#METABOLOMICS WORKBENCH epmosher_20210121_142232 DATATRACK_ID:2414 STUDY_ID:ST001658 ANALYSIS_ID:AN002708 PROJECT_ID:PR001063
VERSION             	1
CREATED_ON             	January 25, 2021, 11:40 am
#PROJECT
PR:PROJECT_TITLE                 	Control of Topoisomerase II Activity and Chemotherapeutic Inhibition by TCA
PR:PROJECT_TITLE                 	Cycle Metabolites
PR:PROJECT_SUMMARY               	Topoisomerase II (topo II) is essential for disentangling newly-replicated
PR:PROJECT_SUMMARY               	chromosomes. DNA unlinking involves the physical passage of one DNA duplex
PR:PROJECT_SUMMARY               	through another and depends on the transient formation of double-strand DNA
PR:PROJECT_SUMMARY               	breaks, a step exploited by frontline chemotherapies to kill cancer cells.
PR:PROJECT_SUMMARY               	Although anti-topo II drugs are efficacious, they also elicit cytotoxic side
PR:PROJECT_SUMMARY               	effects in normal cells; insights into how topo II is regulated in different
PR:PROJECT_SUMMARY               	cellular contexts is essential to improve their targeted use. Using chemical
PR:PROJECT_SUMMARY               	fractionation and mass spectrometry, we have discovered that topo II is subject
PR:PROJECT_SUMMARY               	to metabolic control through the TCA cycle. We show that TCA metabolites
PR:PROJECT_SUMMARY               	stimulate topo II activity in vitro and that levels of TCA flux modulate
PR:PROJECT_SUMMARY               	cellular sensitivity to anti-topo II drugs in vivo. Our works reveals an
PR:PROJECT_SUMMARY               	unanticipated connection between the control of DNA topology and cellular
PR:PROJECT_SUMMARY               	metabolism, a finding with important ramifications for the clinical use of
PR:PROJECT_SUMMARY               	anti-topo II therapies.
PR:INSTITUTE                     	Johns Hopkins University
PR:LAST_NAME                     	Mosher
PR:FIRST_NAME                    	Eric
PR:ADDRESS                       	725 North Wolfe Street, Biophysics 307
PR:EMAIL                         	emosher2@jhmi.edu
PR:PHONE                         	410-952-9154
#STUDY
ST:STUDY_TITLE                   	Control of Topoisomerase II Activity and Chemotherapeutic Inhibition by TCA
ST:STUDY_TITLE                   	Cycle Metabolites
ST:STUDY_SUMMARY                 	Topoisomerase II (topo II) is essential for disentangling newly-replicated
ST:STUDY_SUMMARY                 	chromosomes. DNA unlinking involves the physical passage of one DNA duplex
ST:STUDY_SUMMARY                 	through another and depends on the transient formation of double-strand DNA
ST:STUDY_SUMMARY                 	breaks, a step exploited by frontline chemotherapies to kill cancer cells.
ST:STUDY_SUMMARY                 	Although anti-topo II drugs are efficacious, they also elicit cytotoxic side
ST:STUDY_SUMMARY                 	effects in normal cells; insights into how topo II is regulated in different
ST:STUDY_SUMMARY                 	cellular contexts is essential to improve their targeted use. Using chemical
ST:STUDY_SUMMARY                 	fractionation and mass spectrometry, we have discovered that topo II is subject
ST:STUDY_SUMMARY                 	to metabolic control through the TCA cycle. We show that TCA metabolites
ST:STUDY_SUMMARY                 	stimulate topo II activity in vitro and that levels of TCA flux modulate
ST:STUDY_SUMMARY                 	cellular sensitivity to anti-topo II drugs in vivo. Our works reveals an
ST:STUDY_SUMMARY                 	unanticipated connection between the control of DNA topology and cellular
ST:STUDY_SUMMARY                 	metabolism, a finding with important ramifications for the clinical use of
ST:STUDY_SUMMARY                 	anti-topo II therapies.
ST:INSTITUTE                     	Johns Hopkins University
ST:LAST_NAME                     	Mosher
ST:FIRST_NAME                    	Eric
ST:ADDRESS                       	725 North Wolfe Street, Biophysics 307
ST:EMAIL                         	emosher2@jhmi.edu
ST:PHONE                         	410-952-9154
#SUBJECT
SU:SUBJECT_TYPE                  	Yeast
SU:SUBJECT_SPECIES               	Saccharomyces cerevisiae
SU:TAXONOMY_ID                   	4932
SU:CELL_STRAIN_DETAILS           	BY4741
#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           	-	F4	Treatment:HPLC fraction 4	RAW_FILE_NAME=f4negR1.mzXML f4negR2.mzXML f4negR3.mzXML f4posR1.mzXML f4posR2.mzXML f4posR3.mzXML nf4negR1.mzXML nf4negR2.mzXML nf4negR3.mzXML nf4posR1.mzXML nf4posR2.mzXML nf4posR3.mzXML
SUBJECT_SAMPLE_FACTORS           	-	F5	Treatment:HPLC fraction 5	RAW_FILE_NAME=f5negR1.mzXML f5negR2.mzXML f5negR3.mzXML f5posR1.mzXML f5posR2.mzXML f5posR3.mzXML nf5negR1.mzXML nf5negR2.mzXML nf5negR3.mzXML nf5posR1.mzXML nf5posR2.mzXML nf5posR3.mzXML
SUBJECT_SAMPLE_FACTORS           	-	F6	Treatment:HPLC fraction 6	RAW_FILE_NAME=f6negR1.mzXML f6negR2.mzXML f6negR3.mzXML f6posR1.mzXML f6posR2.mzXML f6posR3.mzXML nf6negR1.mzXML nf6negR2.mzXML nf6negR3.mzXML nf6posR1.mzXML nf6posR2.mzXML nf6posR3.mzXML
#COLLECTION
CO:COLLECTION_SUMMARY            	Yeast cultures were grown in SC-sulfate media and were harvested at OD600
CO:COLLECTION_SUMMARY            	0.4-0.8 by vacuum filtration then washed with 100mM ammonium acetate - TEA (pH
CO:COLLECTION_SUMMARY            	8.0). Metabolites were extracted by the addition of pre-chilled 10mL 90%
CO:COLLECTION_SUMMARY            	methanol, 10mM ammonium acetate - TEA (pH 8.0). Cell debris was removed by
CO:COLLECTION_SUMMARY            	centrifugation at 4000g for 10-15 minutes. Extracts were subsequently passed
CO:COLLECTION_SUMMARY            	through 3 kDa MWCO filters. Filtrate was diluted 2-fold with water and
CO:COLLECTION_SUMMARY            	lyophilized. Lyophilized metabolite extracts were resuspended with water and pH
CO:COLLECTION_SUMMARY            	was adjusted to 10 with TEA. The extract was then passed through a mixed-mode
CO:COLLECTION_SUMMARY            	anion exchange solid phase extraction cartridge and fractionated by
CO:COLLECTION_SUMMARY            	reverse-phase HPLC on a C18 column. One column volume of water plus 0.1% formic
CO:COLLECTION_SUMMARY            	acid and eight column volumes of methanol were passed through the column.
CO:COLLECTION_SUMMARY            	Fractions that eluted during the aqueous phase were then lyophilized.
CO:SAMPLE_TYPE                   	Yeast cells
#TREATMENT
TR:TREATMENT_SUMMARY             	Active fractions were run on a normal-phase HPLC on an amide column and
TR:TREATMENT_SUMMARY             	fractions were collected. Fractions 4, 5, and 6 were subjected to metabolomics
TR:TREATMENT_SUMMARY             	analyses.
#SAMPLEPREP
SP:SAMPLEPREP_SUMMARY            	Fractions of interest were lyophilized then reconstituted in water plus 0.1%
SP:SAMPLEPREP_SUMMARY            	formic acid such that samples reached a final concentration of 20 mg/mL.
#CHROMATOGRAPHY
CH:CHROMATOGRAPHY_TYPE           	Normal phase
CH:INSTRUMENT_NAME               	Thermo Dionex Ultimate 3000 RS
CH:COLUMN_NAME                   	PolyLC Polyhydroxyethyl A (200 x 2.1mm, 5um)
CH:FLOW_GRADIENT                 	0-2min 80% B, 2-13min 80-40% B, 13-15min 40-10% B, 15-16min 10-80% B, 16-20min
CH:FLOW_GRADIENT                 	80% B
CH:FLOW_RATE                     	0.2 mL/min
CH:COLUMN_TEMPERATURE            	30
CH:SOLVENT_A                     	1mM ammonium acetate + 0.1% formic acid in water
CH:SOLVENT_B                     	1mM ammonium acetate + 0.1% formic acid in 20/80 water/acetonitrile
#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                   	MS1 data was acquired at a resolution of 140,000 over a scan range of 65-850
MS:MS_COMMENTS                   	m/z. Data was analyzed with Thermo Compound Discoverer software.
