,2R,3R,7R,7aS)-1b,2-dimethyl-7a-(prop-1-en-2-yl)-1aH,1bH,2H,3H,4H,5H,7H,7aH-naphtho[1,2-b]oxirene-3,7-diol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eunknown\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e56. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e15.64\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e28,287,214.04\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e196.0881\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e196.0900\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e14\u003c/sub\u003eH\u003csub\u003e12\u003c/sub\u003eO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e4-Methylbenzophenone\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eKetones (Benzophenones)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e57. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e14.449\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e27,409,945.13\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e214.135\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e232.1500\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e20\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e(4aR,5R,6R)-6-hydroxy-4a,5-dimethyl-3-(prop-1-en-2-yl)-2,4a,5,6,7,8-hexahydronaphthalen-2-one\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eTerpenoid\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e58. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e16.302\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e27,286,206.71\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e302.2444\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e302.2500\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e17\u003c/sub\u003eH\u003csub\u003e34\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e2,3-dihydroxypropyl 12-methyltridecanoate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e\u0026nbsp;Glyceride\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e59. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e15.864\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e25,328,627.10\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e316.2003\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e316.2000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e28\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eCafestol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eHydrocarbons (Terpenes)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e60. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e14.695\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e24,803,082.67\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e508.263\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e526.2700\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e27\u003c/sub\u003eH\u003csub\u003e37\u003c/sub\u003eF\u003csub\u003e3\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e5\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e[6-Hydroxy-1-(hydroxymethyl)-1,4a-dimethyl-5-(2-oxo-2-pyrrolidin-1-ylethyl)-2,3,4,5,6,7,8,8a-octahydronaphthalen-2-yl] N-[3-(trifluoromethyl)phenyl]carbamate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eOrganofluorine compounds\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e61. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e20.606\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e24,591,569.01\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e308.2339\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e302.2200\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eEicosapentaenoic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eFatty Acids\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e62. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e21.592\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e23,630,078.82\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e313.2967\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e313.3000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e19\u003c/sub\u003eH\u003csub\u003e39\u003c/sub\u003eNO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eR-Palmitoyl-(2-methyl) ethanolamide\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eLipid (Fatty Amide)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e63. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e12.163\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e23,533,439.36\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e370.094\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eCannot be generated\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e21\u003c/sub\u003eH\u003csub\u003e20\u003c/sub\u003eCl\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e2-(2,4-dichlorophenyl)-4,4,7,9-tetramethyl-4,5-dihydro-3H-naphtho[1,2-d]imidazole\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eunknown\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e64. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e12.76\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e23,504,570.02\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e234.1611\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e252.1700\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e24\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eAgeratriol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eTerpenoids\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e65. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e14.233\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e23,426,676.24\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e244.1091\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e262.1200\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e18\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e(3aR,4aS,5R,8S,9aR)-5-hydroxy-4a,8-dimethyl-3-methylidene-2H,3H,3aH,4H,4aH,5H,6H,8H,9H,9aH-azuleno[6,5-b]furan-2,6-dione\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eTerpenes\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e66. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e13.406\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e23,234,665.52\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e232.1455\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eCannot be generated\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e22\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e(1aR,1bR,2R,3R,7R,7aS)-1b,2-dimethyl-7a-(prop-1-en-2-yl)-1aH,1bH,2H,3H,4H,5H,7H,7aH-naphtho[1,2-b]oxirene-3,7-diol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eNuclear receptor\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e67. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e12.099\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e22,988,983.05\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e384.1096\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eCannot be generated\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e19\u003c/sub\u003eF\u003csub\u003e3\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eS\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eethyl 2-(methylthio)-4-tetrahydro-1H-pyrrol-1-yl-8-(trifluoromethyl)quinoline-3-carboxylate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eunknown\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e68. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e18.446\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e22,839,809.05\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e218.1662\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eCannot be generated\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e24\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eNP-004713\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eunknown\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e69. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e20.376\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e22,099,138.42\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e330.2546\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e330.2600\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e22\u003c/sub\u003eH\u003csub\u003e34\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eEicosapentaenoic acid ethyl ester\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eFatty Acids\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e70. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e17.161\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e21,808,214.15\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e270.2183\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eCannot be generated\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e32\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eNP-020214\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eunknown\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e71. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e13.431\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e20,606,367.65\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e261.1354\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e239.1500\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e13\u003c/sub\u003eH\u003csub\u003e21\u003c/sub\u003eNO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eLevalbuterol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eAmines (Phenethylamines)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e72. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e20.074\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e20,450,089.14\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e306.2545\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e306.2600\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e34\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eLinolenic acid ethyl ester\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eFatty Acids\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e73. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e21.707\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e19,935,241.14\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e310.2857\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e310.2900\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e38\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eEthyl oleate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eFatty Acids\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e74. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e14.41\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e19,870,753.40\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e182.0725\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e182.0700\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e13\u003c/sub\u003eH\u003csub\u003e10\u003c/sub\u003eO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eBenzophenone\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eKetones (Benzophenones)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e75. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e17.367\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e18,964,856.34\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e262.2285\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e280.4500\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e32\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eOctadec-9-ynoic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eHydrocarbons (Alkynes)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e76. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e15.997\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e18,954,242.24\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e228.1141\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e246.1300\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e18\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e(3aS,5aS,9bR)-5a,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,5aH,6H,7H,8H,9bH-naphtho[1,2-b]furan-2,5-dione\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eTerpenes\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e77. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e19.433\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e18,184,819.14\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e328.2388\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e328.2400\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e22\u003c/sub\u003eH\u003csub\u003e32\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eDocosahexaenoic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eFatty Acids\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e78. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e26.392\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e18,033,386.90\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e283.3227\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e284.3300\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e19\u003c/sub\u003eH\u003csub\u003e41\u003c/sub\u003eN\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eCetrimonium\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eAmines (Quartenary Ammonium Compounds)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e79. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e17.063\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e17,943,409.82\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e398.169\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e398.1700\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e22\u003c/sub\u003eH\u003csub\u003e26\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003eS\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e3-(3,4-dimethoxyphenethyl)-2-[(4-isopropylphenyl)imino]-1,3-thiazolan-4-one\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eOrganic Chemicals\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e80. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e9.957\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e17,802,168.49\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e236.1402\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e254.1500\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e14\u003c/sub\u003eH\u003csub\u003e22\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e(\u0026plusmn;)-C75\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eOrganic heterocyclic compound\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e81. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e16.951\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e17,509,512.15\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e234.1611\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e234.1600\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e22\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e3,5-di-tert-Butyl-4-hydroxybenzaldehyde\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eAldehydes (Benzaldehydes)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e82. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e20.317\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e17,492,831.93\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e299.2812\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e299.2800\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e37\u003c/sub\u003eNO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003ePalmitoyl ethanolamide\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eAmines (Amino Alcohols)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e83. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e15.118\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e16,405,749.44\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e467.3231\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e467.3100\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e28\u003c/sub\u003eH\u003csub\u003e41\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eOxethazaine\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eAmines (Amino Alcohols)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e84. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e19.858\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e16,337,402.48\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e305.2705\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eCannot be generated\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e35\u003c/sub\u003eNO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eNP-016582\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eunknown\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e85. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e20.015\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e16,138,319.09\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e321.2654\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e299.5000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e37\u003c/sub\u003eNO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eSphingosine (d18:1)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eAmines\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e86. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e16.742\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e15,941,236.73\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e692.3268\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eCannot be generated\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e22\u003c/sub\u003eH\u003csub\u003e22\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e4-(3-methoxy-5,6-dihydrobenzo[c]acridin-7-yl)morpholine\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eunknown\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e87. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e13.152\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e15,540,877.24\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e334.1743\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e334.1700\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e21\u003c/sub\u003eH\u003csub\u003e22\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e(-)-Strychnine\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eAlkaloids (Indole Alkaloids)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e88. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e20.726\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e15,378,473.45\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e304.2391\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e304.2400\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e32\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eArachidonic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eAutacoids (Eicosanoids)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e89. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e16.279\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e15,308,423.13\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e356.0783\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e356.0700\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e12\u003c/sub\u003eN\u003csub\u003e4\u003c/sub\u003eOS\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e3,4-Diphenylpyrimido[4\u0026apos;,5\u0026apos;:4,5]thieno[2,3-c]pyridazin-8(7H)-one\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eThienopyridazine derivatives\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e90. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e17.305\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e14,960,482.55\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e378.2755\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e378.2800\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e23\u003c/sub\u003eH\u003csub\u003e38\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e2-Arachidonoyl glycerol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eGlycerolipid\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e91. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e19.83\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e14,601,900.81\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e442.3432\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e442.3400\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e29\u003c/sub\u003eH\u003csub\u003e46\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eTestosterone decanoate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eGonadal Steroid Hormones (Testosterone congeners)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e92. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e14.886\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e14,357,946.57\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e274.1558\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e252.1700\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e24\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e(5E)-7-methylidene-10-oxo-4-(propan-2-yl)undec-5-enoic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eTerpenes\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e93. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e17.72\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e13,897,675.48\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e312.2651\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e306.2600\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e34\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e\u0026gamma;-Linolenic acid ethyl ester\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eFatty acid derivative\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e94. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e15.669\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e12,500,838.24\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e510.2786\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eCannot be generated\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e27\u003c/sub\u003eH\u003csub\u003e40\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e6\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e6-Hydroxy-1-(hydroxymethyl)-5-{2-[2-(hydroxymethyl)-1-pyrrolidinyl]-2-oxoethyl}-1,4a-dimethyldecahydro-2-naphthalenyl phenylcarbamate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eunknown\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e95. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e19.475\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e12,426,002.76\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e344.195\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e344.2000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e21\u003c/sub\u003eH\u003csub\u003e28\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eNor-9-carboxy-\u0026delta;9- tetrahydrocannabinol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eTerpenes\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e96. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e26.449\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e12,331,286.20\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e131.0942\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e131.0900\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e13\u003c/sub\u003eNO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e6-Aminocaproic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eCarboxyclic Acid (Caproates)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e97. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e17.805\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e9,806,912.19\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e340.1637\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e340.1600\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e24\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eOS\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003ePropionylpromazine\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eSulfur compounds (Phenothiazines)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e98. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e23.138\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e9,589,300.00\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e390.2753\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e390.2800\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e24\u003c/sub\u003eH\u003csub\u003e38\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eDi(2-ethylhexyl) phthalate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eCarboxylic acid (Phthalic acid)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e99. \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e20.548\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e9,339,555.94\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e176.1194\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e194.1300\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e12\u003c/sub\u003eH\u003csub\u003e18\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eSedanolide\u003c/p\u003e\n \u003cp\u003e\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eHeterocyclic Compound (Benzofurans)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e100. \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e19.703\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e9,113,695.23\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e303.2549\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e303.2600\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e33\u003c/sub\u003eNO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eArachidonoyl amide\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eFatty acid derivative (fatty amide)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e101. \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e16.962\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e8,865,034.10\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e248.1766\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e266.1900\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e26\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eTetranor-12(S)-HETE\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eOrganic Hydroxy compound (hydroxy carboxylic acid)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e102. \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e18.548\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e8,618,378.15\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e306.2545\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e306.2600\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e34\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003e8Z,11Z,14Z-Eicosatrienoic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eAutacoids (Eicosanoids)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"56\"\u003e\n \u003cp\u003e103. \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp;\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e21.448\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"104\"\u003e\n \u003cp\u003e8,239,070.91\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e363.3121\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003e357.3000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eC\u003csub\u003e24\u003c/sub\u003eH\u003csub\u003e39\u003c/sub\u003eNO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"152\"\u003e\n \u003cp\u003eOleyl anilide\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"85\"\u003e\n \u003cp\u003eAmines (Anilides)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n\u003c/table\u003e\n\u003cp\u003eRT = Retention time (minutes); * = Calculated exact mass observed from LC-HRMS; Predicted-calculated molecular mass from ChemDraw.\u003c/p\u003e\n\u003cp\u003eFigure 2 indicated the LC-MS/MS total ion chromatogram and mass spectrum of the soxhlet extraction of Sea grapes (\u003cem\u003eC. racemosa\u003c/em\u003e) used to determine the peaks representing the number of annotated ions, the retention time, and the relative abundance of the ions. Just like in the maceration extract, Annotated compounds were automatically identified via mzCloud MS/MS Library (Thermo Scientific Q Exactive Software). Based on non-targeted metabolomic profiling results with Liquid Chromatography-High Resolution Mass Spectrometry (LC-HRMS), within a retention time of 40 minutes, soxhlet of Sea grapes (\u003cem\u003eC. racemosa\u003c/em\u003e) extract (which represents heat extraction) contained a total of 48 compounds that were diluted between 0.00-30.0 minutes (Figure 2A). Forty-eight (48) metabolite derivatives were successfully identified in Sea grapes (\u003cem\u003eC. racemosa\u003c/em\u003e) from soxhlet extraction extracts then presented in Table 2. Figure 2B FTMS + p ESI Full ms. [50.0000-750.0000] was a spectrum with a base peak intensity of 2.52 x 10\u003csup\u003e6\u003c/sup\u003e counts (combination of electrospray ionization (ESI) with Fourier transform mass spectrometry (FTMS)). This FTMS was in positive mode and by electrospray ionization (ESI) continuous measurements from m/z 50 to m/z 670 (NL = normalization rate).\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eTable 2.\u0026nbsp;\u003c/strong\u003eForty-eight Compounds Observed from HPLC-ESI-HRMS/MS Analysis of Soxhlet Extraction of Sea grapes (\u003cem\u003eC. racemosa\u003c/em\u003e).\u003c/p\u003e\n\u003ctable border=\"1\" width=\"728\"\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e\u003cstrong\u003eNo\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e\u003cstrong\u003eRT (min)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e\u003cstrong\u003eAbundance (Area Max.)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e\u003cstrong\u003eObserved HR-ESIMS m/z*\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e\u003cstrong\u003eCalculated HR-ESIMS m/z**\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003e\u003cstrong\u003eMolecular Formula\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003e\u003cstrong\u003eTentatively Identified Compound\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003e\u003cstrong\u003eCategory\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e1.\u0026nbsp;\u0026nbsp;\u0026nbsp;\u0026nbsp;\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e0.902\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e615,708,699.02\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e117.0787\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e117.0800\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e5\u003c/sub\u003eH\u003csub\u003e11\u003c/sub\u003eNO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eBetaine\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eAmines (Quartenary Ammonium Compounds)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e2.\u0026nbsp;\u0026nbsp;\u0026nbsp;\u0026nbsp;\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e21.916\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e353,793,967.91\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e255.25505\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e255.2600\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e33\u003c/sub\u003eNO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eHexadecanamide\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eFatty Acids (Palmitic Acids)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e3.\u0026nbsp;\u0026nbsp;\u0026nbsp;\u0026nbsp;\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e17.877\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e344,623,223.38\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e278.15076\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e276.1400\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e22\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eDiisobutylphthalate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eCarboxylic Acids\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e4.\u0026nbsp;\u0026nbsp;\u0026nbsp;\u0026nbsp;\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e12.294\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e274,478,961.83\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e157.14607\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e156.1400\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e9\u003c/sub\u003eH\u003csub\u003e19\u003c/sub\u003eNO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003e2,2,6,6-Tetramethyl-1-piperidinol (TEMPO)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eHeterocyclic compounds (piperidines)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e5.\u0026nbsp;\u0026nbsp;\u0026nbsp;\u0026nbsp;\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e18.209\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e195,885,637.15\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e296.23405\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003eCannot be generated\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e34\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eNP-008993\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eunknown\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e6.\u0026nbsp;\u0026nbsp;\u0026nbsp;\u0026nbsp;\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e16.424\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e119,602,748.90\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e268.20276\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003eCannot be generated\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eNP-001596\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eunknown\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e7.\u0026nbsp;\u0026nbsp;\u0026nbsp;\u0026nbsp;\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e21.547\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e104,636,468.21\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e281.27056\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e281.2700\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e35\u003c/sub\u003eNO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eOleamide\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eFatty Amides\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e8.