#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