#METABOLOMICS WORKBENCH gauravsarode143_20230718_132137 DATATRACK_ID:4172 STUDY_ID:ST002800 ANALYSIS_ID:AN004556 PROJECT_ID:PR001747
VERSION             	1
CREATED_ON             	July 28, 2023, 1:48 pm
#PROJECT
PR:PROJECT_TITLE                 	Hepatic oxylipin profiles in mouse models of Wilson disease: new insights into
PR:PROJECT_TITLE                 	early hepatic manifestations.
PR:PROJECT_SUMMARY               	Hepatic inflammation is commonly identified in Wilson disease (WD), a genetic
PR:PROJECT_SUMMARY               	disease of hepatic and brain copper accumulation. Copper accumulation is
PR:PROJECT_SUMMARY               	associated with increased reactive oxygen species and activation of the
PR:PROJECT_SUMMARY               	non-enzymatic oxidation of membrane-bound polyunsaturated fatty acids (PUFA),
PR:PROJECT_SUMMARY               	with impairment of cellular structures and function. Products of PUFA oxidation
PR:PROJECT_SUMMARY               	are collectively known as oxylipins (OXL), which can also be produced via
PR:PROJECT_SUMMARY               	enzymatic pathways including lipoxygenases (LOXs), cyclooxygenases (COXs), and
PR:PROJECT_SUMMARY               	cytochrome P450 monooxygenases (CYPs). These bioactive lipids modulate hepatic
PR:PROJECT_SUMMARY               	inflammation. We aimed to examine hepatic OXLs profile at early stages of WD in
PR:PROJECT_SUMMARY               	mouse model of Wilson disease, the toxic milk from The Jackson Laboratory (tx-j)
PR:PROJECT_SUMMARY               	compared to mice with normal copper metabolism (C3H). Targeted lipidomic
PR:PROJECT_SUMMARY               	profiling of OXLs was performed by ultra-high-performance liquid
PR:PROJECT_SUMMARY               	chromatography-electrospray ionization-tandem mass spectrometry (UPLC-ESI-MS/MS)
PR:PROJECT_SUMMARY               	in livers from 16 weeks old male and female mice. Hepatic OXL profiles were
PR:PROJECT_SUMMARY               	altered, with higher levels of PUFA alcohols, diols, and ketones. Markers of
PR:PROJECT_SUMMARY               	oxidative stress, 9-HETE and 9-HEPE were increased in tx-j mice. Hepatic
PR:PROJECT_SUMMARY               	prostaglandin and thromboxane levels in the COX pathway were increased in tx-j
PR:PROJECT_SUMMARY               	mice. tx-j showed altered PUFA-epoxides, suggesting altered CYP(s) activities.
PR:PROJECT_SUMMARY               	Our findings suggest that both non-enzymatic ROS-dependent and enzymatic PUFAs
PR:PROJECT_SUMMARY               	oxidation via COX and LOX pathways are associated with early stages liver
PR:PROJECT_SUMMARY               	disease in WD. It also indicates altered CYPs activities in animal model of WD.
PR:PROJECT_SUMMARY               	These novel pathways could be the target for future therapies.
PR:INSTITUTE                     	University of California, Davis
PR:DEPARTMENT                    	Internal Medicine
PR:LABORATORY                    	Medici's Lab
PR:LAST_NAME                     	Sarode
PR:FIRST_NAME                    	Gaurav
PR:ADDRESS                       	Genome & Biomedical Sciences Facility, 451 E. Health Sciences Dr., Davis, CA,
PR:ADDRESS                       	95616, USA
PR:EMAIL                         	gsarode@ucdavis.edu
PR:PHONE                         	530752-6715
#STUDY
ST:STUDY_TITLE                   	Hepatic oxylipin profiles in mouse models of Wilson disease: new insights into
ST:STUDY_TITLE                   	early hepatic manifestations.
ST:STUDY_SUMMARY                 	Hepatic inflammation is commonly identified in Wilson disease (WD), a genetic
ST:STUDY_SUMMARY                 	disease of hepatic and brain copper accumulation. Copper accumulation is
ST:STUDY_SUMMARY                 	associated with increased reactive oxygen species and activation of the
ST:STUDY_SUMMARY                 	non-enzymatic oxidation of membrane-bound polyunsaturated fatty acids (PUFA),
ST:STUDY_SUMMARY                 	with impairment of cellular structures and function. Products of PUFA oxidation
ST:STUDY_SUMMARY                 	are collectively known as oxylipins (OXL), which can also be produced via
ST:STUDY_SUMMARY                 	enzymatic pathways including lipoxygenases (LOXs), cyclooxygenases (COXs), and
ST:STUDY_SUMMARY                 	cytochrome P450 monooxygenases (CYPs). These bioactive lipids modulate hepatic
ST:STUDY_SUMMARY                 	inflammation. We aimed to examine hepatic OXLs profile at early stages of WD in
ST:STUDY_SUMMARY                 	mouse model of Wilson disease, the toxic milk from The Jackson Laboratory (tx-j)
ST:STUDY_SUMMARY                 	compared to mice with normal copper metabolism (C3H). Targeted lipidomic
ST:STUDY_SUMMARY                 	profiling of OXLs was performed by ultra-high-performance liquid
ST:STUDY_SUMMARY                 	chromatography-electrospray ionization-tandem mass spectrometry (UPLC-ESI-MS/MS)
ST:STUDY_SUMMARY                 	in livers from 16 weeks old male and female mice. Hepatic OXL profiles were
ST:STUDY_SUMMARY                 	altered, with higher levels of PUFA alcohols, diols, and ketones. Markers of
ST:STUDY_SUMMARY                 	oxidative stress, 9-HETE and 9-HEPE were increased in tx-j mice. Hepatic
ST:STUDY_SUMMARY                 	prostaglandin and thromboxane levels in the COX pathway were increased in tx-j
ST:STUDY_SUMMARY                 	mice. tx-j showed altered PUFA-epoxides, suggesting altered CYP(s) activities.
ST:STUDY_SUMMARY                 	Our findings suggest that both non-enzymatic ROS-dependent and enzymatic PUFAs
ST:STUDY_SUMMARY                 	oxidation via COX and LOX pathways are associated with early stages liver
ST:STUDY_SUMMARY                 	disease in WD. It also indicates altered CYPs activities in animal model of WD.
ST:STUDY_SUMMARY                 	These novel pathways could be the target for future therapies.
