#METABOLOMICS WORKBENCH kborkows_20190729_154556 DATATRACK_ID:1786 STUDY_ID:ST001245 ANALYSIS_ID:AN002069 PROJECT_ID:PR000832 VERSION 1 CREATED_ON August 26, 2019, 1:53 pm #PROJECT PR:PROJECT_TITLE Luteal lipids regulate progesterone production and may modulate immune cell PR:PROJECT_TITLE function during the estrous cycle and pregnancy PR:PROJECT_SUMMARY Despite data indicating an important functional role for bioactive lipids in PR:PROJECT_SUMMARY luteal function, little is known about the patterns of abundance of these lipids PR:PROJECT_SUMMARY in corpus luteum (CL) during luteal development, maintenance, and rescue, in any PR:PROJECT_SUMMARY species. Therefore, the abundance of lipid mediators, including endocannabinoids PR:PROJECT_SUMMARY and oxylipins from cyclooxygenase (COX), lipoxygenase (LOX), and cytochrome P450 PR:PROJECT_SUMMARY (CYP)-dependent metabolism were profiled in the CL on days 4, 11, and 18 of the PR:PROJECT_SUMMARY estrous cycle and on day 18 of pregnancy. The objectives of this study were to PR:PROJECT_SUMMARY identify lipid mediators that regulate luteal function during these transitions, PR:PROJECT_SUMMARY to integrate the lipid profile with a previously published mRNA profile of CL PR:PROJECT_SUMMARY during maternal recognition of pregnancy, and to determine the effect of a PR:PROJECT_SUMMARY subset of lipids on in vitro progesterone production. PR:INSTITUTE University of California, Davis PR:DEPARTMENT Genome and Biomedical Sciences Facility PR:LABORATORY WCMC Metabolomics Core PR:LAST_NAME Fiehn PR:FIRST_NAME Oliver PR:ADDRESS 1315 Genome and Biomedical Sciences Facility, 451 Health Sciences Drive, Davis, PR:ADDRESS CA 95616 PR:EMAIL ofiehn@ucdavis.edu PR:PHONE (530) 754-8258 PR:FUNDING_SOURCE NIH U24DK097154 #STUDY ST:STUDY_TITLE Luteal lipids regulate progesterone production and may modulate immune cell ST:STUDY_TITLE function during the estrous cycle and pregnancy ST:STUDY_SUMMARY Despite data indicating an important functional role for bioactive lipids in ST:STUDY_SUMMARY luteal function, little is known about the patterns of abundance of these lipids ST:STUDY_SUMMARY in corpus luteum (CL) during luteal development, maintenance, and rescue, in any ST:STUDY_SUMMARY species. Therefore, the abundance of lipid mediators, including endocannabinoids ST:STUDY_SUMMARY and oxylipins from cyclooxygenase (COX), lipoxygenase (LOX), and cytochrome P450 ST:STUDY_SUMMARY (CYP)-dependent metabolism were profiled in the CL on days 4, 11, and 18 of the ST:STUDY_SUMMARY estrous cycle and on day 18 of pregnancy. The objectives of this study were to ST:STUDY_SUMMARY identify lipid mediators that regulate luteal function during these transitions, ST:STUDY_SUMMARY to integrate the lipid profile with a previously published mRNA profile of CL ST:STUDY_SUMMARY during maternal recognition of pregnancy, and to determine the effect of a ST:STUDY_SUMMARY subset of lipids on in vitro progesterone production. ST:INSTITUTE University of California, Davis ST:DEPARTMENT Genome and Biomedical Sciences Facility ST:LABORATORY WCMC Metabolomics Core ST:LAST_NAME Fiehn ST:FIRST_NAME Oliver ST:ADDRESS 1315 Genome and Biomedical Sciences Facility, 451 Health Sciences Drive, Davis, ST:ADDRESS CA 95616 ST:EMAIL ofiehn@ucdavis.edu ST:PHONE (530) 754-8258 #SUBJECT SU:SUBJECT_TYPE Mammal SU:SUBJECT_SPECIES Bos taurus SU:TAXONOMY_ID 9913 SU:GENDER Female #FACTORS #SUBJECT_SAMPLE_FACTORS: SUBJECT(optional)[tab]SAMPLE[tab]FACTORS(NAME:VALUE pairs separated by |)[tab]Additional sample data SUBJECT_SAMPLE_FACTORS - 575 Treatment:Regressing 4 hour SUBJECT_SAMPLE_FACTORS - 600 Treatment:Regressing 1 hour SUBJECT_SAMPLE_FACTORS - 604 Treatment:Regressing 1 hour SUBJECT_SAMPLE_FACTORS - 616 Treatment:Regressing 4 hour SUBJECT_SAMPLE_FACTORS - 857 Treatment:Regressing 4 hour SUBJECT_SAMPLE_FACTORS - 858 Treatment:Regressing 1 hour SUBJECT_SAMPLE_FACTORS - 862 Treatment:Regressing 4 hour