#METABOLOMICS WORKBENCH epmosher_20210121_142232 DATATRACK_ID:2414 STUDY_ID:ST001658 ANALYSIS_ID:AN002706 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 Reversed phase
CH:INSTRUMENT_NAME Thermo Dionex Ultimate 3000 RS
CH:COLUMN_NAME Thermo Hypersil Gold aQ (150 x 2.1mm, 1.9um)
CH:FLOW_GRADIENT 0-2min 0% B, 2-13min 0-60% B, 13-15min 60-90% B, 15-16min 90-0% B, 16-20min 0% 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
(±)-Abscisic acid 21239912.19 986658.1546 1953660.014
(15R,27R)-18,21,24-Trihydroxy-2,50-dimethyl-27-{[(9Z,11Z)-9,11-octadecadienoyloxy]methyl}-18,24-dioxido-12,29-dioxo-13,17,19,23,25,28-hexaoxa-18lambda~5~,24lambda~5~-diphosphadopentacontan-15-yl 22-methyltetracosanoate 85047.64513 18112177.15 205091.1831
(2R)-4-[(E)-2-{[(1S)-1-Carboxy-4-hydroxybutyl]amino}vinyl]-2,3-dihydro-2,6-pyridinedicarboxylic acid 7096.912169 6177.542648 6471176.836
(2S)-2-Piperazinecarboxamide 8268447.541 1834293.875 17465396.46
(2S)-3-Hydroxy-2-({[(3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]methyl}amino)butanoic acid (non-preferred name) 109761.5009 876110.7193 633221806.2
(4R)-4-{[(4R)-4-Hydroxy-1-methyl-L-prolyl]oxy}-1-methyl-L-proline 2905116.218 7638492.427 7387062.251
(Z)-dehydrobutyrine 8302884.316 9829370.263 764333237.9
(Z)-dehydrobutyrine (2) 4318242.683 3662530.19 27713581.16
[Similar to: (2E)-2-({[(3aR,4R,6E,9S,10Z,11aS)-9-Acetoxy-6,10-dimethyl-3-methylene-2-oxo-2,3,3a,4,5,8,9,11a-octahydrocyclodeca[b]furan-4-yl]oxy}carbonyl)-2-buten-1-yl (2E)-2-(hydroxymethyl)-2-butenoate; ΔMass: 183.0586 Da] 10018488.8 2122253.528 2936992.189
[Similar to: (2E,8S,10R)-10,11-Dihydroxy-6-(methoxymethyl)-1,10-dimethyl-5-oxo-4,14-dioxatricyclo[9.2.1.03,7]tetradeca-2,6-dien-8-yl methacrylate; ΔMass: -173.1239 Da] 28097152.69 2489964.772 1422666.252
[Similar to: (2R)-7-Methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl β-D-glucopyranoside; ΔMass: 139.0873 Da] 25090545.91 540891628.5 1890057.952
[Similar to: (3β,5ξ,9ξ,16α,18ξ)-16-Hydroxy-13,28-epoxyoleanan-3-yl 6-deoxy-α-L-mannopyranosyl-(1->2)-β-D-galactopyranosyl-(1->3)-[β-D-glucopyranosyl-(1->2)]-β-D-glucopyranosiduronic acid; ΔMass: 901.5618 Da] 269491.5126 443233.3552 4480608.668
[Similar to: (3β,5ξ,9ξ,16α,18ξ)-16-Hydroxy-13,28-epoxyoleanan-3-yl 6-deoxy-α-L-mannopyranosyl-(1->2)-β-D-galactopyranosyl-(1->3)-[β-D-glucopyranosyl-(1->2)]-β-D-glucopyranosiduronic acid; ΔMass: 902.5271 Da] 198835.3184 32934758.14 21892851.74
[Similar to: (3β,5ξ,9ξ,16α,18ξ)-16-Hydroxy-13,28-epoxyoleanan-3-yl 6-deoxy-α-L-mannopyranosyl-(1->2)-β-D-galactopyranosyl-(1->3)-[β-D-glucopyranosyl-(1->2)]-β-D-glucopyranosiduronic acid; ΔMass: 902.5272 Da] 11619105.95 147474525 235263170.6
[Similar to: 15-epi Cloprostenol; ΔMass: 182.0395 Da] 2559562.506 6505417.837 341172.4436
[Similar to: 1-Methylhistidine; ΔMass: 46.0058 Da] 1218905111 1799297487 1338723832
[Similar to: 2-[(5-Bromo-4-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol; ΔMass: 235.9666 Da] 11734668.2 653148.9519 3233794.473
[Similar to: 2-[(5-Bromo-4-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol; ΔMass: 235.9934 Da] 14101367.91 1587878.942 1429307.03
[Similar to: 3-(1,3-Benzodioxol-5-yl)-2-cyanoacrylamide ; ΔMass: -17.8996 Da] 5102673.072 261213.7126 569531.5254
[Similar to: 4-Methylumbelliferyl acetate; ΔMass: -185.1399 Da] 49986609.8 5624082.582 8405857.579
[Similar to: 5-Acetoxy-3-(hydroxymethyl)-6-isopropyl-2-oxo-3-cyclohexen-1-yl 3-methylpentanoate; ΔMass: -21.9790 Da] 138889.5359 2964197.737 318125627.5
[Similar to: 5-Acetoxy-3-(hydroxymethyl)-6-isopropyl-2-oxo-3-cyclohexen-1-yl 3-methylpentanoate; ΔMass: -22.9239 Da] 20259.01805 77135.72634 11576254.8
[Similar to: 6-Methyl-4-(2-thienylmethyl)-2,3-dihydropyridazin-3-one; ΔMass: 93.9877 Da] 171083056.7 949248.8951 398041.8007
[Similar to: A-796260; ΔMass: 241.2744 Da] 3322547.679 730632.5258 2000003.889
[Similar to: Amphomycin; ΔMass: 1135.5768 Da] 430016.0941 9999135.226 15498020.82
[Similar to: Artemisinin; ΔMass: -20.9947 Da] 26382.64813 20187.83622 4823610.784
[Similar to: Azithromycin; ΔMass: 589.5471 Da] 6398820.035 770699.2963 839581.5373
[Similar to: Benproperine; ΔMass: 3.0527 Da] 411661.3123 156729.3613 340194.2099
[Similar to: Benproperine; ΔMass: 3.0527 Da] (2) 154106.1994 100418.3559 151717.5155
[Similar to: Benproperine; ΔMass: 66.0156 Da] 439549.6674 356558.411 433116.1024
[Similar to: Benproperine; ΔMass: 95.0419 Da] 1682634.21 649396.3817 1308058.39
[Similar to: Betaine; ΔMass: 0.1409 Da] 561190.2529 317265.4284 777438.3642
