#METABOLOMICS WORKBENCH kpaglia_20210621_094948_mwtab.txt DATATRACK_ID:2708 STUDY_ID:ST001845 ANALYSIS_ID:AN002988 PROJECT_ID:000000 VERSION 1 CREATED_ON June 22, 2021, 8:40 am #PROJECT PR:PROJECT_TITLE Identification of unique metabolite networks between Latino and Caucasian PR:PROJECT_TITLE patients with nonalcoholic fatty liver disease (NAFLD) PR:PROJECT_SUMMARY Nonalcoholic fatty liver disease (NAFLD) is a spectrum of liver pathology PR:PROJECT_SUMMARY ranging from simple steatosis to nonalcoholic steatohepatitis (NASH); the latter PR:PROJECT_SUMMARY is characterized by inflammation and fibrosis. Risk factors for NALFD include PR:PROJECT_SUMMARY obesity, diabetes, hyperlipidemia, and hypertension—all of which are features PR:PROJECT_SUMMARY of metabolic syndrome. NAFLD is a very heterogeneous disease, as it presents in PR:PROJECT_SUMMARY different patterns in males and females and in patients from different PR:PROJECT_SUMMARY ethnicities, with unclear predictors for development and severity of disease. PR:PROJECT_SUMMARY Previous studies have shown that NAFLD is 1.4 times more frequent in Hispanics PR:PROJECT_SUMMARY than in Caucasians. One of the major challenges in NAFLD is the lack of PR:PROJECT_SUMMARY accurate, noninvasive biomarkers for the detection of the most aggressive PR:PROJECT_SUMMARY presentation, NASH. The gold standard for the diagnosis is liver biopsy, which PR:PROJECT_SUMMARY is an invasive procedure associated with possible complications. Noninvasive PR:PROJECT_SUMMARY diagnosis of NASH is a major unmet medical need and there are no PR:PROJECT_SUMMARY ethnicity-specific biomarkers that can diagnose this condition and predict its PR:PROJECT_SUMMARY progression. Therefore, the main gap in knowledge that this proposal and line of PR:PROJECT_SUMMARY research will address is the characterizing the different plasma and liver PR:PROJECT_SUMMARY metabolomics profile of patients with fatty liver from two ethnicities (Latinos PR:PROJECT_SUMMARY vs. Caucasians) and of both sexes. The overall hypothesis of the present study PR:PROJECT_SUMMARY is that the higher incidence of nonalcoholic fatty liver (NAFL) in Latino PR:PROJECT_SUMMARY patients is reflected in a different plasma and liver metabolomics profile PR:PROJECT_SUMMARY compared to Caucasian patients with further sex-related differences. PR:PROJECT_SUMMARY Characterization of metabolite networks can aid in identifying the mechanistic PR:PROJECT_SUMMARY underpinnings of sex and ethnic driven differences in NAFL which could help PR:PROJECT_SUMMARY diagnose and establish a prognosis of this condition, especially in the critical PR:PROJECT_SUMMARY transition from NAFL to the more aggressive nonalcoholic steatohepatitis PR:PROJECT_SUMMARY (NASH).To address this hypothesis, plasma metabolomics profile of samples from PR:PROJECT_SUMMARY male and female Latino and Caucasian bariatric surgery patients with NAFL and PR:PROJECT_SUMMARY from healthy subjects will be compared. Metabolomics findings will be related PR:PROJECT_SUMMARY with liver pathology and liver transcriptome profiles from intraoperatively PR:PROJECT_SUMMARY obtained liver biopsies using correlation, network, and pathway analysis. PR:INSTITUTE University of California, Davis PR:DEPARTMENT Department of Internal Medicine, Division of Gastroenterology and Hepatology PR:LABORATORY Medici Lab PR:LAST_NAME Medici PR:FIRST_NAME Valentina PR:ADDRESS 4150 V Street - PSSB Suite 3500 - 95817 Sacramento CA PR:EMAIL vmedici@ucdavis.edu PR:PHONE (916) 734 3751 PR:FUNDING_SOURCE The National Institutes of Health (NIH)-West Coast Metabolomic Center WCMC) PR:FUNDING_SOURCE grant number DK104770 #STUDY ST:STUDY_TITLE Identification of unique metabolite networks between Latino and Caucasian ST:STUDY_TITLE patients with nonalcoholic fatty liver disease (NAFLD) (part V) ST:STUDY_SUMMARY Nonalcoholic fatty liver disease (NAFLD) is a spectrum of liver pathology ST:STUDY_SUMMARY ranging from simple steatosis to nonalcoholic steatohepatitis (NASH); the latter ST:STUDY_SUMMARY is characterized by inflammation and fibrosis. Risk factors for NALFD include ST:STUDY_SUMMARY obesity, diabetes, hyperlipidemia, and hypertension—all of which are features ST:STUDY_SUMMARY of metabolic syndrome. NAFLD is a very heterogeneous disease, as it presents in ST:STUDY_SUMMARY different patterns in males and females and in patients from different ST:STUDY_SUMMARY ethnicities, with unclear predictors for development and severity of disease. ST:STUDY_SUMMARY Previous studies have shown that NAFLD is 1.4 times more frequent in Hispanics ST:STUDY_SUMMARY than in Caucasians. One of the major challenges in NAFLD is the lack of ST:STUDY_SUMMARY accurate, noninvasive biomarkers for the detection of the most aggressive ST:STUDY_SUMMARY presentation, NASH. The gold standard for the diagnosis is liver biopsy, which ST:STUDY_SUMMARY is an invasive procedure associated with possible complications. Noninvasive