\u0026nbsp;\u0026nbsp;\u0026nbsp;\u0026nbsp;\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e0.901\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e104,452,391.68\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e131.09424\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e131.0900\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e13\u003c/sub\u003eNO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eDL-\u0026beta;-Leucine\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eAmino Acids\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e9.\u0026nbsp;\u0026nbsp;\u0026nbsp;\u0026nbsp;\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e16.928\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e82,954,091.16\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e278.22365\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e278.2200\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003e\u0026alpha;-Eleostearic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eFatty Acids\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e10.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e23.776\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e82,837,237.90\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e283.28606\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e283.2900\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e37\u003c/sub\u003eNO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eStearamide\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eAmides\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e11.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e13.397\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e79,829,227.71\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e276.17153\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003eCannot be generated\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e26\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eNP-020014\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eunknown\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e12.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e18.681\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e75,543,295.89\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e282.25472\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e282.2600\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e34\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eEthyl palmitoleate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eFatty acid ester (Fatty acid ethyl ester)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e13.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e17.587\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e75,423,822.44\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e294.21851\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e312.2300\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e32\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003e(\u0026plusmn;)13-HpODE\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eFatty acid\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e14.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e0.911\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e70,567,131.89\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e87.10485\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e87.1000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e5\u003c/sub\u003eH\u003csub\u003e13\u003c/sub\u003eN\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eIsoamylamine\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eAmines\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e15.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e21.92\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e67,501,000.61\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e307.2863\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e325.3000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e39\u003c/sub\u003eNO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eOleoyl ethanolamide\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eAmines (Amino alcohols)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e16.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e0.906\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e62,987,796.05\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e103.0996\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e104.1100\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e5\u003c/sub\u003eH\u003csub\u003e13\u003c/sub\u003eNO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eCholine\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eAmines (Quartenary Ammonium Compounds)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e17.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e0.835\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e60,193,728.47\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e228.97644\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e228.9800\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e9\u003c/sub\u003eH\u003csub\u003e5\u003c/sub\u003eClFNOS\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003e2-(3-Chloro-2-fluorophenyl)-2,3-dihydroisothiazol-3-one\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eEnzyme\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e18.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e18.938\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e42,693,613.10\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e308.19524\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003eCannot be generated\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eNP-001596\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eunknown\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e19.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e17.881\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e42,504,568.52\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e323.20854\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e306.1800\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e26\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003en-Pentyl isopentyl phthalate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003ePhthalates\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e20.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e16.455\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e39,764,527.54\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e250.19238\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e426.3000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e26\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eOctylphenol Ethoxylates (OPEO)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003ealkylphenols\u003c/p\u003e\n \u003cp\u003e\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e21.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e17.434\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e39,577,349.70\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e316.20043\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e316.2000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e28\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eCafestol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eHydrocarbons (Terpenes)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e22.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e16.654\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e37,079,182.87\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e254.22351\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e254.2200\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003ePalmitoleic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eFatty Acids\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e23.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e22.8\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e33,398,733.18\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e309.30147\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e41\u003c/sub\u003eNO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eStearoyl Ethanolamide\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eFatty Acids\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e24.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e20.591\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e32,595,365.73\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e308.23406\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e302.2200\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eEicosapentaenoic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eFatty Acids\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e25.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e17.87\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e31,871,173.23\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e294.21853\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e294.2200\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003e9-Oxo-10(E),12(E)-octadecadienoic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eFatty Acids\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e26.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e14.577\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e31,454,460.53\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e273.26564\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e256.2400\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e32\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003ePalmitic Acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eFatty acids\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e27.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e7.411\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e31,100,701.46\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e197.11981\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e197.1200\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e14\u003c/sub\u003eH\u003csub\u003e15\u003c/sub\u003eN\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eDibenzylamine\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eAmines\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e28.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e17.367\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e30,483,737.39\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e280.2392\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003eCannot be generated\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e34\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eNP-011548\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eunknown\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e29.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e26.447\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e29,296,796.45\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e131.09427\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e131.0900\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e13\u003c/sub\u003eNO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003e6-Aminocaproic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eCarboxyclic Acid (Caproates)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e30.