[Similar to: Betaine; ΔMass: -0.8559 Da] 9448943.754 2331892.619 4745208.166
[Similar to: Betaine; ΔMass: -0.9326 Da] 1864084.648 297685.728 766611.1473
[Similar to: Bialaphos; ΔMass: -18.0059 Da] 78140.3542 13215604.89 225813357.7
[Similar to: Bialaphos; ΔMass: -19.0364 Da] 97062.45818 132109.6622 44480356.69
[Similar to: Carazolol; ΔMass: 179.0737 Da] 8373056.727 1294294.139 799949.7474
[Similar to: Colistin; ΔMass: 883.5251 Da] 17860916.22 9154492.169 13686146.73
[Similar to: Cyclo(glycyl-N5-acetyl-N5-hydroxyornithyl-N5-acetyl-N5-hydroxyornithyl-N5-acetyl-N5-hydroxyornithylglycylglycyl); ΔMass: 388.1720 Da] 28108.32882 32362.45032 9265090.889
[Similar to: D-(+)-Glucose; ΔMass: -15.9610 Da] 61410.62791 26257538.69 688248.2089
[Similar to: D-Glucosamine; ΔMass: -17.0134 Da] 13489395.3 251403938.9 153995062.7
[Similar to: Dithiopyr; ΔMass: 232.0199 Da] 568241.7067 203293.924 242569040.9
[Similar to: Dithiopyr; ΔMass: 233.0039 Da] 361958.3722 638451.4722 380857673.2
[Similar to: DL-Arginine; ΔMass: 0.0829 Da] 14147747.16 133731.4909 81844.20056
[Similar to: DL-Arginine; ΔMass: -0.8888 Da] 1075108.997 26939798.85 59885.71162
[Similar to: DL-Arginine; ΔMass: -174.0398 Da] 53645.98004 187079.9356 54407053.56
[Similar to: Folinic acid; ΔMass: 147.0580 Da] 26941.23239 2353790.827 90374900.07
[Similar to: Folinic acid; ΔMass: -157.0677 Da] 14686.01942 11918.16381 13412343.96
[Similar to: Folinic acid; ΔMass: 79.0713 Da] 16320.39394 21945.60022 9639992.161
[Similar to: GW 610; ΔMass: 0.9863 Da] 19672.96246 6925475.908 561015.8924
[Similar to: Kanosamine; ΔMass: 19.0662 Da] 6668020.358 442483.7649 489464.2269
[Similar to: Kanosamine; ΔMass: -20.9972 Da] 157465.9483 260704.0493 12562907.87
[Similar to: L-Glutamine; ΔMass: -0.9963 Da] 50927.20854 100938.8954 33463515.8
[Similar to: L-Glutamine; ΔMass: 17.0678 Da] 55540.89704 4170064.36 522084.849
[Similar to: L-Glutamine; ΔMass: 32.9741 Da] 179958.8146 195755.3649 17416487.76
[Similar to: L-Histidine; ΔMass: 0.0507 Da] 128018.0855 142137.3538 13373823.27
[Similar to: L-Histidine; ΔMass: 1.0346 Da] 166434.8508 202919.9524 54797098.84
[Similar to: L-Kynurenine; ΔMass: 0.0033 Da] 1006903.499 7184179.836 36725.92832
[Similar to: Muramic acid; ΔMass: 18.1546 Da] 41679.99878 9327873.9 514752.6435
[Similar to: N-(2,4-Difluorophenyl)-4-(dimethylamino)nicotinamide; ΔMass: 121.0134 Da] 27927857.31 190048.0813 198419.55
[Similar to: N,N-Diisopropylethylamine (DIPEA); ΔMass: -0.8056 Da] 74055926.83 6912110.76 8757465.098
[Similar to: N,N-Diisopropylethylamine (DIPEA); ΔMass: -398.2130 Da] 604195.152 451407.9946 584580.8923
[Similar to: N-[4-(2-Aminopyrimidin-4-yl)phenyl]-N'-(3-chlorophenyl)urea; ΔMass: 127.0221 Da] 87406.44472 130574.3862 13155603.07
[Similar to: N-{[(2R,3S,4S,5S)-5-(2-{[2-(Dimethylamino)ethyl]amino}-2-oxoethyl)-3,4-dihydroxytetrahydro-2-furanyl]methyl}-1,3-benzodioxole-5-carboxamide; ΔMass: 250.2236 Da] 5944530.645 1859080.094 2876484.149
[Similar to: N1-[3-(1H-Imidazol-1-yl)propyl]-2,6-dimethoxy-3-nitrobenzamide; ΔMass: 68.0408 Da] 43409142.13 126147.7827 160930.1032
[Similar to: Nobiletin; ΔMass: 10.9493 Da] 7321355.168 678011.1937 622711.556
[Similar to: n-Pentyl isopentyl phthalate ; ΔMass: -19.1862 Da] 11395748.09 21408580.3 26325990.81
[Similar to: Oleoyl ethylamide; ΔMass: 112.2551 Da] 25140954.81 2320692.918 793181.275
[Similar to: Oleoyl ethylamide; ΔMass: 193.3247 Da] 65834150.56 3833358.992 9074741.432
[Similar to: Oleoyl ethylamide; ΔMass: 211.3349 Da] 13137708.53 1204488.242 1531070.393
[Similar to: Proline; ΔMass: -0.0111 Da] 14669319.76 1028918.954 933149.376
[Similar to: Proline; ΔMass: 1.0342 Da] 19260882.46 3666146.564 2528078.981
[Similar to: Proline; ΔMass: -113.9757 Da] 7752438.278 254384.792 195962.9805
[Similar to: Proline; ΔMass: -114.9722 Da] 26430873.32 1069728.409 210858.4424
[Similar to: Secodihydro-hydramicromelin B; ΔMass: -105.1287 Da] 17908021.33 1984572.803 3583979.347
[Similar to: Secodihydro-hydramicromelin B; ΔMass: -91.1129 Da] 8361264.887 797120.7664 1621351.394
[Similar to: Sulfamethazine; ΔMass: 155.0043 Da] 231454674.9 842713749.4 1017383291
[Similar to: Sulfamethazine; ΔMass: 155.0044 Da] 231454674.9 601423520.8 688591899.5
[Similar to: Tangeritin; ΔMass: -15.9568 Da] 14684.33374 36276.60368 14449409.58
[Similar to: Unguisin E; ΔMass: 616.3379 Da] 13323955.15 549029.3616 215292.7968
[Similar to: Ursolic acid; ΔMass: 228.1410 Da] 48478429.98 48891248.13 40659038.19