ST:STUDY_SUMMARY diagnosis of NASH is a major unmet medical need and there are no ST:STUDY_SUMMARY ethnicity-specific biomarkers that can diagnose this condition and predict its ST:STUDY_SUMMARY progression. Therefore, the main gap in knowledge that this proposal and line of ST:STUDY_SUMMARY research will address is the characterizing the different plasma and liver ST:STUDY_SUMMARY metabolomics profile of patients with fatty liver from two ethnicities (Latinos ST:STUDY_SUMMARY vs. Caucasians) and of both sexes. The overall hypothesis of the present study ST:STUDY_SUMMARY is that the higher incidence of nonalcoholic fatty liver (NAFL) in Latino ST:STUDY_SUMMARY patients is reflected in a different plasma and liver metabolomics profile ST:STUDY_SUMMARY compared to Caucasian patients with further sex-related differences. ST:STUDY_SUMMARY Characterization of metabolite networks can aid in identifying the mechanistic ST:STUDY_SUMMARY underpinnings of sex and ethnic driven differences in NAFL which could help ST:STUDY_SUMMARY diagnose and establish a prognosis of this condition, especially in the critical ST:STUDY_SUMMARY transition from NAFL to the more aggressive nonalcoholic steatohepatitis ST:STUDY_SUMMARY (NASH).To address this hypothesis, plasma metabolomics profile of samples from ST:STUDY_SUMMARY male and female Latino and Caucasian bariatric surgery patients with NAFL and ST:STUDY_SUMMARY from healthy subjects will be compared. Metabolomics findings will be related ST:STUDY_SUMMARY with liver pathology and liver transcriptome profiles from intraoperatively ST:STUDY_SUMMARY obtained liver biopsies using correlation, network, and pathway analysis. ST:INSTITUTE University of California, Davis ST:DEPARTMENT Department of Internal Medicine, Division of Gastroenterology and Hepatology ST:LABORATORY Medici Lab ST:LAST_NAME Medici ST:FIRST_NAME Valentina ST:ADDRESS 4150 V Street - PSSB Suite 3500 - 95817 Sacramento CA ST:EMAIL vmedici@ucdavis.edu ST:PHONE (916) 734 3751 #SUBJECT SU:SUBJECT_TYPE Human SU:SUBJECT_SPECIES Homo sapiens SU:TAXONOMY_ID 9606 SU:AGE_OR_AGE_RANGE 23-73 SU:GENDER Male and female SU:HUMAN_RACE Hispanic and Caucasian #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 - 840422-01_001 factor:NAFLD-CAU RAW_FILE_NAME=840422-01_001.wiff SUBJECT_SAMPLE_FACTORS - 840422-03_002 factor:NAFLD-CAU RAW_FILE_NAME=840422-03_002.wiff SUBJECT_SAMPLE_FACTORS - 840422-04_003 factor:NAFLD-CAU RAW_FILE_NAME=840422-04_003.wiff SUBJECT_SAMPLE_FACTORS - 840422-05_004 factor:NAFLD-CAU RAW_FILE_NAME=840422-05_004.wiff SUBJECT_SAMPLE_FACTORS - 840422-07_005 factor:NAFLD-HIS RAW_FILE_NAME=840422-07_005.wiff SUBJECT_SAMPLE_FACTORS - 840422-08_006 factor:NAFLD-CAU RAW_FILE_NAME=840422-08_006.wiff SUBJECT_SAMPLE_FACTORS - 840422-10_007 factor:NAFLD-HIS RAW_FILE_NAME=840422-10_007.wiff SUBJECT_SAMPLE_FACTORS - 840422-13_008 factor:NAFLD-CAU RAW_FILE_NAME=840422-13_008.wiff SUBJECT_SAMPLE_FACTORS - 840422-14_009 factor:NAFLD-CAU RAW_FILE_NAME=840422-14_009.wiff SUBJECT_SAMPLE_FACTORS - 840422-16_010 factor:NAFLD-CAU RAW_FILE_NAME=840422-16_010.wiff SUBJECT_SAMPLE_FACTORS - 840422-17_011 factor:NAFLD-CAU RAW_FILE_NAME=840422-17_011.wiff SUBJECT_SAMPLE_FACTORS - 840422-18_012 factor:NAFLD-HIS RAW_FILE_NAME=840422-18_012.wiff SUBJECT_SAMPLE_FACTORS - 840422-19_013 factor:NAFLD-CAU RAW_FILE_NAME=840422-19_013.wiff SUBJECT_SAMPLE_FACTORS - 840422-20_014 factor:NAFLD-CAU RAW_FILE_NAME=840422-20_014.wiff SUBJECT_SAMPLE_FACTORS - 840422-21_015 factor:NAFLD-HIS RAW_FILE_NAME=840422-21_015.wiff SUBJECT_SAMPLE_FACTORS - 840422-24_016 factor:NAFLD-CAU RAW_FILE_NAME=840422-24_016.wiff SUBJECT_SAMPLE_FACTORS - 840422-25_017 factor:NAFLD-CAU RAW_FILE_NAME=840422-25_017.wiff SUBJECT_SAMPLE_FACTORS - 840422-27_018 factor:NAFLD-CAU RAW_FILE_NAME=840422-27_018.wiff SUBJECT_SAMPLE_FACTORS - 840422-30_019 factor:NAFLD-CAU RAW_FILE_NAME=840422-30_019.wiff SUBJECT_SAMPLE_FACTORS - 840422-44_020 factor:NAFLD-HIS RAW_FILE_NAME=840422-44_020.wiff SUBJECT_SAMPLE_FACTORS - 840422-28_021 factor:N / A RAW_FILE_NAME=840422-28_021.wiff #COLLECTION CO:COLLECTION_SUMMARY Blood was collected as a part of a routine/pre-operation check up, not more than CO:COLLECTION_SUMMARY 2 weeks prior to operation day (bariatric surgery) for the NAFLD group and among CO:COLLECTION_SUMMARY normal BMI healthy volunteers for the control group. All volunteers were fasted CO:COLLECTION_SUMMARY 10-12 hours before collection. Liver obtained during surgery (no preservatives, CO:COLLECTION_SUMMARY flash-frozen) CO:SAMPLE_TYPE Blood (serum) #TREATMENT TR:TREATMENT_SUMMARY Subjects were divided into two groups either: Healthy control or Nonalcoholic TR:TREATMENT_SUMMARY fatty liver disease (NAFLD) #SAMPLEPREP SP:SAMPLEPREP_SUMMARY 1 Thaw plasma samples on ice 2 Vortex plasma sample and pipette 50µl in SP:SAMPLEPREP_SUMMARY polypropylene Eppendorf tube/Plate 3 Add Surrogate Standards of the 3 lipid SP:SAMPLEPREP_SUMMARY classes (as needed) and