#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