SUBJECT_SAMPLE_FACTORS - 876 Treatment:Regressing 12 hour SUBJECT_SAMPLE_FACTORS - 905 Treatment:Regressing 12 hour SUBJECT_SAMPLE_FACTORS - 909 Treatment:Regressing 12 hour SUBJECT_SAMPLE_FACTORS - 912 Treatment:Regressing 12 hour SUBJECT_SAMPLE_FACTORS - 936 Treatment:Midcycle SUBJECT_SAMPLE_FACTORS - 956 Treatment:Midcycle SUBJECT_SAMPLE_FACTORS - 957 Treatment:Midcycle SUBJECT_SAMPLE_FACTORS - 971 Treatment:D18 cyclic SUBJECT_SAMPLE_FACTORS - 1005 Treatment:Early SUBJECT_SAMPLE_FACTORS - 1006 Treatment:Early SUBJECT_SAMPLE_FACTORS - 1007 Treatment:Early SUBJECT_SAMPLE_FACTORS - 1008 Treatment:D18 cyclic SUBJECT_SAMPLE_FACTORS - 1011 Treatment:D18 pregnant SUBJECT_SAMPLE_FACTORS - 1012 Treatment:D18 cyclic SUBJECT_SAMPLE_FACTORS - 1020 Treatment:D18 pregnant SUBJECT_SAMPLE_FACTORS - 1021 Treatment:D18 pregnant SUBJECT_SAMPLE_FACTORS - 1022 Treatment:D18 cyclic SUBJECT_SAMPLE_FACTORS - 1025 Treatment:D18 pregnant SUBJECT_SAMPLE_FACTORS - 1106 Treatment:Early SUBJECT_SAMPLE_FACTORS - 1129 Treatment:Midcycle SUBJECT_SAMPLE_FACTORS - 1351 Treatment:Regressing 8 hour SUBJECT_SAMPLE_FACTORS - 1352 Treatment:Regressing 8 hour SUBJECT_SAMPLE_FACTORS - 1353 Treatment:Regressing 8 hour SUBJECT_SAMPLE_FACTORS - 1378 Treatment:Regressing 24 hour SUBJECT_SAMPLE_FACTORS - 1379 Treatment:Regressing 24 hour SUBJECT_SAMPLE_FACTORS - 1380 Treatment:Regressing 24 hour SUBJECT_SAMPLE_FACTORS - 1381 Treatment:Regressing 24 hour SUBJECT_SAMPLE_FACTORS - 1342 Treatment:Regressing 8 hour #COLLECTION CO:COLLECTION_SUMMARY For cows assigned to the day 4 group, upon observation of estrus and a dominant CO:COLLECTION_SUMMARY follicle by ultrasound, cows were given an injection of GnRH (Factrel, 100 µg; CO:COLLECTION_SUMMARY Zoetis) in order to precisely time ovulation relative to time of collection for CO:COLLECTION_SUMMARY these early CL. Cows were slaughtered on day 4 following estrus. For samples CO:COLLECTION_SUMMARY collected later than day 4, precise synchrony of ovulation relative to CL CO:COLLECTION_SUMMARY collection was not necessary, so no GnRH was given, and CL were collected via CO:COLLECTION_SUMMARY colpotomy. For CL of pregnancy, cows were bred by artificial insemination and a CO:COLLECTION_SUMMARY uterine flush was performed immediately following CL collection and was examined CO:COLLECTION_SUMMARY for embryo fragments to confirm the presence of a viable pregnancy. For all CO:COLLECTION_SUMMARY samples, tissue was snap frozen in liquid nitrogen immediately following tissue CO:COLLECTION_SUMMARY collection and stored at -80 degrees Celsius thereafter. For in vitro CO:COLLECTION_SUMMARY experiments, three to five dairy cows were used in each group, CL were collected CO:COLLECTION_SUMMARY on day 10-12 of the estrous cycle, and each treatment was applied to cells from CO:COLLECTION_SUMMARY each cow CO:SAMPLE_TYPE Corpus Luteum #TREATMENT TR:TREATMENT_SUMMARY For cows assigned to the day 4 group, upon observation of estrus and a dominant TR:TREATMENT_SUMMARY follicle by ultrasound, cows were given an injection of GnRH (Factrel, 100 µg; TR:TREATMENT_SUMMARY Zoetis) in order to precisely time ovulation relative to time of collection for TR:TREATMENT_SUMMARY these early CL. Cows were slaughtered on day 4 following estrus. For samples TR:TREATMENT_SUMMARY collected later than day 4, precise synchrony of ovulation relative to CL TR:TREATMENT_SUMMARY collection was not necessary, so no GnRH was given, and CL were collected via TR:TREATMENT_SUMMARY colpotomy. For CL of pregnancy, cows were bred by artificial insemination and a TR:TREATMENT_SUMMARY uterine flush was performed immediately following CL collection and was examined TR:TREATMENT_SUMMARY for embryo fragments to confirm the presence of a viable pregnancy. For all TR:TREATMENT_SUMMARY samples, tissue was snap frozen in liquid nitrogen immediately following tissue TR:TREATMENT_SUMMARY collection and stored at -80 degrees