other reagents as in the following table: Plasma SP:SAMPLEPREP_SUMMARY Sample 10x Oxylipid Surrogate STDs CUDA + PHAU Anti-oxidant ACN/MeOH SUM 4 SP:SAMPLEPREP_SUMMARY Vortex for 30sec 5 Centrifuge at 6°C for 5 min at 15,000 g (or 1,800 g for SP:SAMPLEPREP_SUMMARY plates) 6 Take the supernatant (~240µl) into new Eppendorf tube/filter plate 7 SP:SAMPLEPREP_SUMMARY Spin Filter (0.1 um) or plate filter (0.2um) for 5 min @ 12,000 g (1,800g for SP:SAMPLEPREP_SUMMARY plate) 8 place aliquotes of samples into vials, or plate, and cap vials or seal SP:SAMPLEPREP_SUMMARY plates 9 Store in -20°C until analysis #CHROMATOGRAPHY CH:CHROMATOGRAPHY_SUMMARY Targeted oxylipin analysis CH:CHROMATOGRAPHY_TYPE Other CH:INSTRUMENT_NAME Thermo Vanquish CH:COLUMN_NAME Waters Acquity BEH Amide (150 x 2.1mm, 1.7um) #ANALYSIS AN:ANALYSIS_TYPE MS #MS MS:INSTRUMENT_NAME ABI Sciex 4000 QTrap MS:INSTRUMENT_TYPE Other MS:MS_TYPE EI MS:ION_MODE UNSPECIFIED MS:MS_COMMENTS analyzed by a Waters UPLC with a 2.1×150 mm, 1.7 µm Acquity BEH column, ESI MS:MS_COMMENTS (+) and (-) switching and detection by multi-reaction monitoring on an Sciex MS:MS_COMMENTS 6500+ QTRAP mass spectrometer. We validated this method for linearity, limit of MS:MS_COMMENTS detection, limit of quantitation, inter- and intra-day reproducibility, and MS:MS_COMMENTS recovery for all targets, yielding better than 15% relative standard deviation MS:MS_COMMENTS and (spiked) recoveries of greater than 80%. #MS_METABOLITE_DATA MS_METABOLITE_DATA:UNITS nM MS_METABOLITE_DATA_START Samples 840422-01_001 840422-03_002 840422-04_003 840422-05_004 840422-07_005 840422-08_006 840422-10_007 840422-13_008 840422-14_009 840422-16_010 840422-17_011 840422-18_012 840422-19_013 840422-20_014 840422-21_015 840422-24_016 840422-25_017 840422-27_018 840422-30_019 840422-44_020 840422-28_021 Factors factor:NAFLD-CAU factor:NAFLD-CAU factor:NAFLD-CAU factor:NAFLD-CAU factor:NAFLD-HIS factor:NAFLD-CAU factor:NAFLD-HIS factor:NAFLD-CAU factor:NAFLD-CAU factor:NAFLD-CAU factor:NAFLD-CAU factor:NAFLD-HIS factor:NAFLD-CAU factor:NAFLD-CAU factor:NAFLD-HIS factor:NAFLD-CAU factor:NAFLD-CAU factor:NAFLD-CAU factor:NAFLD-CAU factor:NAFLD-HIS factor:N / A Thromboxane B2 0.1605060571 0.06035353425 0.07723503439 0.1133243175 0.07520114023 2.403028872 0.09774261662 0.1645516417 0.16503336 0.08162524764 0.1280020226 0.04204053618 0.1234076953 0.1042829874 0.1138752678 0.1215809452 0.09881785107 0.05905576755 0.1297033318 0.1174054279 0.1870358497 6-Ketoprostaglandin F1 alpha 0.06866651008 0.06481719899 0.08161799949 0.06483063408 0.06577892337 0.01097352811 0.07191570934 0.06394558781 0.8913492161 0.04589573771 0.05021024643 0.04773354635 0.05023183276 0.06201388922 0.03463643246 0.02510219979 0.08778369296 0.03139506105 0.05654383657 0.08212959727 0.08053451477 Prostaglandin E1 0.07167305544 0.03279831927 0.05401936469 0.01879059398 0.02800533452 0.02308956492 0.03878529204 0.03067047735 0.04391607876 0.07677263456 0.04432497836 0.05932582559 0.1153486423 0.09758298174 0.06216565447 0.02994929985 0.04187605233 0.0768508031 0.05066427537 0.05162185329 0.05614958363 Prostaglandin E2 0.01882578342 0.02958881604 0.02488936387 0.06960333399 0.1029932457 0.0202991427 0.05050031295 0.07330310364 0.07612792855 0.02464455099 0.05543391597 0.0343931673 0.1323691173 0.008366113408 0.07026858779 0.09046758473 0.03825969989 0.7395748734 0.6903339237 0.05484861088 1.498267617 Prostaglandin D2 0.1718973172 0.1154438581 0.04216665157 0.102854008 2.000665778 0.1183932862 1.591804722 0.05757986892 0.1822697447 0.1574035589 1.59878219 0.0773344263 0.1383636942 0.08605710563 0.08114146951 0.1229938265 0.1393765998 1.83052997 0.1051298443 1.676104426 0.1164057978 15-Deoxy-delta-12,14-Prostaglandin J2 0.06232994911 0.05434126445 0.08600019435 0.0694682256 0.07843634193 0.03826494464 0.07861473376 0.08774615504 0.7357977446 0.05917820979 0.8300604489 0.07571016171 0.07219272415 0.6353092326 0.1019514205 0.07556146487 0.08203761054 0.04763073392 0.08257706267 0.08717866082 1.138503602 15-Keto-prostaglandin E2 0.03281896296 0.01974662168 0.01331931059 0.1786656264 0.05578369275 0.06105726896 0.120201905 0.1076235205 0.1478481506 0.06966319581 0.1011750317 0.1489879878 0.1516714415 0.1583022369 0.1702162758 0.02936105632 0.1557023196 0.08507678572 0.03826255798 0.05996557081 0.07938143915 Prostaglandin F2a 0.4501913164 0.240611672 0.5318365258 0.5736592454 0.4708964427 0.4492831408 0.4672000744 0.6200192413 0.5768065213 0.3563110362 5.119532001 0.3887212512 0.5085403845 0.9135509722 0.372685567 0.3405797678 0.7144073629 0.2952280199 0.4641201984 0.4472843452 0.379871816 Prostaglandin E3 0.5998358582 7.463410541 1.312192723 1.66955284 1.701853116 112.8827476 1.673799917 0.9702439805 48.74411428 0.6289672149 10.87821156 1.294346923 15.59402023 0.8746667867 1.657694341 1.630808917 0.9790100074 0.60798002 0.8678433374 0.1227166471 5.636240663 9,11,15-trihydroxy-5,13,1Z-prostatrienoic acid 0.2095718034 