#METABOLOMICS WORKBENCH HdZ611_20250804_081408 DATATRACK_ID:6249 STUDY_ID:ST004107 ANALYSIS_ID:AN006809 PROJECT_ID:PR002582
VERSION             	1
CREATED_ON             	August 12, 2025, 10:38 am
#PROJECT
PR:PROJECT_TITLE                 	Reaction-guided metabolomics accelerates high-throughput annotation of
PR:PROJECT_TITLE                 	xenobiotic metabolites for human exposome
PR:PROJECT_SUMMARY               	We present Compound metabolite discovery network (CMDN), a “top-down”
PR:PROJECT_SUMMARY               	untargeted metabolomics-based MS data processing framework to enable
PR:PROJECT_SUMMARY               	high-throughput and automated annotation of reaction-derived xenobiotic
PR:PROJECT_SUMMARY               	metabolites.
PR:INSTITUTE                     	University of North Carolina at Chapel Hill
PR:LAST_NAME                     	Zhao
PR:FIRST_NAME                    	Haoduo
PR:ADDRESS                       	135 DAUER DR, chapel hill, NC, 27599, USA
PR:EMAIL                         	raven456@unc.edu
PR:PHONE                         	9845281428
#STUDY
ST:STUDY_TITLE                   	Pesticide metabolite characterization by human liver S9 fractions
ST:STUDY_SUMMARY                 	We present Compound metabolite discovery network (CMDN), a “top-down”
ST:STUDY_SUMMARY                 	untargeted metabolomics-based MS data processing framework to enable
ST:STUDY_SUMMARY                 	high-throughput and automated annotation of reaction-derived xenobiotic
ST:STUDY_SUMMARY                 	metabolites. S9 fractions were used to generate pesticide metabolites, futher
ST:STUDY_SUMMARY                 	annotated through constructured CMDN framework
ST:STUDY_SUMMARY                 	(https://github.com/LeaveMeNotTonight/CMDN).
ST:INSTITUTE                     	University of North Carolina at Chapel Hill
ST:LAST_NAME                     	Zhao
ST:FIRST_NAME                    	Haoduo
ST:ADDRESS                       	135 DAUER DR, chapel hill, NC, 27599, USA
ST:EMAIL                         	raven456@unc.edu
ST:PHONE                         	19845281428
#SUBJECT
SU:SUBJECT_TYPE                  	Cultured cells
SU:SUBJECT_SPECIES               	Homo sapiens
SU:TAXONOMY_ID                   	9606
#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           	-	CG-1	Sample source:Human Liver S9 fractions | Treatment:Control	Mass spec config=Full MS1; RAW_FILE_NAME(Raw file name)=Gold_300uL_pos_20241114Pesticide-S9_PG1-2-S9-Final_5uL_Control-CG1-1.raw
SUBJECT_SAMPLE_FACTORS           	-	CG-2	Sample source:Human Liver S9 fractions | Treatment:Control	Mass spec config=Full MS1; RAW_FILE_NAME(Raw file name)=Gold_300uL_pos_20241114Pesticide-S9_PG1-2-S9-Final_5uL_Control-CG1-2.raw
SUBJECT_SAMPLE_FACTORS           	-	CG-3	Sample source:Human Liver S9 fractions | Treatment:Control	Mass spec config=Full MS1; RAW_FILE_NAME(Raw file name)=Gold_300uL_pos_20241114Pesticide-S9_PG1-2-S9-Final_5uL_Control-CG1-3.raw
SUBJECT_SAMPLE_FACTORS           	-	CG-4	Sample source:Human Liver S9 fractions | Treatment:Control	Mass spec config=Full MS1; RAW_FILE_NAME(Raw file name)=Gold_300uL_pos_20241114Pesticide-S9_PG1-2-S9-Final_5uL_Control-CG1-4.raw
