#METABOLOMICS WORKBENCH jord001_20250201_151607 DATATRACK_ID:5587 STUDY_ID:ST003998 ANALYSIS_ID:AN006589 PROJECT_ID:PR002503 VERSION 1 CREATED_ON June 23, 2025, 4:27 pm #PROJECT PR:PROJECT_TITLE Untargeted Metabolomics and In silico Screening of Sisymbrium officinale: PR:PROJECT_TITLE Identification of Flavonoid Glycosides as Potential Anti-Inflammatory Agents PR:PROJECT_SUMMARY Sisymbrium officinale (SO), often referred to as "the plant of singers," is a PR:PROJECT_SUMMARY revered traditional Mediterranean medicinal herb known for its applications in PR:PROJECT_SUMMARY treating inflammatory diseases. Despite its historical use, comprehensive PR:PROJECT_SUMMARY metabolomics and in silico studies validating its anti-inflammatory effects PR:PROJECT_SUMMARY remain scarce. The study reported here seeks to uncover and characterize the PR:PROJECT_SUMMARY bioactive compounds within SO, providing a critical step in identifying PR:PROJECT_SUMMARY potential anti-inflammatory agents. To achieve this, we extracted plant PR:PROJECT_SUMMARY compounds using various solvents with differing polarities, i.e., water, PR:PROJECT_SUMMARY methanol, ethanol, acetone, and chloroform. These extractions were followed by PR:PROJECT_SUMMARY phase separation (polar phase and nonpolar phase) of crude extracts. PR:PROJECT_SUMMARY Additionally, we employed GC-MS and LC-MS (polar phase and nonpolar phase) PR:PROJECT_SUMMARY spectroscopy to obtain a preliminary quantification of the diverse functional PR:PROJECT_SUMMARY groups in the SO extracts.We also carried out inflammatory bioassay analysis PR:PROJECT_SUMMARY followed by chemometrics and in silico screening. PR:INSTITUTE King Abdullah University of Science and Technology PR:LAST_NAME Kahfi PR:FIRST_NAME Jordan PR:ADDRESS Thuwal, Thuwal, Makkah, 23955, Saudi Arabia PR:EMAIL jordan.kahfi@kaust.edu.sa PR:PHONE 0541244806 #STUDY ST:STUDY_TITLE Untargeted Metabolomics and In silico Screening of Sisymbrium officinale: ST:STUDY_TITLE Identification of Flavonoid Glycosides as Potential Anti-Inflammatory Agents ST:STUDY_SUMMARY Sisymbrium officinale (SO), often referred to as "the plant of singers," is a ST:STUDY_SUMMARY revered traditional Mediterranean medicinal herb known for its applications in ST:STUDY_SUMMARY treating inflammatory diseases. Despite its historical use, comprehensive ST:STUDY_SUMMARY metabolomics and in silico studies validating its anti-inflammatory effects ST:STUDY_SUMMARY remain scarce. The study reported here seeks to uncover and characterize the ST:STUDY_SUMMARY bioactive compounds within SO, providing a critical step in identifying ST:STUDY_SUMMARY potential anti-inflammatory agents. To achieve this, we extracted plant ST:STUDY_SUMMARY compounds using various solvents with differing polarities, i.e., water, ST:STUDY_SUMMARY methanol, ethanol, acetone, and chloroform. These extractions were followed by ST:STUDY_SUMMARY phase separation (polar phase and nonpolar phase) of crude extracts. ST:STUDY_SUMMARY Additionally, we employed GC-MS and LC-MS (polar phase and nonpolar phase) ST:STUDY_SUMMARY spectroscopy to obtain a preliminary quantification of the diverse functional ST:STUDY_SUMMARY groups in the SO extracts. GC-MS analysis resulted in the identification of SO ST:STUDY_SUMMARY primary metabolites including sugars (rhamnose, trehalose, fructopyranose, ST:STUDY_SUMMARY myo-inositol, etc.), amino acids (glycine, lysine, valine, etc.), and fatty ST:STUDY_SUMMARY acids (linolenic acid, norlinolenic acid, aminovaleric acid, etc.). The LC-MS ST:STUDY_SUMMARY analysis of both polar and nonpolar fraction resulted in diverse secondary ST:STUDY_SUMMARY metabolite groups including alkaloids (tetramethylpyrazine, pilocarpine), ST:STUDY_SUMMARY flavonoids (apigetrin, cynaroside, vitexin 4-O-glucoside, kaempferol, galangin, ST:STUDY_SUMMARY naringenin, etc.), and plant sterols (zymosterol). The bioassay analysis showed ST:STUDY_SUMMARY that methanol, ethanol, and acetone possess the highest anti-inflammatory ST:STUDY_SUMMARY activity through NO suppresion of RAW 264.7 macrophage cells. Further, ST:STUDY_SUMMARY chemometrics and in silico screening (molecular docking and ADMET) resulted in ST:STUDY_SUMMARY two flavonoid glycosides, apigetrin and 3-O-α-L-arabinopyranoside, as potential ST:STUDY_SUMMARY anti-inflammatory compounds that suppress the activity of human inducible NO ST:STUDY_SUMMARY synthase (iNOS, PDB ID: 3E7G), endothelial NOS (eNOS, PDB ID: 6AV7), and ST:STUDY_SUMMARY neuronal NOS (nNOS, PDB ID: 6CID). These findings pave the ways for further ST:STUDY_SUMMARY validation studies including isolation, purification, in vitro, and in vivo ST:STUDY_SUMMARY analysis. ST:INSTITUTE King Abdullah University of Science and Technology ST:LAST_NAME Kahfi ST:FIRST_NAME Jordan ST:ADDRESS Thuwal, Thuwal, Makkah, 23955, Saudi Arabia ST:EMAIL jordan.kahfi@kaust.edu.sa ST:PHONE 0541244806 #SUBJECT SU:SUBJECT_TYPE Plant SU:SUBJECT_SPECIES Sisymbrium officinale SU:TAXONOMY_ID 203582 #FACTORS #SUBJECT_SAMPLE_FACTORS: SUBJECT(optional)[tab]SAMPLE[tab]FACTORS(NAME:VALUE pairs separated by |)[tab]Raw file names and additional sample data SUBJECT_SAMPLE_FACTORS - A1 Sample source:Leaves | Treatment:Acetone Crude Extract Replicate=Technical replicate 1; RAW_FILE_NAME(Raw File Name GC)=A1-GC; RAW_FILE_NAME(Raw File Name LC Positive)=A1-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=A1-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=A1-NP SUBJECT_SAMPLE_FACTORS - A2 Sample source:Leaves | Treatment:Acetone Crude Extract Replicate=Technical replicate 2; RAW_FILE_NAME(Raw File Name GC)=A2-GC; RAW_FILE_NAME(Raw File Name LC Positive)=A2-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=A2-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=A2-NP SUBJECT_SAMPLE_FACTORS - A3 Sample source:Leaves | Treatment:Acetone Crude Extract Replicate=Technical replicate 3; RAW_FILE_NAME(Raw File Name GC)=A3-GC; RAW_FILE_NAME(Raw File Name LC Positive)=A3-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=A3-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=A3-NP SUBJECT_SAMPLE_FACTORS - A4 Sample source:Leaves | Treatment:Acetone Crude Extract Replicate=Technical replicate 4; RAW_FILE_NAME(Raw File Name GC)=A4-GC; RAW_FILE_NAME(Raw File Name LC Positive)=A4-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=A4-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=A4-NP SUBJECT_SAMPLE_FACTORS - A5 Sample source:Leaves | Treatment:Acetone Crude Extract Replicate=Technical replicate 5; RAW_FILE_NAME(Raw File Name GC)=A5-GC; RAW_FILE_NAME(Raw File Name LC Positive)=A5-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=A5-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=A5-NP SUBJECT_SAMPLE_FACTORS - C1 Sample source:Leaves | Treatment:Chloroform Crude Extract Replicate=Technical replicate 1; RAW_FILE_NAME(Raw File Name GC)=C1-GC; RAW_FILE_NAME(Raw File Name LC Positive)=C1-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=C1-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=C1-NP SUBJECT_SAMPLE_FACTORS - C2 Sample source:Leaves | Treatment:Chloroform Crude Extract Replicate=Technical replicate 2; RAW_FILE_NAME(Raw File Name GC)=C2-GC; RAW_FILE_NAME(Raw File Name LC Positive)=C2-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=C2-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=C2-NP SUBJECT_SAMPLE_FACTORS - C3 Sample source:Leaves | Treatment:Chloroform Crude Extract Replicate=Technical replicate 3; RAW_FILE_NAME(Raw File Name GC)=C3-GC; RAW_FILE_NAME(Raw File Name LC Positive)=C3-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=C3-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=C3-NP SUBJECT_SAMPLE_FACTORS - C4 Sample source:Leaves | Treatment:Chloroform