ST:INSTITUTE                     	University of California, Davis
ST:LAST_NAME                     	Sarode
ST:FIRST_NAME                    	Gaurav
ST:ADDRESS                       	Genome & Biomedical Sciences Facility, 451 E. Health Sciences Dr., Davis, CA,
ST:ADDRESS                       	95616, USA
ST:EMAIL                         	gsarode@ucdavis.edu
ST:PHONE                         	530752-6715
#SUBJECT
SU:SUBJECT_TYPE                  	Mammal
SU:SUBJECT_SPECIES               	Mus musculus
SU:TAXONOMY_ID                   	10090
#FACTORS
#SUBJECT_SAMPLE_FACTORS:         	SUBJECT(optional)[tab]SAMPLE[tab]FACTORS(NAME:VALUE pairs separated by |)[tab]Raw file names and additional sample data
SUBJECT_SAMPLE_FACTORS           	-	900	Treatment:C3H 5001	Tissue=Liver; RAW_FILE_NAME=044-1.A09-900_031
SUBJECT_SAMPLE_FACTORS           	-	901	Treatment:C3H 5001	Tissue=Liver; RAW_FILE_NAME=035-1.A10-901_032
SUBJECT_SAMPLE_FACTORS           	-	902	Treatment:C3H 5001	Tissue=Liver; RAW_FILE_NAME=013-1.A11-902_033
SUBJECT_SAMPLE_FACTORS           	-	903	Treatment:C3H 5001	Tissue=Liver; RAW_FILE_NAME=041-1.A12-903_034
SUBJECT_SAMPLE_FACTORS           	-	904	Treatment:C3H 5001	Tissue=Liver; RAW_FILE_NAME=040-1.B01-904_035
SUBJECT_SAMPLE_FACTORS           	-	905	Treatment:C3H 5001	Tissue=Liver; RAW_FILE_NAME=022-1.B02-905_036
SUBJECT_SAMPLE_FACTORS           	-	906	Treatment:C3H 5001	Tissue=Liver; RAW_FILE_NAME=016-1.B03-906_037
SUBJECT_SAMPLE_FACTORS           	-	908	Treatment:tx-J 5001	Tissue=Liver; RAW_FILE_NAME=045-1.B04-908_038
SUBJECT_SAMPLE_FACTORS           	-	909	Treatment:tx-J 5001	Tissue=Liver; RAW_FILE_NAME=046-1.B05-909_039
SUBJECT_SAMPLE_FACTORS           	-	910	Treatment:tx-J 5001	Tissue=Liver; RAW_FILE_NAME=021-1.B06-910_040
SUBJECT_SAMPLE_FACTORS           	-	911	Treatment:tx-J 5001	Tissue=Liver; RAW_FILE_NAME=037-1.B07-911_041
SUBJECT_SAMPLE_FACTORS           	-	912	Treatment:tx-J 5001	Tissue=Liver; RAW_FILE_NAME=014-1.B08-912_042
SUBJECT_SAMPLE_FACTORS           	-	913	Treatment:tx-J 5001	Tissue=Liver; RAW_FILE_NAME=042-1.B09-913_043
SUBJECT_SAMPLE_FACTORS           	-	914	Treatment:tx-J 5001	Tissue=Liver; RAW_FILE_NAME=034-1.B10-914_044
SUBJECT_SAMPLE_FACTORS           	-	915	Treatment:tx-J 5001	Tissue=Liver; RAW_FILE_NAME=038-1.B11-915_045
SUBJECT_SAMPLE_FACTORS           	-	916	Treatment:tx-J 5001	Tissue=Liver; RAW_FILE_NAME=039-1.B12-916_046
SUBJECT_SAMPLE_FACTORS           	-	917	Treatment:tx-J 5001	Tissue=Liver; RAW_FILE_NAME=020-1.C01-917_047
SUBJECT_SAMPLE_FACTORS           	-	918	Treatment:tx-J 5001	Tissue=Liver; RAW_FILE_NAME=032-1.C02-918_048
SUBJECT_SAMPLE_FACTORS           	-	919	Treatment:tx-J 5001	Tissue=Liver; RAW_FILE_NAME=023-1.C03-919_049
SUBJECT_SAMPLE_FACTORS           	-	920	Treatment:tx-J 5001	Tissue=Liver; RAW_FILE_NAME=025-1.C04-920_050
SUBJECT_SAMPLE_FACTORS           	-	921	Treatment:tx-J 5001	Tissue=Liver; RAW_FILE_NAME=033-1.C05-921_051
SUBJECT_SAMPLE_FACTORS           	-	922	Treatment:tx-J 5001	Tissue=Liver; RAW_FILE_NAME=015-1.C06-922_052
SUBJECT_SAMPLE_FACTORS           	-	923	Treatment:tx-J 5001	Tissue=Liver; RAW_FILE_NAME=018-1.C07-923_053
SUBJECT_SAMPLE_FACTORS           	-	924	Treatment:tx-J 5001	Tissue=Liver; RAW_FILE_NAME=036-1.C08-924_054
SUBJECT_SAMPLE_FACTORS           	-	925	Treatment:tx-J 5001	Tissue=Liver; RAW_FILE_NAME=026-1.C09-925_055
SUBJECT_SAMPLE_FACTORS           	-	926	Treatment:C3H 5001	Tissue=Liver; RAW_FILE_NAME=043-1.C10-926_056
SUBJECT_SAMPLE_FACTORS           	-	927	Treatment:C3H 5001	Tissue=Liver; RAW_FILE_NAME=027-1.C11-927_057
SUBJECT_SAMPLE_FACTORS           	-	928	Treatment:C3H 5001	Tissue=Liver; RAW_FILE_NAME=019-1.C12-928_058
SUBJECT_SAMPLE_FACTORS           	-	929	Treatment:C3H 5001	Tissue=Liver; RAW_FILE_NAME=017-1.D01-929_059
SUBJECT_SAMPLE_FACTORS           	-	930	Treatment:C3H 5001	Tissue=Liver; RAW_FILE_NAME=024-1.D02-930_060
#COLLECTION
CO:COLLECTION_SUMMARY            	The liver was isolated. All samples were stored at -80°C until further
CO:COLLECTION_SUMMARY            	analysis.