1-(4-Amino-4-carboxybutanoyl)-2-piperidinecarboxylic acid 65319.01978 119724.5999 8959790.943
1-(5-Decanoyl-4-nonyl-1,4-dihydro-3-pyridinyl)-1-dodecanone 8627053.216 110698.0826 223874.493
1,1'-(2,5-Pyrazinediyl)di(1,2,3,4-butanetetrol) 54810.6184 266222.6611 79728757.5
1-[(3-Carboxypropyl)amino]-1-deoxy-beta-D-fructofuranose 66096.52273 7661846.548 22985099.09
1-{[(3S,4S,5R)-2,3,4-Trihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]methyl}-2-pyrrolidinecarboxylic acid (non-preferred name) 18705.68022 19942118.81 28721949.97
11-Aminoundecanoic acid 69492092.97 14416822.26 10771345.98
1H-Imidazol-2-ol 3478916.299 9983922.373 12975519.37
1H-Imidazol-2-ol (2) 5045845.874 11069724.36 7420701.567
2,3-DIHYDRO-3,5-DIHYDROXY-6-METHYL-4H-PYRAN-4-ONE 4957883.36 17155813.09 75851523.19
2,4,6-triaminotoluene 11409138.54 51955.5532 505156.0376
2-[(2-Methylimidazo[1,2-a]pyridin-3-yl)carbonyl]hydrazine-1-carboxamide 194106.9607 65331503.91 832456947.2
2080745 79253.83736 102307.397 18585627.14
2908 400501.5446 307212.3398 29310224.65
2949 577562.386 303889.7381 543249.5983
2949 (2) 239560.915 82891.63246 191251.7005
2-Acetamido-2-deoxyglucose 100549.5612 3508946.211 7977950.89
2-Amino-3-(1H-imidazol-4-yl)propan-1-ol 58882.09262 79353.76532 5914623.233
2-Amino-4-[(4-aminobutyl)amino]butanoic acid 357911.0285 170972.8603 257185.079
2-Aminonicotinic acid 25885738.55 3555603.226 4822223.061
2'-Deoxyadenosine 20636.37763 26098306.72 101720020.1
2'-Deoxycytosine 41739492.14 8864621.67 28147633.11
2'-deoxymugineic acid 135795.4925 4405297.81 966753764
2-ETHYL-4,5-DIMETHYLOXAZOLE 456577.4827 190996.4925 483729.6964
2-Hydroxyfelbamate 254457.4202 19966089.29 545223.0753
2-Hydroxyhippuric acid 81815.67937 40830200 157846546.4
3,4-Diaminopyridine 108848.8795 126842.9133 24512413.34
3477 170776.001 117607.6635 233275.7254
3635 224082.9386 2979938.594 14688834.09
3-amino-2,3-dideoxy-scyllo-inosose 49429450.04 1289000.615 16297465.4
3-Aminopyrrolidine 2165619.885 2750922.406 5257992.583
3-Pyrroline 393074.8617 151971.2841 42145653.94
4-guanidinobutanal 68518.33647 105410.4937 56155301.09
4-Hydroxyprolylalanine 28321.44694 9262202.243 5306019.994
4-Hydroxyprolylleucine 194565.1593 81667.14197 174394.4911
4-Hydroxyprolylthreonine 13059.14724 70390.56265 31245269.57
4-Imidazolemethanol 7919744.018 11803035.91 10390090.99
4-Imidazolemethanol (2) 6630210.533 2120888.654 1296437.979
4-Morpholinylacetic acid 5756492.178 1285097.313 45577487.6
4-Morpholinylacetic acid (2) 970724.446 661410.8027 2806705.848
5-(4-Hydroxybutyl)-2,4-imidazolidinedione 1285819.237 52216465.28 253675128.2
5-AMINO-3-HYDROXY-2-(2-OXO-AZETIDIN-1-YL)-PENTANOIC ACID 442373.7088 439494.7718 12036592.24
5-AMINO-3-HYDROXY-2-(2-OXO-AZETIDIN-1-YL)-PENTANOIC ACID (2) 27750.33328 128351.6145 22973805.76
5-Oxotetrahydrofuran-2-carboxylic acid 22161707.26 5010880.677 6017076673
6-(5-Hydroxy-2-methyl-4-oxo-1(4H)-pyridinyl)norleucine 8566359.617 117808.4074 49878.6005
6-Oxolysine 974842.2245 5509463.279 4193715.005
6-Oxo-pipecolinic acid 1997928.136 7783093.16 321724581.5
6-Oxo-pipecolinic acid (2) 32845319.65 786481.828 3316084.167
Aceturic acid 13082061.76 393058.8229 474229.2815
Adipamide 2002471.765 455134.3965 705440.7926
Alanylclavam 19099883.22 245910.4115 87871.10047
ALA-PRO 239578938.7 164777149.2 6911188.058
ala-ser 59993.97308 128031.406 8764966.312
aldehydo-D-glucosamine 6-phosphate 30756.41605 6975679.569 98899.85702
Aminolevulinic acid 2563462.171 33019888.48 246702206.1
APM 2864711.081 25570637.98 272362.8733
arg-ala 20150.86096 46210.74104 5690295.25
Benserazide 153046.6391 24809.24 48810518.75
Betaine 87333706.75 148449846.7 14470317.48
Bicine 12125306.47 3307938.213 1486782.129
Bis(methylbenzylidene)sorbitol 70313231.93 7931141.197 12410779.53
Butoctamide semisuccinate 9600021.53 3003788.813 2216976.885
Butoctamide semisuccinate (2) 13868377.48 2606892.307 1686344.746
Cadaverine 45608.83478 47060.00382 12228061.92
Caprolactam 1398182937 161432762.7 3088314.061
capuride 737685.2679 320552.63 581994.642
carisoprodol 621285.6603 294405.0483 494049.9881
Choline 52526095.15 348700.8259 346848.1964
Cyclohexylamine 4081866.22 4951849.759 4708354.697
D-(-)-Glutamine 6385092.332 3457027.246 7602340349
D-(+)-Glucose 24897316.67 323762168.1 2124898978
Deanol 21140092.49 229842.9298 288244.2187
Dehydroglycine 90110.49559 81017.16139 14091804.78
D-Glucosamine 10996601.64 64152877.64 3944185471
Diethylene glycol 43862248.39 70410382.73 26001812.09
Dihydrothymine 23307294.86 9075734.757 35481664.56