Crude Extract Replicate=Technical replicate 4; RAW_FILE_NAME(Raw File Name GC)=C4-GC; RAW_FILE_NAME(Raw File Name LC Positive)=C4-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=C4-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=C4-NP SUBJECT_SAMPLE_FACTORS - C5 Sample source:Leaves | Treatment:Chloroform Crude Extract Replicate=Technical replicate 5; RAW_FILE_NAME(Raw File Name GC)=C5-GC; RAW_FILE_NAME(Raw File Name LC Positive)=C5-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=C5-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=C5-NP SUBJECT_SAMPLE_FACTORS - E1 Sample source:Leaves | Treatment:Ethanol Crude Extract Replicate=Technical replicate 1; RAW_FILE_NAME(Raw File Name GC)=E1-GC; RAW_FILE_NAME(Raw File Name LC Positive)=E1-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=E1-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=E1-NP SUBJECT_SAMPLE_FACTORS - E2 Sample source:Leaves | Treatment:Ethanol Crude Extract Replicate=Technical replicate 2; RAW_FILE_NAME(Raw File Name GC)=E2-GC; RAW_FILE_NAME(Raw File Name LC Positive)=E2-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=E2-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=E2-NP SUBJECT_SAMPLE_FACTORS - E3 Sample source:Leaves | Treatment:Ethanol Crude Extract Replicate=Technical replicate 3; RAW_FILE_NAME(Raw File Name GC)=E3-GC; RAW_FILE_NAME(Raw File Name LC Positive)=E3-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=E3-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=E3-NP SUBJECT_SAMPLE_FACTORS - E4 Sample source:Leaves | Treatment:Ethanol Crude Extract Replicate=Technical replicate 4; RAW_FILE_NAME(Raw File Name GC)=E4-GC; RAW_FILE_NAME(Raw File Name LC Positive)=E4-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=E4-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=E4-NP SUBJECT_SAMPLE_FACTORS - E5 Sample source:Leaves | Treatment:Ethanol Crude Extract Replicate=Technical replicate 5; RAW_FILE_NAME(Raw File Name GC)=E5-GC; RAW_FILE_NAME(Raw File Name LC Positive)=E5-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=E5-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=E5-NP SUBJECT_SAMPLE_FACTORS - M1 Sample source:Leaves | Treatment:Methanol Crude Extract Replicate=Technical replicate 1; RAW_FILE_NAME(Raw File Name GC)=M1-GC; RAW_FILE_NAME(Raw File Name LC Positive)=M1-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=M1-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=M1-NP SUBJECT_SAMPLE_FACTORS - M2 Sample source:Leaves | Treatment:Methanol Crude Extract Replicate=Technical replicate 2; RAW_FILE_NAME(Raw File Name GC)=M2-GC; RAW_FILE_NAME(Raw File Name LC Positive)=M2-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=M2-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=M2-NP SUBJECT_SAMPLE_FACTORS - M3 Sample source:Leaves | Treatment:Methanol Crude Extract Replicate=Technical replicate 3; RAW_FILE_NAME(Raw File Name GC)=M3-GC; RAW_FILE_NAME(Raw File Name LC Positive)=M3-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=M3-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=M3-NP SUBJECT_SAMPLE_FACTORS - M4 Sample source:Leaves | Treatment:Methanol Crude Extract Replicate=Technical replicate 4; RAW_FILE_NAME(Raw File Name GC)=M4-GC; RAW_FILE_NAME(Raw File Name LC Positive)=M4-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=M4-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=M4-NP SUBJECT_SAMPLE_FACTORS - M5 Sample source:Leaves | Treatment:Methanol Crude Extract Replicate=Technical replicate 5; RAW_FILE_NAME(Raw File Name GC)=M5-GC; RAW_FILE_NAME(Raw File Name LC Positive)=M5-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=M5-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=M5-NP SUBJECT_SAMPLE_FACTORS - W1 Sample source:Leaves | Treatment:Water Crude Extract Replicate=Technical replicate 1; RAW_FILE_NAME(Raw File Name