#MS_METABOLITE_DATA
MS_METABOLITE_DATA:UNITS	Peak Area
MS_METABOLITE_DATA_START
Samples	F4	F5	F6
Factors	Treatment:HPLC fraction 4	Treatment:HPLC fraction 5	Treatment:HPLC fraction 6
(+)-Eudesmin	158964747.1	36782994.48	46686351.74
(±)-Abscisic acid	65175333.46	719505.2215	6046618.003
(2S)-2-Piperazinecarboxamide	579026.2889	534543.9202	443920988.1
(2S)-2-Piperazinecarboxamide (2)	42264159.25	14664078.73	81414723.2
(2S)-3-Hydroxy-2-({[(3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]methyl}amino)butanoic acid (non-preferred name)	909103.422	1134365.575	1056314630
(2S)-3-Hydroxy-2-({[(3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]methyl}amino)butanoic acid (non-preferred name) (2)	368303.5837	855290.6831	618968769
(2S)-3-Hydroxy-2-({[(3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]methyl}amino)butanoic acid (non-preferred name) (3)	377014.1898	375194.8874	186308372.5
(2S)-3-Methyl-2-({[(3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]methyl}amino)butanoic acid (non-preferred name) (4)	230986.2467	2710078.005	20865079.44
(2Z)-2-Aminobut-2-enoate	1531470.449	2190933.69	227069785.2
(4R)-4-{[(4R)-4-Hydroxy-1-methyl-L-prolyl]oxy}-1-methyl-L-proline	16256893.92	92632875.51	52887756.14
[(1,2-Dioxo-1,2-ethanediyl)bis(oxy)]diammonium	23346820.17	2870914.815	6016700.913
[Similar to: (2S,3R,4R,5S,6E,14S)-4-Acetoxy-2-ammonio-3,5,14-trihydroxy-6-icosenoate; ΔMass: 229.2344 Da]	317319666.6	27625071.25	34064299.26
[Similar to: (3R,4S)-3-Ethyl-4-{2-[(1-naphthylmethyl)amino]-2-oxoethyl}-N-[3-(trifluoromethyl)phenyl]-1-piperidinecarboxamide; ΔMass: 303.1625 Da]	109516.2155	27743101.04	115381637
[Similar to: (4R,9β,23E)-2-(β-D-Glucopyranosyloxy)-16,20-dihydroxy-9,10,14-trimethyl-1,11,22-trioxo-4,9-cyclo-9,10-secocholesta-2,5,23-trien-25-yl acetate; ΔMass: 416.3763 Da]	340363.6026	108671367.5	399581.4803
[Similar to: (4R,9β,23E)-2-(β-D-Glucopyranosyloxy)-16,20-dihydroxy-9,10,14-trimethyl-1,11,22-trioxo-4,9-cyclo-9,10-secocholesta-2,5,23-trien-25-yl acetate; ΔMass: 476.2302 Da]	28528730.76	124120969.7	24720566.16
[Similar to: 1-({(2R,3S,4R,5S)-3,4-Dihydroxy-5-[2-(4-morpholinyl)-2-oxoethyl]tetrahydro-2-furanyl}methyl)-3-(3-fluorophenyl)urea; ΔMass: 294.0648 Da]	114378552.2	2106726.614	1837161.174
[Similar to: 10-Deacetylbaccatin III; ΔMass: 181.1173 Da]	145801.4298	35792675.49	652066.9569
[Similar to: 15-epi Cloprostenol; ΔMass: 182.2474 Da]	1161218.877	591236.2726	40495435.63
[Similar to: 2-(2,5-dimethyl-1H-pyrrol-1-yl)-N'-(2-furylcarbonyl)-4,5-dimethoxybenzohydrazide; ΔMass: 125.1855 Da]	132265.0202	7802795.43	695409.6189
[Similar to: 2-(2,5-dimethyl-1H-pyrrol-1-yl)-N'-(2-furylcarbonyl)-4,5-dimethoxybenzohydrazide; ΔMass: 125.2564 Da]	144460.3064	17730998.13	765412.0813
[Similar to: 3-(4-Phenylpiperazino)-2-(2-pyridylsulfonyl)acrylonitrile; ΔMass: 142.0187 Da]	489308.335	21866530.03	196201.0209
[Similar to: 3-Chloro-N-{methyl(oxo)[5-(trifluoromethyl)-2-pyridinyl]-λ6-sulfanylidene}-5-(trifluoromethyl)-2-pyridinecarboxamide; ΔMass: 228.9967 Da]	111602.0659	5411585.441	852281.8792
[Similar to: 3-Hydroxy-1-[3-(trifluoromethyl)phenyl]pyrazin-2(1H)-one; ΔMass: -52.0757 Da]	784039.1035	978772.016	483616786.4
[Similar to: 3-Hydroxy-1-[3-(trifluoromethyl)phenyl]pyrazin-2(1H)-one; ΔMass: 65.0293 Da]	3512645.479	832437.2609	46211726.28
[Similar to: 3-Hydroxy-1-[3-(trifluoromethyl)phenyl]pyrazin-2(1H)-one; ΔMass: -74.0574 Da]	146595.4303	172503.5375	21962871.15
[Similar to: 3-Hydroxy-1-[3-(trifluoromethyl)phenyl]pyrazin-2(1H)-one; ΔMass: -80.1178 Da]	180702.8649	202954.744	248794592.2
[Similar to: 4-(1-Methyl-4-nitro-1H-imidazol-5-yl)morpholine; ΔMass: 28.0256 Da]	254611.3561	293334.8593	70495236.34
[Similar to: 4-Allyl-5-[1-(4-chlorophenoxy)ethyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione; ΔMass: 201.0010 Da]	75885225.18	7142593.019	7362511.993
[Similar to: 6-Aminocaproic acid; ΔMass: 19.0306 Da]	78937855.97	3896498.119	4893396.385
[Similar to: 6-Methyl-4-(2-thienylmethyl)-2,3-dihydropyridazin-3-one; ΔMass: 49.0186 Da]	20819691.98	564734.9387	308492.2239
[Similar to: 9-Nitrooleate; ΔMass: 152.1203 Da]	105813941.6	6092876.839	5583183.18
[Similar to: 9-Nitrooleate; ΔMass: 171.1512 Da]	147507258.8	23870924.73	11426937.53
[Similar to: Amobarbital; ΔMass: 0.1878 Da]	3517295.237	219787.4973	624514352.7
[Similar to: Amphomycin; ΔMass: 1069.5860 Da]	201908483.1	1505834.129	19574020.78
[Similar to: Artemisinin; ΔMass: -21.8314 Da]	241877.0737	15407104.6	558135.557
[Similar to: Azoxystrobin; ΔMass: 206.0273 Da]	224225.4304	352555.4761	44395101.55
[Similar to: Butylisopropylamine; ΔMass: 0.0613 Da]	21895137.8	1160587.2	16863747.09
[Similar to: Celiprolol; ΔMass: 259.1854 Da]	135078.2426	267495.6485	435982951.6
[Similar to: Colistin; ΔMass: 996.7933 Da]	1499278.411	226418.9596	239260163.9
[Similar to: Colistin; ΔMass: 997.7171 Da]	1058130.138	54579059.04	455276.7269
[Similar to: DL-Arginine; ΔMass: -0.9967 Da]	233777.1418	225298.9336	583316693.4
[Similar to: Germanasim E; ΔMass: 300.4860 Da]	59799754.55	44827.15807	445885.8036
[Similar to: Germanasim E; ΔMass: 315.9890 Da]	160804.1126	148492.8002	14915605.58
[Similar to: Imidazolelactic acid; ΔMass: 0.0770 Da]	112499224.5	596190.0396	463566.4017
[Similar to: Imidazolelactic acid; ΔMass: -1.0315 Da]	1368687.069	3877762.749	26326770179
[Similar to: L-Aspartic acid; ΔMass: -40.9496 Da]	199246320.8	669513.9773	425011.941
[Similar to: Linezolid; ΔMass: 235.0924 Da]	506373.5932	399835.2302	56069891.52
[Similar to: Linezolid; ΔMass: 236.0956 Da]	3065195.505	5400060.643	1577389222
[Similar to: Linezolid; ΔMass: 236.0956 Da] (2)	822056.9786	2161484.306	376372019.9
[Similar to: Linezolid; ΔMass: 236.0956 Da] (3)	949266.6023	1723546.543	238997235.8
[Similar to: Muramic acid; ΔMass: -0.8542 Da]	304117.4271	7285302.59	1379099.536