Dimethyl octanediimidate 3712733.873 1870970.443 3655687.469
DL-Alanine 31293790.87 973276144 323040197.1
DL-Arginine 852090.4826 1110595.853 13285595370
DL-Citrulline 20225.62897 36235.68668 9439904.239
EJ4025000 249774.8399 110652.0686 265531.9588
EJ4025000 (2) 244586.5648 129005.2922 149346.6057
ethyl argininate 17444.72575 15690.46119 13215200.2
Furfural 3956631.296 394299.3755 7405244.228
g-Guanidinobutyrate 8153950.993 238341.5526 1947849.444
glu-pro 54101212.56 243520.9459 282137.2573
glutaral 8904165.476 522160.6347 110579.367
Gly-l-pro 6499134.151 672098.8839 936768.0291
Gly-Lys 5804433.609 11775.02625 11404.43553
Guvacine 2047516.868 1713427.979 2512899.972
Hexitol 99690.34032 47070733.54 9483851.748
HIDA 576606.3538 163793.4028 12286766.12
Histamine 73927.79082 53903.77389 3317949.448
Homocitrulline 12656813.38 429818.7378 42281.73218
Imidazolelactic acid 48202.92746 8345623.888 941651.3917
ISOXYL 86262.51172 23716.81699 12057965.18
Kanosamine 68249.46244 94838.98319 1251054687
Kanosamine (2) 1598376.964 14866816 1640572766
L-(-)-Serine 239701.4994 436179.5327 385321419.3
L-(+)-Alanine 1065650.193 18567542.98 12127159.26
L-(+)-Aspartic acid 102016.3046 101218.4882 90454950.85
L-Alanyl-L-proline 24735600.85 413309228.7 3117456.355
L-Aspartic acid 17934.61526 11430022.4 913743.2464
lawsone 23296735.16 2547322.04 1807237.312
Leu-Leu 548918.988 273741.412 392469.1697
Leu-Val 242284.055 101794.2849 270361.7074
L-Glutamic acid 37329638.21 58734784.02 11458541965
l-Histidinal 29388046.1 33820256.22 20554196.86
L-Histidine 169107.9641 216407.5804 193903919.7
L-Proline 1479157.889 1115369.818 69880854.61
L-Pyroglutamic acid 1879048.953 65964876.88 54098645.16
L-Pyroglutamic acid (2) 6055257.596 2345592.753 6094413532
L-Theanine 1206433.912 562116.821 5517793.573
LU3453000 527465.7576 7437758.655 38135469.65
lys-leu 9070.642448 9032.560101 5500367.376
Lysylvaline 21158.23826 111304.2131 13240924.34
MA4000000 501731.1121 522593.8166 11046046.08
Maleamic acid 386791.0083 314628.1397 101420686
mebutamate 2856064.949 1187087.315 2325069.599
melamine 2285577.34 501001.8551 581633.7313
Methionine sulfoxide 68664.02749 58564.60985 81936923.42
Methylimidazoleacetic acid 410504.7415 8521089.975 262532731.1
Methylol Dimethylhydantoin 510285.0547 47565510.29 634559183.1
MFCD00037215 123485.3072 161726.4978 69681512.6
MFCD01664827 34557.72618 44658285.8 98219.68976
Miglitol 296052.2406 826810.6899 36485549.51
Muramic acid 567178.4049 452102962.5 4581571852
Muscimol 1306566.708 1369391.976 4122312.295
N-((4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL)FORMAMIDE 136634885.4 157778.6738 229887.5703
N-(4-Amino-1-carboxybutyl)glutamic acid 1114720.217 9238731.499 46448941.33
N,N-diacetyllegionaminic acid 21344.37376 89662.39055 17140823.87
N,N-diacetyllegionaminic acid (2) 38408.11749 130064.9543 132967472.8
N,N-Diethylethanolamine 287729032.6 65631992.33 81548840.66
N~6~,N~6~-Dimethyllysine 88179.40695 96014.10448 15399673.85
N6-METHYLLYSINE 80517.0575 100868.8395 6916401.457
N-Acetylleucylleucine 651050.3831 221069.5991 678250.7647
N-Acetylneuraminic acid 205605.3366 668214.8114 270734333.9
N-Acetylputrescine 1456209685 170235285.6 3789853.115
NI3400000 12161038.1 1007835.016 37859725.84
Nicotinamide 452357.8539 8939777.618 537482.6538
NJ5000000 162645.8047 214205.9989 8272650.199
N-methylethanolamine phosphate 3859387.497 19898399.23 196894.3558
N-methylethanolamine phosphate (2) 4936345.217 4126232.787 607487.0733
NPYR 622503.348 280059.6903 27064664.9
nylon cyclic dimer 1395021.725 2721329.019 6823772.666
nylon cyclic dimer (2) 297989467 169537606.1 257883971.4
Ofloxacin ethyl ester 21433.10081 35617.13411 42178057.84
Oxaceprol 350959.9868 366091.6429 57787684.12
pentobarbital 7263312.554 907951.734 29301.77277
pentobarbital (2) 15489725.68 9922025.158 41473.28491
pentobarbital (3) 49553722.68 19941.23997 18980.42928
Pioglitazone 13911.21094 17425.50826 8914592.492
Piracetam 13553720.73 413960.4726 298820.2566
Piracetam (2) 18191588.05 2073400.404 1218965.415
PPG n10 7782373.664 6561192.039 10125287.17
PPG n10 (2) 1388348 1440872.63 5044372.407
PPG n8 13092275.4 6589945.082 11515028.25
PPG n9 15971154.23 8077722.236 16195836.01
pro-gln 19851.95776 43015.9366 9916955.928
pro-gln (2) 50378.96862 111131.6819 4489060.813
Pro-Glu 1143526.466 9222720.4 9952787.597
Pro-Glu (2) 362644.1844 7028650.572 9952787.597
Proline 240027384.1 2856084492 25234937.53
Pyridoxamine 42532862.27 32780284.76 6525061.322