Celsius thereafter. For in vitro TR:TREATMENT_SUMMARY experiments, three to five dairy cows were used in each group, CL were collected TR:TREATMENT_SUMMARY on day 10-12 of the estrous cycle, and each treatment was applied to cells from TR:TREATMENT_SUMMARY each cow #SAMPLEPREP SP:SAMPLEPREP_SUMMARY Oxylipins and endocannabinoids were isolated using a Waters Ostro™ Sample SP:SAMPLEPREP_SUMMARY Preparation Plate. Luteal samples were homogenized and 40 ± 8 mg were added to SP:SAMPLEPREP_SUMMARY 2 mL polypropylene tubes spiked with a 5 µL antioxidant solution (0.2 mg/ml SP:SAMPLEPREP_SUMMARY solution BHT/EDTA in 1:1 MeOH:water) and 10 μL 1000 nM analytical deuterated SP:SAMPLEPREP_SUMMARY surrogates as previously described (Agrawal et al., 2017; La Frano et al., SP:SAMPLEPREP_SUMMARY 2017). Samples were then mixed with 35 µL methanol, 550 µL isopropanol w/ 10 SP:SAMPLEPREP_SUMMARY mM ammonium formate, 1% formic acid and 100 µL water, and the tube was placed SP:SAMPLEPREP_SUMMARY in a Geno/Grinder 2010 (SPEX SamplePrep) for 30 sec and centrifuged at 10,000 x SP:SAMPLEPREP_SUMMARY g for 5 min at room temperature. Supernatants were transferred into the Ostro SP:SAMPLEPREP_SUMMARY plate wells and captured in glass inserts containing 10 μL of 20% glycerol in SP:SAMPLEPREP_SUMMARY methanol by applying 15 mmHg of vacuum for 10 min. The eluent was dried under SP:SAMPLEPREP_SUMMARY vacuum and reconstituted with 100 µL, 1:1 MeOH/ACN (v/v) containing 100 nM of SP:SAMPLEPREP_SUMMARY 1-cyclohexyl ureido, 3 dodecanoic acid and 1-phenyl ureido, 3-hexanoic acid urea SP:SAMPLEPREP_SUMMARY used as internal standards (gifts from Dr. B.D. Hammock, University of SP:SAMPLEPREP_SUMMARY California, Davis). The samples were then vortexed and filtered at 0.1µm SP:SAMPLEPREP_SUMMARY through PVDF membranes (Millipore) by centrifugation < 4500 x g (rcf) for 3 min SP:SAMPLEPREP_SUMMARY at 6 ºC. The filtrate was transferred to inserts in amber glass and stored at SP:SAMPLEPREP_SUMMARY -20 ºC for less than 48 hours before analysis by UPLC-MS/MS. Analytes in 5 μL SP:SAMPLEPREP_SUMMARY extract aliquot were separated on a 2.1 mm x 150 mm, 1.7 µm Acquity BEH column SP:SAMPLEPREP_SUMMARY (Waters) using published protocols for oxylipins and endocannabinoids (Agrawal SP:SAMPLEPREP_SUMMARY et al., 2017; Pedersen and Newman, 2018). Samples were held at 10ºC. Separated SP:SAMPLEPREP_SUMMARY residues were detected by negative mode electrospray ionization for oxylipins SP:SAMPLEPREP_SUMMARY and positive mode electrospray ionization for endocannabinoids using multiple SP:SAMPLEPREP_SUMMARY reaction monitoring on an API 6500 QTRAP (AB Sciex). Analytes were quantified SP:SAMPLEPREP_SUMMARY using internal standard methods and 5- to 7-point calibration curves (r2 ≥ SP:SAMPLEPREP_SUMMARY 0.997). Calibrants and internal standards were either synthesized [10,11-DHN, SP:SAMPLEPREP_SUMMARY 10,11-DHHep, 10(11)-EpHep] or purchased from Cayman Chemical, Avanti Polar SP:SAMPLEPREP_SUMMARY Lipids Inc., or Larodan Fine Lipids. Data was processed with AB Sciex MultiQuant SP:SAMPLEPREP_SUMMARY version 3.0.2. The internal standards were used to quantify recovery of SP:SAMPLEPREP_SUMMARY surrogate standards #CHROMATOGRAPHY CH:CHROMATOGRAPHY_TYPE Reversed phase CH:INSTRUMENT_NAME Shimadzu Nexera X2 CH:COLUMN_NAME Waters Acquity BEH C18 (150 x 2mm, 1.7um) CH:FLOW_RATE 0.5 mL/min CH:COLUMN_TEMPERATURE 60 #ANALYSIS AN:ANALYSIS_TYPE MS #MS MS:INSTRUMENT_NAME ABI Sciex 6500 QTrap MS:INSTRUMENT_TYPE Triple quadrupole MS:MS_TYPE ESI MS:ION_MODE NEGATIVE MS:MS_COMMENTS Multiquant #MS_METABOLITE_DATA MS_METABOLITE_DATA:UNITS nM MS_METABOLITE_DATA_START Samples 575 600 604 616 857 858 862 876 905 909 912 936 956 957 971 1005 1006 1007 1008 1011 1012 1020 1021 1022 1025 1106 1129 1351 1352 1353 1378 1379 1380 1381 1342 Factors Treatment:Regressing 4 hour Treatment:Regressing 1 hour Treatment:Regressing 1 hour Treatment:Regressing 4 hour