[Similar to: Muramic acid; ΔMass: 0.9482 Da]	155112.4979	604376.7305	78015577.26
[Similar to: Muramic acid; ΔMass: 0.9846 Da]	285569.582	2731049.507	93766526.49
[Similar to: Muramic acid; ΔMass: -1.0029 Da]	557748.2745	5707101.803	1354934327
[Similar to: N,N-Diisopropylethylamine (DIPEA); ΔMass: -40.9899 Da]	16867161.66	5196887.338	6824561.141
[Similar to: N3-(4-Methylbenzyl)pyridin-3-amine; ΔMass: 94.1198 Da]	21647757.19	5914262.959	7217122.261
[Similar to: N3-(4-Methylbenzyl)pyridin-3-amine; ΔMass: 95.0156 Da]	396193861.7	2484402.079	2076741.821
[Similar to: N4-Acetylsulfamethoxazole; ΔMass: -0.0012 Da]	171199.0815	48154774.38	1361877.516
[Similar to: N-Acetylneuraminic acid; ΔMass: -1.0028 Da]	109230.114	98515.408	18964195.8
[Similar to: N-Acetylneuraminic acid; ΔMass: 35.9742 Da]	180658.5704	1055841.391	23382387.57
[Similar to: N-Acetylneuraminic acid; ΔMass: 37.0056 Da]	215233.1032	163400.9641	13135946.86
[Similar to: N-Acetylneuraminic acid; ΔMass: 37.0081 Da]	200204.1871	11442550.13	1267475.576
[Similar to: PEG n6; ΔMass: -16.9798 Da]	185552.5189	543321.1786	55511015.39
[Similar to: PEG n6; ΔMass: -17.9637 Da]	437174.7156	383070.9865	16998496.64
[Similar to: PEG n7; ΔMass: -17.9636 Da]	304694.9569	2396687.241	18055883.22
[Similar to: Phalloidin; ΔMass: 420.0745 Da]	354102.9614	429486.6542	37506687.85
[Similar to: Proline; ΔMass: -39.0107 Da]	130612.0459	83372.5242	14130218.62
[Similar to: Propranolol; ΔMass: 155.1218 Da]	238404.9885	99336697.3	6642422.052
[Similar to: Protirelin; ΔMass: 0.2516 Da]	136015.8691	62445267.08	1105833.686
[Similar to: Sildenafil methylsulfonyl; ΔMass: 137.1792 Da]	39284784.53	1341635.255	3384947.258
[Similar to: Tetraglyme; ΔMass: -15.9944 Da]	64669816.21	11801220.72	9535424.303
[Similar to: Triamcinolone acetonide; ΔMass: 210.1545 Da]	17112622.9	37875524.53	175142.4834
[Similar to: Triamcinolone acetonide; ΔMass: 211.1053 Da]	621629.6106	984506.7501	270607443.1
[Similar to: Triamcinolone acetonide; ΔMass: 211.1676 Da]	172288.587	239789.7589	17842865.61
[Similar to: Tributylamine; ΔMass: 73.1504 Da]	627781682.1	21992479.15	87821168.05
[Similar to: Triethanolamine; ΔMass: 1.0892 Da]	10012414.07	13053444.38	12848800.2
[Similar to: α-Methyl-DL-histidine; ΔMass: 4.1259 Da]	841673.0318	272645986.3	984324.1194
[Similar to: γ-Aminopropyltriethoxysilane; ΔMass: 101.1122 Da]	71658404.58	565915.198	864567.6724
[Similar to: γ-Aminopropyltriethoxysilane; ΔMass: 102.0499 Da]	82000143.08	17309798.87	580262.2895
[Similar to: γ-Aminopropyltriethoxysilane; ΔMass: 124.1607 Da]	373030788.6	69124627.37	76826587.92
[Similar to: γ-Aminopropyltriethoxysilane; ΔMass: 83.1342 Da]	102349644.3	29941602.96	33169690.09
[Similar to: γ-Aminopropyltriethoxysilane; ΔMass: 83.2456 Da]	73465562.12	105506.3684	857689.7244
[Similar to: γ-Aminopropyltriethoxysilane; ΔMass: 84.0917 Da]	12284187.87	509466.2707	839283.8407
[Similar to: γ-Aminopropyltriethoxysilane; ΔMass: 84.0917 Da] (2)	5425063.552	785345.901	197779.2069
[Similar to: Υ-Aminobutyric acid (GABA); ΔMass: -0.9721 Da]	4469137.097	7668132.575	162559313.3
1-(beta-D-Ribofuranosyl)-1,2-dihydropyrimidine	3686062.598	16190548.94	169919.3931
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide	7463786.913	13080200.23	1181902.784
1-{[(3S,4S,5R)-2,3,4-Trihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]methyl}-2-pyrrolidinecarboxylic acid (non-preferred name)	378305.8203	23047244.39	196261633.9
11-Aminoundecanoic acid	209400260.6	101518773.8	45155298.82
2-(Diethylamino)ethanol	1477986928	420252212.7	345840275
2-(Diethylamino)ethanol (2)	626909457.7	311840745.5	206059047
2,2,6,6-Tetramethyl-1-piperidinol (TEMPO)	48760586.55	928390.364	858410.0844
2,4,6-triaminotoluene	42194744.3	173831.9649	3879205.594
2,4-Dimethyloxazole	134877.3733	621030.3462	17964074.02
2-[(2-Methylimidazo[1,2-a]pyridin-3-yl)carbonyl]hydrazine-1-carboxamide	451867.0544	25109645.15	5869938315
2-[(2-Methylimidazo[1,2-a]pyridin-3-yl)carbonyl]hydrazine-1-carboxamide (2)	176234.3564	136304351	13616533.58
2080745	218159.018	238603.4563	210105163.2
2085522	8673358.486	37147681.72	900173.8328
2908	314557.1356	511674.943	306148012.9
2908 (2)	284034.9821	371031.631	75991515.96
2-Acetamido-2-deoxyglucose	215648.3372	175904.6925	28923228.97
2-Acetamido-2-deoxyglucose (2)	158904.8462	322428.5047	8805355.635
2-Amino-1H-benzimidazole	4833567.872	4858541.626	7927757.525
2-Amino-2-deoxy-4-O-beta-D-galactopyranosyl-D-glucose	425674.2834	122937532.7	1861201.372
2-Amino-3-(1H-imidazol-4-yl)propan-1-ol	1011287.253	214303.2262	16814382.03
2'-deamino-2'-hydroxy-6'-dehydroparomamine	370951.7087	476842.6386	333957976.8
2'-Deoxyadenosine	898400.8471	30000679.17	39581207.15
2'-deoxymugineic acid	712698.8985	4274494.25	3883600715
2'-deoxymugineic acid (2)	241705.6999	486358.0179	905494491.9
2-Hydroxyfelbamate	413570.9889	74617138.91	3548415.889
2-Oxo-4-pentenoic acid	455312.0929	600812.5119	109790083.5
3,4-Diaminopyridine	187869.3268	163601.8076	243293768
3302	70602077.31	1147842.353	189819311.3
3-Methyl-6,7,8-trihydropyrrolo[1,2-a]pyrimidin-2-one	3465525.045	28989133.24	422578.202
4-(2-Carboxy-1-azetidinyl)-N-(3-carboxy-3-hydroxypropyl)threonine	808018.2169	853569.6073	277511859.2
4,6-Dimethyl-2(1H)-pyrimidinone	79911359.52	31783330.56	23444398.94
4,6-Dimethyl-2(1H)-pyrimidinone (2)	26291180.11	10175015.44	13095557.33
4129939	172238.4455	123722.0893	391027266.9
4-ACETAMIDOBUTYRIC ACID	436752385.5	4777906436	36484692.23
4-Aminopyridine	54123804.83	155861.5352	1617548.289
4-Aminopyridine (2)	2107087.838	3393092.467	43335198.88
4-Imidazolemethanol	87928563.79	2500673.614	28534316.11
4-methylthio-2-oxobutanoic acid	330182.3837	220019.8583	424255710.4
4-Morpholinylacetic acid	201579757.3	4651829169	34526634.96
4-Nitroaniline	128710495.5	1853248.743	2907489.687