Pyrimidine 5533014.039 15110123.79 10808162.39
Pyrimidine (2) 68605850.82 57303916 55571628.59
Reduced Glutathione 13227.24564 8673.86269 6777879.807
RV0540000 52932153.18 369732.8342 962593.7076
spinacine 112770.2438 134466.6855 9490300.864
Streptamine 199657.1159 444603.0665 25447723.94
Succinyl proline 18459.26088 1863919.223 28484102.68
Sulfuric acid 16017264.79 1513097.178 1913756.395
Tetraacetylethylenediamine 126699.1406 1158854.811 29069347.48
Threonine 3893269.064 1930784.811 2470788910
tiapride 53215.83254 57944.03344 5076470.436
Tiformin 13977356.62 148664.4554 208180.4098
Timonacic 17622281.8 8473394.214 45144.87964
Triethanolamine 11569675.92 3614307.258 681943.2374
Triethylamine 10805068.83 1882573.634 2235330.955
Triisopropanolamine 5491835.935 1246610.482 655069.1385
trimethadione 3070207.408 3891692.43 2178781.831
UB6600000 6601737.86 1055201.835 1511649.598
UB6600000 (2) 148566986.5 945358.646 948063.7835
val-arg 53958.05854 29333.0797 13887480.84
val-asn 26762.05804 77415.39815 8074335.91
Veronal 11129831.75 203343.5035 15206.15669
Veronal (2) 16105047.18 18094.99471 260929.6789
Veronal (3) 7807633.272 114710.0885 217598.8085
Viloxazine 18568235.24 138990.8017 203149.824
Υ-Aminobutyric acid (GABA) 5175775.872 36321383.06 1958944.38
MS_METABOLITE_DATA_END
#METABOLITES
METABOLITES_START
metabolite_name Formula Molecular Weight Retention times [min]
(±)-Abscisic acid C15 H20 O4 286.1152 6.617
(15R,27R)-18,21,24-Trihydroxy-2,50-dimethyl-27-{[(9Z,11Z)-9,11-octadecadienoyloxy]methyl}-18,24-dioxido-12,29-dioxo-13,17,19,23,25,28-hexaoxa-18lambda~5~,24lambda~5~-diphosphadopentacontan-15-yl 22-methyltetracosanoate C90 H172 O17 P2 1587.20949 1.865
(2R)-4-[(E)-2-{[(1S)-1-Carboxy-4-hydroxybutyl]amino}vinyl]-2,3-dihydro-2,6-pyridinedicarboxylic acid C14 H18 N2 O7 326.11211 3.122
(2S)-2-Piperazinecarboxamide C5 H11 N3 O 129.08982 3.21
(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 281.10989 2.059
(4R)-4-{[(4R)-4-Hydroxy-1-methyl-L-prolyl]oxy}-1-methyl-L-proline C12 H20 N2 O5 272.136 2.371
(Z)-dehydrobutyrine C4 H7 N O2 101.0479 1.994
(Z)-dehydrobutyrine (2) C4 H7 N O2 101.04786 2.167
[Similar to: (2E)-2-({[(3aR,4R,6E,9S,10Z,11aS)-9-Acetoxy-6,10-dimethyl-3-methylene-2-oxo-2,3,3a,4,5,8,9,11a-octahydrocyclodeca[b]furan-4-yl]oxy}carbonyl)-2-buten-1-yl (2E)-2-(hydroxymethyl)-2-butenoate; ΔMass: 183.0586 Da] C10 H21 N7 O5 319.16169 13.571
[Similar to: (2E,8S,10R)-10,11-Dihydroxy-6-(methoxymethyl)-1,10-dimethyl-5-oxo-4,14-dioxatricyclo[9.2.1.03,7]tetradeca-2,6-dien-8-yl methacrylate; ΔMass: -173.1239 Da] C25 H45 N O13 567.28671 14.713
[Similar to: (2R)-7-Methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl β-D-glucopyranoside; ΔMass: 139.0873 Da] C4 H11 O8 P 218.01865 1.97
[Similar to: (3β,5ξ,9ξ,16α,18ξ)-16-Hydroxy-13,28-epoxyoleanan-3-yl 6-deoxy-α-L-mannopyranosyl-(1->2)-β-D-galactopyranosyl-(1->3)-[β-D-glucopyranosyl-(1->2)]-β-D-glucopyranosiduronic acid; ΔMass: 901.5618 Da] C3 H9 N O7 S 203.00981 2.066
[Similar to: (3β,5ξ,9ξ,16α,18ξ)-16-Hydroxy-13,28-epoxyoleanan-3-yl 6-deoxy-α-L-mannopyranosyl-(1->2)-β-D-galactopyranosyl-(1->3)-[β-D-glucopyranosyl-(1->2)]-β-D-glucopyranosiduronic acid; ΔMass: 902.5271 Da] C4 H6 N6 O4 202.04449 1.942
[Similar to: (3β,5ξ,9ξ,16α,18ξ)-16-Hydroxy-13,28-epoxyoleanan-3-yl 6-deoxy-α-L-mannopyranosyl-(1->2)-β-D-galactopyranosyl-(1->3)-[β-D-glucopyranosyl-(1->2)]-β-D-glucopyranosiduronic acid; ΔMass: 902.5272 Da] 202.04448 2.026
[Similar to: 15-epi Cloprostenol; ΔMass: 182.0395 Da] C11 H18 N2 O4 242.12575 2.7
[Similar to: 1-Methylhistidine; ΔMass: 46.0058 Da] C6 H9 N3 123.07936 17.112
[Similar to: 2-[(5-Bromo-4-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol; ΔMass: 235.9666 Da] C5 H5 N3 O2 S 171.01049 1.68
[Similar to: 2-[(5-Bromo-4-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol; ΔMass: 235.9934 Da] C4 H2 N3 O3 P 170.98377 1.706
[Similar to: 3-(1,3-Benzodioxol-5-yl)-2-cyanoacrylamide ; ΔMass: -17.8996 Da] C H3 N2 O10 P 233.95304 1.744
[Similar to: 4-Methylumbelliferyl acetate; ΔMass: -185.1399 Da] C18 H25 N7 O4 403.19778 16.456
[Similar to: 5-Acetoxy-3-(hydroxymethyl)-6-isopropyl-2-oxo-3-cyclohexen-1-yl 3-methylpentanoate; ΔMass: -21.9790 Da] C15 H26 N2 O8 362.16763 2.134
[Similar to: 5-Acetoxy-3-(hydroxymethyl)-6-isopropyl-2-oxo-3-cyclohexen-1-yl 3-methylpentanoate; ΔMass: -22.9239 Da] C10 H17 N7 O8 363.11249 2.111
[Similar to: 6-Methyl-4-(2-thienylmethyl)-2,3-dihydropyridazin-3-one; ΔMass: 93.9877 Da] C5 H8 N2 O 112.06368 2.439