0.1313500035 0.6825706629 0.2075199524 1.297512099 0.05802255764 0.1624006595 0.173127705 0.8798595515 0.05351005646 0.1603907364 0.1720036779 0.1963139566 0.08360411299 0.05861069665 0.6707242979 0.7248644472 0.05899991079 0.1445299213 0.07504599148 0.1358909931 9,12,13-trihydroxyoctadec-10-enoic acid 3.04750682 0.4630291812 0.4176739244 0.4787586158 0.1084060476 0.3502292086 0.2371046856 0.1777271643 0.1719740613 0.1894538529 7.079710016 0.2197463393 0.247762405 0.3868753467 0.1863139137 0.07816174193 0.2955062304 0.3075802405 0.4318850437 0.147952419 0.3280146388 5,6,15-trihydroxyeicosa-7,9,11,13-tetraenoic acid 3.095011285 0.3195366166 0.1546185238 11.11234167 1.434019566 0.2417644437 0.3082838875 0.3686908609 4.899347895 0.4051128081 3.985500802 0.25804971 3.704018669 0.2240882216 0.3395379177 0.2254226966 0.4222678658 2.907856621 2.00230445 0.2060819829 2.98018497 Resolvin D1 0.06277323748 0.009411526146 0.02856056914 0.08049093752 0.03486669935 0.04050256688 0.02261015209 0.07966780907 0.06063342657 0.03549893615 0.1098387468 0.04272262426 0.07453864648 0.0870141669 0.05914853313 0.09552112225 0.02788244646 0.04423556575 0.05106093521 0.08401894391 0.05771486389 9S,10R-dihydroxy-stearic acid 0.6791915653 0.610736344 0.2356954174 3.530585427 0.5511612498 3.151782012 4.687149443 0.3505077048 3.370247485 0.4994628492 3.478199631 0.5905255442 5.31177935 0.4014932277 0.4346491268 0.6844222029 0.3882304067 3.099591182 4.702406278 3.190466612 4.832696927 12,13-dihydroxyoctadec-9-enoic acid 2.806252585 2.498545712 1.602632248 4.123039486 2.589903559 9.602487651 14.82462897 1.414057117 3.959409526 2.876397767 3.04535469 1.221290291 5.686576763 1.565879435 1.606548695 3.64638239 2.705546879 7.367612935 4.517426347 4.217713931 7.047206817 9,10-dihydroxyoctadec-12-enoic acid 2.041586223 1.763347555 1.338557787 2.693888415 2.63313482 7.424004326 23.1918602 0.9825216445 3.976056461 3.305662093 1.729993304 0.6929266 2.437596897 1.08205292 1.378093243 2.692290037 1.90967044 3.786703522 4.694419669 3.385818997 5.850296004 15,16-dihydroxyoctadeca-9,12-dienoic acid 6.806912192 6.128063233 5.773365638 17.06161458 11.71918953 22.33744593 15.16031898 2.978959809 11.52281535 10.89576785 7.567324647 3.334503801 12.26494759 10.23155525 6.910802594 9.317794027 11.17493885 17.6473279 13.1774637 10.00184245 13.86838085 12,13-dihydroxyoctadeca-9,15-dienoic acid 0.06233223346 0.07253877754 0.08018115093 0.1343810083 0.06031407657 0.2515745199 0.09834717045 0.07137738235 0.1244962991 0.04688680964 0.156787195 0.04603763561 0.0745265148 0.1054903762 0.1382559731 0.0916526782 0.06879293251 0.06039686797 0.13154252 0.1536702872 0.1156892679 9,10-dihydroxyoctadeca-12,15-dienoic acid 0.04615080143 0.03039995076 0.02427133129 0.05275301382 0.04542662853 0.1302326401 1.243927539 0.01337909924 0.06537492146 0.04638742373 0.03384485076 0.008007428038 0.03233538936 0.0187644662 0.01200856071 0.04344778986 0.03555322903 0.06026681138 0.1317985811 0.06155919239 0.6753711778 14,15-dihydroxyeicosa-5,8,11-trienoic acid 2.712057168 1.079460614 1.715414367 2.029470954 2.053422332 2.286294877 1.376627572 2.195308472 2.774785055 3.512209038 1.898815983 0.1349108604 3.963496268 2.239497273 1.843124314 2.41185128 3.454689375 0.2389034974 1.516105884 0.1258454717 2.14784391 11,12-Dihydroxyicosa-5,8,14-trienoic acid 0.5816026749 0.5658840974 0.1033407637 0.5938356493 0.8558123397 0.6931496195 0.702107271 0.1266928322 1.043770322 0.9156671608 0.119307327 0.07269938308 0.8780761944 0.6094185166 0.09211528006 1.107440336 1.619181156 0.7003140136 0.9378329177 0.1198880172 0.7063934096 8,9-dihydroxyeicosa-5,11,14-trienoic acid 0.1011771219 0.1336088926 0.1004041411 0.103897326 0.1087939111 0.09723763914 0.08801350947 0.1034133636 0.7307969893 0.1476517281 0.06791119779 0.07265010062 0.1778437032 0.1518769615 0.06215634011 0.1326649769 0.5500827858 0.06290787524 0.066565186 0.1135516165 0.1934204221 5,6-dihydroxyeicosa-8,11,14-trienoic acid 0.05692460932 0.03144859576 0.0319261143 0.05434252753 0.03965047695 0.08142127042 0.07719751605 0.03763636863 0.08069230629 0.5868482479 0.07624473745 0.01105846702 0.06818142132 0.06009637355 0.03559942343 0.1035476238 0.09010946183 0.01996706112 0.04872084026 0.03456975599 0.0500070044 17,18-dihydroxyeicosa-5,8,11,14-tetraenoic acid 5.079524374 6.329079117 3.316013223 4.874333367 3.276325137 3.279904463 4.204236371 2.792357506 14.06193324 6.084631006 6.287985523 3.609371535 5.874940865 5.29423213 0.5888372123 3.737422234 5.980885889 0.5489437726 3.633807192 0.3944315493 5.529155128 14,15-dihydroxyeicosa-5,8,11,17-tetraenoic acid 0.1628472378 0.176969224 1.000512408 0.1318768274 0.1169555198 0.133040701 0.1352933222 0.108057781 1.416705183 0.1132933953 1.161996375 0.05741951178 1.251206244 0.1607732731 0.05333533611 1.144771394 1.977675449 0.08932233903 0.05322866688 0.09735208976 1.472789679 19,20-dihydroxydocosa-4,7,10,13,16-pentaenoic acid 0.8700100849 0.7297238401 0.5750923534 