4-Nitroaniline (2)	2286780.479	23073702.16	26749183.07
5-(N,N-Dimethylcarbamimidamido)-2-oxopentanoic acid	177984.5601	2228200.128	41047748.85
6-Oxolysine	344344.8793	2872699.338	54029444.74
6-Oxolysine (2)	159251.6726	6302313.932	40937430.45
6-Oxo-pipecolinic acid	578920.6325	55650484.7	3197165.765
ACPC	1549455.235	2482432.471	1890000255
ACPC (2)	730482.7444	1368555.686	1740956638
agmatine	221605.8829	450386.5897	29669411.32
agmatine (2)	120658.2159	159507.4676	7827827.514
ala-ser	169110.8302	205038.1917	14518806.44
Aminolevulinic acid	1149307.627	4061235.861	228583394.3
Aminolevulinic acid (2)	929831.6367	3407161.607	99127515.11
Aminolevulinic acid (3)	3582459.777	72069386.93	7928072.548
Aminolevulinic acid (4)	308643.1678	1513861.979	47929973.12
Aminolevulinic acid (5)	523297.2531	2365154.1	33330646.17
Aminolevulinic acid (6)	287663.3738	410136.5337	14325229.29
APM	170028.8223	36275076.46	444997.3396
arg-ala	184036.0568	213238.4113	36144213.39
Arg-pro	276159.7461	23136946.05	589948.3834
Arg-pro (2)	113117.0974	153458.5575	10309598.31
Betaine	31666871.22	1017550874	21910031.43
Betaine (2)	481655678.7	19978137.8	34294000.78
Boc-Asn-Oh	1325461.715	1948748.571	79033027.34
Butabarbital	18522218.75	30816640.44	1680542.733
butalbital	20044071.15	4098379.401	743718.4186
Butoctamide semisuccinate	70395915.2	41100692.26	16578209.78
Caprolactam	4722492473	406127862.9	16354785.5
Caprolactam (2)	818702361.2	1012476704	19680653.24
Caprolactam (3)	20348223.42	37453599.61	6422425.437
Carbofuran	209912.4047	4034941.966	20053677.23
Choline	79486273.5	9420361.191	10925870.45
Choline Alfoscerate	376720.7024	5153862.569	962194118.8
Coprine	4745804.574	22221069.75	193705072.1
Cyclohexylamine	267151089.2	154914674.6	162546876.7
Cyprodenate	84363086.17	11556532.58	21456819.24
Cyprodenate (2)	7962776.963	8858045.954	7094156.673
D-(-)-Glutamine	652700.7756	514071.8883	20058629155
Daminozide	255467.1255	2309020.327	48956676.78
Desoxymycin	74013079.1	15974158.38	8829712.198
D-Glucosamine	438965.6241	1690979.409	3584308790
D-Glucosamine (2)	2181939.431	122564335.5	13712783.82
D-Glucosamine (3)	240450.1187	38259261.08	9649924.871
Dibutyl phthalate	4151309.514	6707372.107	5435145.988
DL-Arginine	1353914.418	1242737.226	39646928501
DL-Arginine (2)	150767.4691	102818.3085	7132408411
DL-Arginine (3)	104620.8186	203512.7876	1038076005
DL-Carnitine	29641241.36	6991453.387	442289.6949
DL-Glutamine	205152.9797	228079.5166	17665414.44
DL-Histidine	146418.3885	395280.5661	1071240223
DL-Histidine (2)	172619.7744	176145.1095	66583096.15
D-Serine	339327.1779	359367.415	105685274.5
Dulcin	6802755.751	20404178.61	857262.0296
Ethephon	37375570.86	10050928.77	10735772.94
Fucosamine	114361694.9	51369222.17	13101529.64
Gabapentin	16928274.31	5384818.168	7838828.893
gaboxadol	11739192.71	20606051.8	1519385.483
Galactosamine	876332.5435	1546643.198	13955874326
gamma-Aminobutyric acid	34666473.3	115702700.4	4254629.847
g-Butyrobetaine	25442572.78	709866.6261	1711215.897
g-Guanidinobutyrate	24523687.36	1500424.026	17297914.24
glu-pro	1324308.92	30109102.21	144496613.4
glu-thr	577911.9433	647293.0365	20602957.81
glyceraldehyde 3-phosphate	46008734.88	10715634.48	11953333.62
Glycine	499972.3351	809888.334	12491106.74
Glycyl-4-hydroxyproline	360767.4152	532720.1089	37808015.14
Gly-l-pro	11681948.46	114413644.3	1049213031
Gly-Lys	48978337.01	334420.5173	260675.2882
Guvacine	666046.9297	28825734.32	2713401.067
HEPES	216280.0255	228081.4631	51475387.65
Hexaconazole	326771.2207	41211363.46	3200601.025
Hexaconazole (2)	468788.8229	39205127.69	4718634.222
Histamine	134462.7832	162171.0282	23394716.92
Homoanserine	133248.9249	111307.9368	12506207.79
Homocitrulline	33799363.29	2964652.603	553189.0116
Homo-L-arginine	144661.2068	120244.2519	36676529.11
Homo-L-arginine (2)	157342.882	190770.1592	17411756.03
Imidazolepropionic acid	1285960.735	42750123.83	1250665758
Kanosamine	2308528.317	3798041.996	17485098952
Kanosamine (2)	1462243.5	2401009.944	6251175858
Kanosamine (3)	5648668.61	403870833.2	21898939.63
L-(-)-Asparagine	506189.1921	382687.3405	836740693.5
L-(-)-Serine	265371.0174	553382.9083	2005240228
L-(+)-Alanine	264766.3112	145870.7728	10091939.89
L-(+)-Aspartic acid	175800.3966	10452218.41	901738.2074
L-Alanyl-L-proline	473719661.4	4383471912	29346948.21
L-Alanyl-L-proline (2)	353715874.9	874149006.1	170539615.4
L-Alanyl-L-proline (3)	366155172.2	91180246.83	816465.677
L-Aspartic acid	2053563.48	276410.8526	1991700019
Lauramide	11819031.85	14152949.71	14203506.68
lentiginosine	52237640.41	2760668.71	2273708.43
L-Glutamic acid	903116.8696	2114555.968	26894123120
L-Glutamic acid (2)	433807.132	1123692.584	8157580873
L-Glutamic acid (3)	140308.2561	172494.5158	6462095532
L-Glutamic acid (4)	91226684.64	15594910.39	1240432458
L-Glutamic acid (5)	44303.04058	38616.08948	16183840.44
Linamarin	192473.9709	958957.4945	15961659.23
L-Proline	4617776.504	79308096.47	309329836.1
L-Pyroglutamic acid	732908.9033	1456313.054	27920167574
L-Pyroglutamic acid (2)	14735276.27	2672588.252	4700252869
L-Pyroglutamic acid (3)	280481.2705	1455768	2864482262
L-Pyroglutamic acid (4)	235591.5619	278497.0302	1950015778
L-Theanine	149546.0907	198841.1666	23963699.14
LU3453000	1605642.48	6017551.077	782870417.1
LU3453000 (2)	389651.2017	661869.0136	190676494.1
Lysylvaline	152670.0631	241955.2387	42048150.71
MA4000000	47394346.47	55064300.41	19380141.71
MA4000000 (2)	680838.826	837819.1033	26435674.37
metharbital	640751.6243	5378731.372	81798886.1
MFCD00037215	399063.8202	301011.6515	377374173.4
MFCD00041932	44878702.79	2288133.766	193581.0293
MFCD00055782	485899.1825	1845545.12	11185552.48
MFCD01664827	169885.5637	26725161.68	956068.0945
Midodrine	1748505.199	24114520.6	1148263.779
Miglitol	4333489.047	2235048.809	72095932.22
Muramic acid	540866.6464	26892511.43	20422243194