[Similar to: A-796260; ΔMass: 241.2744 Da] 112.95637 1.742
[Similar to: Amphomycin; ΔMass: 1135.5768 Da] C7 H10 N2 O2 154.07357 2.085
[Similar to: Artemisinin; ΔMass: -20.9947 Da] C8 H17 N9 O4 303.14137 2.753
[Similar to: Azithromycin; ΔMass: 589.5471 Da] 158.96138 3.053
[Similar to: Benproperine; ΔMass: 3.0527 Da] C16 H22 N2 O4 306.15654 11.319
[Similar to: Benproperine; ΔMass: 3.0527 Da] (2) C16 H22 N2 O4 306.15654 11.106
[Similar to: Benproperine; ΔMass: 66.0156 Da] C12 H25 N3 O2 243.19371 6.959
[Similar to: Benproperine; ΔMass: 95.0419 Da] C11 H22 N2 O2 214.16736 11.333
[Similar to: Betaine; ΔMass: 0.1409 Da] 116.93807 1.753
[Similar to: Betaine; ΔMass: -0.8559 Da] 117.9349 1.748
[Similar to: Betaine; ΔMass: -0.9326 Da] 118.01155 1.753
[Similar to: Bialaphos; ΔMass: -18.0059 Da] C10 H26 N5 O2 P3 341.13056 1.974
[Similar to: Bialaphos; ΔMass: -19.0364 Da] C9 H26 N8 O2 S2 342.16107 1.921
[Similar to: Carazolol; ΔMass: 179.0737 Da] C5 H13 N O2 119.09446 1.976
[Similar to: Colistin; ΔMass: 883.5251 Da] C14 H29 N3 O2 271.22485 8.983
[Similar to: Cyclo(glycyl-N5-acetyl-N5-hydroxyornithyl-N5-acetyl-N5-hydroxyornithyl-N5-acetyl-N5-hydroxyornithylglycylglycyl); ΔMass: 388.1720 Da] C13 H21 N3 O5 299.14678 2.328
[Similar to: D-(+)-Glucose; ΔMass: -15.9610 Da] C4 H9 N2 O5 P 196.02435 1.936
[Similar to: D-Glucosamine; ΔMass: -17.0134 Da] C4 H8 N10 196.0928 1.898
[Similar to: Dithiopyr; ΔMass: 232.0199 Da] C3 H3 N7 O2 169.03434 2.035
[Similar to: Dithiopyr; ΔMass: 233.0039 Da] C3 H4 N8 O 168.05041 1.96
[Similar to: DL-Arginine; ΔMass: 0.0829 Da] C6 H2 N6 O 174.02878 2.185
[Similar to: DL-Arginine; ΔMass: -0.8888 Da] C H2 N7 O2 P 175.00049 2.167
[Similar to: DL-Arginine; ΔMass: -174.0398 Da] C18 H26 N2 O P2 348.15146 1.997
[Similar to: Folinic acid; ΔMass: 147.0580 Da] C10 H14 N8 O5 326.10794 3.213
[Similar to: Folinic acid; ΔMass: -157.0677 Da] C21 H38 N6 O16 630.23363 3.145
[Similar to: Folinic acid; ΔMass: 79.0713 Da] C10 H19 N8 O5 P S 394.09464 3.147
[Similar to: GW 610; ΔMass: 0.9863 Da] C9 H12 N4 O7 288.07094 1.988
[Similar to: Kanosamine; ΔMass: 19.0662 Da] 160.01313 2.016
[Similar to: Kanosamine; ΔMass: -20.9972 Da] C3 H12 N4 O6 200.07661 1.823
[Similar to: L-Glutamine; ΔMass: -0.9963 Da] 147.06542 1.97
[Similar to: L-Glutamine; ΔMass: 17.0678 Da] 129.00131 1.935
[Similar to: L-Glutamine; ΔMass: 32.9741 Da] C5 H11 N3 113.09501 1.929
[Similar to: L-Histidine; ΔMass: 0.0507 Da] C3 H12 N P3 155.01878 1.881
[Similar to: L-Histidine; ΔMass: 1.0346 Da] C2 H2 N8 O 154.03484 1.882
[Similar to: L-Kynurenine; ΔMass: 0.0033 Da] C6 H8 N8 O 208.08153 2.273
[Similar to: Muramic acid; ΔMass: 18.1546 Da] C6 H5 N O3 P2 S 232.94587 1.934
[Similar to: N-(2,4-Difluorophenyl)-4-(dimethylamino)nicotinamide; ΔMass: 121.0134 Da] C7 H12 N2 O2 156.08931 2.727
[Similar to: N,N-Diisopropylethylamine (DIPEA); ΔMass: -0.8056 Da] 129.95732 1.751
[Similar to: N,N-Diisopropylethylamine (DIPEA); ΔMass: -398.2130 Da] C25 H53 N O10 527.36479 16.757
[Similar to: N-[4-(2-Aminopyrimidin-4-yl)phenyl]-N'-(3-chlorophenyl)urea; ΔMass: 127.0221 Da] C4 H13 N4 O4 P 212.06659 1.889
[Similar to: N-{[(2R,3S,4S,5S)-5-(2-{[2-(Dimethylamino)ethyl]amino}-2-oxoethyl)-3,4-dihydroxytetrahydro-2-furanyl]methyl}-1,3-benzodioxole-5-carboxamide; ΔMass: 250.2236 Da] 158.96133 1.751
[Similar to: N1-[3-(1H-Imidazol-1-yl)propyl]-2,6-dimethoxy-3-nitrobenzamide; ΔMass: 68.0408 Da] C9 H21 N2 O P3 266.08688 4.654
[Similar to: Nobiletin; ΔMass: 10.9493 Da] C11 H30 N5 O8 P 391.18218 14.419
[Similar to: n-Pentyl isopentyl phthalate ; ΔMass: -19.1862 Da] C22 H47 N 325.36934 16.949
[Similar to: Oleoyl ethylamide; ΔMass: 112.2551 Da] C4 H13 N3 O2 P2 197.04808 1.751
[Similar to: Oleoyl ethylamide; ΔMass: 193.3247 Da] 115.97849 1.752
[Similar to: Oleoyl ethylamide; ΔMass: 211.3349 Da] 97.96826 1.739
[Similar to: Proline; ΔMass: -0.0111 Da] C4 H9 N3 O 115.07445 2.43
[Similar to: Proline; ΔMass: 1.0342 Da] 114.02917 2.101
[Similar to: Proline; ΔMass: -113.9757 Da] 229.03901 2.09
[Similar to: Proline; ΔMass: -114.9722 Da] C4 H8 N8 P2 230.03558 2.09
[Similar to: Secodihydro-hydramicromelin B; ΔMass: -105.1287 Da] C24 H33 N O6 431.22885 16.458
[Similar to: Secodihydro-hydramicromelin B; ΔMass: -91.1129 Da] C19 H27 N7 O4 417.21306 16.458
[Similar to: Sulfamethazine; ΔMass: 155.0043 Da] C6 H9 N3 123.07943 17.285
[Similar to: Sulfamethazine; ΔMass: 155.0044 Da] C6 H9 N3 123.07931 17.239
[Similar to: Tangeritin; ΔMass: -15.9568 Da] C13 H17 N4 O8 P 388.07766 3.143
[Similar to: Unguisin E; ΔMass: 616.3379 Da] C7 H12 N2 O2 156.08929 2.878