0.578578131 1.052985736 0.6461207524 1.220778898 0.7788557934 1.031689946 1.057255119 0.6663596789 0.5666419396 1.090818391 0.6534097836 0.6799380711 1.472423652 1.479630774 1.029410306 1.081641134 0.5263017808 1.168201913 8,15-dihydroxyeicosa-5,9,11,13-tetraenoic acid 0.1385602562 0.1500692408 0.1630297568 0.1095508913 0.117010042 0.1144971833 0.1061173834 0.2178073675 0.1539884072 0.1757126486 0.2643196268 0.1335809754 0.09445262576 0.0659062111 0.2245643005 0.155911417 0.06396060821 0.1444649298 0.05856002344 0.06261920607 0.1236953573 5,15-dihydroxyeicosa-6,8,11,13-tetraenoic acid 0.09129068646 0.05455578862 0.04912330296 0.1171488071 0.110724051 0.04166951865 0.1077900313 0.08141428365 0.1031522054 0.09161731741 0.1728695127 0.07621228186 0.151032454 0.06989525335 0.07762119254 0.08754461769 0.0442430297 0.09490416718 0.12824576 0.5639691057 0.1045513836 6-trans-Leukotriene B4 0.01334462259 0.00968807685 0.0184504086 0.0353582716 0.02136950985 0.01478952224 0.02669191828 0.03656047438 0.06009701278 0.02984447177 0.02576608225 0.008176657442 0.04023306596 0.01436806617 0.01338807932 0.04990649156 0.02153273863 0.01766418952 0.0534578012 0.01589779611 0.03441785984 Leukotriene B4 0.03366382293 0.03572225632 0.06662351237 0.02543092869 0.1105030883 0.01901313992 0.02695443148 0.03093097961 0.1334347626 0.03451713009 0.03069438986 0.0288308467 0.05555614327 0.01574122494 0.04329513382 0.08184775149 0.0377289205 0.03178231569 0.03701416212 0.04877285618 0.129236169 Leukotriene B5 0.01243969673 0.006145543896 0.009866662038 0.00986713503 0.01318294714 0.004181483397 0.01118307795 0.009474623813 0.01421130655 0.007127457679 0.02231972196 0.006676692019 0.02497785339 0.009091896388 0.01484099787 0.01568277998 0.01152914669 0.008779811449 0.01107377504 0.009318162417 0.01516905592 13-Hydroxyoctadecadienoic acid 7.763260327 7.309819543 8.362872342 8.411974341 9.866667905 15.86230307 43.37291766 7.161718925 11.38872926 9.683126995 7.411981913 3.789666566 16.32601383 8.380504657 5.890345957 9.206825281 7.063235502 13.42807945 11.90287752 12.44881819 16.78507162 9-Hydroxylinoleic acid 6.386379869 3.829182396 5.229432428 7.421816829 6.94304816 9.619464019 43.84665134 7.259780925 10.54928172 7.276252713 6.916174778 3.206273755 11.71610254 7.542666849 6.013462893 5.674280612 5.661883665 10.55097111 9.257882652 7.76334496 10.90301089 13-hydroxyoctadeca-9,11,15-trienoic acid 0.075962968 0.1614000522 0.06304153188 0.07851438401 0.3208588445 0.2695560673 2.575477367 0.0975842604 0.1863428859 0.1469458763 0.08371328437 0.04792736429 0.2076495857 0.2901589349 0.08033023481 0.1503637624 0.3641733191 0.08448054669 0.1194751083 0.1816574271 0.4431374292 9-hydroxyoctadeca-10,12,15-trienoic acid 0.06720074165 0.04219213657 0.08797524094 0.1406497243 0.1616120112 0.1107698623 0.2979195449 0.1096822691 0.173914249 0.1602317114 0.05677356686 0.05634596948 0.0965875131 0.1391629162 0.04595937572 0.09206097452 0.1883621747 0.1104463191 0.158386754 0.1094038796 0.1685530946 20-Hydroxyarachidonic acid 0.4279853251 0.5932982002 0.5547412854 0.3949949235 0.4263382279 0.1549961741 0.4513912879 0.6849497288 0.5002948934 0.3842850662 0.4964659325 0.6716655233 0.3461254333 0.5098787708 0.6161976082 0.6337382644 0.6753796299 0.5141286024 0.4918055168 0.2552004737 0.5748660153 15-hydroxyeicosa-5,8,11,13-tetraenoic acid 1.407838439 1.282701661 0.7869901682 1.149214358 1.367810669 1.46972856 1.519063994 0.9274471863 0.8584641478 1.008275948 1.429702935 0.5763939796 0.1433939356 1.09830725 1.151060919 0.8801469794 1.176722715 1.088963126 1.205992525 1.770423307 3.68566457 12-Hydroxy-5,8,10,14-eicosatetraenoic acid 5.863748532 2.610561725 3.267251538 3.001917509 1.521230228 20.00350103 1.030140131 1.208864068 1.074798524 0.8487635721 1.198433019 0.818494323 0.6677870642 2.346403952 0.8018951724 1.197435335 0.1471634053 0.9682014223 1.918578781 0.6756759261 1.021286341 8-hydroxyeicosa-5,9,11,14-tetraenoic acid 0.1226164419 0.1420488147 0.2356751975 0.1431183219 0.0780164664 0.1239823312 0.2220670929 0.1177057106 0.2268049462 0.1566673303 1.403308343 0.1549240299 0.1492433444 0.1472741808 0.1541105946 0.2327346152 0.222363985 0.1360928229 0.206635123 0.1698321386 0.1573371508 11-Hydroxy-arachidonic acid 0.5761876533 0.1205324195 0.1276920933 0.08891667367 0.8243280535 0.682876237 0.09829077998 0.1189500711 0.1140560173 0.1041118093 0.1069294361 0.0872546864 0.05554628639 0.09739156659 0.06943585069 0.07685768636 0.07520689504 0.6302148368 0.0514779825 0.5537951198 0.7337767519 9-hydroxyeicosa-5,7,11,14-tetraenoic acid 0.02780417321 0.06173318996 0.05013395705 0.04722335841 0.05582229407 0.100635992 0.06883966071 0.0732753295 0.186103541 0.08839029305 0.1679652232 0.04190840556 0.02649323305 0.07604129085 0.07257375534 0.048763892 0.02991462728 0.05215720492 0.1026948627 0.07739685257 0.1357265123 5-Hydroxy-6,8,11,14-eicosatetraenoic acid 0.3373841805 0.2663043226 0.2267375783 0.1409102848 0.4895614665 0.365826476 