CO:SAMPLE_TYPE                   	Liver
#TREATMENT
TR:TREATMENT_SUMMARY             	NA
#SAMPLEPREP
SP:SAMPLEPREP_SUMMARY            	Weigh 1-15 mg tissue aliquots on dry ice, record exact weights, place in 2-mL
SP:SAMPLEPREP_SUMMARY            	eppendorf tubes labeled on cap, keep frozen Add 10 µL anti-oxidant soln, (0.2
SP:SAMPLEPREP_SUMMARY            	mg/ml solution BHT/EDTA in 1:1 meoh:water) Add 10 uL of surrogate standards Add
SP:SAMPLEPREP_SUMMARY            	500 uL of cold methanol as extraction solvent and stainless steel grinding balls
SP:SAMPLEPREP_SUMMARY            	Homogenize using GenoGrinder 2x30 sec, centrifuge, transfer supernatant to a
SP:SAMPLEPREP_SUMMARY            	1.5-mL eppendorf tube (Cryo-label on side) containing 10 µL 20% glycerol
SP:SAMPLEPREP_SUMMARY            	solution in MeOH Add a second aliquot of 500 uL of cold methanol to
SP:SAMPLEPREP_SUMMARY            	centrifugation pellet Homogenize using GenoGrinder 2x30 sec, centrifuge, combine
SP:SAMPLEPREP_SUMMARY            	this second supernatant with the first one in the 1.5-mL eppendorf tube Transfer
SP:SAMPLEPREP_SUMMARY            	vials to Speed-vac and evaporate to dryness or transfer to 96 well plate and
SP:SAMPLEPREP_SUMMARY            	Gene-Vac to dryness. Assure samples are dry before removing from evaporation
SP:SAMPLEPREP_SUMMARY            	process. Reconstitute samples for LC-MS in PHAU/CUDA 50 nM in methanol/ACN
SP:SAMPLEPREP_SUMMARY            	50:50, vortex for 10 sec, then sonicate for 5 min. Set rack of samples on wet
SP:SAMPLEPREP_SUMMARY            	ice for 15min Centrifuge for 3 min at highest speed, then transfer supernatant
SP:SAMPLEPREP_SUMMARY            	to glass insert in amber HPLC vial / 96 well plate Store at -20°C until LCMS
SP:SAMPLEPREP_SUMMARY            	analysis
#CHROMATOGRAPHY
CH:CHROMATOGRAPHY_TYPE           	Reversed phase
CH:INSTRUMENT_NAME               	Shimadzu Nexera X2
CH:COLUMN_NAME                   	Waters ACQUITY UPLC BEH C18 (100 x 2.1mm,1.7um)
CH:SOLVENT_A                     	100% water; 0.1% acetic acid
CH:SOLVENT_B                     	90% acetonitrile/ 10% isopropanol
CH:FLOW_GRADIENT                 	75% ACN:IPA 90:10 (v/v) with 0.1% Acetic acid
CH:FLOW_RATE                     	0.6 mL/min
CH:COLUMN_TEMPERATURE            	65°C
#ANALYSIS
AN:ANALYSIS_TYPE                 	MS
AN:ANALYSIS_PROTOCOL_FILE        	Oxy-EC_analysis_protocol.pdf
#MS
MS:INSTRUMENT_NAME               	ABI Sciex 6500 QTrap
MS:INSTRUMENT_TYPE               	Triple quadrupole
MS:MS_TYPE                       	ESI
MS:ION_MODE                      	UNSPECIFIED
MS:MS_COMMENTS                   	LC/MS on Thermo Scientific Vanquish UPLC/Sciex Qtrap with targeted MRM method
MS:MS_COMMENTS                   	(developed by Newman lab, optimized for Fiehn lab setup). See protocol file.
#MS_METABOLITE_DATA
MS_METABOLITE_DATA:UNITS	nM
MS_METABOLITE_DATA_START
Samples	900	901	902	903	904	905	906	908	909	910	911	912	913	914	915	916	917	918	919	920	921	922	923	924	925	926	927	928	929	930
Factors	Treatment:C3H 5001	Treatment:C3H 5001	Treatment:C3H 5001	Treatment:C3H 5001	Treatment:C3H 5001	Treatment:C3H 5001	Treatment:C3H 5001	Treatment:tx-J 5001	Treatment:tx-J 5001	Treatment:tx-J 5001	Treatment:tx-J 5001	Treatment:tx-J 5001	Treatment:tx-J 5001	Treatment:tx-J 5001	Treatment:tx-J 5001	Treatment:tx-J 5001	Treatment:tx-J 5001	Treatment:tx-J 5001	Treatment:tx-J 5001	Treatment:tx-J 5001	Treatment:tx-J 5001	Treatment:tx-J 5001	Treatment:tx-J 5001	Treatment:tx-J 5001	Treatment:tx-J 5001	Treatment:C3H 5001	Treatment:C3H 5001	Treatment:C3H 5001	Treatment:C3H 5001	Treatment:C3H 5001
Thromboxane B2	0.944	18.524	2.209	0.781	2.111	2.255	1.729	2.465	1.588	5.256	8.955	1.801	1.104	1.392	1.838	10.926	4.922	4.345	2.087	3.794	5.555	4.903	7.924	2.02	1.575	1.079	1.622	3.597	4.347	2.749
6-Ketoprostaglandin F1 alpha	0.264	0.102	0.108	0.071	0.298	1	1.041	2.63	1.463	2.538	13.004	3.211	1.412	4.627	13.505	16.213	3.013	2.526	0.661	5.798	1.245	2.678	37.373	3.371	2.703	1.682	0.677	2.123	1.884	1.083
Prostaglandin E1	0.027	0.022	0.085	0.028	0.028	0.016	0.047	0.065	0.006	0.055	0.183	0.037	0.002	0.052	0.091	1.694	0.048	0.042	0.038	0.067	0.008	0.019	0.085	0.007	0.003	0.002	0.024	0.096	0.021	0.053