GC)=W1-GC; RAW_FILE_NAME(Raw File Name LC Positive)=W1-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=W1-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=W1-NP SUBJECT_SAMPLE_FACTORS - W2 Sample source:Leaves | Treatment:Water Crude Extract Replicate=Technical replicate 2; RAW_FILE_NAME(Raw File Name GC)=W2-GC; RAW_FILE_NAME(Raw File Name LC Positive)=W2-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=W2-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=W2-NP SUBJECT_SAMPLE_FACTORS - W3 Sample source:Leaves | Treatment:Water Crude Extract Replicate=Technical replicate 3; RAW_FILE_NAME(Raw File Name GC)=W3-GC; RAW_FILE_NAME(Raw File Name LC Positive)=W3-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=W3-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=W3-NP SUBJECT_SAMPLE_FACTORS - W4 Sample source:Leaves | Treatment:Water Crude Extract Replicate=Technical replicate 4; RAW_FILE_NAME(Raw File Name GC)=W4-GC; RAW_FILE_NAME(Raw File Name LC Positive)=W4-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=W4-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=W4-NP SUBJECT_SAMPLE_FACTORS - W5 Sample source:Leaves | Treatment:Water Crude Extract Replicate=Technical replicate 5; RAW_FILE_NAME(Raw File Name GC)=W5-GC; RAW_FILE_NAME(Raw File Name LC Positive)=W5-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=W5-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=W5-NP #COLLECTION CO:COLLECTION_SUMMARY The leaf sample was collected from wild Sisymbrium officinale Plant grown in in CO:COLLECTION_SUMMARY the mountainous regions of Hebron, Palestine in February 2023. CO:SAMPLE_TYPE Leaves #TREATMENT TR:TREATMENT_SUMMARY Sisymbrium officinale leaves were lyophilized and extracted with different type TR:TREATMENT_SUMMARY of solvent (water, ethanol, methanol, acetone, and chloroform). The dried crude TR:TREATMENT_SUMMARY extracts were subjected for liquid-liquid phase separation: polar phase and TR:TREATMENT_SUMMARY nonpolar phase prior GC-MS and LC-MS analysis #SAMPLEPREP SP:SAMPLEPREP_SUMMARY SO powder (25 mg) was mixed with 2.0 mL of each different solvent: water, SP:SAMPLEPREP_SUMMARY methanol, ethanol, ethyl acetate, and acetone. The mixtures were sonicated in SP:SAMPLEPREP_SUMMARY ice bath (15 minutes) to avoid excessive heating, macerated on a shaker SP:SAMPLEPREP_SUMMARY overnight (25 °C, 1400 rpm, 17 hours) to ensure maximum extraction, and SP:SAMPLEPREP_SUMMARY centrifuged (25 °C, 14,000X g, 10 minutes) to separate the debris and extracted SP:SAMPLEPREP_SUMMARY materials. The supernatant was transferred into new labelled tubes (water, SP:SAMPLEPREP_SUMMARY methanol, ethanol, ethyl acetate, and acetone) and stored at -20 °C. #CHROMATOGRAPHY CH:CHROMATOGRAPHY_SUMMARY A Thermo Trace 1310, was used for the analysis of the primary metabolites. CH:CHROMATOGRAPHY_SUMMARY Helium was used as the carrier gas, with a flow rate of 1.2mL/min. CH:CHROMATOGRAPHY_TYPE GC CH:INSTRUMENT_NAME Thermo Trace 1310 CH:COLUMN_NAME Thermo Scientific Trace GOLD TG-5SilMS (30m × 0.25mm, 0.25um) CH:SOLVENT_A - CH:SOLVENT_B - CH:FLOW_GRADIENT - CH:FLOW_RATE 1.2 mL/min CH:COLUMN_TEMPERATURE Programmed temperature gradient: The oven temperature was maintained initially CH:COLUMN_TEMPERATURE at 70°C for 2 min and increased to 220 °C at a rate of 8°C/min, then CH:COLUMN_TEMPERATURE increased to 325 °C at a rate of 16°C/min and was held for 10 min. #ANALYSIS AN:ANALYSIS_TYPE MS #MS MS:INSTRUMENT_NAME Thermo Orbitrap Exploris 240 MS:INSTRUMENT_TYPE Orbitrap MS:MS_TYPE EI MS:ION_MODE POSITIVE MS:MS_COMMENTS The Thermo Orbitrap Exploris 240 mass spectrometer was used. This instrument was MS:MS_COMMENTS operated in electron ionization (EI) which was set at 300 ˚C, and the electron MS:MS_COMMENTS energy was set to 70eV with an emission current of 50µA. The acquisition mode MS:MS_COMMENTS was set to full scan