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e19.991\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e29,136,008.89\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e278.22365\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e278.4400\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003e\u0026alpha;-Linolenic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eEssential fatty acid\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e31.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e13.398\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e25,493,790.28\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e261.13552\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e239.1500\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e13\u003c/sub\u003eH\u003csub\u003e21\u003c/sub\u003eNO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eLevalbuterol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eAmines (Phenethylamines)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e32.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e22.054\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e19,542,351.23\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e361.2968\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e361.3000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e23\u003c/sub\u003eH\u003csub\u003e39\u003c/sub\u003eNO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eMethanandamide\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eFatty acid derivative\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e33.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e16.914\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e17,243,572.51\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e234.16117\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e234.1600\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e22\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003e3,5-di-tert-Butyl-4-hydroxybenzaldehyde\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eAldehydes (Benzaldehydes)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e34.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e13.132\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e16,983,601.06\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e276.17153\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e276.1700\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e17\u003c/sub\u003eH\u003csub\u003e24\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eShogaol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003ePhenols\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e35.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e20.295\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e16,462,133.15\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e299.28127\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e299.2800\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e37\u003c/sub\u003eNO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003ePalmitoyl ethanolamide\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eAmines (Amino Alcohols)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e36.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e14.576\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e14,874,891.90\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e414.20268\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e414.2000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e24\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e6\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eBis(4-ethylbenzylidene)sorbitol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eSugar alcohol\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e37.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e19.986\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e14,176,669.67\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e321.26558\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e299.5000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e37\u003c/sub\u003eNO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eSphingosine (d18:1)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eAmines\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e38.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e19.715\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e13,852,334.54\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e336.20778\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e336.2100\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e29\u003c/sub\u003eFO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eFluoxymesterone\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eHormones\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e39.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e17.688\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e13,159,097.66\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e350.24193\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e328.2600\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e19\u003c/sub\u003eH\u003csub\u003e36\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003e2,4-dihydroxyheptadec-16-en-1-yl acetate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eUnsaturated Fatty Acids\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e40.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e26.392\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e12,768,022.53\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e283.32268\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e284.3300\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e19\u003c/sub\u003eH\u003csub\u003e41\u003c/sub\u003eN\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eCetrimonium\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eAmines (Quartenary Ammonium Compounds)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e41.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e23.12\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e12,428,205.36\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e390.2755\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e390.2800\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e24\u003c/sub\u003eH\u003csub\u003e38\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eBis(2-ethylhexyl) phthalate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eCarboxylic Acids\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e42.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e16.474\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e11,621,213.91\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e266.16368\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e266.1600\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e12\u003c/sub\u003eH\u003csub\u003e27\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003eP\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eTributyl phosphate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eOrganophosphorus Compounds\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e43.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e16.926\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e10,593,568.28\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e248.17679\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e266.1900\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e26\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eTetranor-12(S)-HETE\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eOrganic Hydroxy compound (hydroxy carboxylic acid)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e44.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e20.537\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e9,753,652.00\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e176.11943\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e194.1300\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e12\u003c/sub\u003eH\u003csub\u003e18\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eSedanolide\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eHeterocyclic Compound (Benzofurans)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e45.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e21.427\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e8,882,476.13\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e363.31224\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e357.3000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e24\u003c/sub\u003eH\u003csub\u003e39\u003c/sub\u003eNO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eOleyl anilide\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eAmines (Anilides)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e46.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e11.188\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e8,843,434.72\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e294.21855\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e294.2200\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003e13(S)-HOTrE\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eUnsaturated Fatty Acids\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e47.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e11.662\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e8,423,640.09\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e191.13033\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e191.11300\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e12\u003c/sub\u003eH\u003csub\u003e17\u003c/sub\u003eNO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eDiethyltoluamide or DEET\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eCarboxylic Acids\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e48.\u0026nbsp; \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"57\"\u003e\n \u003cp\u003e21.688\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"98\"\u003e\n \u003cp\u003e7,026,193.73\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"74\"\u003e\n \u003cp\u003e310.28584\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"80\"\u003e\n \u003cp\u003e310.2900\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"92\"\u003e\n \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e38\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"166\"\u003e\n \u003cp\u003eEthyl oleate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"105\"\u003e\n \u003cp\u003eFatty Acids\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n\u003c/table\u003e\n\u003cp\u003eRT = Retention time (minutes); * = Calculated exact mass observed from LC-HRMS; Predicted-calculated molecular mass from ChemDraw.\u003c/p\u003e\n\u003cp\u003e\u003cem\u003e3.2. Identification of the peptide in purified fraction 1 of C. racemosa\u003c/em\u003e\u003c/p\u003e\n\u003cp\u003ePF1 of \u003cem\u003eC. racemosa\u003c/em\u003e found a bioactive peptide named (2S,5S,8S,11S,14S,17S)-11-((1H-indol-3-yl)methyl)-17-amino-8-(4-aminobutyl)-2-benzyl-5-((R)-1-hydroxyethyl)-14-isobutyl-4,7,10,13,16-pentaoxo-3,6,9,12,15-pentaazaicosanedioic acid or ELWKTF (Glu-Leu-Trp-Lys-Thr-Phe) which was eluted at a retention time of 30.9 minutes with a peak area of 815,602,581.03 (Table 3). The structural visualization of ELWKTF is shown in Figure 3.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eTable 3.