Prostaglandin E2	1.549	0.051	0.033	0.463	0.042	0.086	0.235	0.681	0.087	0.024	4.748	53.001	0.601	0.031	0.063	8.194	0.125	0.046	0.029	1.921	0.009	0.008	0.581	0.055	0.05	0.148	1.229	0.118	0.078	0.086
Prostaglandin D2	1.137	0.154	0.031	1.026	0.082	0.07	1.89	0.805	0.414	0.07	5.264	62.083	1.216	0.102	0.034	9.623	0.068	0.038	0.03	0.436	0.026	0.049	0.489	0.147	0.266	1.905	0.065	0.157	0.072	0.275
15-Deoxy-delta-12,14-Prostaglandin J2	0.399	0.548	0.908	0.355	0.309	0.694	0.956	0.535	0.423	0.83	0.757	0.793	0.41	0.473	0.354	0.508	0.526	0.518	0.488	0.076	0.719	0.93	0.607	0.375	0.781	0.059	0.557	0.323	0.321	0.07
15-Keto-prostaglandin E2	1.158	1.54	6.687	0.964	1.476	0.927	2.003	2.868	2.332	2.971	2.805	5.292	2.587	3.208	215.698	4.258	2.674	2.296	1.741	5.306	2.916	10.493	4.9	4.53	0.977	0.556	9.936	4.575	3.427	1.953
Prostaglandin F2a	0.094	0.229	1.205	0.524	0.068	0.271	1.251	9.851	1.765	1.849	64.762	1.749	1.367	1.552	5.709	62.378	1.766	0.287	0.778	11.38	1.849	1.031	10.962	2.175	0.986	0.593	0.11	0.243	0.311	0.201
Prostaglandin E3	0.032	0.741	83.751	0.261	0.08	0.074	30.325	0.102	0.066	1.533	0.642	0.157	0.03	0.159	0.096	1.23	0.046	0.037	0.017	0.093	0.166	0.071	0.054	0.027	0.098	0.075	2.066	2.775	0.457	0.963
9,11,15-trihydroxy-5,13,1Z-prostatrienoic acid	0.947	2.285	1.624	0.051	0.503	2.095	0.735	2.158	0.057	0.084	7.835	7.766	0.329	0.67	11.486	5.376	0.027	0.013	5.843	1.782	0.01	0.901	1.457	5.042	0.565	0.026	0.365	3.36	0.54	0.89
9,12,13-trihydroxyoctadec-10-enoic acid	46.614	74.574	21.701	8.876	9.928	18.106	11.077	21.096	12.93	13.309	11.727	3.454	7.064	12.459	11.443	25.962	12.06	26.38	15.679	10.532	32.398	6.1	13.791	21.126	22.587	10.315	13.757	9.171	16.527	15.065
5,6,15-trihydroxyeicosa-7,9,11,13-tetraenoic acid	0.132	0.86	0.559	0.445	0.292	0.405	0.366	0.218	0.278	0.071	0.274	8.408	0.126	0.591	4.07	1.316	1.105	4.478	0.156	6.22	0.309	0.718	0.364	0.741	0.396	0.173	0.884	3.877	2.479	0.227
Resolvin D1	0.029	0.071	0.249	0.05	0.021	0.057	0.034	0.04	0.045	0.152	0.087	3.849	0.024	0.065	0.108	0.024	0.283	0.116	0.159	0.015	0.12	0.056	0.033	0.034	0.039	0.073	0.136	0.212	0.138	0.256
9S,10R-dihydroxy-stearic acid	42.286	70.153	57.491	29.827	35.871	61.013	44.013	26.572	27.197	34.645	25.49	25.699	14.169	29.261	26.714	41.018	32.307	55.17	25.971	20.26	37.716	20.913	32.133	39.371	35.428	39.799	60.053	47.381	51.836	45.084
12,13-dihydroxyoctadec-9-enoic acid	24.12	33.76	34.187	24.041	13.323	31.169	32.146	12.587	15.732	21.923	23.199	14.073	10.22	17.711	14.448	27.045	17.485	16.555	18.508	14.449	15.01	20.643	13.878	24.93	18.428	23.294	32.326	17.685	25.779	25.061
9,10-dihydroxyoctadec-12-enoic acid	2.022	2.592	1.97	0.911	0.833	1.942	2.356	1.079	1.018	1.565	1.624	0.803	0.701	1.142	0.668	1.835	1.235	1.485	1.251	0.799	1.889	1.575	0.903	1.82	1.541	1.495	1.823	1.451	1.876	1.416
15,16-dihydroxyoctadeca-9,12-dienoic acid	7.832	9.92	14.453	9.423	3.953	19.541	16.013	6.516	9.582	16.369	13.692	7.285	5.763	12.242	8.308	15.322	10.179	8.935	8.418	8.007	3.998	12.329	6.387	19.36	9.009	12.342	14.827	6.331	12.119	14.421
12,13-dihydroxyoctadeca-9,15-dienoic acid	0.257	0.411	0.46	0.26	0.184	1.902	0.434	0.164	0.231	0.411	0.324	0.412	0.168	0.318	0.236	0.267	0.218	0.193	0.183	0.132	0.201	0.373	0.172	1.373	0.229	1.198	0.47	0.237	0.426	1.67
9,10-dihydroxyoctadeca-12,15-dienoic acid	1.006	1.394	1.238	0.741	0.431	1.891	1.454	0.501	0.89	1.761	1.306	0.422	0.771	1.053	0.793	1.05	0.745	0.657	0.52	0.386	0.827	1.98	0.664	2.344	0.924	1.577	1.509	0.636	1.366	1.604
14,15-dihydroxyeicosa-5,8,11-trienoic acid	62.382	119.331	94.965	75.877	63.005	107.602	192.589	42.432	43.222	58.622	94.856	55.942	28.58	52.719	54.075	106.775	69.832	38.075	63.092	82.194	79.509	62.489	67.053	63.07	54.592	67.047	149.252	205.538	150.056	80.451
11,12-Dihydroxyicosa-5,8,14-trienoic acid	3.175	5.936	4.656	3.171	3.506	6.094	12.809	2.657	2.907	3.244	5.562	3.199	1.757	2.62	3.162	6.271	4.252	2.106	3.391	4.799	5.101	3.648	4.537	3.537	3.15	3.2	6.115	14.509	8.57	4.308
8,9-dihydroxyeicosa-5,11,14-trienoic acid	14.334	22.494	23.45	12.857	12.477	29.301	64.724	17.906	19.434	20.035	36.056	20.312	9.417	14.429	13.266	32.246	22.083	13.864	18.289	20.762	25.78	19.791	24.852	17.831	17.345	13.777	27.722	57.374	39.539	17.77