with a scan range of 35-700 Da and an orbitrap resolution MS:MS_COMMENTS of 60000 (FWHM, measured at m/z 200). The AGC target was set to standard and the MS:MS_COMMENTS maximum injection time was set to auto mode. The data acquisition was lock-mass MS:MS_COMMENTS corrected using GC column bleed siloxane masse of m/z 207. The Trace 1310 GC MS:MS_COMMENTS operated with an injection volume of 1 µl of sample that was injected using a MS:MS_COMMENTS 10 µL syringe into a single gooseneck with glass wool Thermo Scientific™ MS:MS_COMMENTS Liner GOLD. The inlet mode was set to Split mode with a split flow of 40ml/min MS:MS_COMMENTS and a purge flow of 5 ml/min. The helium carrier rate was set to 1.2 ml/min. The MS:MS_COMMENTS oven temperature was maintained initially at 70°C for 2 min and increased to MS:MS_COMMENTS 220 °C at a rate of 8°C/min, then increased to 325 °C at a rate of 16°C/min MS:MS_COMMENTS and was held for 10 min. #MS_METABOLITE_DATA MS_METABOLITE_DATA:UNITS AUC MS_METABOLITE_DATA_START Samples A1 A2 A3 A4 A5 C1 C2 C3 C4 C5 E1 E2 E3 E4 E5 M1 M2 M3 M4 M5 W1 W2 W3 W4 W5 Factors Sample source:Leaves | Treatment:Acetone Crude Extract Sample source:Leaves | Treatment:Acetone Crude Extract Sample source:Leaves | Treatment:Acetone Crude Extract Sample source:Leaves | Treatment:Acetone Crude Extract Sample source:Leaves | Treatment:Acetone Crude Extract Sample source:Leaves | Treatment:Chloroform Crude Extract Sample source:Leaves | Treatment:Chloroform Crude Extract Sample source:Leaves | Treatment:Chloroform Crude Extract Sample source:Leaves | Treatment:Chloroform Crude Extract Sample source:Leaves | Treatment:Chloroform Crude Extract Sample source:Leaves | Treatment:Ethanol Crude Extract Sample source:Leaves | Treatment:Ethanol Crude Extract Sample source:Leaves | Treatment:Ethanol Crude Extract Sample source:Leaves | Treatment:Ethanol Crude Extract Sample source:Leaves | Treatment:Ethanol Crude Extract Sample source:Leaves | Treatment:Methanol Crude Extract Sample source:Leaves | Treatment:Methanol Crude Extract Sample source:Leaves | Treatment:Methanol Crude Extract Sample source:Leaves | Treatment:Methanol Crude Extract Sample source:Leaves | Treatment:Methanol Crude Extract Sample source:Leaves | Treatment:Water Crude Extract Sample source:Leaves | Treatment:Water Crude Extract Sample source:Leaves | Treatment:Water Crude Extract Sample source:Leaves | Treatment:Water Crude Extract Sample source:Leaves | Treatment:Water Crude Extract (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl 2,2-dihydroxyacetate 37115023 9951976 44717046 48088.891 56689923 49247850 48841166 35068992 39570413 49013180 9815618 14436386 5081118 7529602 17165556 25889091 14267650 13424924 14093275 4789323 3804932 2774385 1088962 1775701 2854443 (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(2-methylbutoxy)oxane-3,4,5-triol 4111800121 4122125405 4457843435 6716810.58 3004734812 208364921 286531531 230856898 591839473 200993119 2894573320 2636934640 2301846440 3849455985 2143160516 1663217152 2285036669 2192263472 1508497782 2165223128 65744815 57420047 60763537 60511719 64456879 1-Aminopentan-2-ol 120706 1228247 1188408 2593.12 320781 12731 15668 5871 38785.02 39851 1365116 1082863 2447248 2018756 1418675 1188323 1668068 902848 1631664 1127492 10779058 9216337 11579205 12556060 12188443 2-Phenylethyl β-D-glucopyranoside 9291756 8902901 10425162 428693.23 6815937 2072783 2340350 1409489 2000510 1010951 6542212 5938616 5246301 8111406 4817488 4286492 5870200 5444681 4479467 5050537 458972 386937 403349 482510.18 265171 2-β-D-glucosyloxy-4-methoxycinnamic acid 3289405 3582269 2909893 556 1673281 28123 616 1885 10005 193861 7662548 7860625 7710826 9803471 5802656 6739606 8876272 7263906 8138126 7452593 26877046 25070261 25441772 19926172 26634164 3-Hydroxy-3-(4'-hydroxy-3'-methoxyphenyl)propionic acid 19509066 21325690 