muramic acid (2)	351091.0455	11233521.73	2110117199
muramic acid (3)	289824.2372	4318247.707	1760900213
Muramic acid (4)	1221023.452	611023851.7	22822056.23
Muramic acid (5)	293708.675	90215712.71	31767842.63
N-((4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL)FORMAMIDE	371922915.4	282451.8901	1088345.778
N,N-diacetyllegionaminic acid	242489.4455	315588.8736	600965048.5
N,N-diacetyllegionaminic acid (2)	201828.4956	244706.6798	113773097.1
N,N-diacetyllegionaminic acid (3)	182092.1705	167713.0105	110404877.2
N,N-dimethylarginine	150182.6929	195455.8756	113530843.6
N,N-Dimethylglycine	621047.0449	73316836.03	1158038.842
N~1~-Isopropyl-2-methylpropan-1,2-diamin	20032146.62	39011294.69	901876.9817
N~6~,N~6~-Dimethyllysine	157802.5867	196366.9638	256015731.1
N6-METHYLLYSINE	189081.8975	190397.7812	89175319.22
N6-METHYLLYSINE (2)	150339.2875	174194.7279	63390708.68
N-Acetyl-D-mannosaminolactone	106115.465	330527.4607	9338902.574
N-acetyl-LL-2,6-diaminopimelic acid	148423.1064	772592.4494	14711410.24
N-Acetylneuraminic acid	1454729.124	3869665.889	975622665.2
N-Acetylputrescine	3173753968	796666955.2	2198130.691
NI3400000	12279731.54	1768028.138	28740942.51
nicotianamine	355172.3142	416965.4948	108762114
NJ5000000	186426.1107	233711.2468	121347613
NJ5000000 (2)	167634.1324	139339.6425	57523230.23
N-methylethanolamine phosphate	360701126.8	7720643.589	315853.063
N-Methylglutamate	43715902.14	1754548.405	2242557.667
N-Nitrosoguvacoline	384852.8162	372157.4506	412492167.1
NPYR	23775602.82	14121484.14	26302081.74
NPYR (2)	25792467.39	18401693.77	25254816.04
N-succinyl-LL-2,6-diaminopimelic acid	408600.9129	399930.6805	38264496.4
N-tetracosanoylsphinganine-1-phosphocholine	10356545.42	36967.41064	432612.1703
N-Undecanoylglycine	35429253.45	9698416.966	5013010.467
nylon cyclic dimer	14116315.6	6387831.412	6240335.61
Oryzalin metabolite	1197743607	1030349828	12741365.75
Paracetamol	34878708.47	1680959.752	35931934.63
PEG-4	136129656.8	43366840.81	39865334.93
pentetrazol	150801.451	125348.1017	18635734.76
pentobarbital	284127285	117089195.7	941713.0326
Phenylhydrazine	793256.6489	14013564.3	1964492.527
Phenylisocyanate	11527632.05	112505.6599	176968.0116
Picolinamide	2908983.892	89675539.69	178205422.9
Proacacipetalin	163050.2563	5040954.436	38597367.18
pro-gln	320742.9548	3555738.008	78723908.23
Proline	1040340.66	8374289644	80806937.84
Proline (2)	239571479.9	131067851.5	22608036.63
Pulcherriminic acid	14267476.84	17810751.54	667122.8679
PYRIDOXAMINE	146424246.8	451792244	1890100.517
Pyrogallol	183639.0176	238997.7453	57089875.55
Reduced Glutathione	153700.1479	134629.9534	23412344.89
RG8841500	8876211.942	16104420.08	516924.1906
S-Allyl propanethioate	138442.9901	99446.18303	230033128.4
spinacine	191544.8317	123329.735	102714293.7
Streptamine	448428.8398	693192.1013	221490547.3
Streptamine (2)	231138.867	1368849.217	122258227.3
tert-Butyl 3-amino-1-methyl-2,3-dioxopropylcarbamate	907439.2329	5034903.52	20412539.78
Tetraacetylethylenediamine	733157.2782	34846167.01	242417039.9
THP(A)	2539434.313	5100437.479	2573542874
Threonine	1988325.385	11143311.03	26839802722
Threonylserine	183207.5789	189680.226	11686971.33
Tiformin	75572326.82	847365.4664	349550.871
tin(ii) hydride	163288918.7	296074427.8	13140728.45
Triethanolamine	59438906.76	36727006.18	6663634.066
Triethylamine	45274353.62	1748997.008	17284600.27
Triethylamine (2)	13375653.29	1333271.215	1771494.409
trimethadione	1601120.981	1775869.608	2038884700
trimethadione (2)	892134.5988	945445.0183	702224323.5
trimethadione (3)	1577475.704	2779330.893	716102886.8
trimethadione (4)	55497190.51	2615913.651	4492577.175
trimethylglycine	437303126.6	109476467	39479416.15
Tris(hydroxymethyl)aminomethane	312937.2912	399549.2443	41301629.25
UB6600000	837828444.7	13909529.98	13181440.19
val-arg	163436.9616	299577.0451	106138127.4
Val-lys	164276.5768	217169.9669	31514471.82
Veronal	135049416.9	8306220.782	859877.996
Veronal (2)	7834142.966	1802088.755	16119564.66
YU0650000	1293817.077	1238442.107	20776850.54
ZV4	776703456.2	11794276.02	26647662.35
β-Alanine	8619658.282	62818299.6	2396410660
β-Alanine (2)	5708691.056	32905884.2	584682535.1
β-Alanine (3)	2749406.513	31553350.21	141874585.3
MS_METABOLITE_DATA_END
#METABOLITES
METABOLITES_START
metabolite_name	Formula	Molecular Weight	Retention times [min]
(+)-Eudesmin	C22 H26 O6	386.17247	2.751
(±)-Abscisic acid	C15 H20 O4	286.11605	3.806
(2S)-2-Piperazinecarboxamide	C5 H11 N3 O	129.09018	5.846
(2S)-2-Piperazinecarboxamide (2)	C5 H11 N3 O	129.09034	3.19
(2S)-3-Hydroxy-2-({[(3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]methyl}amino)butanoic acid (non-preferred name)	C10 H19 N O8	281.11063	5.423
(2S)-3-Hydroxy-2-({[(3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]methyl}amino)butanoic acid (non-preferred name) (2)	C10 H19 N O8	281.11068	5.643
(2S)-3-Hydroxy-2-({[(3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]methyl}amino)butanoic acid (non-preferred name) (3)	C10 H19 N O8	281.11069	6.014
(2S)-3-Methyl-2-({[(3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]methyl}amino)butanoic acid (non-preferred name) (4)	C11 H21 N O7	279.13134	3.613
(2Z)-2-Aminobut-2-enoate	C4 H7 N O2	101.04818	5.767
(4R)-4-{[(4R)-4-Hydroxy-1-methyl-L-prolyl]oxy}-1-methyl-L-proline	C12 H20 N2 O5	272.13667	3.447
[(1,2-Dioxo-1,2-ethanediyl)bis(oxy)]diammonium	C2 H6 N2 O4	122.03303	6.776
[Similar to: (2S,3R,4R,5S,6E,14S)-4-Acetoxy-2-ammonio-3,5,14-trihydroxy-6-icosenoate; ΔMass: 229.2344 Da]	C6 H12 N4 P2	202.05392	8.362
[Similar to: (3R,4S)-3-Ethyl-4-{2-[(1-naphthylmethyl)amino]-2-oxoethyl}-N-[3-(trifluoromethyl)phenyl]-1-piperidinecarboxamide; ΔMass: 303.1625 Da]	C5 H6 N8 O	194.06652	3.593