0.5258447302 0.4179614577 0.5143411613 0.5380262533 0.4578845826 0.2582474875 0.3840784044 0.4083341687 0.353772809 0.4830542792 0.4202632042 2.538985488 0.464141354 0.5895464455 0.2958942269 15-hydroxyeicosa-5,8,11,13,17-pentaenoic acid 0.0218216026 0.03773691646 0.02557560061 0.05187973278 0.05235062406 0.01606441821 0.04395480377 0.03114637974 0.05866189558 0.05369444968 0.03644880408 0.03134029761 0.04036555372 0.1007609569 0.03054188395 0.03864999776 0.02424271063 0.02229309998 0.02907782212 0.03555025117 0.7860695077 12-Hydroxy-5,8,10,14,17-eicosapentaenoic acid 0.07559557497 0.05166177634 0.7514865055 0.1017032056 0.03329167017 0.6911893345 0.03392350905 0.02140274519 0.0367404099 0.0343347471 0.05571793139 0.01251296596 0.03546875246 0.1190248449 0.02770224105 0.01355334553 0.04935728286 0.01262463892 0.04039607894 0.02928882872 0.05901872701 9-Hydroxy-5,7,11,14,17-icosapentaenoic acid 0.0258842388 0.03010183041 0.03552147756 0.06569634817 0.08494168371 0.05532878962 0.04417780122 0.02019800491 0.04421209345 0.05130781574 0.02204641087 0.057101218 0.07935238806 0.06425013575 0.046157196 0.04376571529 0.0255510765 0.02859162416 0.06619118031 0.03158633721 0.08333712697 5-Hydroxy-6,8,11,14,17-eicosapentaenoic acid 0.06392573474 0.1416032666 0.22828414 0.1057088518 0.09623357456 0.1315270236 0.1053001274 0.2859915057 1.47583076 0.1637358342 1.252265157 0.1098074587 1.326304324 0.1842730975 0.1371485146 0.1308691414 0.2261783259 0.0537945239 0.08567317036 0.2126856236 0.08952865631 17-hydroxy-4,7,10,13,15,19-docosahexaenoic acid 2.711605978 0.3535489606 0.2437765147 0.9006647777 0.4795113489 0.2858620374 0.6305406201 0.3234598961 3.291501682 0.4613576801 0.7611936163 0.4552646878 7.584749743 0.693140714 3.04580577 0.7557542233 0.591894094 5.117726152 0.6853587759 2.852054674 0.451209622 14-hydroxydocosa-4,7,10,12,16,19-hexaenoic acid 5.679091303 0.579302199 4.043687859 0.4425558588 3.185702757 7.823115161 5.235837349 0.3236709085 0.1353332838 2.530036153 0.2097610228 0.2789569514 0.3921267436 3.933077881 0.4183060775 0.5612994339 3.227847887 0.4015040132 3.287626498 0.3951353784 0.5877303422 4-hydroxydocosa-5,7,10,13,16,19-hexaenoic acid 0.0815551341 0.187424228 1.278231361 1.240061651 0.2650940979 0.1548470766 0.1894844649 0.2874487048 1.206502846 0.1198545067 0.1524073197 0.235288123 1.75265401 0.3151799553 0.2549779163 0.1040987704 1.973377246 0.1277675931 0.09766158697 1.113767507 0.2457773084 13-ketooctadeca-9,11-dienoic acid 0.423406294 0.2612667133 0.4462493848 0.5216459476 0.6518788831 0.3444572697 0.3092742984 0.2833314459 0.5459570274 0.7012111142 0.4152648889 0.3019683268 0.2736591949 0.6821897374 0.7024315962 0.6538042764 0.2970592436 0.3132908725 0.5725659734 0.3622095389 0.6276168082 9-ketooctadeca-10,12-dienoic acid 0.3600078173 0.3368150882 2.327409717 1.333418394 1.494118936 2.30619002 0.3000936932 0.2238269279 0.3150823207 1.059848197 2.413370871 1.002222731 0.1511336183 0.4054902367 2.006919402 0.3968536715 0.3260286992 2.136234565 2.822907085 1.1706401 3.369522837 15-ketoeicosa-5,8,11,13-tetraenoic acid 0.3290829405 3.780701855 6.186690126 0.5226370906 0.5704318429 0.5459525288 3.608264602 2.76916999 3.213537358 0.09650305711 5.755039399 3.468852945 2.905071822 5.449789446 6.427103697 2.549435937 2.889441851 0.5101139606 2.836795765 3.351900633 4.483259639 5-ketoeicosa-6,8,11,14-tetraenoic acid 1.44698428 1.007561165 8.868363882 0.3631376352 1.38455201 0.3953313106 0.3824576261 4.658781715 4.759577799 0.4355844958 9.686028082 0.4804661869 4.504389729 0.4922216422 0.2199062845 0.4664141709 4.45838005 1.527346918 3.590386899 1.604640973 11.03524264 9,10-Epoxystearic acid 0.3463488873 0.3219812162 0.2742200356 0.4689092421 0.1895650319 0.2157353902 0.1961003888 0.2587433501 0.4982716288 1.405056492 3.717039257 0.1382521764 0.3436159912 0.354028306 0.2888661651 0.3434838895 0.3468744727 0.495972609 0.5070486436 0.5010841795 1.424431813 trans-12,13-epoxy-11-oxo-trans-9-octadecenoic acid 0.1099397553 88.35738562 4.094290977 17.87620928 0.1140623995 124.251697 0.1129246013 0.2862746901 177.9039664 19.57224338 11.37988995 0.09467941173 19.86266412 0.09120741898 0.08135212589 24.79350745 0.07563970371 0.3657537921 32.01891276 28.66913755 8.658361663 12,13-epoxy-9-octadecenoic acid 0.3332313795 0.3287320866 0.391436151 9.003130351 0.3597880945 3.717095122 9.215806345 0.2966895475 0.4768803807 0.5646544973 0.271599844 0.2954176894 0.5530985425 0.2807412449 0.1210294898 0.2260066593 0.2214004449 0.3974951174 0.3964940962 4.014242712 0.6562490425 9(10)-epoxy-12Z-octadecenoic acid 0.903652557 0.1169777367 0.03240805668 0.811316269 0.125718898 0.1121894272 2.868382679 0.1486325262 0.1320019449 1.341957661 0.06652969177 0.07688055911 0.1129050682 0.1048633946 0.162779802 0.1324353008 0.156245464 0.68665636 0.1456931395 0.9729414981 0.8434712057 15(16)-epoxy-9,12-octadecadienoic acid 0.2226490913 0.3308372227 0.04837331102 4.545101506 0.4946257901 4.90436514 5.150603618 