18358161.19 4022.6 12251419 6456 587 608 491573 173748 21888637 21503619 20306307.45 24998858.99 15799237 18887146 23818893 19480561 22763057 22186388 12083256 7652700 7389930 8575992 8963896 4-Aminobutanoic acid 3082491761 9640546038 5765246226 1597947.56 6098534271 16429210 8729095 7573683 495739123 745234326 25681274591 14149737369 10012870824 31718046405 14660408970 32163338826 25103655173 7492634880 28681994516 30564284416 24742082263 19424835569 22479265235 29835970949 27476461136 5-Aminolevulinic acid hexyl ester 586290265 534311681 503602474 1625799.7 365588879 4302622 3096280.02 3296394.46 48385220 40081653 1276631057 1329060158 1395355243 1350300227 1007848599 932307932 801878114 603559962 871007169 960024417 6710243919 5431456514 6895952790 6720356755 7035977168 5-Aminovaleric acid 8297541 6304064 6425629 39188.51 5153804 62448 45910 29345 611171.12 619622 51833794 56587855 50820799 62588472 40515229 48107311 48525182 44657284 53948711 51438982 64640336 71159437 76546569 63406540 67215355 5-hydroxy-2-(2-hydroxy-3-([2-(1H-indol-3-yl)-1,1-dimethylethyl]amino)propoxy)benzonitrile 933974 976847 953294 18156.33 577015.86 32896.71 29000.59 28009.08 61306.83 42494.28 1749708 1751835 1823247 1890874 1253501 2234224 2183037 1854480 2126872 2179623 53080 34104 38581 34039 25447 5-Trifluoromethoxytryptamine 494039780 501403699 427093088 1654771.06 289407657 7044922 2942128 1824157 44904150 34719369 1434809476 1388691131 1471387780 1580065435 1087032885 907530900 974688258 717775239 856133524 837023891 14618484044 12378752484 14427808353 14120787923 14689665827 Benzoic acid, 4-[2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-(hydroxymethyl)ethoxy]-3-methoxy-, methyl ester 4627504 4800450 4321998 6699.2 2828118 18816.47 1461 700 25634 11310 4516335 5142523 4604329 5482125 3494154 4109400 5673796 4453967 20928 86867 11669342 9778628 11172691 11644050 12268878 Cadaverine 7631945 5627912 5617765.55 29510.89 4453364 67745 8953 25922.96 271681 7052 21773817.15 19860318 19666161 19076950 15847189 12043381 18348002 13505724 14383605 14601501 140199563 153391392 141679507 132225612 131804304 Citric acid 3742793 625236 694610 482 381678 326127 1344007 1250675 27978661 4466198 3516438 15531137 14523198 4111717 18067305 117342985.7 124359963 93323418.56 55230879 37804860 533536648 593707591 416070794 394133857 432310938 D,L-O-tyrosine 310113377 361355392 304008198 4085367.03 161363950 901150 412093 551784.12 5357667 2837889 592979045 569100166 672562439 691220134 496823433 650334096 615281577 460506600 544485863 524013631 1304245875 1156452177 1347027040 1430620338 1395228079 D-(+)-cellobiose, (isomer 1) 175747497 122688125 147486217 125200.33 99512191 400881 213873 186632 2943245 8403617 1550539763 1610779556 1546126839 1825282183 1147530594 1692606298 2290596790 1955474909 2041000494 2166428382 1080807553 1034811960 1064674227 839455323 1125692903 D-(+)-cellobiose, (isomer 2) 7994063 8322398 7493909 527 4892767 457510 569554 392869 1359887 1973812.6 33190269 34630903 31043032 35662485.93 22459818 46367387.88 56418566 44113294 45982741 49186336 141695095 127481074 125164490 123795317 151484063 D-(-)-fructopyranose, 5TMS (isomer 2) 353306 211814 65981 13308.34 231094.4 4312 15243.9 738 13675 2581 9580327 49150 12242121 20967325.01 23008526 154359313 35558370 164413365 169471229 267748189 9274435 25751327 4155679 4285341 5144478 D-galactonic acid 81035638 43134370 59396305 601 44780267 961835 5569 726893 11854539 110607951 150264184 163233073 161241988 1288145021 124798752 162179607 285652866 202943766 195919673 210183239 753807579 705184810 710584139 671938471 813975690 D-gluconic acid 64524254 40073806 67624043 533 25077086 408676 515082 402768 25883946 56635010 236042685 120401583 206131710 584970197 181853408 212245264 256447330 106025499 94812422 87157429 527114286 495586638 486044533 469179233 558275501 