SUBJECT_SAMPLE_FACTORS           	-	CG-5	Sample source:Human Liver S9 fractions | Treatment:Control	Mass spec config=Full MS1; RAW_FILE_NAME(Raw file name)=Gold_300uL_pos_20241114Pesticide-S9_PG1-2-S9-Final_5uL_Control-CG1-5.raw
SUBJECT_SAMPLE_FACTORS           	-	PG-1	Sample source:Human Liver S9 fractions | Treatment:Pesiticide exposure	Mass spec config=Full MS1; RAW_FILE_NAME(Raw file name)=Gold_300uL_pos_20241114Pesticide-S9_PG1-2-S9-Final_5uL_Pesticide-PG1-1.raw
SUBJECT_SAMPLE_FACTORS           	-	PG-2	Sample source:Human Liver S9 fractions | Treatment:Pesiticide exposure	Mass spec config=Full MS1; RAW_FILE_NAME(Raw file name)=Gold_300uL_pos_20241114Pesticide-S9_PG1-2-S9-Final_5uL_Pesticide-PG1-2.raw
SUBJECT_SAMPLE_FACTORS           	-	PG-3	Sample source:Human Liver S9 fractions | Treatment:Pesiticide exposure	Mass spec config=Full MS1; RAW_FILE_NAME(Raw file name)=Gold_300uL_pos_20241114Pesticide-S9_PG1-2-S9-Final_5uL_Pesticide-PG1-3.raw
SUBJECT_SAMPLE_FACTORS           	-	PG-4	Sample source:Human Liver S9 fractions | Treatment:Pesiticide exposure	Mass spec config=Full MS1; RAW_FILE_NAME(Raw file name)=Gold_300uL_pos_20241114Pesticide-S9_PG1-2-S9-Final_5uL_Pesticide-PG1-4.raw
SUBJECT_SAMPLE_FACTORS           	-	PG-5	Sample source:Human Liver S9 fractions | Treatment:Pesiticide exposure	Mass spec config=Full MS1; RAW_FILE_NAME(Raw file name)=Gold_300uL_pos_20241114Pesticide-S9_PG1-2-S9-Final_5uL_Pesticide-PG1-5.raw
SUBJECT_SAMPLE_FACTORS           	-	PG-PRM-1	Sample source:Human Liver S9 fractions | Treatment:PRM for treatment pooled mix	Mass spec config=PRM MS2; RAW_FILE_NAME(Raw file name)=Gold_300uL_pos_20241117_Pesticide-S9_PG1-2-S9-PRM_PG1QC_5uL_IL1.raw
SUBJECT_SAMPLE_FACTORS           	-	PG-PRM-2	Sample source:Human Liver S9 fractions | Treatment:PRM for treatment pooled mix	Mass spec config=PRM MS2; RAW_FILE_NAME(Raw file name)=Gold_300uL_pos_20241117_Pesticide-S9_PG1-2-S9-PRM_PG1QC_5uL_IL2.raw
SUBJECT_SAMPLE_FACTORS           	-	PG-PRM-3	Sample source:Human Liver S9 fractions | Treatment:PRM for treatment pooled mix	Mass spec config=PRM MS2; RAW_FILE_NAME(Raw file name)=Gold_300uL_pos_20241117_Pesticide-S9_PG1-2-S9-PRM_PG1QC_5uL_IL3.raw
SUBJECT_SAMPLE_FACTORS           	-	PG-PRM-4	Sample source:Human Liver S9 fractions | Treatment:PRM for treatment pooled mix	Mass spec config=PRM MS2; RAW_FILE_NAME(Raw file name)=Gold_300uL_pos_20241117_Pesticide-S9_PG1-2-S9-PRM_PG1QC_5uL_IL4.raw
SUBJECT_SAMPLE_FACTORS           	-	PG-PRM-5	Sample source:Human Liver S9 fractions | Treatment:PRM for treatment pooled mix	Mass spec config=PRM MS2; RAW_FILE_NAME(Raw file name)=Gold_300uL_pos_20241117_Pesticide-S9_PG1-2-S9-PRM_PG1QC_5uL_IL5.raw
SUBJECT_SAMPLE_FACTORS           	-	PG-PRM-6	Sample source:Human Liver S9 fractions | Treatment:PRM for treatment pooled mix	Mass spec config=PRM MS2; RAW_FILE_NAME(Raw file name)=Gold_300uL_pos_20241117_Pesticide-S9_PG1-2-S9-PRM_PG1QC_5uL_IL6.raw