[Similar to: (4R,9β,23E)-2-(β-D-Glucopyranosyloxy)-16,20-dihydroxy-9,10,14-trimethyl-1,11,22-trioxo-4,9-cyclo-9,10-secocholesta-2,5,23-trien-25-yl acetate; ΔMass: 416.3763 Da]	C7 H14 O5 P4	301.98011	4.713
[Similar to: (4R,9β,23E)-2-(β-D-Glucopyranosyloxy)-16,20-dihydroxy-9,10,14-trimethyl-1,11,22-trioxo-4,9-cyclo-9,10-secocholesta-2,5,23-trien-25-yl acetate; ΔMass: 476.2302 Da]	C11 H18 N2 O4	242.12628	3.432
[Similar to: 1-({(2R,3S,4R,5S)-3,4-Dihydroxy-5-[2-(4-morpholinyl)-2-oxoethyl]tetrahydro-2-furanyl}methyl)-3-(3-fluorophenyl)urea; ΔMass: 294.0648 Da]	C5 H13 N O	103.1001	3.068
[Similar to: 10-Deacetylbaccatin III; ΔMass: 181.1173 Da]	C10 H17 N7 O8	363.11357	6.065
[Similar to: 15-epi Cloprostenol; ΔMass: 182.2474 Da]		241.91782	3.779
[Similar to: 2-(2,5-dimethyl-1H-pyrrol-1-yl)-N'-(2-furylcarbonyl)-4,5-dimethoxybenzohydrazide; ΔMass: 125.1855 Da]	C4 H8 N2 O5 P2 S	257.96266	5.449
[Similar to: 2-(2,5-dimethyl-1H-pyrrol-1-yl)-N'-(2-furylcarbonyl)-4,5-dimethoxybenzohydrazide; ΔMass: 125.2564 Da]	C3 H2 Cl N2 O4 P3	257.8917	5.418
[Similar to: 3-(4-Phenylpiperazino)-2-(2-pyridylsulfonyl)acrylonitrile; ΔMass: 142.0187 Da]	C11 H17 O2 P	212.0964	3.52
[Similar to: 3-Chloro-N-{methyl(oxo)[5-(trifluoromethyl)-2-pyridinyl]-λ6-sulfanylidene}-5-(trifluoromethyl)-2-pyridinecarboxamide; ΔMass: 228.9967 Da]	C6 H7 N2 O2 P S	201.99628	5.736
[Similar to: 3-Hydroxy-1-[3-(trifluoromethyl)phenyl]pyrazin-2(1H)-one; ΔMass: -52.0757 Da]	C11 H20 N2 O8	308.12163	6.03
[Similar to: 3-Hydroxy-1-[3-(trifluoromethyl)phenyl]pyrazin-2(1H)-one; ΔMass: 65.0293 Da]	C6 H10 N O2 P S	191.01669	6.05
[Similar to: 3-Hydroxy-1-[3-(trifluoromethyl)phenyl]pyrazin-2(1H)-one; ΔMass: -74.0574 Da]	C11 H19 N6 O2 P S	330.10334	6.107
[Similar to: 3-Hydroxy-1-[3-(trifluoromethyl)phenyl]pyrazin-2(1H)-one; ΔMass: -80.1178 Da]	C12 H24 N4 O7	336.1638	5.97
[Similar to: 4-(1-Methyl-4-nitro-1H-imidazol-5-yl)morpholine; ΔMass: 28.0256 Da]	C9 H13 O2 P	184.06532	3.741
[Similar to: 4-Allyl-5-[1-(4-chlorophenoxy)ethyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione; ΔMass: 201.0010 Da]		94.0536	3.264
[Similar to: 6-Aminocaproic acid; ΔMass: 19.0306 Da]	C5 H8 N2 O	112.06398	3.479
[Similar to: 6-Methyl-4-(2-thienylmethyl)-2,3-dihydropyridazin-3-one; ΔMass: 49.0186 Da]		157.03283	4.818
[Similar to: 9-Nitrooleate; ΔMass: 152.1203 Da]	C8 H17 N O3	175.12063	3.406
[Similar to: 9-Nitrooleate; ΔMass: 171.1512 Da]	C7 H12 N2 O2	156.08973	3.281
[Similar to: Amobarbital; ΔMass: 0.1878 Da]	C4 H4 O7 P2	225.94399	3.849
[Similar to: Amphomycin; ΔMass: 1069.5860 Da]	C6 H14 N4 O P2	220.06432	8.323
[Similar to: Artemisinin; ΔMass: -21.8314 Da]	C6 H9 Cl N2 O8 S	303.97817	4.717
[Similar to: Azoxystrobin; ΔMass: 206.0273 Da]	C6 H15 N O6	197.08955	4.615
[Similar to: Butylisopropylamine; ΔMass: 0.0613 Da]	C4 H9 N3 O	115.07476	3.333
[Similar to: Celiprolol; ΔMass: 259.1854 Da]		120.06167	5.413
[Similar to: Colistin; ΔMass: 996.7933 Da]		157.95665	3.854
[Similar to: Colistin; ΔMass: 997.7171 Da]		157.0328	4.411
[Similar to: DL-Arginine; ΔMass: -0.9967 Da]		175.10841	5.84
[Similar to: Germanasim E; ΔMass: 300.4860 Da]		335.68299	5.838
[Similar to: Germanasim E; ΔMass: 315.9890 Da]	C11 H24 N6 O5	320.18007	5.621
[Similar to: Imidazolelactic acid; ΔMass: 0.0770 Da]	C2 H5 Cl N2 O2 S	155.97652	8.351
[Similar to: Imidazolelactic acid; ΔMass: -1.0315 Da]	C6 H11 N3 O2	157.08497	5.893
[Similar to: L-Aspartic acid; ΔMass: -40.9496 Da]	C2 H7 Cl N2 O3 S	173.98708	8.354
[Similar to: Linezolid; ΔMass: 235.0924 Da]		102.05142	5.905
[Similar to: Linezolid; ΔMass: 236.0956 Da]		101.0482	5.972
[Similar to: Linezolid; ΔMass: 236.0956 Da] (2)		101.0482	5.9
[Similar to: Linezolid; ΔMass: 236.0956 Da] (3)		101.0482	5.837
[Similar to: Muramic acid; ΔMass: -0.8542 Da]	C5 H8 N2 O2 P4	251.95471	5.394
[Similar to: Muramic acid; ΔMass: 0.9482 Da]	C10 H22 N2 O5	250.15234	5.946
[Similar to: Muramic acid; ΔMass: 0.9846 Da]	C9 H18 N2 O6	250.11594	6.008
[Similar to: Muramic acid; ΔMass: -1.0029 Da]	C3 H12 N10 O4	252.10341	4.498
[Similar to: N,N-Diisopropylethylamine (DIPEA); ΔMass: -40.9899 Da]	C9 H18 N2 O	170.14161	2.934
[Similar to: N3-(4-Methylbenzyl)pyridin-3-amine; ΔMass: 94.1198 Da]		103.99588	3.09
[Similar to: N3-(4-Methylbenzyl)pyridin-3-amine; ΔMass: 95.0156 Da]	C5 H13 N O	103.10011	3.234
[Similar to: N4-Acetylsulfamethoxazole; ΔMass: -0.0012 Da]	C8 H13 N3 O9	295.06392	5.654
[Similar to: N-Acetylneuraminic acid; ΔMass: -1.0028 Da]		310.10875	6.901
[Similar to: N-Acetylneuraminic acid; ΔMass: 35.9742 Da]	C5 H20 N7 O4 P	273.1318	5.948
[Similar to: N-Acetylneuraminic acid; ΔMass: 37.0056 Da]	C11 H16 N2 O6	272.10038	6.024
[Similar to: N-Acetylneuraminic acid; ΔMass: 37.0081 Da]	C7 H12 N8 O4	272.09786	6
[Similar to: PEG n6; ΔMass: -16.9798 Da]	C13 H21 N3 O5	299.14761	3.594
[Similar to: PEG n6; ΔMass: -17.9637 Da]	C13 H20 N2 O6	300.13151	3.604
[Similar to: PEG n7; ΔMass: -17.9636 Da]	C15 H24 N2 O7	344.15769	3.445
[Similar to: Phalloidin; ΔMass: 420.0745 Da]	C18 H32 N4 O4	368.24178	3.618
[Similar to: Proline; ΔMass: -39.0107 Da]	C7 H10 N2 O2	154.07401	5.018
[Similar to: Propranolol; ΔMass: 155.1218 Da]		104.03545	5.615
[Similar to: Protirelin; ΔMass: 0.2516 Da]	C5 H4 N2 O13 P2	361.91862	5.633
[Similar to: Sildenafil methylsulfonyl; ΔMass: 137.1792 Da]	C4 H6 N3 O5 P3	268.95194	8.376
[Similar to: Tetraglyme; ΔMass: -15.9944 Da]	C10 H22 O6	238.1411	3.232
[Similar to: Triamcinolone acetonide; ΔMass: 210.1545 Da]	C6 H13 N2 O5 P	224.05595	3.684
[Similar to: Triamcinolone acetonide; ΔMass: 211.1053 Da]	C8 H17 N O6	223.10514	4.002
[Similar to: Triamcinolone acetonide; ΔMass: 211.1676 Da]	C7 H14 N O3 P S	223.04285	3.959
[Similar to: Tributylamine; ΔMass: 73.1504 Da]	C5 H8 N2 O	112.06391	3.281
[Similar to: Triethanolamine; ΔMass: 1.0892 Da]	C8 H4 O3	148.01599	19.043
[Similar to: α-Methyl-DL-histidine; ΔMass: 4.1259 Da]		164.95928	3.926