Treatment:Regressing 4 hour Treatment:Regressing 1 hour Treatment:Regressing 4 hour Treatment:Regressing 12 hour Treatment:Regressing 12 hour Treatment:Regressing 12 hour Treatment:Regressing 12 hour Treatment:Midcycle Treatment:Midcycle Treatment:Midcycle Treatment:D18 cyclic Treatment:Early Treatment:Early Treatment:Early Treatment:D18 cyclic Treatment:D18 pregnant Treatment:D18 cyclic Treatment:D18 pregnant Treatment:D18 pregnant Treatment:D18 cyclic Treatment:D18 pregnant Treatment:Early Treatment:Midcycle Treatment:Regressing 8 hour Treatment:Regressing 8 hour Treatment:Regressing 8 hour Treatment:Regressing 24 hour Treatment:Regressing 24 hour Treatment:Regressing 24 hour Treatment:Regressing 24 hour Treatment:Regressing 8 hour 10-Nitrooleate 42.7 36.5 28.8 25.4 18.2 44.6 70.3 20.6 41.4 21.2 12.7 54.1 31.2 45 24.7 31.2 20.1 46.3 83.6 23 27.8 46.1 30.7 39.2 26.7 15.5 88.2 4.87 44.6 2.68 37.1 11.4 19.8 85.2 41 11(12)-EpETE 1.72 2.3 1.19 1.61 0.666 0.776 0.624 3.05 1.87 4.31 3.44 0.476 16.9 1.12 14.2 0.489 0.451 0.702 1.63 0.623 1.16 0.982 1.44 3.1 1.7 0.833 1.03 0.588 0.737 0.361 0.655 1.17 1.08 0.667 1.3 11(12)-EpETrE 16.9 17.9 15.7 17.1 3.04 5.54 12.8 20.3 5.98 23.3 14.5 3.04 47.8 1.83 119 1.27 2.89 1.72 12 2.11 4.66 8.01 9.8 22.5 9.85 2.23 5.75 8.15 12.1 1.93 9.85 13.2 2.28 8.95 5.98 11_12-DiHETrE 9.13 18 21.2 10.9 5.38 16.8 20 10.1 19.3 8.45 28.6 7.53 19 4.93 196 4.98 6.6 6.56 8.31 5.53 8.79 5.81 21.7 10.6 17.1 9.47 34.5 8.6 9.82 8.37 13.3 6.68 8.87 7.99 12 11-HETE 494 159 187 103 73.8 228 168 67 134 107 114 53.7 94.1 35.1 1280 14.6 28.8 40.5 49 45.2 70.2 48.9 145 32 51.5 34.4 109 23.8 30.7 27.2 32.3 21.3 43.6 19.7 50.8 12(13)-Ep-9-KODE 9.49 38.2 40.6 26.5 4.93 34.1 21.2 11.5 32.9 12.2 13.6 19.9 73.6 22.9 109 5.98 10.2 16.5 231 16.2 49 24.4 6.82 26.6 57.4 17.1 32.9 11.2 10.2 11.2 11.2 10.2 7.39 8.73 41.6 12(13)-EpODE 2.35 5.48 1.11 2.55 0.358 0.493 1.7 3.41 0.889 5.71 1.96 0.722 16.4 1.18 14.9 0.88 0.553 0.421 1.76 0.215 0.628 2.89 1.26 3.62 1.5 1.52 0.672 0.949 1.3 0.091 1.05 0.838 0.397 1.01 1.11 12(13)-EpOME 35.6 41.5 35.5 54.6 9.68 15.2 40.4 42.1 20.2 59.1 33.9 12.2 54.1 8.71 152 2.59 8.98 5.3 25.6 4.73 7.24 33.5 27.9 60.9 22.6 10.1 9.4 21.8 23.3 8.4 26.5 29.7 8.67 22.3 21.1 12_13-DiHODE 4.35 10.4 6.36 7.28 2.6 7.21 8.74 4.65 30.8 3.25 8.21 16.2 26.6 14.8 159 6.12 2.82 0.6 9.87 4.99 5.51 7.51 31.3 9.53 29.3 14.2 4.73 5.63 5.96 5.19 10.4 3.42 8.91 5.88 8.05 12_13-DiHOME 57.4 77.7 222 185 81.9 303 399 112 411 57.3 122 116 63.7 66.9 1230 35.3 28 18.7 48.1 112 64.1 72.5 401 114 177 143 258 110 86 111 305 102 208 148 106 12-HEPE 44.9 46.2 17.9 14.1 3.46 6.55 15.9 9.05 12.3 28.6 14.9 7.11 28.1 8.54 115 127 4.17 6.79 7.2 3.34 7.6 7.42 10.1 4.75 4.82 48 3.22 2.27 2.09 1.25 1.31 1.02 1.45 1.22 6.37 12-HETE 935 448 540 562 97.5 258 604 88.9 146 165 144 59.4 141 41.2 1680 995 45.5 259 145 42.8 98.9 97.4 181 65 79.2 267 134 55.8 53.6 26.4 36 34.2 33.8 32.3 94.4 13-HODE 2500 857 1610 875 562 1450 1040 625 997 674 869 381 350 288 4300 165 103 150 323 311 390 595 567 257 337 358 315 167 141 176 246 148 199 129 481 13-HOTE 99.7 107 44.5 25.4 13.3 41.6 26.2 25.9 95.8 83.4 60.1 73.8 49.8 81.3 332 55.5 17.6 20.7 13.2 21.5 57.1 29.2 19.9 12.3 10.2 144 18.9 10.9 10 13.7 13.9 6.45 15.6 6.17 38.7 13-KODE 25.5 15.9 48.1 22.9 12.3 76.5 34.9 25.7 116 32.1 38.6 50 21.5 19.1 194 8.99 10.6 29.1 49.9 51.3 35.9 38.2 10.3 35.8 20.5 45.1 27.2 17 12.9 21.2 17.2 13.9 11.8 13 107 14(15)-EpETrE 28.6 28.6 29 35.4 7.77 17 28.9 40.7 10.9 37.1 21.5 7.9 64.9 4.7 181 2.16 7.22 2.66 18.4 4.66 5.55 16.5 40.7 40.5 17 5 11.4 14.8 28.4 6.56 29 28.2 8.24 17.1 10.5 14_15-DiHETE 97.5 224 205 202 88.5 309 258 228 1280 97.9 171 418 349 339 2730 136 87 22 184 234 81.9 110 959 186 493 231 426 179 253 138 213 113 198 165 116 14_15-DiHETrE 178 203 723 663 215 1040 1210 311 908 56.4 135 218 59.9 94.9 2160 63.8 61.8 19.7 102 320 83.4 76.1 793 153 359 200 1070 397 365 273 886 325 495 372 116 15(16)-EpODE 3.67 7.36 3.08 