SUBJECT_SAMPLE_FACTORS           	-	PG-PRM-7	Sample source:Human Liver S9 fractions | Treatment:PRM for treatment pooled mix	Mass spec config=PRM MS2; RAW_FILE_NAME(Raw file name)=Gold_300uL_pos_20241117_Pesticide-S9_PG1-2-S9-PRM_PG1QC_5uL_IL7.raw
SUBJECT_SAMPLE_FACTORS           	-	PG-PRM-8	Sample source:Human Liver S9 fractions | Treatment:PRM for treatment pooled mix	Mass spec config=PRM MS2; RAW_FILE_NAME(Raw file name)=Gold_300uL_pos_20241117_Pesticide-S9_PG1-2-S9-PRM_PG1QC_5uL_IL8.raw
SUBJECT_SAMPLE_FACTORS           	-	PG-PRM-9	Sample source:Human Liver S9 fractions | Treatment:PRM for treatment pooled mix	Mass spec config=PRM MS2; RAW_FILE_NAME(Raw file name)=Gold_300uL_pos_20241117_Pesticide-S9_PG1-2-S9-PRM_PG1QC_5uL_IL9.raw
SUBJECT_SAMPLE_FACTORS           	-	PG-PRM-10	Sample source:Human Liver S9 fractions | Treatment:PRM for treatment pooled mix	Mass spec config=PRM MS2; RAW_FILE_NAME(Raw file name)=Gold_300uL_pos_20241117_Pesticide-S9_PG1-2-S9-PRM_PG1QC_5uL_IL10.raw
SUBJECT_SAMPLE_FACTORS           	-	STD-PRM-1	Sample source:STD | Treatment:NA	Mass spec config=PRM MS2; RAW_FILE_NAME(Raw file name)=Gold_300uL_pos_20241117_Pesticide-S9_PG1-2-S9-PRM_PG1STD_5uL_IL1.raw
SUBJECT_SAMPLE_FACTORS           	-	STD-PRM-2	Sample source:STD | Treatment:NA	Mass spec config=PRM MS2; RAW_FILE_NAME(Raw file name)=Gold_300uL_pos_20241117_Pesticide-S9_PG1-2-S9-PRM_PG1STD_5uL_IL2.raw
SUBJECT_SAMPLE_FACTORS           	-	STD-PRM-3	Sample source:STD | Treatment:NA	Mass spec config=PRM MS2; RAW_FILE_NAME(Raw file name)=Gold_300uL_pos_20241117_Pesticide-S9_PG1-2-S9-PRM_PG1STD_5uL_IL3.raw
SUBJECT_SAMPLE_FACTORS           	-	STD-PRM-4	Sample source:STD | Treatment:NA	Mass spec config=PRM MS2; RAW_FILE_NAME(Raw file name)=Gold_300uL_pos_20241117_Pesticide-S9_PG1-2-S9-PRM_PG1STD_5uL_IL4.raw
SUBJECT_SAMPLE_FACTORS           	-	STD-PRM-5	Sample source:STD | Treatment:NA	Mass spec config=PRM MS2; RAW_FILE_NAME(Raw file name)=Gold_300uL_pos_20241117_Pesticide-S9_PG1-2-S9-PRM_PG1STD_5uL_IL5.raw
#COLLECTION
CO:COLLECTION_SUMMARY            	Pesticide metabolite generated by liver S9 fraction and identified via CMDN.
CO:SAMPLE_TYPE                   	Liver
#TREATMENT
TR:TREATMENT_SUMMARY             	Pesticide mixtures were diluted in 50 mM phosphate buffer (pH 7.4)
TR:TREATMENT_SUMMARY             	containing 10 mM magnesium chloride and 10 mM DL-dithiothreitol (DTT) to a
TR:TREATMENT_SUMMARY             	final concentration of 1 ppm per compound. The liver S9 fraction (2 mg/ mL)
TR:TREATMENT_SUMMARY             	was combined with pesticide mixtures in 96-well plates (N = 5), and
TR:TREATMENT_SUMMARY             	pre-incubated at 37 ºC for 5 min. The biotransformation reaction was initiated
TR:TREATMENT_SUMMARY             	by the addition of coenzyme NADPH (5mM), yielding a final volume of 200 μL.
#SAMPLEPREP
SP:SAMPLEPREP_SUMMARY            	After 2h of incubation, reactions were quenched by adding 200 µL ice-cold
SP:SAMPLEPREP_SUMMARY            	acetone and stored at -80 ℃ to ensure deproteinization. Samples were
SP:SAMPLEPREP_SUMMARY            	centrifuged at 13,000 rpm, and supernatants were freeze-dried and
SP:SAMPLEPREP_SUMMARY            	reconstituted in 100 μL of 50% acetonitrile prior to analysis.