[Similar to: γ-Aminopropyltriethoxysilane; ΔMass: 101.1122 Da]	C6 H4 N2 O	120.03249	3.763
[Similar to: γ-Aminopropyltriethoxysilane; ΔMass: 102.0499 Da]	C5 H13 N O2	119.09478	3.485
[Similar to: γ-Aminopropyltriethoxysilane; ΔMass: 124.1607 Da]		96.984	8.355
[Similar to: γ-Aminopropyltriethoxysilane; ΔMass: 83.1342 Da]	C2 H8 N2 O P2	138.0105	8.325
[Similar to: γ-Aminopropyltriethoxysilane; ΔMass: 83.2456 Da]		137.89907	5.984
[Similar to: γ-Aminopropyltriethoxysilane; ΔMass: 84.0917 Da]		137.05306	6.005
[Similar to: γ-Aminopropyltriethoxysilane; ΔMass: 84.0917 Da] (2)		137.05297	6.234
[Similar to: Υ-Aminobutyric acid (GABA); ΔMass: -0.9721 Da]		104.03539	3.853
1-(beta-D-Ribofuranosyl)-1,2-dihydropyrimidine	C9 H14 N2 O4	214.09506	3.121
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide	C11 H16 N2 O5	256.1054	3.612
1-{[(3S,4S,5R)-2,3,4-Trihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]methyl}-2-pyrrolidinecarboxylic acid (non-preferred name)	C11 H19 N O7	277.1157	5.243
11-Aminoundecanoic acid	C11 H23 N O2	201.17264	3.072
2-(Diethylamino)ethanol	C6 H15 N O	117.11562	3.053
2-(Diethylamino)ethanol (2)	C6 H15 N O	117.11565	2.953
2,2,6,6-Tetramethyl-1-piperidinol (TEMPO)	C9 H19 N O	157.14645	3.017
2,4,6-triaminotoluene	C7 H11 N3	137.09506	3.269
2,4-Dimethyloxazole	C5 H7 N O	97.05316	5.304
2-[(2-Methylimidazo[1,2-a]pyridin-3-yl)carbonyl]hydrazine-1-carboxamide	C10 H11 N5 O2	233.08971	4.507
2-[(2-Methylimidazo[1,2-a]pyridin-3-yl)carbonyl]hydrazine-1-carboxamide (2)	C10 H11 N5 O2	233.08971	6.063
2080745	C9 H20 N2 O2	188.15209	4.224
2085522	C7 H10 N2 O	138.07908	3.49
2908	C5 H11 N	85.08961	4.902
2908 (2)	C5 H11 N	85.0896	4.074
2-Acetamido-2-deoxyglucose	C8 H15 N O6	221.08954	5.055
2-Acetamido-2-deoxyglucose (2)	C8 H15 N O6	221.08957	3.646
2-Amino-1H-benzimidazole	C7 H7 N3	133.06384	2.93
2-Amino-2-deoxy-4-O-beta-D-galactopyranosyl-D-glucose	C12 H23 N O10	341.13178	6.07
2-Amino-3-(1H-imidazol-4-yl)propan-1-ol	C6 H11 N3 O	141.09005	3.3
2'-deamino-2'-hydroxy-6'-dehydroparomamine	C12 H22 N2 O8	322.13705	4.325
2'-Deoxyadenosine	C10 H13 N5 O3	273.0843	6.224
2'-deoxymugineic acid	C12 H20 N2 O7	304.12669	4.483
2'-deoxymugineic acid (2)	C12 H20 N2 O7	304.12672	4.615
2-Hydroxyfelbamate	C11 H14 N2 O5	254.08982	3.575
2-Oxo-4-pentenoic acid	C5 H6 O3	114.03198	4.157
3,4-Diaminopyridine	C5 H7 N3	109.06427	5.915
3302	C5 H6 N2 O	110.0483	3.736
3-Methyl-6,7,8-trihydropyrrolo[1,2-a]pyrimidin-2-one	C8 H10 N2 O	150.0791	3.523
4-(2-Carboxy-1-azetidinyl)-N-(3-carboxy-3-hydroxypropyl)threonine	C12 H20 N2 O8	320.12142	4.857
4,6-Dimethyl-2(1H)-pyrimidinone	C6 H8 N2 O	142.07416	3.51
4,6-Dimethyl-2(1H)-pyrimidinone (2)	C6 H8 N2 O	124.06361	3.601
4129939	C5 H11 N O3 S	165.04576	5.429
4-ACETAMIDOBUTYRIC ACID	C6 H11 N O3	145.07367	3.644
4-Aminopyridine	C5 H6 N2	94.053	3.25
4-Aminopyridine (2)	C5 H6 N2	94.05348	5.034
4-Imidazolemethanol	C4 H6 N2 O	98.04831	3.515
4-methylthio-2-oxobutanoic acid	C5 H8 O3 S	148.01928	5.402
4-Morpholinylacetic acid	C6 H11 N O3	145.07369	3.467
4-Nitroaniline	C6 H6 N2 O2	138.04289	3.725
4-Nitroaniline (2)	C6 H6 N2 O2	138.0429	3.534
5-(N,N-Dimethylcarbamimidamido)-2-oxopentanoic acid	C8 H15 N3 O3	201.11089	5.958
6-Oxolysine	C6 H12 N2 O3	160.08448	6.086
6-Oxolysine (2)	C6 H12 N2 O3	160.08463	4.381
6-Oxo-pipecolinic acid	C6 H9 N O3	143.05814	6.037
ACPC	C4 H7 N O2	101.04806	5.299
ACPC (2)	C4 H7 N O2	101.04806	5.415
agmatine	C5 H14 N4	130.12175	4.851
agmatine (2)	C5 H14 N4	130.12177	4.054
ala-ser	C6 H12 N2 O4	176.07938	4.411
Aminolevulinic acid	C5 H9 N O3	131.05838	6.133
Aminolevulinic acid (2)	C5 H9 N O3	131.05837	6.338
Aminolevulinic acid (3)	C5 H9 N O3	131.05809	3.486
Aminolevulinic acid (4)	C5 H9 N O3	131.05837	6.012
Aminolevulinic acid (5)	C5 H9 N O3	131.05837	6.467
Aminolevulinic acid (6)	C5 H9 N O3	131.05814	6.257
APM	C7 H13 N O4	175.08424	4.952
arg-ala	C9 H19 N5 O3	245.14836	4.43
Arg-pro	C11 H21 N5 O3	271.16397	6.068
Arg-pro (2)	C11 H21 N5 O3	271.1639	4.157
Betaine	C5 H11 N O2	117.07894	4.417
Betaine (2)	C5 H11 N O2	117.07893	4.832
Boc-Asn-Oh	C9 H16 N2 O5	232.10558	3.671
Butabarbital	C10 H16 N2 O3	212.1156	3.446
butalbital	C11 H16 N2 O3	224.11572	3.104
Butoctamide semisuccinate	C16 H29 N O5	315.20431	2.764
Caprolactam	C6 H11 N O	113.08414	3.494
Caprolactam (2)	C6 H11 N O	113.08419	3.294
Caprolactam (3)	C6 H11 N O	113.0843	3.137
Carbofuran	C12 H15 N O3	221.10473	4.335
Choline	C5 H13 N O	71.07409	3.468
Choline Alfoscerate	C8 H20 N O6 P	257.10261	5.292
Coprine	C8 H14 N2 O4	202.09505	3.656
Cyclohexylamine	C6 H13 N	99.10524	2.984
Cyprodenate	C13 H25 N O2	227.1883	2.79
Cyprodenate (2)	C13 H25 N O2	227.18831	19.085
D-(-)-Glutamine	C5 H10 N2 O3	146.06895	5.53
Daminozide	C6 H12 N2 O3	160.08433	5.951
Desoxymycin	C21 H41 N7 O11	567.28891	2.743
D-Glucosamine	C6 H13 N O5	179.07919	4.32
D-Glucosamine (2)	C6 H13 N O5	179.07921	6.06
D-Glucosamine (3)	C6 H13 N O5	179.07915	6.297
Dibutyl phthalate	C16 H22 O4	278.15157	19.046
DL-Arginine	C6 H14 N4 O2	174.11145	5.762
DL-Arginine (2)	C6 H14 N4 O2	174.1115	5.428
DL-Arginine (3)	C6 H14 N4 O2	174.11149	4.745
DL-Carnitine	C7 H15 N O3	161.10497	3.172
DL-Glutamine	C5 H10 N2 O3	146.06893	4.083
DL-Histidine	C6 H9 N3 O2	155.06933	5.903
DL-Histidine (2)	C6 H9 N3 O2	155.06938	5.218
D-Serine	C3 H7 N O3	105.04289	6.126
Dulcin	C9 H12 N2 O2	180.08956	3.165
Ethephon	C2 H6 Cl O3 P	143.97477	2.746
Fucosamine	C6 H13 N O4	163.08428	3.648
Gabapentin	C9 H17 N O2	171.12565	3.015
gaboxadol	C6 H8 N2 O2	140.05839	3.309
Galactosamine	C6 H13 N O5	179.07915	4.139
gamma-Aminobutyric acid	C4 H9 N O2	103.06367	3.519
g-Butyrobetaine	C7 H15 N O2	145.11008	3.344
g-Guanidinobutyrate	C5 H11 N3 O2	145.08492	3.193
glu-pro	C10 H16 N2 O5	244.10568	3.594
glu-thr	C9 H16 N2 O6	248.10036	4.321
glyceraldehyde 3-phosphate	C3 H7 O6 P	169.99813	8.367
Glycine	C2 H5 N O2	75.0322	5.453
Glycyl-4-hydroxyproline	C7 H12 N2 O4	188.07938	3.923