3.78 1.55 2.45 2.63 7.32 6.85 9.63 5.16 4.81 14.9 8.67 21.6 1.32 1.3 1.73 4.13 0.911 3.82 5.18 2.04 7.7 3.34 7.14 1.6 3.25 3.15 1.49 3.21 1.91 1.49 2.42 4.44 15_16-DiHODE 15.6 27.4 17.8 13.3 6.83 21.2 13.9 17.5 39.3 16.9 43.5 39.9 117 36.9 481 7.67 3.6 9.55 101 16.1 43.2 19.5 33 48.5 161 25.7 11.8 10.4 14.8 10.7 11.4 7.9 7.83 6.82 29.4 15-deoxy PGJ2 0.39 0.655 0.342 0.479 0.425 0.873 0.784 0.226 0.426 0.242 0.522 0.546 2.51 0.277 2.66 0.209 0.801 1.37 3.42 0.424 0.407 0.291 0.831 0.435 1.91 0.361 8.23 0.918 1.64 0.508 0.183 0.269 0.312 0.198 0.705 15-HEPE 37.5 28.8 16.5 9.11 4.44 9.18 10.6 11 35.1 37 22.8 15.6 27.1 12.3 189 17.9 4.85 0.851 5.82 7.88 9.83 5.54 23.2 3.94 6.89 11.9 7.53 3.74 4.94 3.66 5.94 3.78 6.2 4.33 7.28 15-HETE 755 468 652 207 178 1000 320 220 609 298 395 277 240 115 2870 58.4 68.9 154 162 249 294 145 395 116 124 154 319 89.2 71.7 122 140 80.6 190 70.7 304 15-KETE 10.3 26.7 20.7 7.38 5.15 48.6 14.5 16.7 32.5 14.8 14.4 28.9 29.7 5.62 95.4 4.93 6.85 18.1 25.3 22.6 25.1 8.94 8.49 24.2 7.78 10.5 17.8 13.7 11.8 8.86 8.48 12.5 7.85 6.4 50.7 17(18)-EpETE 2.84 6.72 1.93 2.57 1.14 0.904 2.87 5.44 4 6.47 3.09 2.8 17.3 4.42 16.1 1.1 0.927 0.45 2.36 0.547 1.84 3.38 2.82 3.97 2.44 1.23 0.874 1.67 2.27 0.776 2.51 1.55 1.2 2.14 3.43 17_18-DiHETE 82.2 166 91 81.3 34.6 152 72.8 137 360 178 218 244 761 272 1790 50.7 34.3 37.5 289 118 218 87.6 235 167 421 112 117 75.5 104 97.1 62.4 42.1 81.3 44.2 182 17-HDoHE 55.9 55 64 41.3 12.9 45.6 37.6 28.7 110 26.3 58.3 72.2 42.6 38.8 692 37 20.8 22.5 7.17 35 32.6 20 155 14.4 28.4 44.1 269 33.7 60.5 41.7 124 42.2 101 52.1 40.5 19(20)-EpDPE 2.38 5.77 1.09 0.831 0.35 0.291 0.897 2.45 3.28 6.07 3.12 1.3 9.16 3.3 20.6 1.22 0.672 0.426 0.832 0.229 1.73 0.62 1.16 4.01 1.98 1.04 2.36 2.59 2.52 2.06 2.12 2.12 1.25 2.4 2.66 19_20-DiHDoPA 5.45 6.52 5.64 3.4 1.43 2.08 2.88 4.13 7.11 6.86 19.4 7.72 18.5 4.91 75.5 1.44 1.5 0.782 2.23 3.5 5.54 1.2 3.75 5.85 8.12 1.33 8.8 2.01 3.17 2.91 3.55 1.71 3.5 3.88 7.51 20-HETE 8.92 18.1 26.7 13.4 7.63 30.6 14.7 10.9 38.3 34.4 37.5 30.7 18.4 23.5 71 4.45 4.72 13.2 2.41 36.5 68.4 4.95 5.16 8.02 9.23 13.5 33.8 10.2 12.2 25.8 19.3 11.4 19.1 13.7 63.1 4-HDoHE 3.71 2.24 1.45 1.23 1.14 1.28 0.85 1.42 4.1 0.907 3.53 2.3 1.9 1.66 15.8 1.05 0.993 2.69 1.06 3.42 2.53 2.11 1.92 1.6 1.61 1.13 3.22 0.451 0.446 1.99 0.91 0.501 0.727 0.554 1.74 5_15-DiHETE 41.4 4.39 12.5 4.68 5.53 9.54 6.3 3.96 3.38 4.39 5.71 1.72 18.3 2.43 161 0.297 0.379 0.691 2.16 0.67 1.37 7.49 9.38 1.18 4.27 0.731 1.02 0.773 0.986 0.749 0.311 0.172 0.678 0.5 0.28 5_6-DiHETrE 1.47 2.22 2.98 0.916 0.933 3.61 3.09 2.26 3.61 5.63 5.46 0.96 11.9 1.13 107 0.808 0.6 0.579 7.88 0.969 1.23 1.69 5.76 3.21 11.5 2.14 3.4 1.14 1.44 0.611 1.58 1.08 0.806 1.61 1.27 5-HEPE 8.46 9.3 6.06 2.86 1.79 5.42 3.23 6.63 9.97 17 15.8 8.78 18.6 4.7 73.9 4.84 2.08 1.83 10.2 4.03 3.77 2.64 7.08 3.47 2.93 7.13 2.43 2.68 1.41 1.75 1.3 1.58 1.99 1.79 5.4 5-HETE 144 75.8 119 48.3 46.1 154 65.2 54.7 97.6 119 129 56 89.2 20.7 1360 20.6 15.5 36.7 91.5 55.3 50 29.8 96.4 50 37.2 34.9 52.8 29 28.9 26 21.4 23.3 33 19.2 81.5 5-KETE 7.75 17.9 27.6 8.34 5.4 53.2 15.6 16.3 31.8 12.3 12.4 26.1 24.7 7.1 88 5.16 6.11 13.3 24.9 32.6 24.5 8.55 6.85 19.7 8.78 12.4 24.5 12.6 10.1 10.6 9.97 10.1 7.88 5.97 35 6-keto PGF1a 14.4 55.4 6.54 56.9 6.81 5.79 64.6 1.37 2.37 6.56 19.3 15.8 30.4 1.74 83.7 16.3 50.8 68 217 22 8.66 2.06 62.5 8.52 61.9 11.5 193 22.6 74 20.4 7.13 6.48 6.59 8.89 10.2 6-trans-LTB4 19.4 8.62 9.28 2.65 2.5 5.63 4.71 1.81 3.45 2.68 4.16 1.14 9.51 2.5 63.8 1.31 1.55 1.13 5.42 1.28 2.69 6.58 5.69 2.2 4.42 1.42 2.49 0.914 0.787 0.982 0.394 0.262 0.735 0.66 1.39 8(9)-EpETrE 19.7 22.4 15.8 21.2 3.81 5.34 14.2 24.9 6.22 26.9 13.4 3.76 59 1.98 132 1.57 4.04 1.39 12.6 1.62 2.89 9.9 11 28 11 1.61 3.89 9.83 13.7 1.58 11.9 15.5 1.85 10.6 4.05 8_15-DiHETE 121 12.3 25.1 17.5 14.8 18.4 15.3 5.28 8.66 5.48 12.9 1.68 40.9 5.16 198 3.26 1.02 1.56 12.2 1.73 5.19 21.3 22 2.78 22.3 1.45 1.9 1.41 