[Similar to: Ursolic acid; ΔMass: 228.1410 Da] C13 H28 N2 O 228.21932 16.135
1-(4-Amino-4-carboxybutanoyl)-2-piperidinecarboxylic acid C11 H18 N2 O5 258.12051 2.152
1-(5-Decanoyl-4-nonyl-1,4-dihydro-3-pyridinyl)-1-dodecanone C36 H65 N O2 543.50195 1.868
1,1'-(2,5-Pyrazinediyl)di(1,2,3,4-butanetetrol) C12 H20 N2 O8 320.12073 2.225
1-[(3-Carboxypropyl)amino]-1-deoxy-beta-D-fructofuranose C10 H19 N O7 265.11506 2.17
1-{[(3S,4S,5R)-2,3,4-Trihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]methyl}-2-pyrrolidinecarboxylic acid (non-preferred name) C11 H19 N O7 277.11514 2.478
11-Aminoundecanoic acid C11 H23 N O2 201.17218 5.12
1H-Imidazol-2-ol C3 H4 N2 O 84.03268 16.806
1H-Imidazol-2-ol (2) C3 H4 N2 O 84.03269 16.872
2,3-DIHYDRO-3,5-DIHYDROXY-6-METHYL-4H-PYRAN-4-ONE C6 H8 O4 144.04175 1.998
2,4,6-triaminotoluene C7 H11 N3 137.09476 2.255
2-[(2-Methylimidazo[1,2-a]pyridin-3-yl)carbonyl]hydrazine-1-carboxamide C10 H11 N5 O2 233.08914 2.023
2080745 C9 H20 N2 O2 188.15156 1.915
2908 C5 H11 N 85.08935 1.777
2949 C12 H22 N2 O4 258.157 8.604
2949 (2) C12 H22 N2 O4 258.157 8.349
2-Acetamido-2-deoxyglucose C8 H15 N O6 221.08899 2.26
2-Amino-3-(1H-imidazol-4-yl)propan-1-ol C6 H11 N3 O 141.08978 1.789
2-Amino-4-[(4-aminobutyl)amino]butanoic acid C8 H19 N3 O2 189.14708 4.187
2-Aminonicotinic acid C6 H6 N2 O2 138.04252 5.325
2'-Deoxyadenosine C10 H13 N5 O3 273.08109 2.054
2'-Deoxycytosine C4 H7 N3 97.06425 17.406
2'-deoxymugineic acid C12 H20 N2 O7 304.12602 3.143
2-ETHYL-4,5-DIMETHYLOXAZOLE C7 H11 N O 125.08385 12.274
2-Hydroxyfelbamate C11 H14 N2 O5 254.08919 2.522
2-Hydroxyhippuric acid C9 H9 N O4 217.03449 1.872
3,4-Diaminopyridine C5 H7 N3 109.06395 1.887
3477 C12 H20 N2 O3 240.14626 7.425
3635 C5 H6 O3 114.03169 1.892
3-amino-2,3-dideoxy-scyllo-inosose C6 H11 N O4 161.06817 2.366
3-Aminopyrrolidine C4 H10 N2 86.08472 17.005
3-Pyrroline C4 H7 N 69.05812 1.934
4-guanidinobutanal C5 H11 N3 O 129.0898 1.924
4-Hydroxyprolylalanine C8 H14 N2 O4 202.09457 2.458
4-Hydroxyprolylleucine C11 H20 N2 O4 244.14142 7.776
4-Hydroxyprolylthreonine C9 H16 N2 O5 232.10508 2.346
4-Imidazolemethanol C4 H6 N2 O 98.04811 17.253
4-Imidazolemethanol (2) C4 H6 N2 O 98.04814 16.598
4-Morpholinylacetic acid C6 H11 N O3 145.07334 2.03
4-Morpholinylacetic acid (2) C6 H11 N O3 145.07348 6.689
5-(4-Hydroxybutyl)-2,4-imidazolidinedione C7 H12 N2 O3 172.08426 2.145
5-AMINO-3-HYDROXY-2-(2-OXO-AZETIDIN-1-YL)-PENTANOIC ACID C8 H14 N2 O4 202.09442 2.196
5-AMINO-3-HYDROXY-2-(2-OXO-AZETIDIN-1-YL)-PENTANOIC ACID (2) C8 H14 N2 O4 202.09442 2.062
5-Oxotetrahydrofuran-2-carboxylic acid C5 H6 O4 130.02603 2.015
6-(5-Hydroxy-2-methyl-4-oxo-1(4H)-pyridinyl)norleucine C12 H18 N2 O4 254.12567 8.112
6-Oxolysine C6 H12 N2 O3 160.08417 2.099
6-Oxo-pipecolinic acid C6 H9 N O3 143.05775 1.889
6-Oxo-pipecolinic acid (2) C6 H9 N O3 143.05765 2.345
Aceturic acid C4 H7 N O3 117.0424 2.787
Adipamide C6 H12 N2 O2 144.08944 4.276
Alanylclavam C8 H12 N2 O4 200.07891 3.22
ALA-PRO C8 H14 N2 O3 186.09984 2.273
ala-ser C6 H12 N2 O4 176.07905 2.122
aldehydo-D-glucosamine 6-phosphate C6 H14 N O8 P 259.04463 2.141
Aminolevulinic acid C5 H9 N O3 131.05768 2.091
APM C7 H13 N O4 175.08388 2.301
arg-ala C9 H19 N5 O3 245.14772 2.037
Benserazide C10 H15 N3 O5 257.10164 2.06
Betaine C5 H11 N O2 117.0788 2.1
Bicine C6 H13 N O4 163.08388 2.165
Bis(methylbenzylidene)sorbitol C22 H26 O6 386.17116 16.458
Butoctamide semisuccinate C16 H29 N O5 315.20341 9.226
Butoctamide semisuccinate (2) C16 H29 N O5 315.20341 8.658
Cadaverine C5 H14 N2 102.1158 1.733
Caprolactam C6 H11 N O 113.0838 2.612
capuride C9 H18 N2 O2 186.13616 8.61
carisoprodol C12 H24 N2 O4 260.17256 14.622
Choline C5 H13 N O 103.09984 2.055
Cyclohexylamine C6 H13 N 99.10498 8.986
D-(-)-Glutamine C5 H10 N2 O3 146.06866 1.978
D-(+)-Glucose C6 H12 O6 197.08918 1.992
Deanol C4 H11 N O 89.08434 2.111
Dehydroglycine C2 H3 N O2 73.01657 1.929
D-Glucosamine C6 H13 N O5 179.07876 1.888
Diethylene glycol C4 H10 O3 106.06279 3.618
Dihydrothymine C5 H8 N2 O2 128.05836 2.15
Dimethyl octanediimidate C10 H20 N2 O2 200.15164 8.894
DL-Alanine C3 H7 N O2 89.04803 1.942
DL-Arginine C6 H14 N4 O2 174.11102 1.926
DL-Citrulline C6 H13 N3 O3 175.09497 2.052
EJ4025000 C8 H18 N2 O 158.14154 6.547
EJ4025000 (2) C8 H18 N2 O 158.14154 8.892
ethyl argininate C8 H18 N4 O2 202.14238 2.451
Furfural C5 H4 O2 96.02139 1.739
g-Guanidinobutyrate C5 H11 N3 O2 145.08456 3.332
glu-pro C10 H16 N2 O5 244.10491 4.641
glutaral C5 H8 O2 100.05255 2.172