SP:SAMPLEPREP_SUMMARY            	Heat-inactivated S9 fractions (pre-incubated at 80 °C for 5 min) were used as
SP:SAMPLEPREP_SUMMARY            	negative controls (N = 5).
#CHROMATOGRAPHY
CH:CHROMATOGRAPHY_TYPE           	Reversed phase
CH:INSTRUMENT_NAME               	Vanquish
CH:COLUMN_NAME                   	Thermo Hypersil GOLD aQ C18 Polar Endcapped HPLC Column (100 × 2.1mm, 1.9um)
CH:SOLVENT_A                     	100% water; 4 mM ammonium formate; 0.1% formic acid in
CH:SOLVENT_B                     	100% Methanol; 4 mM ammonium formate; 0.1% formic acid
CH:FLOW_GRADIENT                 	12% B, 0 min; 12 to 95% B, 0-8 min; 95 to 100% B, 8–9 min; 100% B, 9-11 min;
CH:FLOW_GRADIENT                 	100-12% B, 11–11.1 min; 12% B, 11.1–14 min
CH:FLOW_RATE                     	0.3mL/min
CH:COLUMN_TEMPERATURE            	40
#ANALYSIS
AN:ANALYSIS_TYPE                 	MS
#MS
MS:INSTRUMENT_NAME               	Thermo Q Exactive Orbitrap
MS:INSTRUMENT_TYPE               	Orbitrap
MS:MS_TYPE                       	ESI
MS:ION_MODE                      	POSITIVE
MS:MS_COMMENTS                   	Only HESI positive mode was performed, with following ion source setting: sheath
MS:MS_COMMENTS                   	gas 60 L/min, aux gas 10 L/min, sweep gas 1 L/min, spray voltage 2.75 kV,
MS:MS_COMMENTS                   	capillary 325 °C, and aux gas heater 400 °C. For MS1 full scan, the AGC target
MS:MS_COMMENTS                   	is set as 3e6, with maximum IT set as 250 ms. For MS2 PRM scan, following
MS:MS_COMMENTS                   	parameters were set: resolution 17,500, AGC target 2e5, Maxmium IT 100ms, loop
MS:MS_COMMENTS                   	count 12, MSX count 1, isolation window 0.7 m/z, stepped NCE 20, 50, 100. All QE
MS:MS_COMMENTS                   	data were acquired and processed by MSDial, including MS1 full scan data for
MS:MS_COMMENTS                   	metabolic feature profiling and MS/MS spectra data for unknown identification
MS:MS_COMMENTS                   	and structure elucidation.
#MS_METABOLITE_DATA
MS_METABOLITE_DATA:UNITS	intensity
MS_METABOLITE_DATA_START
Samples	CG-1	CG-2	CG-3	CG-4	CG-5	PG-1	PG-2	PG-3	PG-4	PG-5
Factors	Sample source:Human Liver S9 fractions | Treatment:Control	Sample source:Human Liver S9 fractions | Treatment:Control	Sample source:Human Liver S9 fractions | Treatment:Control	Sample source:Human Liver S9 fractions | Treatment:Control	Sample source:Human Liver S9 fractions | Treatment:Control	Sample source:Human Liver S9 fractions | Treatment:Pesiticide exposure	Sample source:Human Liver S9 fractions | Treatment:Pesiticide exposure	Sample source:Human Liver S9 fractions | Treatment:Pesiticide exposure	Sample source:Human Liver S9 fractions | Treatment:Pesiticide exposure	Sample source:Human Liver S9 fractions | Treatment:Pesiticide exposure