1.2 0.756 0.384 0.236 0.601 0.398 0.877 8_9-DiHETrE 2.63 6.17 5.13 3.45 1.87 7.3 3.88 2.19 6.47 8.33 10.8 2.02 12 1.66 110 1.28 1.91 2.05 4.95 1.49 3.31 1.94 7.45 3.26 5.54 2.41 4.21 1.86 2.31 1.86 2.07 0.975 1.67 1.76 2.02 8-HETE 335 91.1 93.4 50.8 46.8 109 83.9 38.5 60.8 68.6 71.7 25.8 63 18.8 834 11.7 12.2 15.2 24.6 17.9 41.1 26.9 81.4 22.1 23.9 20.7 38.9 10.9 8.25 11.2 10.1 7.67 17.7 7.67 28 9(10)-EpODE 6.69 10.9 3.39 4.55 1.98 1.39 2.8 7.31 5.45 17.7 7.86 5.99 33.2 5.6 49 1.4 2.4 0.954 5.99 1.59 2.78 7.16 1.95 10.1 4.47 6.14 1.79 2.78 2.76 1.5 2.37 2.6 0.944 2.47 5.34 9(10)-EpOME 38.5 38 41.4 59.1 8.88 11.5 42.3 52 17 72.4 40.5 10.4 59.5 7.34 231 3.3 8.33 4.55 27.3 5.76 8.18 30.9 15.7 69.6 30.6 9.3 7.71 18.5 17.9 5.59 25.4 29.1 5.59 21.7 17.1 9_10-DiHODE 1.02 3.11 1.55 1.47 0.437 1.06 0.987 1.01 3.07 1.45 2.46 2.83 12.4 3.09 20.2 1.49 0.714 0.712 8.28 0.667 1.28 2.42 5.16 2.47 6.77 2.22 1.69 0.803 1.52 0.615 1.54 0.799 1.12 0.952 1.62 9_10-DiHOME 11.4 18.5 29.6 23.8 9.2 34.4 30.3 17.2 34.6 21.2 29.1 20.1 15.9 16.1 149 7.94 7.05 13.1 12 14.2 22.6 14.8 26.3 23.5 16.3 22.8 34.9 10.6 11.7 12.4 27.5 11.5 17.3 15.4 22.3 9_10-e-DiHO 17.8 16.5 14.2 13.9 6.9 23.8 18 10.3 25.7 2.61 26.1 15.3 27.9 22.3 81 8.73 19.9 54.8 46.4 9.27 15.3 13.3 35 21.9 40.3 12.9 50.2 9.94 12.1 20 76.2 22.9 19.4 15.8 27.8 9_10-EpO 18.3 30.9 12.8 26.2 5.86 9.5 19.1 11.2 18.3 22.7 14.3 14.6 78.4 17.5 178 2.95 14.3 14.4 75.2 8.62 30.3 27.9 20.7 33.8 106 12.6 10.1 8.71 14.9 13.6 6.85 9.06 7.35 14.9 15.6 9_12_13-TriHOME 188 75 151 104 41.4 121 70.7 58.5 92.2 74.2 74.1 36.7 73.1 36.2 381 13.4 17.7 19.4 114 26.4 31.7 42.8 88.5 33.4 45.2 24 50.4 16.7 17.1 14.6 56.4 27.3 12.8 15.6 45.7 9-HEPE 34.5 9.39 4.05 4.41 3.8 4.33 4.78 4.28 8.61 13.5 11.3 3.98 19.4 6.23 76 1.61 1.65 0.713 3.09 1.87 8.65 2.89 7.03 2.61 2.7 4.84 1.86 0.428 1.44 0.703 0.417 0.363 0.988 0.642 5.39 9-HETE 448 90.8 96.5 60.8 57.2 130 105 38.6 78.9 124 100 31.5 69.9 17.8 1160 4.83 12 18.6 21.1 22.9 39.2 25.5 115 17.7 25.6 12.1 31 7.8 5.92 8.68 5.84 6.46 13.5 6.11 18.8 9-HODE 869 341 417 378 245 570 433 195 401 218 316 175 143 124 1220 35.8 63 81.8 130 144 126 212 204 99 124 134 150 78.1 67.5 78.8 80.5 57 87.8 55.1 204 9-HOTE 2.01 8.12 1.94 2.09 0.518 1.27 1.2 4.45 2.03 9.2 3.99 2.2 19.7 2.55 19.2 0.382 1.11 0.425 3.95 0.715 1.39 3.71 0.836 5.61 1.96 2.29 0.227 1.09 1.47 0.377 0.977 1.38 0.445 1.23 2.36 9-KODE 72.4 43.3 72.9 60.1 19.2 149 62.7 40.6 157 42.8 45.9 86 37.6 30.2 234 16.4 23.4 34.7 91.4 69.6 56.7 54.4 18.7 57.1 37.9 80.1 47.6 29 18.9 33.3 24.4 20.6 16.7 16.2 164 AA 2 4.24 3.59 2.33 1.53 5.17 3.48 2.87 4.38 3.48 5.15 2.43 2.03 1.77 7.93 1.03 1.23 1.37 1.88 2.74 2.43 1.75 2.38 2.87 2.27 2.21 4.3 1.72 1.59 1.83 2.07 1.46 1.78 1.77 2.33 ALA 1.69 6.5 2.28 1.75 0.802 1.87 1.55 2.79 5.36 6.11 6.17 3.64 3.27 4.14 11 1.71 1.28 0.448 1.55 1.79 2.96 2.31 1.24 3.27 1.97 4.71 0.831 0.824 0.976 0.969 1.29 0.58 1.16 1.13 2.44 DHA 2.35 3.19 2.24 1.45 0.449 0.682 1.15 2.47 2.75 3.41 6.59 2.05 5.01 1.76 21.4 1.32 1.38 0.82 0.486 0.705 1.7 1.62 2.69 2.64 1.62 2.17 5.25 0.838 2.07 0.827 1.79 1.18 2.08 2 2.94 EPA 1.38 5.95 2.57 1.92 1.03 1.93 1.49 3.64 4.9 7.18 8.05 3.05 4.49 3.07 12.6 1.2 1.01 0.278 1.44 1.99 3.09 1.32 2.14 3.03 1.9 3.66 1.66 0.651 0.821 0.733 1.26 0.641 0.908 0.877 1.61 LA 2.04 3.68 3.77 2.9 1.67 4.34 4.14 2.77 5.66 3.48 5.39 2.52 1.3 2.2 5.79 1.22 1.16 1.26 1.87 3.04 2.23 1.95 1.83 2.92 2.5 3.41 3.36 1.64 1.26 2.16 2.13 1.45 1.66 1.74 2.85 Lipoxin A4 3.25 0.615 2.23 1.09 1.73 3.67 3.35 3.18 2.49 4.31 5.66 0.797 2.72 0.554 25.5 1.27 0.564 2.15 2.02 0.883 0.267 0.83 4.39 3.09 1.28 0.885 0.69 1.67 1.71 1.29 1.9 0.944 2.46 1.39 0.971 PGD2 30 47.4 66.8 99.7 80.6 61.2 93.4 14.8 19.9 26.9 57.7 44.2 82.4 97.7 161 34.3 70.2 97.2 127 78 1.51 27.9 42.3 55 57 52 303 142 108 47.2 31.9 35 20.9 24.5 43.4 PGE1 2.19 9.11 2.21 7.86 7.75 0.626 11.7 0.661 0.789 2.22 4.84 2.32 11.2 1.53 4.88 0.361 11.1 7.43 4.72 2.99 0.714 0.159 3.22 1.58 5.15 