5,6-dihydroxyeicosa-8,11,14-trienoic acid	8.312	12.453	10.835	6.691	6.228	19.81	38.985	14.125	16.257	18.462	30.189	18.89	4.147	11.346	6.542	23.581	13.682	18.498	13.239	14.54	24.59	17.392	19.71	19.918	21.304	5.437	15.423	22.261	17.02	10.058
17,18-dihydroxyeicosa-5,8,11,14-tetraenoic acid	13.927	17.801	17.574	12.73	6.502	17.847	20.957	8.775	10.406	12.474	14.349	13.373	6.601	14.114	14.606	18.639	13.707	10.084	12.896	14.316	9.076	13.452	11.011	17.608	13.79	17.05	28.129	17.075	18.386	16.326
14,15-dihydroxyeicosa-5,8,11,17-tetraenoic acid	45.75	69.121	50.765	45.873	26.412	68.986	75.783	22.416	25.095	28.755	45.721	26.659	13.728	30.47	31.632	42.652	29.659	21.347	32.904	36.19	34.455	35.928	29.363	52.567	37.682	54.213	149.27	99.504	81.2	55.165
19,20-dihydroxydocosa-4,7,10,13,16-pentaenoic acid	21.174	39.736	37.606	28.681	18.765	51.811	67.708	11.774	12.976	19.555	20.588	18.246	8.651	18.983	17.924	34.588	18.11	13.715	16.066	24.154	14.753	20.743	20.384	21.429	16.822	30.862	57.665	55.23	57.318	39.496
8,15-dihydroxyeicosa-5,9,11,13-tetraenoic acid	0.125	0.155	0.107	0.067	0.077	0.293	0.191	0.1	0.161	0.225	0.361	0.278	0.053	0.12	0.064	1.47	0.097	0.137	0.203	0.278	0.106	0.108	0.151	0.146	0.167	0.062	0.144	0.22	0.354	0.104
6-trans-Leukotriene B4	0.016	0.028	0.045	0.016	0.005	0.034	0.015	0.013	0.009	0.061	0.011	0.006	0.006	0.016	0.018	0.055	0.027	0.021	0.023	0.018	0.01	0.019	0.057	0.038	0.008	0.002	0.008	0.037	0.071	0.029
Leukotriene B4	0.014	0.021	0.031	0.017	0.007	0.015	0.032	0.01	0.235	0.033	0.037	0.029	0.014	0.031	0.055	0.655	0.012	0.032	0.001	0.061	0.02	0.014	0.046	0.016	0.025	0.007	0.021	0.039	0.043	0.038
Leukotriene B5	3.378	13.583	1.277	8.369	3.318	4.833	51.717	0.378	0.929	0.497	0.262	0.279	0.252	0.446	6.871	3.072	4.78	3.728	4.617	8.231	7.689	2.02	2.745	1.119	3.923	3.87	8.125	25.078	9.748	3.595
13-Hydroxyoctadecadienoic acid	74.215	140.119	79.184	44.833	55.302	101.96	116.522	95.374	83.698	65.959	137.466	100.776	42.182	63.014	66.955	233.921	90.005	68.5	69.593	73.171	103.671	62.732	113.564	78.885	86.439	37.312	81.095	60.136	93.891	62.716
9-Hydroxylinoleic acid	79.262	152.144	64.095	34.377	42.138	63.544	67.509	74.902	49.602	45.568	88.94	49.331	26.937	39.088	43.415	173.139	59.322	49.895	50.962	59.372	91.786	35.109	58.835	50.551	67.337	27.912	51.43	36.03	47.629	37.309
13-hydroxyoctadeca-9,11,15-trienoic acid	0.396	0.576	0.29	1.11	0.388	0.624	0.283	1.42	3.232	0.646	2.136	0.488	0.338	2.309	1.579	3.372	1.799	0.453	0.504	0.335	0.526	0.541	6.681	0.427	0.318	0.334	0.545	0.301	3.691	0.17
9-hydroxyoctadeca-10,12,15-trienoic acid	1.309	2.096	1.414	1.001	0.735	1.452	1.429	0.926	2.318	1.328	1.76	0.929	0.694	1.074	0.848	2.879	1.126	0.942	1.281	0.878	0.33	1.004	1.261	1.179	0.996	0.792	1.805	0.25	0.689	0.819
20-Hydroxyarachidonic acid	3.38	1.674	10.588	19.075	4.98	11.197	18.028	14.484	6.682	21.684	34.963	1.166	3.316	14.25	7.177	52.502	1.087	1.522	15.292	31.037	17.169	10.172	8.759	14.855	41.704	8.378	40.054	12.937	22.703	13.423
15-hydroxyeicosa-5,8,11,13-tetraenoic acid	9.031	12.602	11.888	8.667	9.31	22.84	19.375	15.785	13.829	12.065	30.656	13.19	6.512	10.729	13.365	43.994	12.587	9.26	12.263	21.882	18.024	8.885	15.13	12.276	11.926	7.345	16.448	18.416	18.08	15.142
12-Hydroxy-5,8,10,14-eicosatetraenoic acid	4.831	10.309	9.136	8.343	9.496	24.954	25.433	29.065	50.099	16.431	89.449	13.817	6.154	23.409	18.521	140.157	29.078	7.313	10.388	32.899	21.086	8.383	60.159	16.665	9.593	10.259	20.784	27.244	55.176	6.34
8-hydroxyeicosa-5,9,11,14-tetraenoic acid	1.717	2.329	3.833	1.765	1.514	2.814	4.586	2.698	7.23	3.762	8.202	5.228	0.829	2.444	2.771	7.681	2.694	2.096	4.076	4.907	2.916	3.839	5.102	2.395	2.471	1.363	2.593	2.464	4.206	1.853
11-Hydroxy-arachidonic acid	3.365	7.005	7.275	4.52	4.329	10.218	12.601	7.884	8.693	7.731	21.619	8.528	3.671	6.012	7.122	26.223	7.08	4.458	6.403	10.876	8.902	6.11	10.125	6.599	6.038	3.818	7.639	8.038	7.836	6.975
9-hydroxyeicosa-5,7,11,14-tetraenoic acid	3.588	5.32	6.939	3.652	2.563	4.904	6.515	4.535	13.809	7.534	11.468	6.597	2.897	5.317	8.529	14.089	5.729	6.076	8.411	10.044	6.613	5.431	7.571	3.862	6.583	3.612	4.933	3.991	5.673	3.124