Ethiofencarb:+O	72714248	52939456	57366592	65664804	47247072	546386752	645238656	770355968	517498368	529220992
Sethoxydim:-C2H4-CH2	3140314	1342996	694926	222081	124663	143116256	150122496	152572000	152108960	151393136
Pirimiphos ethyl: Dearylation of organphosphosulfur compound-l-1	4520656	4391726	2061584	2825332	1440470	95740608	104949160	98039736	98839008	101217696
Chlortoluron:+O	570976	1067418	666251	925223	334606	305935104	298106816	293775648	292181888	297463040
Isoproturon:+O-2	18634944	35857788	34198612	32447548	39394328	68500024	83495912	87829160	71459568	99924424
Isoproturon:+O-1	3332929	3089415	6458952	7385642	3136015	55968208	50620044	60609524	53949528	52574596
Fenthion sulfoxide:-S+O	21620478	49933988	50819184	49933092	47713076	203432464	186340672	189155936	207434832	248994576
Bensulide:-C2H4-CH2	85157	103892	147457	148494	27179	98773824	97310280	103324168	109078616	107758056
Mepronil:-C2H4-CH2-2	1286173	1364543	895831	1134585	992136	197539008	231209744	235394864	206305344	253913216
Etrimfos:-C2H4	13487630	13070563	9811404	13862575	13227903	29518346	34630048	36263380	32196336	38099868
Cafenstrole:+O-1	108179	160411	42527	109735	74460	53283956	70650296	57376832	103596320	119561512
Iprovalicarb:+O-1	410717.475	410717.475	410717.475	410717.475	410717.475	12054255	8499310	4107175	14746624	24515456
Mepronil:+O-4	1435.300488	1435.300488	65511	1435.300488	14353	9327232	5603910	1356603	4829449	18466806
Phenthoate:-S+O-CH2	9210.071875	92101	9210.071875	149609	9210.071875	33616436	22190876	16116910	27739288	67444576
Mepronil:+O-1	616890	1476147	1329144	2570278	2399820	37741692	30208402	18019250	21979670	79123960
Crufomate:+O	1727.535938	21391	22360	17275	1727.535938	33983668	43177460	18700178	33947740	73756352
Chlorthiophos:-S+O+O	214276.425	214276.425	214276.425	214276.425	214276.425	8216098	5334066	2142764	9627355	23837908
Triflusulfuron-methyl:+O-1	8990.239844	8990.239844	8990.239844	8990.239844	8990.239844	246295	401724	89902	830965	1495850
Bensulide:-S+O	226343.15	226343.15	226343.15	226343.15	226343.15	2575186	2537720	2263432	4232330	8215030
Propiconazole:+O-1	61394	6139.417578	6139.417578	6139.417578	6139.417578	52853596	46879880	42394764	72378848	142905552
Etrimfos:-S+O	552734	643316	900244	875761	162436	259116720	151198128	231608736	323395360	481593216
Propiconazole:+O-2	1012.691406	10127	10947	51275	31534	78170744	56923400	66808684	136765184	40520036