0.899 5.71 2.14 5.89 3.77 0.784 1.29 1.11 0.814 1.05 PGE2 9.52 87.7 7.56 88.3 40.3 6.52 149 5.29 4.76 10.9 29.6 10.9 61 3.05 44 4.43 166 45.1 62.9 16.5 1.58 0.432 37.7 15 41.2 5.35 143 28.6 85.1 32.9 7.79 14.3 12.6 8.85 8.81 PGF2a 7.13 65.3 10.6 51 34.1 10.5 85.2 3.09 2.1 8.22 28.1 6.9 46.3 1.42 54.8 2.04 12.8 23.5 30.9 8.73 2.75 0.732 15.8 7.76 20.6 1.64 57.7 14.4 56.9 21.2 3.96 8.14 7.03 5.53 6.3 MS_METABOLITE_DATA_END #METABOLITES METABOLITES_START metabolite_name Report Order LOD LOQ Ionisation mede Observed InChIKey PubChem ID Chemical class Enzyme Parent FA Units quantitated m/z Q3 Retention times 10-Nitrooleate 93 0.895 2.98 Negative No WRADPCFZZWXOTI-UHFFFAOYSA-N 53394576 Nitro-FA NOS OA nM 326.2 279.5 11.16086096 11(12)-EpETE 81 1.03 3.43 Negative No QHOKDYBJJBDJGY-BVILWSOJSA-N 16061087 Epox CYP EPA nM 317.202 167.2 9.007136568 11(12)-EpETrE 77 0.243 0.811 Negative Yes DXOYQVHGIODESM-IQCOFVSKSA-N 53480479 Epox CYP AA nM 319.203 167.1 10.11252215 11_12-DiHETrE 39 0.0991 0.532 Negative Yes LRPPQRCHCPFBPE-KROJNAHFSA-N 5283146 vic-Diol sEH AA nM 337.3 167.1 6.994004679 11-HETE 52 0.256 1.19 Negative Yes GCZRCCHPLVMMJE-RSPKXIRXSA-N 5312981 R-OH LOX AA nM 319.201 167.1 8.938483441 12(13)-Ep-9-KODE 65 1.29 4.29 Negative No RCMABBHQYMBYKV-BUHFOSPRSA-N 5283007 R=0 ADH LA nM 309.2 291.2 7.15756084 12(13)-EpODE 74 0.202 0.674 Negative Yes BKKGUKSHPCTUGE-OOHFSOINSA-N 16061061 Epox CYP aLA nM 293.2 183.2 8.752930865 12(13)-EpOME 71 0.48 1.44 Negative Yes CCPPLLJZDQAOHD-FLIBITNWSA-N 5356421 Epox CYP LA nM 295.202 195.2 9.661290014 12_13-DiHODE 36 0.296 0.986 Negative Yes RGRKFKRAFZJQMS-OOHFSOINSA-N 16061067 vic-Diol sEH aLA nM 311.2 183.2 5.095371563 12_13-DiHOME 33 0.175 1.01 Negative Yes CQSLTKIXAJTQGA-FLIBITNWSA-N 10236635 vic-Diol sEH LA nM 313.3 183.2 5.979625048 12-HEPE 57 0.238 1.48 Negative Yes MCRJLMXYVFDXLS-QGQBRVLBSA-N 10041593 R-OH LOX EPA nM 317.2 179.1 7.931722367 12-HETE 51 0.202 0.819 Negative Yes ZNHVWPKMFKADKW-FYMOKONMSA-N 5312983 R-OH LOX AA nM 319.2 179.1 9.102943013 13-HODE 45 1.87 5.62 Negative Yes HNICUWMFWZBIFP-IRQZEAMPSA-N 6443013 R-OH LOX LA nM 295.201 195.2 8.322103244 13-HOTE 47 0.383 1.92 Negative Yes KLLGGGQNRTVBSU-JDTPQGGVSA-N 10469728 R-OH LOX aLA nM 293.2 195.2 7.301577503 13-KODE 63 1.15 6.03 Negative Yes JHXAZBBVQSRKJR-BSZOFBHHSA-N 6446027 R=0 ADH LA nM 293.2 179.1 8.616131233 14(15)-EpETrE 76 0.287 0.903 Negative Yes WLMZMBKVRPUYIG-LTCHCNGXSA-N 11954058 Epox CYP AA nM 319.202 219.2 9.753586248 14_15-DiHETE 42 1.67 5.56 Negative Yes BLWCDFIELVFRJY-QXBXTPPVSA-N 16061119 vic-Diol sEH EPA nM 335.3 207.2 5.659792118 14_15-DiHETrE 38 0.074 0.816 Negative Yes SYAWGTIVOGUZMM-ILYOTBPNSA-N 5283147 vic-Diol sEH AA nM 337.3 207.2 6.538077643 15(16)-EpODE 73 0.789 2.37 Negative Yes HKSDVVJONLXYKL-OHPMOLHNSA-N 16061062 Epox CYP aLA nM 293.201 275.2 8.596848125 15_16-DiHODE 35 0.493 1.48 Negative Yes LKLLJYJTYPVCID-OHPMOLHNSA-N 16061068 vic-Diol sEH aLA nM 311.2 235.2 5.037245131 15-deoxy PGJ2 7 0.085 0.283 Negative No VHRUMKCAEVRUBK-GODQJPCRSA-N 5311211 PGs COX2 AA nM 315.2 271.2 7.458262862 15-HEPE 56 0.303 0.909 Negative Yes UDXLGBLAJBYLSZ-XBCQTNLFSA-N 53480357 R-OH LOX EPA nM 317.2 219.2 7.656163137 15-HETE 50 0.296 0.989 Negative Yes JSFATNQSLKRBCI-VAEKSGALSA-N 5280724 R-OH LOX AA nM 319.201 219.2 8.621058577 15-KETE 66 1.14 3.81 Negative No YGJTUEISKATQSM-USWFWKISSA-N 5280701 R=0 ADH AA nM 317.2 273.2 8.854762609 17(18)-EpETE 79 0.134 0.445 Negative No GPQVVJQEBXAKBJ-JPURVOHMSA-N 16061089 R-OH LOX EPA nM 317.2 259.2 8.552215894 17_18-DiHETE 43 1.71 5.13 Negative Yes XYDVGNAQQFWZEF-JPURVOHMSA-N 16061120 vic-Diol sEH EPA nM 335.3 247.2 5.375933313 17-HDoHE 60 2.05 6.85 Negative Yes SWTYBBUBEPPYCX-VIIQGJSXSA-N 6439179 R-OH LOX DHA nM 343.301 281.2 8.730402221 19(20)-EpDPE 82 0.854 2.85 Negative No OSXOPUBJJDUAOJ-MBYQGORISA-N 11631565 Epox CYP DHA nM 343.303 281.2 9.595908173 19_20-DiHDoPA 44 0.269 1 Negative Yes FFXKPSNQCPNORO-MBYQGORISA-N 16061148 