5-Hydroxy-6,8,11,14-eicosatetraenoic acid	5.893	9.329	19.192	5.382	4.018	15.69	28.151	10.63	23.88	17.813	40.205	29.82	5.417	11.97	10.928	25.872	15.761	12.676	14.518	16.2	11.753	27.012	28.716	7.461	13.952	6.6	8.144	5.715	12.555	9.378
12-Hydroxy-5,8,10,14,17-eicosapentaenoic acid	5.824	10.997	4.512	13.916	5.621	22.827	13.127	29.988	43.117	10.59	46.573	6.582	4.966	15.932	9.484	141.117	24.205	5.271	11.301	23.827	17.892	3.072	17.74	16.246	9.778	8.748	22.757	11.403	18.404	5.206
9-Hydroxy-5,7,11,14,17-icosapentaenoic acid	1.661	3.066	4.105	3.04	0.928	1.755	3.231	2.825	7.643	4.449	4.842	4.321	1.336	4.535	3.84	6.896	3.509	3.408	3.45	3.32	1.619	4.609	4.351	2.52	4.345	1.871	3.293	2.03	2.135	1.228
5-Hydroxy-6,8,11,14,17-eicosapentaenoic acid	3.743	4.775	6.373	4.416	2.752	8.314	7.887	4.936	13.238	8.989	9.708	7.324	3.808	9.253	7.406	14.3	9.71	7.65	7.8	10.098	5.023	8.777	9.043	6.456	8.353	3.515	7.279	3.179	5.574	5.467
17-hydroxy-4,7,10,13,15,19-docosahexaenoic acid	10.662	14.201	23.342	18.243	11.781	25.811	16.881	11.588	25.418	12.703	22.184	11.869	7.068	15.694	19.156	49.634	23.603	14.589	18.001	31.884	12.317	14.887	41.879	14.527	11.855	10.395	16.245	18.32	25.739	6.217
14-hydroxydocosa-4,7,10,12,16,19-hexaenoic acid	8.233	11.35	15.524	14.458	14.964	40.437	21.627	19.051	41.165	10.389	27.354	27.999	6.923	27.015	13.104	130.666	29.753	6.507	7.707	23.453	18.858	8.768	51.257	22.359	8.135	12.006	28.004	28.181	128.129	9.655
4-hydroxydocosa-5,7,10,13,16,19-hexaenoic acid	3.13	2.754	7.615	3.14	2.054	3.084	4.058	0.621	3.191	0.268	0.367	0.968	0.095	0.408	1.127	2.792	2.006	0.407	0.316	0.383	0.236	1.32	0.357	0.284	0.397	3.293	3.952	3.235	7.947	0.293
13-ketooctadeca-9,11-dienoic acid	6.002	4.159	4.649	4.217	7.683	9.988	6.997	4.208	9.87	0.328	7.901	4.645	0.867	5.507	1.108	12.003	5.026	5.017	1.337	0.878	5.375	5.583	7.111	4.555	4.487	0.888	1.064	0.788	5.313	4.488
9-ketooctadeca-10,12-dienoic acid	11.952	11.898	9.765	5.34	8.019	12.18	9.172	7.753	19.503	7.694	13.445	8.122	3.968	6.368	5.28	22.733	6.474	7.813	7.513	6.675	9.178	9.992	7.774	8.104	7.913	2.333	6.774	3.375	5.056	0.823
15-ketoeicosa-5,8,11,13-tetraenoic acid	0.719	1.098	0.305	1.171	0.442	1.782	0.242	1.419	3.709	0.849	3.265	1.181	1.174	1.283	2.422	2.464	0.24	1.458	2.811	0.249	2.927	0.824	0.186	0.241	2.223	0.466	1.498	1.325	1.293	0.241
5-ketoeicosa-6,8,11,14-tetraenoic acid	1.373	2.229	7.745	1.638	1.449	5.604	11.623	2.85	12.655	7	12.882	9.554	1.582	3.907	0.312	13.502	5.594	0.848	1.343	4.992	5.005	10.519	6.702	3.88	1.534	1.508	1.889	3.838	5.825	1.005
9,10-Epoxystearic acid	12.957	10.76	34.913	11.7	11.013	32.909	47.329	16.331	31.818	41.122	31.654	39.058	5.554	14.038	19.582	32.638	23.709	66.284	17.29	15.559	14.147	30.854	36.519	25.739	11.622	9.215	14.408	19.862	33.482	12.161
trans-12,13-epoxy-11-oxo-trans-9-octadecenoic acid	1.638	1.904	0.693	1.821	2.613	4.778	2.106	6.728	14.849	2.294	14.072	1.151	5.528	7.963	5.735	7.203	2.417	9.049	4.85	5.343	5.119	1.779	2.729	3.095	5.367	2.825	3.025	2.002	1.807	2.881
12,13-epoxy-9-octadecenoic acid	83.769	129.953	44.623	56.457	53.506	68.711	60.32	89.182	65.304	45.81	114.537	45.637	35.549	54.045	63.232	208.445	61.53	51.807	68.998	81.814	95.197	27.685	68.187	58.442	87.33	36.48	88.615	47.92	66.714	54.663
9(10)-epoxy-12Z-octadecenoic acid	3.079	1.669	1.535	1.604	2.067	1.423	0.544	1.795	6.434	3.278	4.53	0.584	1.51	3.169	1.427	5.549	2.277	3.578	2.307	3.164	1.566	1.093	1.098	4.787	3.875	1.997	2.907	0.411	0.783	1.199
15(16)-epoxy-9,12-octadecadienoic acid	1.585	0.757	0.63	1.434	1.983	0.619	0.276	0.074	1.828	0.432	0.532	0.061	0.149	0.299	0.268	0.29	0.482	0.496	0.218	0.602	0.45	0.255	0.134	0.34	0.431	0.588	2	0.426	0.445	2.624
9(10)-epoxy-12,15-octadecadienoic acid	0.361	0.33	0.15	0.226	0.302	0.253	0.292	0.207	0.322	0.294	0.255	0.072	0.228	0.182	0.214	0.545	0.259	0.241	0.022	0.344	0.202	0.363	0.121	0.262	0.294	0.158	0.465	0.222	0.034	0.235
12(13)-epoxy-9,15-octadecadienoic acid	0.056	0.053	0.057	0.101	0.075	0.159	0.058	0.097	0.074	0.1	0.142	0.033	0.211	0.092	0.213	0.247	0.081	0.103	0.121	0.564	0.178	0.033	0.036	0.115	0.151	0.108	0.11	0.079	0.082	0.097
11-Hydroxy-14,15-epoxyeicosatrienoic acid	0.551	0.197	0.145	0.672	0.865	0.817	0.342	1.063	1.434	0.391	1.276	0.13	0.123	0.108	0.471	1.28	0.497	0.423	0.356	1.198	0.381	0.365	0.176	0.127	0.634	0.527	0.76	0.605	0.628	0.163