\u0026nbsp;\u003c/strong\u003eAmino Acids (ELWKTF) Analysis\u003cem\u003e.\u003c/em\u003e\u003c/p\u003e\n\u003ctable border=\"1\" cellpadding=\"0\" cellspacing=\"0\" width=\"698\"\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd width=\"11.908177905308465%\"\u003e\n \u003cp\u003e\u003cstrong\u003ePeptide Sequence\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"17.50358680057389%\"\u003e\n \u003cp\u003e\u003cstrong\u003eAverage Local Confidence (ALC, %)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.75609756097561%\"\u003e\n \u003cp\u003e\u003cstrong\u003eLength*\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"10.760401721664275%\"\u003e\n \u003cp\u003e\u003cstrong\u003em/\u003cem\u003ez\u003c/em\u003e\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"12.195121951219512%\"\u003e\n \u003cp\u003e\u003cstrong\u003eRetention Time (RT)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.946915351506455%\"\u003e\n \u003cp\u003e\u003cstrong\u003eTheoretical Mass/Observed Mass (Da)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.929698708751793%\"\u003e\n \u003cp\u003e\u003cstrong\u003ePeak Area (max)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"11.908177905308465%\"\u003e\n \u003cp\u003eELWKTF\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"17.50358680057389%\"\u003e\n \u003cp\u003e97\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.75609756097561%\"\u003e\n \u003cp\u003e6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"10.760401721664275%\"\u003e\n \u003cp\u003e412.2320\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"12.195121951219512%\"\u003e\n \u003cp\u003e30.9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.946915351506455%\"\u003e\n \u003cp\u003e822.43/822.428\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.929698708751793%\"\u003e\n \u003cp\u003e815,602,581.03\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n\u003c/table\u003e\n\u003cp\u003e\u003cem\u003e\u003cstrong\u003eChemical Formula\u003c/strong\u003e: C41H58N8O10. \u003cstrong\u003eExact Mass\u003c/strong\u003e: 822.43. \u003cstrong\u003eMolecular Weight\u003c/strong\u003e: 822.96. \u003cstrong\u003em/z\u003c/strong\u003e: 822.43 (100.0%), 823.43 (45.4%), 824.43 (13.0%), 823.42 (3.0%), 825.44 (2.4%). \u003cstrong\u003eElemental Analysis\u003c/strong\u003e: C, 59.84; H, 7.10; N, 13.62; O, 19.44. *, The number of amino acids on the peptide.\u003c/em\u003e\u003c/p\u003e\n\u003cp\u003e\u003cem\u003e3.3. The DPPH Radical Scavenging Activity of C. racemosa\u003c/em\u003e\u003c/p\u003e\n\u003cp\u003eFigure 4 showed the results of an in vitro study inhibiting DPPH radical scavenging activity. The inhibitory activity of DPPH was compared among \u003cem\u003eC. racemosa\u003c/em\u003e macerated extract (EM), Soxhlet extract (ES), purified fraction 1 (PF1), and glutathione (GSH). The results showed lesser DPPH inhibition activities than GSH or control at 1 \u0026mu;g/mL, 2 \u0026mu;g/mL, 3 \u0026mu;g/mL, and 4 \u0026mu;g/mL of EM; and 1 \u0026mu;g/mL, 2 \u0026mu;g/mL, 3 \u0026mu;g/mL, 4 \u0026mu;g/mL, 5 \u0026mu;g/mL of ES and PF1(p \u0026lt; 0.0001). The DPPH inhibition of EM was to close with GSH at a dose of 5 \u0026mu;g/mL with a percentage of 87.43 \u0026plusmn; 0.67% and 86.73 \u0026plusmn; 0.61%, respectively (Figure 4).\u003c/p\u003e\n\u003cp\u003eAs shown in Figure 5, the EC\u003csub\u003e50\u003c/sub\u003e yields of EM, ES, PF1, and GSH were 2.945 \u0026mu;g/mL, 2.297 \u0026mu;g/mL, 2.302 \u0026mu;g/mL, and 2.691 \u0026mu;g/mL, respectively. ES and PF1 show good potential effectiveness in DPPH radical elimination activity because the EC\u003csub\u003e50\u003c/sub\u003e values are lower than the control or GSH.\u003c/p\u003e\n\u003cp\u003e\u003cem\u003e3.4. ABTS Radical Scavenging Activity of C. racemosa\u003c/em\u003e\u003c/p\u003e\n\u003cp\u003eFigure 6 showed the results of an \u003cem\u003ein vitro\u003c/em\u003e study inhibiting the radical scavenging activity of ABTS. The inhibitory activity of ABTS was compared among the macerated extract of \u003cem\u003eC. rasemosa\u003c/em\u003e (EM), the soxhletated extract (ES), the purified fraction 1 (PF1), and the Trolox or control. The results showed lesser of ABTS inhibition activities at doses 1 \u0026mu;g/mL, 2 \u0026mu;g/mL, 3 \u0026mu;g/mL, 4 \u0026mu;g/mL and 5 \u0026mu;g/mL for ES and PF1, compared to Trolox or control (p \u0026lt; 0.0001).\u003c/p\u003e\n\u003cp\u003eAs shown in Figure 7, the EM, ES, PF1, and Trolox yield was EC\u003csub\u003e50\u003c/sub\u003e of 3.306 \u0026mu;g/mL, 3.244 \u0026mu;g/mL, 2.508 \u0026mu;g/mL, and 2.547 \u0026mu;g/mL, respectively. PF1 showed good potential effectiveness in the radical elimination activity of ABTS because it has a lower EC\u003csub\u003e50\u003c/sub\u003e value than the control or Trolox.\u003c/p\u003e\n\u003cp\u003e\u003cem\u003e3.5.\u0026nbsp;\u003c/em\u003e\u003cem\u003eCytotoxicity Evaluation of C. racemosa using MTT Assay\u0026nbsp;\u003c/em\u003e\u003c/p\u003e\n\u003cp\u003eFigure 8 showed the difference in the viability percentage of normal cells or fibroblasts from the human Caucasian cell line. There was a significant difference (p\u0026lt;0.05) between each concentration between the groups during 24 hours of incubation and 48 hours. The sequence of LC\u003csub\u003e50\u003c/sub\u003e samples that are lowest or show the highest cytotoxicity to the lowest cytotoxicity is EM 914.78 \u0026mu;g/mL, PF1 2069.21 \u0026mu;g/mL, and ES 2227.85 \u0026mu;g/mL at 24 hours; and, ES 1816.17 \u0026mu;g/mL, PF1 2173.02 \u0026mu;g/mL, and EM 2971.15 \u0026mu;g/mL at 48 hours (Table 4). This result suggested EM, ES, and PF1 as antioxidant agents in the observed EC\u003csub\u003e50\u003c/sub\u003e were safe. Furthermore, in terms of cytotoxicity, it was observed that \u003cem\u003eC. racemosa\u003c/em\u003e was safe to be potentially developed into various products. In addition, the value of LC\u003csub\u003e50\u003c/sub\u003e is presented in Table 4.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eTable 4\u003c/strong\u003e. LC\u003csub\u003e50\u003c/sub\u003e Value of \u003cem\u003eC. racemosa\u003c/em\u003e on Cytotoxicity Test in BUD-8 Cell Lines\u003c/p\u003e\n\u003ctable border=\"1\" cellpadding=\"0\" cellspacing=\"0\"\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" width=\"22.596153846153847%\"\u003e\n \u003cp\u003e\u003cstrong\u003eHours of incubation\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd colspan=\"3\" valign=\"top\" width=\"77.40384615384616%\"\u003e\n \u003cp\u003e\u003cstrong\u003eLC\u003csub\u003e50\u003c/sub\u003e (\u0026mu;g/ml)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" width=\"22.596153846153847%\"\u003e\n \u003cp\u003e\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" width=\"25.641025641025642%\"\u003e\n \u003cp\u003eEM\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" width=\"25.641025641025642%\"\u003e\n \u003cp\u003eES\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" width=\"26.121794871794872%\"\u003e\n \u003cp\u003ePF1\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" width=\"22.596153846153847%\"\u003e\n \u003cp\u003e24 hours\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" width=\"25.641025641025642%\"\u003e\n \u003cp\u003e914.78\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" width=\"25.641025641025642%\"\u003e\n \u003cp\u003e2227.85\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" width=\"26.121794871794872%\"\u003e\n \u003cp\u003e2069.21\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" width=\"22.596153846153847%\"\u003e\n \u003cp\u003e48 hours\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" width=\"25.641025641025642%\"\u003e\n \u003cp\u003e2971.15\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" width=\"25.641025641025642%\"\u003e\n \u003cp\u003e1816.17\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" width=\"26.121794871794872%\"\u003e\n \u003cp\u003e2173.02\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n\u003c/table\u003e"},{"header":"4 Discussions","content":"\u003cp\u003eSeaweed is traditionally used as a sea vegetable in Asian countries, especially Indonesia, but its consumption is still minimal. \u003cem\u003eC. racemosa\u003c/em\u003e is one of the green seaweeds whose metabolite profiles, health properties, and potential use as functional ingredients in food, supplements, and pharmaceuticals should be further explored. This will be a new opportunity to introduce \u003cem\u003eC. racemosa\u003c/em\u003e indirectly into the human food chain in western countries, especially in Europe.\u003c/p\u003e\n\u003cp\u003eFoodomics is a discipline that studies the domain of food and nutrition through the application and integration of advanced technology \u0026quot;-omics\u0026quot; to improve the well-being, health, and knowledge of consumers \u003csup\u003e22,23\u003c/sup\u003e. One part of Foodomics is the metabolomic study \u003csup\u003e29\u003c/sup\u003e which was applied in this study and successfully profiled the secondary metabolites of \u003cem\u003eC. racemosa\u003c/em\u003e with different extraction methods. On the other hand, the bioactive peptides were also successfully identified using proteomics approaches. Secondary metabolites and bioactive peptides are expected to be a data challenge for other researchers or follow-up research to find their continued effects on health and product development based on \u003cem\u003eC. racemosa\u003c/em\u003e. This untargeted metabolomic profiling study that we conducted has succeeded in profiling secondary metabolites of \u003cem\u003eC. racemosa\u003c/em\u003e, which was previously a challenge from the research of Pangestuti \u003cem\u003eet al\u003c/em\u003e. (2021) \u003csup\u003e30\u003c/sup\u003e. Study by Pangestuti \u003cem\u003eet al\u003c/em\u003e. (2021) only observed at phytochemicals of \u003cem\u003eC. racemosa\u003c/em\u003e in terms of total phenolic, saponins, and flavonoid contents without the metabolite compounds \u003csup\u003e30\u003c/sup\u003e.\u003c/p\u003e\n\u003cp\u003eThere was a difference in the number of compounds identified in the maceration (cold) and soxhletation (heat) methods of extraction of sea grapes Sea grapes (\u003cem\u003eC. racemosa\u003c/em\u003e) extract through the extraction-maceration method had higher bioactive compound than the Sea grapes extracted using a Soxhlet. The soxhlet extraction method integrates the advantages of reflux and percolation extraction, which utilizes the principle of reflux and siphon to continuously extract the herb with fresh solvent \u003csup\u003e13\u003c/sup\u003e. Extraction using the soxhlet method has the advantage of an automatic continuous extraction method with less extraction time and less solvent use than maceration or percolation \u003csup\u003e13\u003c/sup\u003e. However, high temperatures and long extraction times in soxhlet extraction will increase the likelihood of thermal degradation. This is what is strongly suspected to cause differences in the results of compounds from the two extracts in this \u003cem\u003eC. racemosa\u003c/em\u003e study. In line with the results of our study, other studies showed that the degradation of catechins in tea was also observed in soxhlet extraction due to the high extraction temperature \u003csup\u003e31\u003c/sup\u003e. The total polyphenol and total alkaloid concentrations of the soxhlet extraction method decreased compared to the maceration method \u003csup\u003e31,32\u003c/sup\u003e.