Metolachlor:-CH2	14073779	8247564	5836686	4154785	4636582	226792160	311626048	230308432	349315008	130167464
Bromuconazole, cis-:+O-1	61034.80625	61034.80625	61034.80625	61034.80625	61034.80625	2535064	3838125	1774603	4529454	610348
Sethoxydim:+O	16687	100542	23424	16883	4258	42358536	65330912	27547450	75731328	18587266
Etrimfos:+O	10606799	5348316	2685005	1515253	1230675	183936912	240460608	133899656	272974720	110198664
Benalaxyl:+O-2	1875551	2096534	1533335	1898721	1479625	50699192	70469016	38573280	80641312	19747134
Famoxadone:-CO2-NH3	3535950	2414408	3604489	2421996	3250349	6848859	11819293	11441365	12672887	3079880
Mepronil:-C2H4-CH2-1	852979	1028499	332221	1283076	326191	11001043	12686785	11909095	13752525	8759710
Pirimiphos ethyl:-C2H4-2	92819.6375	92819.6375	92819.6375	92819.6375	92819.6375	928196	1819636	4213946	1927681	1835401
Propyzamide:+H2O	581194	178729	48101	25747	47793	18580190	22625830	22051612	23079914	13596567
Benalaxyl:+O-1	246970	300975	302924	151081	215698	45974452	55552520	54443972	58222668	31183844
Bensulide:+NH	113487	108394	63356	67906	191779	7238850	9040621	9227714	9881435	3709641
Pirimiphos ethyl:-S+O	27034010	34648788	35885672	30761010	31431732	185726064	233712576	223649728	231896560	103805624
Antimycin A:-CH2+O-2	566556.35	566556.35	566556.35	566556.35	566556.35	21432782	23908616	35243316	31429358	5665564
Bromuconazole, cis-:-Br+H+C2H2O	524803.95	524803.95	524803.95	524803.95	524803.95	6736328	9844057	9368074	11940835	5248040
Carbophenothion:+O	2458767	3371500	1918629	2732795	2236422	134804272	153899952	144250624	100312376	84788272
Antimycin A:-H2+O	675180.75	675180.75	675180.75	675180.75	675180.75	21532340	18243094	12763520	17408010	6751808
Clethodim:-C2H4	770170.25	770170.25	770170.25	770170.25	770170.25	10738202	10566751	8999266	7701702	9953351
Antimycin A:+O	4344007.2	4344007.2	4344007.2	4344007.2	4344007.2	75957160	76719936	75494280	72001056	43440072
Sethoxydim:-C2H4	2769752	3049100	2919631	2460799	3096900	11084460	12418046	11892119	11468317	8875434
Antimycin A:+CO+H2	88306.05625	88306.05625	88306.05625	88306.05625	88306.05625	1206570	1460691	1587081	900149	883061
Cyhalothrin iso 1:-NH	1347109	1268787	706531	867215	1295378	3776813	2616558	2109591	1794301	2368921
Sethoxydim:-C2H4+NH-2	570219	927732	900408	830046	533864	8823331	7632908	6931310	6441812	6739295
MS_METABOLITE_DATA_END
#METABOLITES
METABOLITES_START
metabolite_name	mz	rt	Molecular Formula	INCHIKEY	SMILES
Antimycin A:+CO+H2	579.29211	8.781	C29H42N2O10	KFYHDQRFNYYWFW-PROVFDEWSA-N	CC(C)CC(O[C@H]([C@H]1CCCCCC)[C@H](C)OC([C@@H](NC(C2=CC=CC(NCO)=C2OC=O)=O)[C@@H](C)OC1=O)=O)=O