11,12-Epoxyeicosa-5,8,14-trienoic acid	0.855	0.378	0.567	0.473	1.227	0.881	1.549	0.375	2.204	1.936	1.906	1.018	0.355	0.855	1.752	0.882	0.659	0.96	1.198	2.068	0.943	1.292	1.828	1.145	0.818	0.744	1.189	1.111	1.205	1.682
8,9-Epoxyeicosa-5,11,14-trienoic acid	1.203	0.296	2.525	0.654	1.55	0.862	2.428	1.283	3.898	3.696	3.261	2.647	1.049	1.301	0.307	2.941	1.537	1.276	0.293	1.481	1.157	2.671	3.062	2.983	0.266	0.848	0.267	0.87	2.032	0.212
17,18-Epoxy-5,8,11,14-eicosatetraenoic acid	1.305	2.069	0.81	1.021	1.448	0.65	0.325	0.584	0.696	0.272	0.276	0.218	0.352	0.697	1.204	1.187	0.547	0.675	0.744	0.282	0.279	0.46	0.803	1.003	1.028	1.339	2.726	0.69	0.882	2.07
14(15)-epoxy-5,8,11,17-eicosatetraenoic acid	0.08	1.906	0.198	1.883	0.833	0.422	1.744	0.586	0.51	0.801	0.638	0.532	0.212	0.741	1.209	0.466	1.127	0.467	0.414	0.662	0.351	0.901	0.368	1.083	0.159	0.311	0.383	0.605	0.307	0.187
11(12)-epoxy-5,8,14,17- eicosatetraenoic acid	0.212	0.064	0.084	0.701	0.439	0.469	0.058	0.423	0.58	0.38	0.683	0.435	0.316	0.649	0.085	1.436	0.688	0.681	0.056	0.036	0.341	0.561	0.778	0.7	0.644	0.251	0.466	0.378	0.307	0.655
18-(3-ethyloxiran-2-yl)octadeca-4,7,10,13,16-pentaenoic acid	4.735	3.822	4.63	6.502	4.582	3.491	3.137	1.098	3.468	1.005	2.216	1.483	0.861	1.082	2.166	3.788	3.207	0.796	1.202	2.964	1.099	0.567	2.048	1.149	1.117	3.821	5.316	3.975	4.081	3.319
16(17)-epoxy-4,7,10,13,19-docosapentaenoic acid	0.484	0.583	0.242	0.678	0.314	0.771	0.3	2.757	0.238	0.853	0.383	0.274	0.364	0.493	0.498	0.637	0.391	0.803	8.949	0.44	0.316	0.349	0.465	0.949	0.559	0.352	0.666	0.363	0.696	5.735
10-nitrooleic acid	0.029	0.069	0.029	0.034	0.398	0.12	0.077	0.074	0.089	0.562	0.137	0.045	0.055	0.035	0.132	0.077	0.009	0.108	0.06	0.073	0.067	0.099	0.029	0.03	0.066	0.02	0.156	0.008	0.023	0.733
9-nitrooleic acid	0.421	0.767	0.113	2.098	0.386	7.478	0.431	2.454	6.847	0.425	0.529	0.39	1.2	0.439	4.608	6.721	0.358	0.575	0.48	0.734	0.596	0.508	0.532	0.664	5.446	0.278	5.525	0.336	0.317	1.631
10-nitrolinoleic acid	0.142	0.084	0.109	0.09	0.046	1.078	0.168	0.061	0.111	0.263	1.402	0.126	0.063	0.131	0.136	1.83	0.183	0.089	1.33	0.053	0.095	0.177	0.028	0.082	0.226	0.061	0.134	0.132	0.075	1.315
MS_METABOLITE_DATA_END
#METABOLITES
METABOLITES_START
metabolite_name	approved short names	InChI Key	PubChem	Ret.Time
Thromboxane B2	TXB2	XNRNNGPBEPRNAR-JQBLCGNGSA-N	5283137	3.97
6-Ketoprostaglandin F1 alpha	6-keto-PGF1alpha	KFGOFTHODYBSGM-ZUNNJUQCSA-N	5280888	3.19
Prostaglandin E1	PGE1	GMVPRGQOIOIIMI-DWKJAMRDSA-N	5280723	4.7
Prostaglandin E2	PGE2	XEYBRNLFEZDVAW-ARSRFYASSA-N	5280360	4.54
Prostaglandin D2	PGD2	BHMBVRSPMRCCGG-OUTUXVNYSA-N	448457	4.83
15-Deoxy-delta-12,14-Prostaglandin J2	15-deoxy PGJ2	VHRUMKCAEVRUBK-GODQJPCRSA-N	5311211	9.85
15-Keto-prostaglandin E2	15-Keto PGE2	YRTJDWROBKPZNV-KMXMBPPJSA-N	5280719	4.87
Prostaglandin F2a	PGF2alpha	PXGPLTODNUVGFL-YNNPMVKQSA-N	5280363	4.42
Prostaglandin E3	PGE3	CBOMORHDRONZRN-QLOYDKTKSA-N	5280937	3.84
9,11,15-trihydroxy-5,13,1Z-prostatrienoic acid	PGF3alpha	SAKGBZWJAIABSY-SAMSIYEGSA-N	5280940	3.7
9,12,13-trihydroxyoctadec-10-enoic acid	91213-TriHOME	MDIUMSLCYIJBQC-MVFSOIOZSA-N	9858729	4.36
5,6,15-trihydroxyeicosa-7,9,11,13-tetraenoic acid	Lipoxin A4	IXAQOQZEOGMIQS-SSQFXEBMSA-N	5280914	5.48
Resolvin D1	Resolvin D1	OIWTWACQMDFHJG-CCFUIAGSSA-N	44251266	5.37
9S,10R-dihydroxy-stearic acid	910-e-DiHO	VACHUYIREGFMSP-SJORKVTESA-N	441460	9.39
12,13-dihydroxyoctadec-9-enoic acid	12_13-DiHOME	CQSLTKIXAJTQGA-FLIBITNWSA-N	10236635	8.03
9,10-dihydroxyoctadec-12-enoic acid	910-DiHOME	XEBKSQSGNGRGDW-YFHOEESVSA-N	9966640	8.44
15,16-dihydroxyoctadeca-9,12-dienoic acid	1516-DiHODE	LKLLJYJTYPVCID-OHPMOLHNSA-N	16061068	6.96
12,13-dihydroxyoctadeca-9,15-dienoic acid	1213-DiHODE	RGRKFKRAFZJQMS-OOHFSOINSA-N	16061067	7.04
9,10-dihydroxyoctadeca-12,15-dienoic acid	910-DiHODE	QRHSEDZBZMZPOA-ZJSQCTGTSA-N	16061066	7.08
14,15-dihydroxyeicosa-5,8,11-trienoic acid	1415-DiHETrE	SYAWGTIVOGUZMM-ILYOTBPNSA-N	5283147	8.68
11,12-Dihydroxyicosa-5,8,14-trienoic acid	1112-DiHETrE	LRPPQRCHCPFBPE-KROJNAHFSA-N	5283146	9.24
8,9-dihydroxyeicosa-5,11,14-trienoic acid	89-DiHETrE	DCJBINATHQHPKO-TYAUOURKSA-N	5283144	9.78
5,6-dihydroxyeicosa-8,11,14-trienoic acid	56-DiHETrE	GFNYAPAJUNPMGH-QNEBEIHSSA-N	5283142	10.56