vic-Diol sEH DHA nM 361.3 273.2 6.550541632 20-HETE 49 2.04 6.79 Negative Yes NNDIXBJHNLFJJP-DTLRTWKJSA-N 5283157 R-OH CYP AA nM 319.2 275.2 7.687978319 4-HDoHE 62 0.457 1.37 Negative Yes IFRKCNPQVIJFAQ-JGDWKEERSA-N 53394255 R-OH LOX DHA nM 343.304 281.2 9.842290968 5_15-DiHETE 22 0.557 1.67 Negative Yes UXGXCGPWGSUMNI-BVHTXILBSA-N 5283158 Diol LOX AA nM 335.3 173.1 5.433374486 5_6-DiHETrE 41 0.324 0.644 Negative Yes GFNYAPAJUNPMGH-QNEBEIHSSA-N 5283142 vic-Diol sEH AA nM 337.3 145.1 8.01321217 5-HEPE 59 1.12 3.36 Negative Yes FTAGQROYQYQRHF-FCWZHQICSA-N 6439678 R-OH LOX EPA nM 317.2 115.1 8.381515221 5-HETE 55 0.383 1.28 Negative Yes KGIJOOYOSFUGPC-JGKLHWIESA-N 5280733 R-OH LOX AA nM 319.2 115.1 9.595958437 5-KETE 67 5.36 17.9 Negative No MEASLHGILYBXFO-XTDASVJISA-N 5283159 R=0 ADH AA nM 317.2 203.2 8.867206051 6-keto PGF1a 2 0.34 1.13 Negative No KFGOFTHODYBSGM-ZUNNJUQCSA-N 5280888 PGs COX1 AA nM 369.3 163.1 2.143426161 6-trans-LTB4 18 0.283 0.942 Negative No VNYSSYRCGWBHLG-UKNWISKWSA-N 5283128 Diol LOX AA nM 335.301 195.2 5.532185664 8(9)-EpETrE 78 15 49.9 Negative No DBWQSCSXHFNTMO-TYAUOURKSA-N 5283203 Epox CYP AA nM 319.202 155.1 10.25109749 8_15-DiHETE 21 0.343 1.14 Negative No NNPWRKSGORGTIM-RCDCWWQHSA-N 53480358 Diol LOX AA nM 335.3 235.2 5.145709479 8_9-DiHETrE 40 0.472 1.57 Negative Yes DCJBINATHQHPKO-TYAUOURKSA-N 5283144 vic-Diol sEH AA nM 337.3 127.1 7.413812268 8-HETE 54 1.01 3.09 Negative Yes NLUNAYAEIJYXRB-VYOQERLCSA-N 5283154 R-OH LOX AA nM 319.201 155.1 9.192668375 9(10)-EpODE 75 0.336 2.1 Negative Yes JTEGNNHWOIJBJZ-ZJSQCTGTSA-N 16061060 Epox CYP aLA nM 293.201 275.2 8.596848125 9(10)-EpOME 72 0.211 0.632 Negative Yes FBUKMFOXMZRGRB-YFHOEESVSA-N 6246154 Epox CYP LA nM 295.202 171.1 9.823069438 9_10-DiHODE 37 0.25 1.52 Negative Yes QRHSEDZBZMZPOA-ZJSQCTGTSA-N 16061066 vic-Diol sEH aLA nM 311.2 201.2 5.12728795 9_10-DiHOME 34 0.0802 0.977 Negative Yes XEBKSQSGNGRGDW-YFHOEESVSA-N 9966640 vic-Diol sEH LA nM 313.3 201.2 6.318673114 9_10-e-DiHO 32 1.82 6.06 Negative Yes VACHUYIREGFMSP-SJORKVTESA-N 441460 vic-Diol sEH OA nM 315.2 297.2 7.132185199 9_10-EpO 70 4.1 13.7 Negative Yes IMYZYCNQZDBZBQ-UHFFFAOYSA-N 15868 Epox CYP OA nM 297.3 279.2 10.85346028 9_12_13-TriHOME 23 0.267 1.31 Negative Yes MDIUMSLCYIJBQC-MVFSOIOZSA-N 9858729 Triol LOX LA nM 329.2 211.2 2.927883672 9-HEPE 58 1.04 3.45 Negative Yes OXOPDAZWPWFJEW-FPRWAWDYSA-N 5283187 R-OH LOX EPA nM 317.201 167.2 8.084324688 9-HETE 53 0.267 0.891 Negative Yes KATOYYZUTNAWSA-DLJQHUEDSA-N 5312978 R-OH LOX AA nM 319.202 167.1 9.340233127 9-HODE 46 1.02 3.07 Negative Yes NPDSHTNEKLQQIJ-SIGMCMEVSA-N 5282945 R-OH LOX LA nM 295.201 171.1 8.459276674 9-HOTE 48 0.0927 0.983 Negative Yes YUPHIKSLGBATJK-OBKPXJAFSA-N 53480359 R-OH LOX aLA nM 293.2 171.1 7.196218581 9-KODE 64 1.79 5.95 Negative Yes LUZSWWYKKLTDHU-ZJHFMPGASA-N 9839084 R=0 ADH LA nM 293.2 185.2 8.938323416 AA 88 Negative Yes YZXBAPSDXZZRGB-DOFZRALJSA-N 444899 PUFA D5D AA Rel Abs 303.4 259.2 11.88464188 ALA 87 Negative Yes DTOSIQBPPRVQHS-PDBXOOCHSA-N 5280934 PUFA Diet aLA Rel Abs 277.4 259.2 11.28471376 DHA 90 Negative Yes MBMBGCFOFBJSGT-KUBAVDMBSA-N 445580 PUFA D6D DHA Rel Abs 327.2 283.2 11.67053992 EPA 89 Negative Yes JAZBEHYOTPTENJ-JLNKQSITSA-N 446284 PUFA D6D EPA Rel Abs 301.4 257.2 11.20821464 LA 86 Negative Yes OYHQOLUKZRVURQ-HZJYTTRNSA-N 5280450 PUFA Diet LA Rel Abs 279.4 261.2 12.02070333 Lipoxin A4 26 0.596 1.99 Negative No IXAQOQZEOGMIQS-SSQFXEBMSA-N 5280914 Triol LOX AA nM 351.3 217.2 3.724527834 PGD2 6 0.393 1.31 Negative Yes BHMBVRSPMRCCGG-OUTUXVNYSA-N 448457 PGs COX2 AA nM 351.303 271.2 3.230825903 PGE1 3 0.899 3 Negative No GMVPRGQOIOIIMI-DWKJAMRDSA-N 5280723 PGs COX2 DGLA nM 353.3 317.2 3.181344629 PGE2 4 0.125 0.415 Negative Yes XEYBRNLFEZDVAW-ARSRFYASSA-N 5280360 PGs COX2 AA nM 351.302 271.2 3.042327283 PGF2a 8 0.473 1.58 Negative Yes PXGPLTODNUVGFL-UAAPODJFSA-N 5283078 PGs COX2 AA nM 353.3 193.2 2.980062116 METABOLITES_END #END