0.09522340465 4.699028318 2.974521823 0.244611502 0.3884061236 2.783227672 3.06570874 0.255995542 0.3447971116 8.063036298 7.138593652 0.4548984825 3.075905478 8.803274462 9(10)-epoxy-12,15-octadecadienoic acid 0.173957938 0.2231029597 0.07892605518 0.192351054 0.06945502342 4.177487634 0.2130869755 0.07508344182 4.36070234 0.1411945724 0.1911173868 0.3034655475 2.505400944 0.07649974139 0.2000118499 0.1695532172 0.07100217796 0.02759932279 0.1293247029 0.1719732167 0.200397782 12(13)-epoxy-9,15-octadecadienoic acid 0.07737182826 0.02302673625 0.03320673876 0.1094145412 0.05423631868 0.07070764701 0.1013850235 0.0342563427 0.05785605246 0.04353881301 0.03097260311 0.04490731558 0.06347487045 0.064986028 0.04688879862 0.02808401942 0.03074168719 0.03883863467 0.04106523083 0.02040671935 0.07970046579 11-Hydroxy-14,15-epoxyeicosatrienoic acid 0.04530450039 0.02661329329 0.06988710335 0.08332272484 0.03384055689 0.03314287896 0.02487682091 0.03266036061 0.119658271 0.08238154497 0.06098363342 0.05201025308 0.072230297 0.03815016703 0.0290283146 0.06866598149 0.009417041271 0.04684465211 0.05090119167 0.04917473409 0.03770161322 11,12-Epoxyeicosa-5,8,14-trienoic acid 0.03590011741 0.02800081541 0.05068106419 0.02089888352 0.06496774473 0.01933961539 0.05487866031 0.0273154275 0.01805896773 0.02633161795 0.03549791484 0.02583613448 0.01613715361 0.04832314806 0.04213468305 0.07380958696 0.02088397859 0.03040477091 0.04995750803 0.03273619231 0.04835268832 8,9-Epoxyeicosa-5,11,14-trienoic acid 0.1699532728 0.1162879046 0.1998767617 0.1342388178 0.1679273305 0.0485528761 0.5086783521 0.1864547116 0.1332672611 0.2296160141 0.1068760111 0.1405713316 0.13764721 0.09499244957 0.3017901294 0.1211072977 0.1018252844 0.2487976914 0.1777028376 0.08264319702 0.129484503 17,18-Epoxy-5,8,11,14-eicosatetraenoic acid 0.09914331778 0.0840030449 0.1534662823 0.06101328816 0.1172737766 0.04843473465 0.1219532516 0.1375841593 0.1394587825 1.006579863 0.06857700058 0.04972213641 0.1372862942 0.6052271129 0.1077933058 0.1523336095 0.1209677297 0.04829681555 0.6307947187 0.08859047082 0.08896542608 14(15)-epoxy-5,8,11,17-eicosatetraenoic acid 0.1682665955 0.1362716957 0.1501863537 0.06455563114 0.2257389221 0.04731391798 0.2916367723 0.1716127881 2.536454662 0.07955763169 0.08157548504 1.274951824 0.1846129542 0.1420957139 0.3024266827 0.1676079613 0.07184265279 0.04339675699 0.2867354969 0.07446784882 1.040413165 11(12)-epoxy-5,8,14,17- eicosatetraenoic acid 0.06400619981 0.06498104672 0.6746270879 0.03857655928 0.04453158208 0.01806096831 0.1178334804 0.05686109746 0.06107118558 0.1123408603 0.01878665819 0.06314293328 0.03924052472 0.04540174545 0.1157570537 0.05149655194 0.08116546088 0.04131966712 0.09950243085 0.02763863512 0.07603121644 18-(3-ethyloxiran-2-yl)octadeca-4,7,10,13,16-pentaenoic acid 0.1540571096 0.09829356521 1.016956004 0.1132602116 0.3081350596 0.1221220333 0.2352621586 0.1198974591 0.3344689792 0.1828972961 0.1714546483 0.1899722566 0.2674359903 0.2720647921 0.1024819302 0.284659686 0.06290351627 0.1155768236 1.297464825 0.2748299623 1.601504097 16(17)-epoxy-4,7,10,13,19-docosapentaenoic acid 0.1697903207 0.05913516196 0.3705310094 0.07211347815 0.260121566 0.07473607383 0.22673971 0.1963775019 0.1806183626 0.06212133096 0.054682606 0.1228770141 0.1185230959 0.1106955931 0.2205025639 0.2358703418 0.1632667791 0.03517660772 0.3535735181 0.1364697059 0.4477895333 10-nitrooleic acid 2.655349915 0.1212758806 3.814624601 0.3364250351 3.552425162 0.5120313677 2.98184083 0.4336521143 0.4119315351 0.3471361185 7.355698582 0.2663961817 7.294967769 6.025321337 0.3403669118 0.3517043329 2.852832189 3.001071883 0.4773856815 0.4464848526 3.805026119 9-nitrooleic acid 0.1600533863 1.009078581 0.1752842411 0.3556582342 0.1276149822 0.2013218168 2.213261052 0.1522086636 2.385030342 1.593170409 0.377641317 0.427397265 1.20704476 0.3841214867 0.3044472123 4.408377719 1.062390624 0.4026986405 2.186193835 0.3261991144 13.8429086 10-nitrolinoleic acid 0.341404762 0.2825535478 5.853797491 0.2207255407 0.5133179999 0.9884683081 0.6484944561 0.4000542036 1.117035019 0.2860791193 0.7213569992 0.377472633 0.4194694416 0.1990548907 0.2257115865 0.4597014027 0.5067212546 0.1876314638 0.4335639905 0.5206402317 1.15141733 MS_METABOLITE_DATA_END #METABOLITES METABOLITES_START metabolite_name InChI Key PubChem Ret.Time Thromboxane B2 XNRNNGPBEPRNAR-JQBLCGNGSA-N 5283137 3.97 6-Ketoprostaglandin F1 alpha KFGOFTHODYBSGM-ZUNNJUQCSA-N 5280888 3.19 Prostaglandin E1 GMVPRGQOIOIIMI-DWKJAMRDSA-N 5280723 4.7 Prostaglandin E2 XEYBRNLFEZDVAW-ARSRFYASSA-N 5280360 4.54 Prostaglandin D2 BHMBVRSPMRCCGG-OUTUXVNYSA-N 448457 4.83 15-Deoxy-delta-12,14-Prostaglandin J2 VHRUMKCAEVRUBK-GODQJPCRSA-N 5311211 9.85 15-Keto-prostaglandin E2 YRTJDWROBKPZNV-KMXMBPPJSA-N 5280719 4.87 Prostaglandin F2a PXGPLTODNUVGFL-YNNPMVKQSA-N 5280363 4.42 Prostaglandin E3 CBOMORHDRONZRN-QLOYDKTKSA-N 5280937 3.84 9,11,15-trihydroxy-5,13,1Z-prostatrienoic