17,18-dihydroxyeicosa-5,8,11,14-tetraenoic acid	1718-DiHETE	XYDVGNAQQFWZEF-JPURVOHMSA-N	16061120	7.34
14,15-dihydroxyeicosa-5,8,11,17-tetraenoic acid	1415-DiHETE	BLWCDFIELVFRJY-QXBXTPPVSA-N	16061119	7.67
19,20-dihydroxydocosa-4,7,10,13,16-pentaenoic acid	1920-DiHDPE	FFXKPSNQCPNORO-MBYQGORISA-N	16061148	8.66
8,15-dihydroxyeicosa-5,9,11,13-tetraenoic acid	815-DiHETE	NNPWRKSGORGTIM-RCDCWWQHSA-N	53480358	7.06
6-trans-Leukotriene B4	6-trans-LTB4	VNYSSYRCGWBHLG-UKNWISKWSA-N	5283128	7.53
Leukotriene B4	LTB4	VNYSSYRCGWBHLG-AMOLWHMGSA-N	5280492	7.78
Leukotriene B5	LTB5	BISQPGCQOHLHQK-HDNPQISLSA-N	5283125	6.52
13-Hydroxyoctadecadienoic acid	13S-HODE	HNICUWMFWZBIFP-IRQZEAMPSA-N	6443013	10.89
9-Hydroxylinoleic acid	9-HODE	NPDSHTNEKLQQIJ-ZJHFMPGASA-N	5282944	11.08
13-hydroxyoctadeca-9,11,15-trienoic acid	13-HOTE	KLLGGGQNRTVBSU-JDTPQGGVSA-N	10469728	9.62
9-hydroxyoctadeca-10,12,15-trienoic acid	9-HOTE	YUPHIKSLGBATJK-OBKPXJAFSA-N	53480359	9.5
20-Hydroxyarachidonic acid	20-HETE	NNDIXBJHNLFJJP-DTLRTWKJSA-N	123803	10.05
15-hydroxyeicosa-5,8,11,13-tetraenoic acid	15-HETE	JSFATNQSLKRBCI-VAEKSGALSA-N	5280724	11.27
12-Hydroxy-5,8,10,14-eicosatetraenoic acid	12S-HETE	ZNHVWPKMFKADKW-LQWMCKPYSA-N	5283155	11.96
8-hydroxyeicosa-5,9,11,14-tetraenoic acid	8S-HETE	NLUNAYAEIJYXRB-VYOQERLCSA-N	5283154	12.1
11-Hydroxy-arachidonic acid	11-HETE	GCZRCCHPLVMMJE-RSPKXIRXSA-N	5312981	11.71
9-hydroxyeicosa-5,7,11,14-tetraenoic acid	9-HETE	KATOYYZUTNAWSA-OIZRIKEUSA-N	14123398	12.31
5-Hydroxy-6,8,11,14-eicosatetraenoic acid	5-HETE	KGIJOOYOSFUGPC-JGKLHWIESA-N	5280733	12.68
12-Hydroxy-5,8,10,14,17-eicosapentaenoic acid	12S-HEPE	MCRJLMXYVFDXLS-UOLHMMFFSA-N	5283191	10.4
9-Hydroxy-5,7,11,14,17-icosapentaenoic acid	9-HEPE	OXOPDAZWPWFJEW-IMCWFPBLSA-N	16061129	10.61
5-Hydroxy-6,8,11,14,17-eicosapentaenoic acid	5S-HEPE	FTAGQROYQYQRHF-GHWNLOBHSA-N	5283193	11
17-hydroxy-4,7,10,13,15,19-docosahexaenoic acid	17-HDoHE	SWTYBBUBEPPYCX-VIIQGJSXSA-N	6439179	11.39
14-hydroxydocosa-4,7,10,12,16,19-hexaenoic acid	14-HDoHE	ZNEBXONKCYFJAF-BGKMTWLOSA-N	11566378	11.7
4-hydroxydocosa-5,7,10,13,16,19-hexaenoic acid	4-HDoHE	IFRKCNPQVIJFAQ-PQVBWYSWSA-N	14429109	13.02
13-ketooctadeca-9,11-dienoic acid	13-KODE	JHXAZBBVQSRKJR-BSZOFBHHSA-N	6446027	11.33
9-ketooctadeca-10,12-dienoic acid	9-KODE	LUZSWWYKKLTDHU-ZJHFMPGASA-N	9839084	11.78
15-ketoeicosa-5,8,11,13-tetraenoic acid	15-KETE	YGJTUEISKATQSM-USWFWKISSA-N	5280701	11.63
5-ketoeicosa-6,8,11,14-tetraenoic acid	5-KETE	MEASLHGILYBXFO-XTDASVJISA-N	5283159	13.39
9,10-Epoxystearic acid	910-EpO	IMYZYCNQZDBZBQ-UHFFFAOYSA-N	15868	14.44
trans-12,13-epoxy-11-oxo-trans-9-octadecenoic acid	12(13)Ep-9-KODE	RCMABBHQYMBYKV-BUHFOSPRSA-N	5283007	9.5
12,13-epoxy-9-octadecenoic acid	12(13)-EpOME	CCPPLLJZDQAOHD-FLIBITNWSA-N	5356421	12.81
9(10)-epoxy-12Z-octadecenoic acid	9(10)-EpOME	FBUKMFOXMZRGRB-YFHOEESVSA-N	6246154	13.04
15(16)-epoxy-9,12-octadecadienoic acid	1516-EpODE	HKSDVVJONLXYKL-OHPMOLHNSA-N	16061062	11.15
9(10)-epoxy-12,15-octadecadienoic acid	Alpha-9(10)-EpODE	JTEGNNHWOIJBJZ-ZJSQCTGTSA-N	16061060	11.35
12(13)-epoxy-9,15-octadecadienoic acid	alpha-12(13)-EpODE	BKKGUKSHPCTUGE-OOHFSOINSA-N	16061061	11.55
11-Hydroxy-14,15-epoxyeicosatrienoic acid	1415-EpETrE	JBSCUHKPLGKXKH-ILYOTBPNSA-N	5283205	12.91
11,12-Epoxyeicosa-5,8,14-trienoic acid	1112-EpETrE	DXOYQVHGIODESM-KROJNAHFSA-N	5283204	13.39
8,9-Epoxyeicosa-5,11,14-trienoic acid	8(9)-EpETrE	DBWQSCSXHFNTMO-TYAUOURKSA-N	5283203	13.59
17,18-Epoxy-5,8,11,14-eicosatetraenoic acid	17(18)-EpETE	GPQVVJQEBXAKBJ-JPURVOHMSA-N	16061089	11.25
14(15)-epoxy-5,8,11,17-eicosatetraenoic acid	14(15)-EpETE	RGZIXZYRGZWDMI-QXBXTPPVSA-N	16061088	11.72
11(12)-epoxy-5,8,14,17- eicosatetraenoic acid	11(12)-EpETE	QHOKDYBJJBDJGY-BVILWSOJSA-N	16061087	11.87
18-(3-ethyloxiran-2-yl)octadeca-4,7,10,13,16-pentaenoic acid	19(20)-EpDPE	OSXOPUBJJDUAOJ-MBYQGORISA-N	11631565	12.65
16(17)-epoxy-4,7,10,13,19-docosapentaenoic acid	16(17)-EpDPE	BCTXZWCPBLWCRV-ZYADFMMDSA-N	14392758	13.04
10-nitrooleic acid	10-Nitrooleate	WRADPCFZZWXOTI-BMRADRMJSA-N	24836820	14.84
9-nitrooleic acid	9-Nitrooleate	CQOAKBVRRVHWKV-SAPNQHFASA-N	11645581	14.79
10-nitrolinoleic acid	10-Nitrolinoleate	LELVHAQTWXTCLY-XYWKCAQWSA-N	5282259	13.85
METABOLITES_END
#END