Antimycin A:+O	565.27527	8.487	C28H40N2O10	JADURWQKSAPKBP-CIOBJBERSA-N	CC(C)CC(O[C@H]([C@H]1CCCCCC)[C@H](C)OC([C@@H](NC(C2=CC(O)=CC(NC=O)=C2O)=O)[C@@H](C)OC1=O)=O)=O
Antimycin A:-CH2+O-2	551.25989	8.206	C27H38N2O10	CDGVLDAHZARAGE-JUUKQFNXSA-N	CC(C)CC(O[C@H]([C@H]1CCCCCC)[C@H](C)OC([C@@H](NC(C2=CC(O)=CC(NC=O)=C2O)=O)COC1=O)=O)=O
Antimycin A:-H2+O	563.25946	8.393	C28H38N2O10	GEOSOEDDUNCTCH-XRPFWVRRSA-N	CC(C)CC(O[C@H]([C@H]1C/C=C/CCC)[C@H](C)OC([C@@H](NC(C2=CC(O)=CC(NC=O)=C2O)=O)[C@@H](C)OC1=O)=O)=O
Benalaxyl:+O-1	342.17004	8.03	C20H23NO4	OLGHWHXXVCIRAJ-UHFFFAOYSA-N	COC(C(N(C1=C(C)C=CC=C1C)C(CC2=CC=C(O)C=C2)=O)C)=O
Benalaxyl:+O-2	342.17004	7.398	C20H23NO4	RZKGAOMPYNEIRU-UHFFFAOYSA-N	COC(C(N(C1=C(C)C=CC=C1O)C(CC2=CC=CC=C2)=O)C)=O
Bensulide:+NH	413.07864	8.115	C14H25N2O4PS3	WSZOHPMYCBWPGQ-UHFFFAOYSA-N	S=P(OC(C)C)(OC(CN)C)SCCNS(=O)(C1=CC=CC=C1)=O
Bensulide:-C2H4-CH2	356.02087	5.58	C11H18NO4PS3	FRKQYKAGWDQFJF-UHFFFAOYSA-N	S=P(OC(C)C)(O)SCCNS(=O)(C1=CC=CC=C1)=O
Bensulide:-S+O	382.09073	7.159	C14H24NO5PS2	XFTSUNODOZMOBM-UHFFFAOYSA-N	O=P(OC(C)C)(OC(C)C)SCCNS(=O)(C1=CC=CC=C1)=O
Bromuconazole, cis-:+O-1	391.95657	7.299	C13H12BrCl2N3O2	AXVQQMHYPYVKTA-UHFFFAOYSA-N	ClC1=C(O)C(Cl)=CC=C1C2(OCC(Br)C2)CN3N=CN=C3
Bromuconazole, cis-:-Br+H+C2H2O	340.06052	8.206	C15H15Cl2N3O2	WUXANIXFLJONQP-UHFFFAOYSA-N	ClC1=CC(Cl)=CC=C1C2(OCC(C(C)=O)C2)CN3N=CN=C3
Cafenstrole:+O-1	367.14432	6.381	C16H22N4O4S	FRTHITAIKLGSRB-UHFFFAOYSA-N	O=C(N(CC)CCO)N1N=C(S(C2=C(C)C=C(C)C=C2C)(=O)=O)N=C1
Carbophenothion:+O	358.97565	8.312	C11H16ClO3PS3	DJNAUSCKTRSLHN-UHFFFAOYSA-N	ClC1=CC=C(SCSP(OCCO)(OCC)=S)C=C1
Chlorthiophos:-S+O+O	360.98218	7.065	C11H15Cl2O5PS	NJLONVAOYMFCAI-UHFFFAOYSA-N	O=P(OCCO)(OCC)OC1=CC(Cl)=C(SC)C=C1Cl
Chlortoluron:+O	229.07407	4.721	C10H13ClN2O2	BPEWOVZUTZDINP-UHFFFAOYSA-N	ON(C(NC1=CC=C(C)C(Cl)=C1)=O)C
Clethodim:-C2H4	332.10721	8.446	C15H22ClNO3S	VSFUZUNLXMPGMY-QQTWPTJBSA-N	O=C1C(C(CC)=NOC/C=C/Cl)=C(O)CC(CC(S)C)C1
Crufomate:+O	308.08139	6.753	C12H19ClNO4P	LDNCSERCQDVUII-UHFFFAOYSA-N	CC(C)(CO)C1=CC=C(OP(OC)(NC)=O)C(Cl)=C1
Cyhalothrin iso 1:-NH	452.12451	9.141	C23H21NClF3O3	JZPCENLQXQIJEC-QTSMVKJYSA-N	CC1(C)C(C(OC(C=N)C2=CC=CC(OC3=CC=CC=C3)=C2)=O)C1/C=C(Cl)/C(F)(F)F
Ethiofencarb:+O	242.08479	4.238	C11H15NO3S	GJYMUGYQGASZJF-UHFFFAOYSA-N	O=C(NC)OC1=CC=CC=C1CSCCO
Etrimfos:+O	309.06757	7.367	C10H17N2O5PS	XMGRLKCPHWEXFW-UHFFFAOYSA-N	S=P(OC)(OC)OC1=CC(OCCO)=NC(CC)=N1
Etrimfos:-C2H4	265.04132	5.854	C8H13N2O4PS	XYNNOOLMQIVIQK-UHFFFAOYSA-N	OC1=NC(CC)=NC(OP(OC)(OC)=S)=C1
Etrimfos:-S+O	277.09445	7.176	C10H17N2O5P	WLTKMXYMVTXVPF-UHFFFAOYSA-N	O=P(OC)(OC)OC1=CC(OCC)=NC(CC)=N1