Gly-l-pro	C7 H12 N2 O3	172.08473	3.634
Gly-Lys	C8 H17 N3 O3	203.12674	3.255
Guvacine	C6 H9 N O2	127.06328	4.831
HEPES	C8 H18 N2 O4 S	238.09817	4.956
Hexaconazole	C14 H17 Cl2 N3 O	313.07666	5.796
Hexaconazole (2)	C14 H17 Cl2 N3 O	291.09479	5.832
Histamine	C5 H9 N3	111.07988	5.034
Homoanserine	C11 H18 N4 O3	254.13738	5.035
Homocitrulline	C7 H15 N3 O3	189.11097	3.677
Homo-L-arginine	C7 H16 N4 O2	188.12695	5.076
Homo-L-arginine (2)	C7 H16 N4 O2	188.12705	4.415
Imidazolepropionic acid	C6 H8 N2 O2	140.05846	3.673
Kanosamine	C6 H13 N O5	161.06861	4.14
Kanosamine (2)	C6 H13 N O5	161.06864	4.524
Kanosamine (3)	C6 H13 N O5	161.06871	6.06
L-(-)-Asparagine	C4 H8 N2 O3	132.0534	6.009
L-(-)-Serine	C3 H7 N O3	105.04292	5.773
L-(+)-Alanine	C3 H7 N O2	89.04765	5.008
L-(+)-Aspartic acid	C4 H7 N O4	133.03734	5.428
L-Alanyl-L-proline	C8 H14 N2 O3	186.10026	3.52
L-Alanyl-L-proline (2)	C8 H14 N2 O3	154.07405	3.613
L-Alanyl-L-proline (3)	C8 H14 N2 O3	186.10022	3.841
L-Aspartic acid	C4 H7 N O4	133.03747	7.884
Lauramide	C12 H25 N O	199.1934	19.049
lentiginosine	C8 H15 N O2	157.10994	3.381
L-Glutamic acid	C5 H9 N O4	147.05296	5.958
L-Glutamic acid (2)	C5 H9 N O4	147.05294	5.814
L-Glutamic acid (3)	C5 H9 N O4	130.0264	5.836
L-Glutamic acid (4)	C5 H9 N O4	147.05299	6.153
L-Glutamic acid (5)	C5 H9 N O4	147.05483	6.205
Linamarin	C10 H17 N O6	247.10504	5.299
L-Proline	C5 H9 N O2	115.06351	5.862
L-Pyroglutamic acid	C5 H7 N O3	129.04254	5.57
L-Pyroglutamic acid (2)	C5 H7 N O3	129.04258	5.975
L-Pyroglutamic acid (3)	C5 H7 N O3	129.04249	5.753
L-Pyroglutamic acid (4)	C5 H7 N O3	129.04259	5.418
L-Theanine	C7 H14 N2 O3	174.10017	4.054
LU3453000	C4 H4 O2	84.02153	6.01
LU3453000 (2)	C4 H4 O2	84.02112	4.189
Lysylvaline	C11 H23 N3 O3	245.17351	4.683
MA4000000	C5 H7 N O2	113.04767	3.491
MA4000000 (2)	C5 H7 N O2	113.04781	4.183
metharbital	C9 H14 N2 O3	198.10021	3.511
MFCD00037215	C8 H14 N2 O5	218.08999	5.184
MFCD00041932	C6 H13 N O	115.09995	3.205
MFCD00055782	C8 H13 N O6	219.07387	6.076
MFCD01664827	C5 H8 N2 O5	176.04311	5.452
Midodrine	C12 H18 N2 O4	254.12603	3.394
Miglitol	C8 H17 N O5	207.11031	3.646
Muramic acid	C9 H17 N O7	251.10026	4.526
muramic acid (2)	C9 H17 N O7	251.10029	4.289
muramic acid (3)	C9 H17 N O7	251.10033	4.179
Muramic acid (4)	C9 H17 N O7	251.10029	6.03
Muramic acid (5)	C9 H17 N O7	251.10033	5.864
N-((4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL)FORMAMIDE	C7 H10 N4 O	166.08532	3.258
N,N-diacetyllegionaminic acid	C13 H22 N2 O8	334.13723	4.195
N,N-diacetyllegionaminic acid (2)	C13 H22 N2 O8	334.13719	4.402
N,N-diacetyllegionaminic acid (3)	C13 H22 N2 O8	334.13719	4.583
N,N-dimethylarginine	C8 H18 N4 O2	202.14267	4.103
N,N-Dimethylglycine	C4 H9 N O2	103.06364	4.765
N~1~-Isopropyl-2-methylpropan-1,2-diamin	C7 H18 N2	130.14697	6.051
N~6~,N~6~-Dimethyllysine	C8 H18 N2 O2	174.13657	4.305
N6-METHYLLYSINE	C7 H16 N2 O2	160.12096	5.108
N6-METHYLLYSINE (2)	C7 H16 N2 O2	160.12096	4.462
N-Acetyl-D-mannosaminolactone	C8 H13 N O6	219.07398	6.374
N-acetyl-LL-2,6-diaminopimelic acid	C9 H16 N2 O5	232.10549	6.015
N-Acetylneuraminic acid	C11 H19 N O9	309.10556	7.042
N-Acetylputrescine	C6 H14 N2 O	89.08407	3.473
NI3400000	C5 H6 N2 O	110.04829	3.464
nicotianamine	C12 H21 N3 O6	303.14238	4.211
NJ5000000	C8 H15 N3 O2	185.11609	4.173
NJ5000000 (2)	C8 H15 N3 O2	185.11612	5.074
N-methylethanolamine phosphate	C3 H10 N O4 P	155.03471	4.821
N-Methylglutamate	C6 H11 N O4	161.06857	3.265
N-Nitrosoguvacoline	C7 H10 N2 O3	170.06895	5.563
NPYR	C4 H8 N2 O	100.06413	19.661
NPYR (2)	C4 H8 N2 O	100.0641	19.479
N-succinyl-LL-2,6-diaminopimelic acid	C11 H18 N2 O7	290.11075	6.042
N-tetracosanoylsphinganine-1-phosphocholine	C47 H97 N2 O6 P	816.70549	5.866
N-Undecanoylglycine	C13 H25 N O3	243.18314	2.817
nylon cyclic dimer	C12 H22 N2 O2	226.16773	3.189
Oryzalin metabolite	C6 H14 N2 O	130.11062	3.368
Paracetamol	C8 H9 N O2	151.06312	3.867
PEG-4	C8 H18 O5	194.11515	3.263
pentetrazol	C6 H10 N4	138.0904	5.086
pentobarbital	C11 H18 N2 O3	226.13144	3.252
Phenylhydrazine	C6 H8 N2	108.06902	3.525
Phenylisocyanate	C7 H5 N O	119.03742	8.355
Picolinamide	C6 H6 N2 O	122.04811	3.669
Proacacipetalin	C11 H17 N O6	259.10512	5.232
pro-gln	C10 H17 N3 O4	243.12152	3.599
Proline	C5 H9 N O2	115.06354	4.779
Proline (2)	C5 H9 N O2	115.06355	5.167
Pulcherriminic acid	C12 H20 N2 O4	256.14168	3.348
PYRIDOXAMINE	C8 H12 N2 O2	168.08965	3.491
Pyrogallol	C6 H6 O3	126.03153	4.17
Reduced Glutathione	C10 H17 N3 O6 S	307.08331	6.203
RG8841500	C8 H20 N2	144.16247	6.046
S-Allyl propanethioate	C6 H10 O S	130.04584	5.453
spinacine	C7 H9 N3 O2	167.06922	5.975
Streptamine	C6 H14 N2 O4	178.09509	6.136
Streptamine (2)	C6 H14 N2 O4	178.09509	6.316
tert-Butyl 3-amino-1-methyl-2,3-dioxopropylcarbamate	C9 H16 N2 O4	216.11067	3.557
Tetraacetylethylenediamine	C10 H16 N2 O4	228.11077	3.52
THP(A)	C6 H10 N2 O3	158.06903	3.734
Threonine	C4 H9 N O3	119.05838	5.323
Threonylserine	C7 H14 N2 O5	206.08994	4.524
Tiformin	C5 H12 N4 O	144.10095	3.647
tin(ii) hydride	H2 Sn	121.91734	3.735
Triethanolamine	C6 H15 N O3	149.10501	3.501
Triethylamine	C6 H15 N	101.12082	2.914
Triethylamine (2)	C6 H15 N	101.12086	3.026
trimethadione	C6 H9 N O3	143.05814	4.193
trimethadione (2)	C6 H9 N O3	143.05806	4.059
trimethadione (3)	C6 H9 N O3	143.05809	4.576
trimethadione (4)	C6 H9 N O3	143.05807	3.501
trimethylglycine	C5 H11 N O2	117.07919	3.352
Tris(hydroxymethyl)aminomethane	C4 H11 N O3	121.07398	3.781
UB6600000	C6 H15 N O2	133.11021	3.197
val-arg	C11 H23 N5 O3	273.17939	4.69
Val-lys	C11 H23 N3 O3	245.17347	4.072
Veronal	C8 H12 N2 O3	184.08464	3.165
Veronal (2)	C8 H12 N2 O3	184.08457	3.672
YU0650000	C7 H8 N2 O	136.06353	3.634
ZV4	C5 H11 N O	101.08397	3.204
β-Alanine	C3 H7 N O2	89.04827	5.013
β-Alanine (2)	C3 H7 N O2	89.04828	4.875
β-Alanine (3)	C3 H7 N O2	89.0483	5.144
METABOLITES_END
#END