D-trehalose 53899711 58146700 46087460 954 32210467 133030.42 56687.37 2704 2558560.24 5706511.07 93158778 108535950 99052214 109539366 70974028 102683991 138514472 112179980 130509008 128800816 78370189 67774786 70717133 74535235 75452865 Glycerol monostearate 2851641 2782779 2834472 419443.015 2554633 15567092 21307449 17152758 15275582 10855142 2395235 2425535 2168808 2658464 2298319 2120834 2248252 1998050 2503715 2274047 3322438 3076271 2102075 1891964 2269120 Glycine 182789006 102800185 106036369 380143.93 81092292 9582027 7370422 6141852 10062476 40557342 1686837152 1384838438 1471031152 1420414389 1357401163 1631500090 1776450596 1325892137 1864547611 1900073582 3112217703 3076636281 3354156780 2929343340 2825085916 Gulose 2748744 2091248 3066032 659 2147783 39208.65 49181 1738 68878 3458 4184349.47 3569961.4 3473707.72 1912480 3183706.91 15974860 6150604.47 14945784 21030382 24636729 21043989 26388617 19096536 22074388 15737943 Kaempferol-3-O-α-L-arabinopyranoside 12238635 15171206 8885511 27878.97 7387325 135206.92 147494.63 143087.31 736334.13 301208.93 11026356 13892914 13546810 12081776 9607171 8995456 11006282 8930302 11903102 10143937 80765 41568 73736 53950 50885 L-glutamic acid 3296503 2107669 3346423 148580.23 2032270 463613 164318 816 855051 5671015 299939551 119202112 159386877 278848791 133511187 102798 285416387 339663318 344588455 375580393 299018284 299456228 321982060 293130225 295063310 L-lysine 67163653 32374966 40225739 683957.09 27368944 6659140 1972840 1279867 11187204 65434143 1589379509 1579748973 1746420761 1580186681 1186190369 1739630420 2057005510 1595073370 1763520028 1764517620 6689139574 6425215799 6788615002 6925341334 6815822536 L-ornithine 140272363 71183298 86381268 4495184.04 63636284 4574826 1729437 1003826 4743117 23632479 1341889014 1426542283 1500470060 1547750106 1134500843 1077611720 1173961043 1082743799 1199011011 1160003419 2652556857 2415847870 2612242720 2813199303 2605215299 L-rhamnose 10215317 7798134 28312231 7312.68 14452411.39 7589 3438 5239 340472 241028 49591982 52164842 55521890 58122082 39651585 50260577 65954373 52715769 59895471 60388248 43538326 34550266 38989860 43908169 40815409 L-valine 2378750195 1717092263 1373028637 2001335.13 1324826161 10921267 4827960 3024763 125461 74184 2877643297 2435986578 2486001495 2684636359 2344628651 2511369000 2802697425 2900955232 2898332911 3174347587 2628752489 2409196349 3495489429 2935787072 2794846326 Maltose 929762.81 832797.51 705744.21 616 511152.04 2488 1558 4653.49 1507 3273 96627 259098.93 4256 51110 4225 953960.44 1049491 856498.49 1162487.67 1026457 8202826 6763585 6437414 7441859 6392526.88 Myo-inositol 449015370 370099377 386965649 517 277635777 5573475 5114 688755 24846479 89884144 2584736785 2459306763 2737313514 2693696738 1967329408 3313791782 3539872499 3059621465 3186902464 3475076813 5962234608 5418331226 6103799266 6504060878 6375366003 Norlinolenic acid 15954476 12848233 10691090 114842.62 13375244 28527580 36937924 27181332 21249631 10176000 12181793 12238423 7729633 14388373 9897655 17219114 20404837 17894003 19846570 19674947 1524583 587918 319576 1647021 1939863 Pseudo uridine 64767376 69261807 59011212 533 43874547 29397 6873 4659 2668525 623062 75010933 80210681 79286286 72509441 59626809 69988141 82992413 66865465 80547765 79960383 114771464 100821071 112127719 120355430 111015249 Sedoheptulose 9247807.26 10882011 9071971.97 35811.35 6023648 3705 16989 18584.86 241776 248955 11375781 11141193 11600419 12453150 8594676 22486297 19028891 22873491.17 23152324 27194779 38178175.46 32023240 35990342 41010163 42555582 Tyramine 2269712 2297518 1406012 22332.81 1339836 32908 4523 8560 144387.33 800944 6571725 6600870.71 7063929.93 7016271 5863623.94 6286370 10905952 6555706.09 6732746.76 5432242 77240384 79670986 95484077 86159448 98294874 α-Linolenic acid 12228284 11351607 9699193 