acid SAKGBZWJAIABSY-SAMSIYEGSA-N 5280940 3.7 9,12,13-trihydroxyoctadec-10-enoic acid MDIUMSLCYIJBQC-MVFSOIOZSA-N 9858729 4.36 5,6,15-trihydroxyeicosa-7,9,11,13-tetraenoic acid IXAQOQZEOGMIQS-SSQFXEBMSA-N 5280914 5.48 Resolvin D1 OIWTWACQMDFHJG-CCFUIAGSSA-N 44251266 5.37 9S,10R-dihydroxy-stearic acid VACHUYIREGFMSP-SJORKVTESA-N 441460 9.39 12,13-dihydroxyoctadec-9-enoic acid CQSLTKIXAJTQGA-FLIBITNWSA-N 10236635 8.03 9,10-dihydroxyoctadec-12-enoic acid XEBKSQSGNGRGDW-YFHOEESVSA-N 9966640 8.44 15,16-dihydroxyoctadeca-9,12-dienoic acid LKLLJYJTYPVCID-OHPMOLHNSA-N 16061068 6.96 12,13-dihydroxyoctadeca-9,15-dienoic acid RGRKFKRAFZJQMS-OOHFSOINSA-N 16061067 7.04 9,10-dihydroxyoctadeca-12,15-dienoic acid QRHSEDZBZMZPOA-ZJSQCTGTSA-N 16061066 7.08 14,15-dihydroxyeicosa-5,8,11-trienoic acid SYAWGTIVOGUZMM-ILYOTBPNSA-N 5283147 8.68 11,12-Dihydroxyicosa-5,8,14-trienoic acid LRPPQRCHCPFBPE-KROJNAHFSA-N 5283146 9.24 8,9-dihydroxyeicosa-5,11,14-trienoic acid DCJBINATHQHPKO-TYAUOURKSA-N 5283144 9.78 5,6-dihydroxyeicosa-8,11,14-trienoic acid GFNYAPAJUNPMGH-QNEBEIHSSA-N 5283142 10.56 17,18-dihydroxyeicosa-5,8,11,14-tetraenoic acid XYDVGNAQQFWZEF-JPURVOHMSA-N 16061120 7.34 14,15-dihydroxyeicosa-5,8,11,17-tetraenoic acid BLWCDFIELVFRJY-QXBXTPPVSA-N 16061119 7.67 19,20-dihydroxydocosa-4,7,10,13,16-pentaenoic acid FFXKPSNQCPNORO-MBYQGORISA-N 16061148 8.66 8,15-dihydroxyeicosa-5,9,11,13-tetraenoic acid NNPWRKSGORGTIM-RCDCWWQHSA-N 53480358 7.06 5,15-dihydroxyeicosa-6,8,11,13-tetraenoic acid UXGXCGPWGSUMNI-BVHTXILBSA-N 5283158 7.4 6-trans-Leukotriene B4 VNYSSYRCGWBHLG-UKNWISKWSA-N 5283128 7.53 Leukotriene B4 VNYSSYRCGWBHLG-AMOLWHMGSA-N 5280492 7.78 Leukotriene B5 BISQPGCQOHLHQK-HDNPQISLSA-N 5283125 6.52 13-Hydroxyoctadecadienoic acid HNICUWMFWZBIFP-IRQZEAMPSA-N 6443013 10.89 9-Hydroxylinoleic acid NPDSHTNEKLQQIJ-ZJHFMPGASA-N 5282944 11.08 13-hydroxyoctadeca-9,11,15-trienoic acid KLLGGGQNRTVBSU-JDTPQGGVSA-N 10469728 9.62 9-hydroxyoctadeca-10,12,15-trienoic acid YUPHIKSLGBATJK-OBKPXJAFSA-N 53480359 9.5 20-Hydroxyarachidonic acid NNDIXBJHNLFJJP-DTLRTWKJSA-N 123803 10.05 15-hydroxyeicosa-5,8,11,13-tetraenoic acid JSFATNQSLKRBCI-VAEKSGALSA-N 5280724 11.27 12-Hydroxy-5,8,10,14-eicosatetraenoic acid ZNHVWPKMFKADKW-LQWMCKPYSA-N 5283155 11.96 8-hydroxyeicosa-5,9,11,14-tetraenoic acid NLUNAYAEIJYXRB-VYOQERLCSA-N 5283154 12.1 11-Hydroxy-arachidonic acid GCZRCCHPLVMMJE-RSPKXIRXSA-N 5312981 11.71 9-hydroxyeicosa-5,7,11,14-tetraenoic acid KATOYYZUTNAWSA-OIZRIKEUSA-N 14123398 12.31 5-Hydroxy-6,8,11,14-eicosatetraenoic acid KGIJOOYOSFUGPC-JGKLHWIESA-N 5280733 12.68 15-hydroxyeicosa-5,8,11,13,17-pentaenoic acid WLKCSMCLEKGITB-XWJJKCKWSA-N 16061131 10.04 12-Hydroxy-5,8,10,14,17-eicosapentaenoic acid MCRJLMXYVFDXLS-UOLHMMFFSA-N 5283191 10.4 9-Hydroxy-5,7,11,14,17-icosapentaenoic acid OXOPDAZWPWFJEW-IMCWFPBLSA-N 16061129 10.61 5-Hydroxy-6,8,11,14,17-eicosapentaenoic acid FTAGQROYQYQRHF-GHWNLOBHSA-N 5283193 11 17-hydroxy-4,7,10,13,15,19-docosahexaenoic acid SWTYBBUBEPPYCX-VIIQGJSXSA-N 6439179 11.39 14-hydroxydocosa-4,7,10,12,16,19-hexaenoic acid ZNEBXONKCYFJAF-BGKMTWLOSA-N 11566378 11.7 4-hydroxydocosa-5,7,10,13,16,19-hexaenoic acid IFRKCNPQVIJFAQ-PQVBWYSWSA-N 14429109 13.02 13-ketooctadeca-9,11-dienoic acid JHXAZBBVQSRKJR-BSZOFBHHSA-N 6446027 11.33 9-ketooctadeca-10,12-dienoic acid LUZSWWYKKLTDHU-ZJHFMPGASA-N 9839084 11.78 15-ketoeicosa-5,8,11,13-tetraenoic acid YGJTUEISKATQSM-USWFWKISSA-N 5280701 11.63 5-ketoeicosa-6,8,11,14-tetraenoic acid MEASLHGILYBXFO-XTDASVJISA-N 5283159 13.39 9,10-Epoxystearic acid IMYZYCNQZDBZBQ-UHFFFAOYSA-N 15868 14.44 trans-12,13-epoxy-11-oxo-trans-9-octadecenoic acid RCMABBHQYMBYKV-BUHFOSPRSA-N 5283007 9.5 12,13-epoxy-9-octadecenoic acid CCPPLLJZDQAOHD-FLIBITNWSA-N 5356421 12.81 9(10)-epoxy-12Z-octadecenoic acid FBUKMFOXMZRGRB-YFHOEESVSA-N 6246154 13.04 15(16)-epoxy-9,12-octadecadienoic acid HKSDVVJONLXYKL-OHPMOLHNSA-N 16061062 11.15 9(10)-epoxy-12,15-octadecadienoic acid JTEGNNHWOIJBJZ-ZJSQCTGTSA-N 16061060 11.35 12(13)-epoxy-9,15-octadecadienoic acid BKKGUKSHPCTUGE-OOHFSOINSA-N 16061061 11.55 11-Hydroxy-14,15-epoxyeicosatrienoic acid JBSCUHKPLGKXKH-ILYOTBPNSA-N 5283205 12.91 11,12-Epoxyeicosa-5,8,14-trienoic acid DXOYQVHGIODESM-KROJNAHFSA-N 5283204 13.39 8,9-Epoxyeicosa-5,11,14-trienoic acid DBWQSCSXHFNTMO-TYAUOURKSA-N 5283203 13.59 17,18-Epoxy-5,8,11,14-eicosatetraenoic acid GPQVVJQEBXAKBJ-JPURVOHMSA-N 16061089 11.25 14(15)-epoxy-5,8,11,17-eicosatetraenoic acid RGZIXZYRGZWDMI-QXBXTPPVSA-N 16061088 11.72 11(12)-epoxy-5,8,14,17- eicosatetraenoic acid QHOKDYBJJBDJGY-BVILWSOJSA-N 16061087 11.87 18-(3-ethyloxiran-2-yl)octadeca-4,7,10,13,16-pentaenoic acid OSXOPUBJJDUAOJ-MBYQGORISA-N 11631565 12.65 16(17)-epoxy-4,7,10,13,19-docosapentaenoic acid BCTXZWCPBLWCRV-ZYADFMMDSA-N 14392758 13.04 10-nitrooleic acid WRADPCFZZWXOTI-BMRADRMJSA-N 24836820 14.84 9-nitrooleic acid CQOAKBVRRVHWKV-SAPNQHFASA-N 11645581 14.79 10-nitrolinoleic acid LELVHAQTWXTCLY-XYWKCAQWSA-N 5282259 13.85 METABOLITES_END #END