\u003c/p\u003e\n\u003cp\u003eThe bioactive compounds found in this study showed both health benefits and toxic effects based on other literature (see Supplementary). However, not all bioactive compounds will have a significant effect since the dose of each metabolite should be considered. For example, an \u003cem\u003ein vivo\u003c/em\u003e intervention study using 450 mg/kgBW of sea grapes extract on rats showed no adverse effects \u003csup\u003e10\u003c/sup\u003e.\u003c/p\u003e\n\u003cp\u003eProteins in foods sourced from marine resources and their by-products have high structural diversity and are a considerable resource for exploring bioactive peptides \u003csup\u003e33\u003c/sup\u003e. Previous literature suggests that the types of amino acids in Bioactive Peptides (BPs) are considered a critical factor in their activity \u003csup\u003e34\u003c/sup\u003e. Residual hydrophobic groups from hydrophobic amino acids such as Pro, Met, Ala, Leu, and Ile, can strongly react with hydrophobic polyunsaturated fatty acids (PUFAs) to inhibit lipid peroxidation in lipid-rich foods \u003csup\u003e35,36\u003c/sup\u003e. The EC\u003csub\u003e50\u003c/sub\u003e of PF1 which was allegedly derived from ELWKTF activity in this study was more potential than Trolox (in ABTS inhibition assay) and GSH (DPPH inhibition Assay) as a control based on the EC\u003csub\u003e50\u003c/sub\u003e value. Carboxyl and amino groups in polar amino acid residues are essential to capture hydroxyl radicals and the metal-ion chelating capacity of BPs \u003csup\u003e36,37\u003c/sup\u003e. In addition, Glu and Leu residues can maintain the high flexibility of the polypeptide skeleton, and its single hydrogen atom can be donated to neutralize Reactive Oxygen Species (ROS) \u003csup\u003e34,38\u003c/sup\u003e. Therefore, polar amino acids, including -Glu and -Leu residues in ELWKTF, may have played an essential role in hydroxyl radical capture activities. \u003cem\u003eC. racemosa,\u003c/em\u003e which has an abundance of ELWKTF, can be a source of free radical inhibition activity through the mechanism presented in the previous sentence. Recent scientific evidence suggested that dietary proteins may have function as nutrients and can also modulate the body\u0026apos;s physiological functions \u003csup\u003e39\u003c/sup\u003e. This physiological function is mainly regulated by several encrypted peptides in the original protein sequence. This bioactive peptide can provide beneficial properties for health and is therefore considered a significant compound for developing nutraceuticals or functional foods to fight metabolic syndrome, obesity, cancer, diabetes, and aging, which are associated with cardiovascular disease. This study that we conducted showed novelty on the measurement of bioactive peptides and their antioxidant activity, which in previous studies had never been reported or carried out \u003csup\u003e30,40\u003c/sup\u003e.\u003c/p\u003e\n\u003cp\u003eLethal concentration (LC\u003csub\u003e50\u003c/sub\u003e) is the lowest concentration of samples that inhibits 50% of cells. In general, a low LC\u003csub\u003e50\u003c/sub\u003e value indicates high toxicity. Extracts with high LC\u003csub\u003e50\u003c/sub\u003e are preferred for use due to their lower toxicity effect on host cells \u003csup\u003e28\u003c/sup\u003e. The interpretation of the LC\u003csub\u003e50\u003c/sub\u003e value was based on the National Cancer Institute \u003csup\u003e41\u003c/sup\u003e, LC\u003csub\u003e50\u003c/sub\u003e value of 20 \u0026mu;g/mL indicates strong cytotoxic properties, 21-200 \u0026mu;g/mL indicates moderate cytotoxicity, 201-500 \u0026mu;g/mL exhibits weak cytotoxicity, and \u0026gt; 500 \u0026mu;g/mL indicates no cytotoxic properties. \u003cem\u003eC. racemosa\u003c/em\u003e has a potential antioxidant activity of EC\u003csub\u003e50\u003c/sub\u003e value accompanied by an LC\u003csub\u003e50\u003c/sub\u003e value which was in a safe category. This is in line with similar studies that observed at the cytotoxicity of \u003cem\u003eC. racemosa\u003c/em\u003e in subcritical water extraction, which did not show significant cytotoxicity activity \u003csup\u003e30\u003c/sup\u003e. Furthermore, a review study by Aroyehun \u003cem\u003eet al\u003c/em\u003e. (2020) stated that in addition to minimal toxicity, \u003cem\u003eC. racemosa\u003c/em\u003e has bioprospecting as a promising nutraceutical due to its nutritional values \u003csup\u003e9\u003c/sup\u003e.\u003c/p\u003e\n\u003cp\u003e\u003cem\u003e4.1 The Potential and Prospects of Caulerpa racemosa as Nutraceuticals and Pharmaceuticals in Terms of Cultivation and Use in Commercial Industrial Production Applications.\u003c/em\u003e\u003c/p\u003e\n\u003cp\u003eFewer incidences of diet-related diseases, especially non-communicable diseases and including cancer and cardiovascular disease have been observed in countries that consume high amounts of seaweed as a supplement or food \u003csup\u003e42,43\u003c/sup\u003e. Seaweed consumption has been shown to reduce the prevalence of different non-communicable diseases due to the metabolites and other bioactive compounds working as a defense mechanism \u003csup\u003e43\u003c/sup\u003e. Studies carried out with seaweed extracts or their specific metabolites proved that they have cytotoxins, which prevent the proliferation of cancer cells \u003csup\u003e44\u003c/sup\u003e. In this study, the results showed that. ES and PF1 show good potential effectiveness in DPPH radical elimination activity because the EC\u003csub\u003e50\u003c/sub\u003e values are lower than the control or GSH. This was in line with a review study by Collins \u003cem\u003eet al.,\u0026nbsp;\u003c/em\u003e2016, which focused on the potential use of bioactive seaweed derivatives, including polysaccharides, antioxidants, and fatty acids, among others, to treat chronic non-communicable diseases \u003csup\u003e42\u003c/sup\u003e. Furthermore, the main compounds resulting from the identification of \u003cem\u003eC. racemosa\u0026nbsp;\u003c/em\u003emetabolomic profiling\u003cem\u003e,\u003c/em\u003e such as choline\u003csup\u003e45\u003c/sup\u003e, betaine\u003csup\u003e45\u003c/sup\u003e, oleamide\u003csup\u003e46\u003c/sup\u003e, hexadecanamide\u003csup\u003e47\u003c/sup\u003e, palmitoleic acid\u003csup\u003e48\u003c/sup\u003e, and \u0026alpha;-eleostearic acid\u003csup\u003e49\u003c/sup\u003e may become therapeutic drugs for non-communicable diseases. Furthermore, we also explored the antioxidant activity of each secondary metabolite of metabolomic profiling results by a review approach, which can be seen in \u003cstrong\u003eSupplementary Table 1\u003c/strong\u003e.\u003c/p\u003e\n\u003cp\u003eThe therapeutic activity of food-derived bioactive proteins and peptides \u0026ndash; such as from medicinal plants \u0026ndash; is attracting increasing attention in the research community \u003csup\u003e39\u003c/sup\u003e. Bioactive peptides offer promising potential as antiviral drugs, and therapeutic peptides are an exciting alternative to be developed into anti-Dengue virus drugs due to their safety and diverse biological and chemical properties\u003csup\u003e50\u003c/sup\u003e. In addition, many potential compounds were identified from \u003cem\u003eC. racemosa\u0026nbsp;\u003c/em\u003emetabolites profiles\u003cem\u003e,\u003c/em\u003e such as choline\u003csup\u003e51\u003c/sup\u003e, betaine\u003csup\u003e52\u003c/sup\u003e, oleamide\u003csup\u003e53\u003c/sup\u003e, hexadecanamide\u003csup\u003e54\u003c/sup\u003e, palmitoleic acid\u003csup\u003e55\u003c/sup\u003e, and \u0026alpha;-eleostearic acid\u003csup\u003e56\u003c/sup\u003e. More research is needed to examine the clinical effects of \u003cem\u003eC. racemosa\u003c/em\u003e as a nutraceutical.\u003c/p\u003e\n\u003cp\u003e\u003cem\u003e4.2 Potential for Future Research.\u003c/em\u003e\u003c/p\u003e\n\u003cp\u003eMany strategies are needed to further develop \u003cem\u003eC. racemosa\u003c/em\u003e products to explore their secondary metabolites and health benefits. In addition, environmental factors play an essential role in influencing the composition of secondary metabolites in \u003cem\u003eC. racemosa\u003c/em\u003e \u003csup\u003e57\u003c/sup\u003e\u003csup\u003e,\u003c/sup\u003e\u003csup\u003e58\u003c/sup\u003e, which is important to be considered. To ensure the validity and safety of Sea grapes research development, the drug discovery process should be carried out through various steps as recommended by the Food and Drug Administration (FDA, US), which can be seen in Figure 10.\u003c/p\u003e\n\u003cp\u003eThe process initiated by metabolomic profiling identifies what processes/pathways can be targeted to affect the disease/condition. Compound screening can also be done to identify compounds that can be promising candidates for further development. Next, an \u003cem\u003ein silico\u003c/em\u003e study is needed for target validation, determining whether the drug can provide therapeutic benefit to the target, and lead discovery to identify the lead compound to be observed for further studies. Subsequently, preclinical trials are needed to evaluate therapeutic index and dose using \u003cem\u003ein vitro\u003c/em\u003e and \u003cem\u003ein vivo\u003c/em\u003e approaches and evaluate the aspects of pharmacokinetics and pharmacodynamics in experimental animals (Figure 10). Finally, to ensure efficacy and safety, three phases of clinical trials need to be conducted, first on healthy patients and then on obese or patients with other cardiovascular diseases.\u003c/p\u003e\n\u003cp\u003e\u003cem\u003e4.3 Strengths and Limitations of Study\u003c/em\u003e\u003c/p\u003e\n\u003cp\u003eThe results of this study complemented the published data related to secondary metabolites from \u003cem\u003eCaulerpa racemosa\u003c/em\u003e found and grown in Asia, especially in Indonesia waters. Furthermore, this study succeeded in profiling the bioactive peptide and their bioactivity properties from the purified fraction 1 of \u003cem\u003eCaulerpa racemosa\u003c/em\u003e (Graphical Abstract). In addition, the synthesis and purification of their respective compounds (metabolites and bioactive peptides) for the development of food and drug products and the exploration of bioactive carbohydrates and other bioactive peptides is a limitation of this research. It is hoped that more research will be carried out in the future. Seeing the metabolomic results which show indications of several compounds that are thought to be anti-nutrients, further studies are needed to confirm whether they are naturally present in Sea grapes or as contaminants. References indicating the activity of the health benefits of each metabolite that have been successfully identified are still very few and limited, so computational molecular docking or \u003cem\u003ein silico\u003c/em\u003e studies are needed for various disease-causing receptors.