Famoxadone:-CO2-NH3	331.14401	7.776	C21H15NO2	LATMRUOXLJMGBH-UHFFFAOYSA-N	O=C1OC(C2=CC=C(OC3=CC=CC=C3)C=C2)=CN1C4=CC=CC=C4
Fenthion sulfoxide:-S+O	279.04456	4.869	C10H15O5PS	GTZCKTIZOGTWQO-UHFFFAOYSA-N	O=P(OC)(OC)OC1=CC=C(S(C)=O)C(C)=C1
Iprovalicarb:+O-1	337.21219	6.47	C18H28N2O4	ZLAFRCXFUSAZGF-XUJLQICISA-N	CC(C)[C@@H](C(NC(C1=CC=C(C)C=C1)C)=O)NC(OC(CO)C)=O
Isoproturon:+O-1	223.14426	4.813	C12H18N2O2	MPUWAWYJXIJYDM-UHFFFAOYSA-N	O=C(N(C)C)NC1=CC=C(C(CO)C)C=C1
Isoproturon:+O-2	223.14426	4.721	C12H18N2O2	JGVRUCYSFDZYCB-UHFFFAOYSA-N	O=C(N(C)CO)NC1=CC=C(C(C)C)C=C1
Mepronil:+O-1	286.14359	6.701	C17H19NO3	MURGMZFAAWGRSD-UHFFFAOYSA-N	O=C(NC1=CC=CC(OC(CO)C)=C1)C2=CC=CC=C2C
Mepronil:+O-4	286.14359	6.561	C17H19NO3	XQBNIENMVJDKSE-UHFFFAOYSA-N	O=C(NC1=CC=CC(OC(C)C)=C1)C2=CC=CC=C2CO
Mepronil:-C2H4-CH2-1	228.10181	7.861	C14H13NO2	UCXCRDPOWBLPHN-UHFFFAOYSA-N	O=C(NC1=CC=CC(OC)=C1)C2=CC=CC=C2
Mepronil:-C2H4-CH2-2	228.10181	5.804	C14H13NO2	SEZMBJGKTFAUDD-UHFFFAOYSA-N	O=C(NC1=CC=CC(O)=C1)C2=CC=CC=C2C
Metolachlor:-CH2	270.12552	7.292	C14H20ClNO2	RNRZTRIOAPZEME-UHFFFAOYSA-N	O=C(N(C1=C(C)C=CC=C1CC)C(CO)C)CCl
Phenthoate:-S+O-CH2	291.04578	6.58	C11H15O5PS	LQRNWJQHZCTTTD-UHFFFAOYSA-N	CCOC(C(C1=CC=CC=C1)SP(O)(OC)=O)=O
Pirimiphos ethyl: Dearylation of organphosphosulfur compound-l-1	182.12935	4.496	C9H15N3O	NQCPECCCWDWTJJ-UHFFFAOYSA-N	CC1=CC(O)=NC(N(CC)CC)=N1
Pirimiphos ethyl:-C2H4-2	306.10349	7.939	C11H20N3O3PS	WDDBAKLOWAZKGE-UHFFFAOYSA-N	CC1=CC(OP(O)(OCC)=S)=NC(N(CC)CC)=N1
Pirimiphos ethyl:-S+O	318.15799	8.118	C13H24N3O4P	WSPIMFPJZBRGMD-UHFFFAOYSA-N	CC1=CC(OP(OCC)(OCC)=O)=NC(N(CC)CC)=N1
Propiconazole:+O-1	358.07169	7.159	C15H17Cl2N3O3	GZZNFYOGUUPAEU-UHFFFAOYSA-N	ClC1=C(C=CC(Cl)=C1)C2(OC(CCCO)CO2)CN3N=CN=C3
Propiconazole:+O-2	358.07169	7.223	C15H17Cl2N3O3	UNJMVBHVQWFXGJ-UHFFFAOYSA-N	CCCC(CO1)OC1(C2=C(Cl)C(O)=C(Cl)C=C2)CN3N=CN=C3
Propyzamide:+H2O	274.03912	7.984	C12H13Cl2NO2	LCOYVBMZPXAXRN-UHFFFAOYSA-N	O=C(NC(C=C)(CO)C)C1=CC(Cl)=CC(Cl)=C1
Sethoxydim:+O	344.18896	7.323	C17H29NO4S	SIOPPXAEQAEEFS-NBVRZTHBSA-N	OC1=C(/C(CCCO)=N/OCC)C(CC(CC(C)SCC)C1)=O
Sethoxydim:-C2H4	300.16339	8.611	C15H25NO3S	FMTRAUJQPVQBJA-FOWTUZBSSA-N	OC1=C(/C(CCC)=N/O)C(CC(CC(C)SCC)C1)=O
Sethoxydim:-C2H4+NH-2	315.17429	9.275	C15H26N2O3S	VAPBUOQYFNLULL-SFQUDFHCSA-N	OC1=C(/C(CCCN)=N/O)C(CC(CC(C)SCC)C1)=O
Sethoxydim:-C2H4-CH2	286.14685	4.496	C14H23NO3S	IDKWNDOZZYDTTM-OQLLNIDSSA-N	OC1=C(/C=N/OCC)C(CC(CC(C)SCC)C1)=O
Triflusulfuron-methyl:+O-1	509.10608	7.068	C17H19F3N6O7S	SDNJNMGTELWTCD-UHFFFAOYSA-N	O=C(OC)C1=CC(O)=CC(C)=C1S(=O)(NC(NC2=NC(N(C)C)=NC(OCC(F)(F)F)=N2)=O)=O
METABOLITES_END
#END