1590 10238604 22980518 31549230 21896745 19720753 11369911 12877803 10338997 6945307 12019602 9355860 17901390 15663459 12441772 15917145 13926956 1002227 773009 991539 753760 958500 MS_METABOLITE_DATA_END #METABOLITES METABOLITES_START metabolite_name RT [min] NIST Lib Hit Formula NIST Theo. Mol. Mass Pubchem CID INCHI_KEY (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl 2,2-dihydroxyacetate 7.302 C18 H38 O4 Si2 374.2303 7373179 BWZMJRSMHQDFIT-KXUCPTDWSA-N   (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(2-methylbutoxy)oxane-3,4,5-triol 17.4 C23 H54 O6 Si4 538.2992 13944078   DMALNKYCYUUBGC-RSDOQXBQSA-N   1-Aminopentan-2-ol 13.283 C14 H37 N O Si3 319.2178 95299 ZRUPXAZUXDFLTG-UHFFFAOYSA-N   2-Phenylethyl β-D-glucopyranoside 19.511 C26 H52 O6 Si4 572.2836 468284 MLRIJUWUQTVDQE-UHFFFAOYSA-N 2-β-D-glucosyloxy-4-methoxycinnamic acid 24.315 C31 H60 O9 Si5 716.3078 129850462 FQWZGEBZILOCET-YJUJGKJLSA-N 3-Hydroxy-3-(4'-hydroxy-3'-methoxyphenyl)propionic acid 22.73 C19 H36 O5 Si3 428.1865 24871597   ABTZMSOARGMKMK-UHFFFAOYSA-N   4-Aminobutanoic acid 10.271 C13 H33 N O2 Si3 319.1814 119 BTCSSZJGUNDROE-UHFFFAOYSA-N 5-Aminolevulinic acid hexyl ester 12.592 C17 H37 N O3 Si2 359.2307 6433083   RYQOILLJDKPETL-UHFFFAOYSA-N   5-Aminovaleric acid 11.395 C14 H35 N O2 Si3 333.197 138 JJMDCOVWQOJGCB-UHFFFAOYSA-N 5-hydroxy-2-(2-hydroxy-3-([2-(1H-indol-3-yl)-1,1-dimethylethyl]amino)propoxy)benzonitrile 25.098 C31 H49 N3 O3 Si3 595.3076 550909   AMMJVFKSVGGOPS-UHFFFAOYSA-N   5-Trifluoromethoxytryptamine 13.654 C20 H35 F3 N2 O Si3 460.2004 21071596   OMDUIRZSXDJSEX-UHFFFAOYSA-N   Benzoic acid, 4-[2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-(hydroxymethyl)ethoxy]-3-methoxy-, methyl ester 23.445 C28 H46 O8 Si3 594.2495 10541338 IANXOBHKQWFRAH-UHFFFAOYSA-N Cadaverine 11.252 C14 H38 N2 Si3 318.2337 273 VHRGRCVQAFMJIZ-UHFFFAOYSA-N Citric acid 13.517 C18 H40 O7 Si4 480.1846 311 KRKNYBCHXYNGOX-UHFFFAOYSA-N D,L-O-tyrosine 14.684 C18 H35 N O3 Si3 397.1919 91482   WRFPVMFCRNYQNR-UHFFFAOYSA-N   D-(+)-cellobiose, (isomer 1) 24.388 C36 H86 O11 Si8 918.4319 519729   QJZFVYJIGWEKIR-UHFFFAOYSA-N   D-(+)-cellobiose, (isomer 2) 22.703 C36 H86 O11 Si8 918.4319 519729   QJZFVYJIGWEKIR-UHFFFAOYSA-N   D-(-)-fructopyranose, 5TMS (isomer 2) 13.856 C21 H52 O6 Si5 540.2605 56606411   BGTCZSJLWAMWRH-ARQDHWQXSA-N   D-galactonic acid 15.198 C24 H60 O7 Si6 628.2949 128869 RGHNJXZEOKUKBD-MGCNEYSASA-N D-gluconic acid 15.245 C24 H60 O7 Si6 628.2949 10690 RGHNJXZEOKUKBD-SQOUGZDYSA-N D-trehalose 25.954 C36 H86 O11 Si8 918.4319 7427 HDTRYLNUVZCQOY-LIZSDCNHSA-N Glycerol monostearate 21.629 C27 H58 O4 Si2 502.3868 24699   VBICKXHEKHSIBG-UHFFFAOYSA-N   Glycine 7.409 C11 H29 N O2 Si3 291.1501 750 DHMQDGOQFOQNFH-UHFFFAOYSA-N Gulose 15.87 C21 H52 O6 Si5 540.2605 441033 WQZGKKKJIJFFOK-CBPJZXOFSA-N Kaempferol-3-O-α-L-arabinopyranoside 27.064 C38 H66 O10 Si6 850.3266 44258911   RNVUDWOQYYWXBJ-RLDUMJPOSA-N   L-glutamic acid 11.338 C14 H33 N O4 Si3 363.1712 33032 WHUUTDBJXJRKMK-VKHMYHEASA-N L-lysine 14.538 C18 H46 N2 O2 Si4 434.2631 5962 KDXKERNSBIXSRK-YFKPBYRVSA-N L-ornithine 13.448 C17 H44 N2 O2 Si4 420.2474 6262 AHLPHDHHMVZTML-BYPYZUCNSA-N L-rhamnose 23.099 C18 H44 O5 Si4 452.226 25310 SHZGCJCMOBCMKK-JFNONXLTSA-N L-valine 6.219 C11 H27 N O2 Si2 261.1575 6287 KZSNJWFQEVHDMF-BYPYZUCNSA-N Maltose 28.224 C36 H86 O11 Si8 918.4319 439186 GUBGYTABKSRVRQ-PICCSMPSSA-N Myo-inositol 16.111 C24 H60 O6 Si6 612.3 892 CDAISMWEOUEBRE-GPIVLXJGSA-N Norlinolenic acid 15.433 C20 H36 O2 Si 336.2479 16061034 FAFSAZIEJFMBBY-PDBXOOCHSA-N Pseudo uridine 18.214 C24 H52 N2 O6 Si5 604.2666 15047 PTJWIQPHWPFNBW-GBNDHIKLSA-N Sedoheptulose 22.407 C25 H62 O7 Si6 642.3106 5459879 HSNZZMHEPUFJNZ-SHUUEZRQSA-N Tyramine 14.409 C17 H35 N O Si3 353.2021 5610 DZGWFCGJZKJUFP-UHFFFAOYSA-N α-Linolenic acid 17.235 C21 H38 O2 Si 350.2636 5280934 DTOSIQBPPRVQHS-PDBXOOCHSA-N METABOLITES_END #END