\u003c/p\u003e"},{"header":"5 Conclusions","content":"\u003cp\u003eThe abundance of secondary metabolites and bioactive compounds in Sea grapes \u003cem\u003e(Caulerpa racemosa)\u003c/em\u003e was obtained from the maceration method\u0026apos;s extraction process. The bioactive peptide purified fraction 1 (PF1), as shown in ELWKTF, was also analyzed for its antioxidant and cytotoxicity activity. These metabolites were responsible for high biochemical activity (antioxidants, scavenging, and reducing) and have good prospects of cytotoxicity. The study revealed that \u003cem\u003eC\u003c/em\u003e. \u003cem\u003eracemosa\u003c/em\u003e contained antioxidant nutrients, metabolites, and bioactive peptides (Graphical Abstract); these factors make it a promising functional food and pharmaceutical. From a future perspective, \u003cem\u003eC. racemosa\u003c/em\u003e is a potential candidate for development as a functional food and other nutraceutical applications, including pharmaceuticals.\u003c/p\u003e"},{"header":"6 Patents","content":"\u003cp\u003ePatent Number S00202107179 (Fahrul Nurkolis is a patent holder, https://pdki-indonesia.dgip.go.id/detail/S00202107179?type=patent\u0026amp;keyword=Formula+Anggur+Laut).\u003c/p\u003e"},{"header":"Abbreviations ","content":"\u003cp\u003e\u003cstrong\u003eABTS\u003c/strong\u003e = 2,2\u0026apos;-Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid); \u003cstrong\u003eBPs\u003c/strong\u003e = Bioactive Peptides; \u003cstrong\u003eDENV\u003c/strong\u003e = Dengue virus; \u003cstrong\u003eDMEM\u003c/strong\u003e = Dulbecco\u0026apos;s Modified Essential Medium; \u003cstrong\u003eDMSO\u003c/strong\u003e = Dimethyl sulfoxide; \u003cstrong\u003eDPPH\u003c/strong\u003e = 2,2-diphenyl-1-picrylhydrazyl; \u003cstrong\u003eELWKTF\u003c/strong\u003e: Glu-Leu-Trp-Lys-Thr-Phe; \u003cstrong\u003eEM\u003c/strong\u003e = Macerated Extract (Extract Maceration); \u003cstrong\u003eES\u003c/strong\u003e = Soxhletated Extract (Extract-Soxhletation); \u003cstrong\u003eESI\u003c/strong\u003e = Electrospray ionization; \u003cstrong\u003eFBS\u003c/strong\u003e = Fetal bovine serum; \u003cstrong\u003eGSH\u003c/strong\u003e = Glutathione; \u003cstrong\u003eHPLC\u003c/strong\u003e = High Performance Liquid Chromatography; \u003cstrong\u003eHRMS\u003c/strong\u003e = High Resolution Mass Spectrometry; \u003cstrong\u003eIUPAC\u003c/strong\u003e = International Union of Pure and Applied Chemistry; \u003cstrong\u003eMTT\u003c/strong\u003e = 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide; \u003cstrong\u003ePS\u003c/strong\u003e = Protein Supernatant; \u003cstrong\u003ePSN\u003c/strong\u003e = Penicillin-Streptomycin-Neomycin; \u003cstrong\u003ePUFAs\u003c/strong\u003e = Polyunsaturated fatty acids; \u003cstrong\u003eROS\u003c/strong\u003e = Reactive Oxygen Species.\u003c/p\u003e"},{"header":"Declarations","content":"\u003cp\u003e\u003cstrong\u003eAuthor Contributions or\u0026nbsp;\u003c/strong\u003e\u003cstrong\u003eAuthors CRediT (Contributor Roles Taxonomy)\u003c/strong\u003e\u003cstrong\u003e:\u003c/strong\u003e FN and HH: conduct experiments, analyzed data, write the manuscript, design research, and conceptualize ideas; while HH, VMY, MY, RJK: contribute to data analysis, critiquing manuscript, interpret manuscript results, assisting in the processing of data, as well as helping to revise and graphical abstract editing. IWH, WBG, SR, NAT, NM, NS, AT, RK: critiquing, writing \u0026ndash; review \u0026amp; editing manuscript. TET, RK, SR, EI, and CFT reviewed and edited the final manuscript text. All authors have read and also approved this final manuscript.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eFunding:\u003c/strong\u003e This research received no external funding.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eData Availability Statement:\u0026nbsp;\u003c/strong\u003eThe data presented in this study are available on request from the corresponding author and/or the original contributions presented in the study are publicly available. The datasets generated and/or analysed during the current study are available in the [Figshare] repository, [https://doi.org/10.6084/m9.figshare.20518485.v1].\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eAcknowledgments:\u003c/strong\u003e The authors thank all of the contributors for their outstanding help in research and also in formatting the paper. I also want to express my gratitude to my two special people, who have provided suggestions and comments on the research and writing of this manuscript, as well as the motivation that has led the authors to keep the passion for research during the pandemic: 1. \u003cem\u003eProfessor Hardinsyah, MS, Ph.D\u003c/em\u003e. (the President of the Federations of Asian Nutrition Societies; President of the Food and Nutrition Society of Indonesia; and Member of the Southeast Asian Probiotic Scientific and Regulatory Experts Network), and 2. \u003cem\u003eProfessor Dr. Nurpudji A Taslim, MD., MPH, Sp.GK (K)\u0026nbsp;\u003c/em\u003e(Chair of the Indonesian Clinical Nutrition Physician Association). Also to \u003cem\u003eJulia M. L. Menon\u003c/em\u003e (Netherlands Heart Institute: Utrecht, NL), for providing her time and assistance in making this manuscript more readable. The study was conducted with the researcher\u0026apos;s funds.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eConflicts of Interest:\u003c/strong\u003e The authors and/or contributors to the study stated that they had no conflict of interest.\u003c/p\u003e"},{"header":"References","content":"\u003col\u003e\n\u003cli\u003eHamed, I., \u0026Ouml;zogul, F., \u0026Ouml;zogul, Y. \u0026amp; Regenstein, J. M. Marine Bioactive Compounds and Their Health Benefits: A Review. \u003cem\u003eCompr. Rev. Food Sci. Food Saf.\u003c/em\u003e \u003cstrong\u003e14\u003c/strong\u003e, 446\u0026ndash;465 (2015).\u003c/li\u003e\n\u003cli\u003ePooja, S. Algae used as Medicine and Food-A Short Review. \u003cem\u003eJ. Appl. Pharm. Sci. Res.\u003c/em\u003e \u003cstrong\u003e6\u003c/strong\u003e, 33\u0026ndash;35 (2014).\u003c/li\u003e\n\u003cli\u003eCircuncis\u0026atilde;o, A. R., Catarino, M. D., Cardoso, S. M. \u0026amp; Silva, A. M. S. 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Influence of abiotic stress signals on secondary metabolites in plants. \u003cem\u003ehttps://doi.org/10.4161/psb.6.11.17613\u003c/em\u003e \u003cstrong\u003e6\u003c/strong\u003e, 1720\u0026ndash;1731 (2011).\u003c/li\u003e\n\u003cli\u003eShi, Y. \u003cem\u003eet al.\u003c/em\u003e Seasonal variation influences flavonoid biosynthesis path and content, and antioxidant activity of metabolites in Tetrastigma hemsleyanum Diels \u0026amp; Gilg. \u003cem\u003ePLoS One\u003c/em\u003e \u003cstrong\u003e17\u003c/strong\u003e, e0265954 (2022).\u003c/li\u003e\n\u003c/ol\u003e"}],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":true,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":true,"hideJournal":true,"highlight":"","institution":"","isAcceptedByJournal":false,"isAuthorSuppliedPdf":false,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":false,"isPdf":false,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"researchsquare","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":true,"externalIdentity":"","sideBox":"","snPcode":"","submissionUrl":"/submission","title":"Research Square","twitterHandle":"researchsquare","acdcEnabled":true,"dfaEnabled":false,"editorialSystem":"","reportingPortfolio":"","inReviewEnabled":false,"inReviewRevisionsEnabled":true},"keywords":"Caulerpa racemosa, metabolites, nutraceuticals, antioxidants, green algae","lastPublishedDoi":"10.21203/rs.3.rs-2158307/v2","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-2158307/v2","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eMarine macroalgae are nutraceuticals rich in nutritional profile and secondary bioactive metabolites. However, they have varied nutritional and biochemical qualities due to a variety of reasons. This study aimed to determine the phytochemical profile and biological activities of \u003cem\u003eCaulerpa racemosa\u003c/em\u003e, edible green algae also known as Sea grapes. The study successfully identified secondary metabolites through metabolomic profiling untargeted by LC-HRMS as well as a bioactive peptide. In addition, antioxidant activity and cytotoxicity of extracts and compounds were determined. A total of 103 metabolites were identified in \u003cem\u003eC. racemosa\u003c/em\u003e extract obtained by the maceration, while 48 were detected in the soxhlet extract. A peptide with the sequence ELWKTF (Glu-Leu-Trp-Lys-Thr-Phe; C\u003csub\u003e41\u003c/sub\u003eH\u003csub\u003e58\u003c/sub\u003eN\u003csub\u003e8\u003c/sub\u003eO) and its abundance was identified in the α-chymotrypsin hydrolysate of \u003cem\u003eC. racemosa\u003c/em\u003e. In the antioxidant activity test, Soxhletated-extract (ES) and purified fraction 1 (PF1) had half-maximal effective concentration (EC\u003csub\u003e50\u003c/sub\u003e) \u0026lt; EC\u003csub\u003e50\u003c/sub\u003e of control/GSH (DPPH inhibition) and PF1 had EC\u003csub\u003e50\u003c/sub\u003e \u0026lt; EC\u003csub\u003e50\u003c/sub\u003e of control/Trolox (ABTS inhibition). The cytotoxicity results showed that macerated-extract (EM), ES, and PF1 as antioxidant agents in the observed EC\u003csub\u003e50\u003c/sub\u003e were safe. In general, \u003cem\u003eC. racemosa\u003c/em\u003e contains antioxidant nutrients, metabolites, and bioactive peptides, a factor that makes it a promising functional food and pharmaceutical.\u003c/p\u003e","manuscriptTitle":"Metabolomic Profiling, In Vitro Antioxidant and Cytotoxicity Properties of Caulerpa racemosa : Functional Food of the Future from Algae","msid":"","msnumber":"","nonDraftVersions":[{"code":2,"date":"2024-08-15 17:13:50","doi":"10.21203/rs.3.rs-2158307/v2","editorialEvents":[{"type":"communityComments","content":0}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"researchsquare","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":true,"externalIdentity":"","sideBox":"","snPcode":"","submissionUrl":"/submission","title":"Research Square","twitterHandle":"researchsquare","acdcEnabled":true,"dfaEnabled":false,"editorialSystem":"","reportingPortfolio":"","inReviewEnabled":false,"inReviewRevisionsEnabled":true}},{"code":1,"date":"2022-10-13 16:23:25","doi":"10.21203/rs.3.rs-2158307/v1","editorialEvents":[{"type":"communityComments","content":0}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"researchsquare","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":true,"externalIdentity":"","sideBox":"","snPcode":"","submissionUrl":"/submission","title":"Research Square","twitterHandle":"researchsquare","acdcEnabled":true,"dfaEnabled":false,"editorialSystem":"","reportingPortfolio":"","inReviewEnabled":false,"inReviewRevisionsEnabled":true}}],"origin":"","ownerIdentity":"629b32ef-a9b6-4f24-bd88-7e10283e704b","owner":[],"postedDate":"August 15th, 2024","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"posted","subjectAreas":[{"id":16227034,"name":"Food Chemistry"},{"id":16227035,"name":"Food Science \u0026 Technology"},{"id":16227036,"name":"Marine and Freshwater Biology"},{"id":16227037,"name":"Molecular Biology"},{"id":16227038,"name":"Drug Discovery, Design, \u0026 Development"}],"tags":[],"updatedAt":"2022-10-13T16:23:25+00:00","versionOfRecord":[],"versionCreatedAt":"2024-08-15 17:13:50","video":"","vorDoi":"","vorDoiUrl":"","workflowStages":[]},"version":"v2","identity":"rs-2158307","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-2158307","identity":"rs-2158307","version":["v2"]},"buildId":"qtupq5eGEP_6zYnWcrvyt","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}