Gly-l-pro C7 H12 N2 O3 172.08416 2.501
Gly-Lys C8 H17 N3 O3 203.12632 6.453
Guvacine C6 H9 N O2 127.06305 4.189
Hexitol C6 H14 O6 182.07815 1.983
HIDA C6 H11 N O5 177.06307 2.206
Histamine C5 H9 N3 111.0796 1.792
Homocitrulline C7 H15 N3 O3 189.11062 3.132
Imidazolelactic acid C6 H8 N2 O3 156.05302 2.324
ISOXYL C10 H17 N3 O2 211.13136 2.626
Kanosamine C6 H13 N O5 201.06061 1.865
Kanosamine (2) C6 H13 N O5 161.0682 2.031
L-(-)-Serine C3 H7 N O3 105.04263 1.904
L-(+)-Alanine C3 H7 N O2 89.048 2.175
L-(+)-Aspartic acid C4 H7 N O4 133.03698 1.918
L-Alanyl-L-proline C8 H14 N2 O3 186.09986 2.578
L-Aspartic acid C4 H7 N O4 133.03712 2.465
lawsone C10 H6 O3 174.03246 1.756
Leu-Leu C12 H24 N2 O3 244.17764 7.616
Leu-Val C11 H22 N2 O3 230.16226 7.771
L-Glutamic acid C5 H9 N O4 147.05251 2.005
l-Histidinal C6 H9 N3 O 139.0739 17.102
L-Histidine C6 H9 N3 O2 155.06898 1.887
L-Proline C5 H9 N O2 115.06315 1.929
L-Pyroglutamic acid C5 H7 N O3 129.0423 3.636
L-Pyroglutamic acid (2) C5 H7 N O3 129.04218 1.969
L-Theanine C7 H14 N2 O3 174.09986 2.154
LU3453000 C4 H4 O2 84.02152 1.982
lys-leu C12 H25 N3 O3 259.18852 3.07
Lysylvaline C11 H23 N3 O3 245.17299 2.192
MA4000000 C5 H7 N O2 113.04764 1.768
Maleamic acid C4 H5 N O3 115.02648 1.908
mebutamate C10 H20 N2 O4 232.14133 12.272
melamine C3 H6 N6 126.06518 2.46
Methionine sulfoxide C5 H11 N O3 S 165.04526 2.052
Methylimidazoleacetic acid C6 H8 N2 O2 140.05806 1.959
Methylol Dimethylhydantoin C6 H10 N2 O3 158.0686 1.956
MFCD00037215 C8 H14 N2 O5 218.08958 2.575
MFCD01664827 C5 H8 N2 O5 176.04272 2.471
Miglitol C8 H17 N O5 207.10979 2.061
Muramic acid C9 H17 N O7 251.09953 2.015
Muscimol C4 H6 N2 O2 114.04244 17.447
N-((4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL)FORMAMIDE C7 H10 N4 O 166.08487 3.241
N-(4-Amino-1-carboxybutyl)glutamic acid C10 H18 N2 O6 262.11555 2.38
N,N-diacetyllegionaminic acid C13 H22 N2 O8 334.13627 3.063
N,N-diacetyllegionaminic acid (2) C13 H22 N2 O8 334.13649 2.103
N,N-Diethylethanolamine C6 H15 N O 117.11525 2.695
N~6~,N~6~-Dimethyllysine C8 H18 N2 O2 174.13618 1.917
N6-METHYLLYSINE C7 H16 N2 O2 160.1206 1.885
N-Acetylleucylleucine C14 H26 N2 O4 286.18804 9.685
N-Acetylneuraminic acid C11 H19 N O9 309.1047 2.09
N-Acetylputrescine C6 H14 N2 O 130.11028 2.62
NI3400000 C5 H6 N2 O 110.04795 1.96
Nicotinamide C6 H6 N2 O 122.04777 2.521
NJ5000000 C8 H15 N3 O2 185.11564 1.829
N-methylethanolamine phosphate C3 H10 N O4 P 155.03427 2.08
N-methylethanolamine phosphate (2) C3 H10 N O4 P 155.03426 1.814
NPYR C4 H8 N2 O 100.06384 1.976
nylon cyclic dimer C12 H22 N2 O2 226.16724 9.213
nylon cyclic dimer (2) C12 H22 N2 O2 226.16725 8.984
Ofloxacin ethyl ester C20 H24 F N3 O4 389.17785 2.06
Oxaceprol C7 H11 N O4 173.06798 2.032
pentobarbital C11 H18 N2 O3 226.13098 6.446
pentobarbital (2) C11 H18 N2 O3 226.13097 5.662
pentobarbital (3) C11 H18 N2 O3 226.13098 4.285
Pioglitazone C19 H20 N2 O3 S 356.1183 3.048
Piracetam C6 H10 N2 O2 142.07369 2.675
Piracetam (2) C6 H10 N2 O2 142.07377 2.287
PPG n10 C30 H62 O11 615.45444 16.65
PPG n10 (2) C30 H62 O11 615.45458 16.567
PPG n8 C24 H50 O9 499.37064 15.202
PPG n9 C27 H56 O10 557.41247 16.034
pro-gln C10 H17 N3 O4 243.12092 2.405
pro-gln (2) C10 H17 N3 O4 243.1209 2.724
Pro-Glu C10 H16 N2 O5 244.10491 2.423
Pro-Glu (2) C10 H16 N2 O5 244.10498 2.555
Proline C5 H9 N O2 115.06314 2.174
Pyridoxamine C8 H12 N2 O2 168.08925 2.119
Pyrimidine C4 H4 N2 80.03736 17.269
Pyrimidine (2) C4 H4 N2 80.0378 17.234
Reduced Glutathione C10 H17 N3 O6 S 307.08242 3.243
RV0540000 C5 H12 O4 136.07302 2.173
spinacine C7 H9 N3 O2 167.06878 1.855
Streptamine C6 H14 N2 O4 178.09474 1.771
Succinyl proline C9 H13 N O5 215.07833 2.013
Sulfuric acid H2 O4 S 97.96759 1.738
Tetraacetylethylenediamine C10 H16 N2 O4 228.11015 2.148
Threonine C4 H9 N O3 119.05808 1.973
tiapride C15 H24 N2 O4 S 328.14535 1.904
Tiformin C5 H12 N4 O 144.10056 2.598
Timonacic C4 H7 N O2 S 133.01931 2.238
Triethanolamine C6 H15 N O3 149.10465 2.002
Triethylamine C6 H15 N 101.12053 3.838
Triisopropanolamine C9 H21 N O3 191.15125 3.257
trimethadione C6 H9 N O3 143.05774 2.78
UB6600000 C6 H15 N O2 133.10984 3.535
UB6600000 (2) C6 H15 N O2 133.10987 2.542
val-arg C11 H23 N5 O3 273.17893 2.607
val-asn C9 H17 N3 O4 231.12094 2.251
Veronal C8 H12 N2 O3 184.08413 3.639
Veronal (2) C8 H12 N2 O3 184.08414 4.537
Veronal (3) C8 H12 N2 O3 184.08415 4.172
Viloxazine C13 H19 N O3 237.13734 2.098
Υ-Aminobutyric acid (GABA) C4 H9 N O2 103.06341 2.083
METABOLITES_END
#END