#METABOLOMICS WORKBENCH epmosher_20210121_142232 DATATRACK_ID:2414 STUDY_ID:ST001658 ANALYSIS_ID:AN002707 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 NEGATIVE
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
(±)-Ibotenic acid 9540737.349 44452.64866 334588.7782
(1R,2R,3S,5R,7R)-2-Acetamido-7-(1,2-dihydroxyethyl)-3-hydroxy-6,8-dioxabicyclo[3.2.1]octane-5-carboxylic acid 1446887.385 51910445.09 20059523.08
(1R,2R,3S,5R,7R)-2-Acetamido-7-(1,2-dihydroxyethyl)-3-hydroxy-6,8-dioxabicyclo[3.2.1]octane-5-carboxylic acid (2) 409229.6609 6963219.568 5217140.513
(2S)-2-({[(3S,4S,5R)-2,3,4-Trihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]methyl}amino)propanoic acid (non-preferred name) 140312.5155 61999860.06 202544290.5
(2S)-3-Hydroxy-2-({[(3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]methyl}amino)butanoic acid (non-preferred name) 85017.00804 610761.7381 302258175.3
[Similar to: (2-{[(1S,11aS)-7-(1,3-Benzodioxol-5-yl)-5,11-dioxo-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-1-yl]amino}-2-oxoethoxy)acetic acid; ΔMass: 305.0813 Da] 2271432.095 25991345.78 52658334.14
[Similar to: (2-{[(1S,11aS)-7-(1,3-Benzodioxol-5-yl)-5,11-dioxo-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-1-yl]amino}-2-oxoethoxy)acetic acid; ΔMass: 306.0654 Da] 108952.6459 10995521.48 30121306.41
[Similar to: (2-{[7-(2-Fluorophenyl)-5,11-dioxo-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-1-yl]amino}-2-oxoethoxy)acetic acid; ΔMass: 106.0721 Da] 64482.58995 43474871.62 21536961.28
[Similar to: (2-{[7-(2-Fluorophenyl)-5,11-dioxo-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-1-yl]amino}-2-oxoethoxy)acetic acid; ΔMass: 278.0869 Da] 93018.43073 249763.5055 17548427.85
[Similar to: (3R,4R,6R)-6-{[4-(1-Hydroxycyclopentyl)-1H-1,2,3-triazol-1-yl]methyl}-N-(2-methoxybenzyl)quinuclidine-3-carboxamide; ΔMass: 301.1805 Da] 2553051.337 14657356.15 43537.99421
[Similar to: (4S,6S)-N-(Cyclopropylmethyl)-6-isobutyl-1-[(1-methyl-1H-imidazol-2-yl)methyl]-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indole-4-carboxamide; ΔMass: 142.1527 Da] 11984.03968 5739785.708 6323601.988
[Similar to: (4S,6S)-N-(Cyclopropylmethyl)-6-isobutyl-1-[(1-methyl-1H-imidazol-2-yl)methyl]-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indole-4-carboxamide; ΔMass: 247.1849 Da] 33181.98808 10404801.1 14944115.49
[Similar to: 2-Methoxy-N-{2-[1-(2-naphthyl)-1H-1,2,3,4-tetraazol-5-yl]vinyl}-5-(trifluoromethyl)aniline; ΔMass: 43.0187 Da] 44113.04533 18292988.55 57228293.75
[Similar to: 2-Methoxy-N-{2-[1-(2-naphthyl)-1H-1,2,3,4-tetraazol-5-yl]vinyl}-5-(trifluoromethyl)aniline; ΔMass: 43.2561 Da] 616930.9926 17492918.87 433282.9275
[Similar to: 2-Methoxy-N-{2-[1-(2-naphthyl)-1H-1,2,3,4-tetraazol-5-yl]vinyl}-5-(trifluoromethyl)aniline; ΔMass: 44.0152 Da] 62548.9873 19690062.81 23559367.49
[Similar to: 4-Guanidinobutyric acid; ΔMass: 43.0549 Da] 2926865.168 31214369.51 72334998.83
[Similar to: 4-Oxoproline; ΔMass: -0.9228 Da] 91839007.76 63348124.67 2325794.071
[Similar to: 4-Oxoproline; ΔMass: -0.9825 Da] 78309.40354 770076.5059 10375369.51
[Similar to: 4-Oxoproline; ΔMass: -67.9864 Da] 245187.9668 12327821.8 7583362.223
[Similar to: Argininosuccinic acid; ΔMass: 158.0342 Da] 112287.7725 78267.69396 207646775.2
[Similar to: Argininosuccinic acid; ΔMass: 158.1592 Da] 7100825.405 80900492.86 423799.3258
[Similar to: Argininosuccinic acid; ΔMass: 159.1223 Da] 5204505.731 47144.07436 262912.4296
[Similar to: D-(-)-Glutamine; ΔMass: -71.9041 Da] 38196.38007 4803452.923 45109.00764
[Similar to: DL-Arginine; ΔMass: 0.1561 Da] 1347863.565 13032309.99 562774.8554
[Similar to: DL-Arginine; ΔMass: 1.0828 Da] 69012.18631 65380.54409 43182292.95
[Similar to: DL-Homoserine ; ΔMass: -161.0380 Da] 55427.50573 3164047.383 1414936.46
[Similar to: DL-Malic acid; ΔMass: 0.9854 Da] 89572.5854 13937171.73 608977.4718
[Similar to: Guanidinosuccinic acid; ΔMass: 43.0073 Da] 203781.2851 165463.8067 94509107.54
[Similar to: L-(-)-Malic acid; ΔMass: -156.0032 Da] 9069.583177 2214338.769 11425.197
[Similar to: L-Glutamic acid; ΔMass: 0.0481 Da] 42909.6235 44803.68093 7722835.007
[Similar to: L-Glutamic acid; ΔMass: -147.0028 Da] 88407.6981 15219565.6 3454727.853
[Similar to: L-Glutamic acid; ΔMass: -161.0684 Da] 47801.12506 51500.40876 76906907.02
[Similar to: L-Glutamic acid; ΔMass: -168.0507 Da] 79376.445 59148.23729 45544875.22
[Similar to: L-Glutamic acid; ΔMass: -168.6796 Da] 116112985.2 199683.6544 624895.6296
[Similar to: L-Glutamic acid; ΔMass: -169.0348 Da] 71878.2626 82855.15019 233585524.2
[Similar to: L-Glutamic acid; ΔMass: -184.6535 Da] 115351455.3 130395.9992 336129.3037
[Similar to: L-Glutamic acid; ΔMass: -250.1156 Da] 82102.10185 57950.94874 13484818.5
[Similar to: L-Glutamic acid; ΔMass: -251.0997 Da] 61250.90347 54770.41534 127150760.5
[Similar to: L-Histidine; ΔMass: -0.8350 Da] 41157152.81 142735.5264 861135.6052
[Similar to: Microcystin LF; ΔMass: 855.5507 Da] 99832171.41 1104853913 6463195.797
[Similar to: N-(2,3-Dihydro-1,4-benzodioxin-6-yl)-1,2-dimethyl-1H-imidazole-4-sulfonamide; ΔMass: 122.9789 Da] 755798.4658 34536491.91 335434.9508
[Similar to: N-1-({2-[4-(Dimethylamino)benzoyl]hydrazino}carbothioyl)-2-methylbut-2-enamide; ΔMass: 118.1227 Da] 36174.236 10273961.97 69661.57013
[Similar to: N'1-(2-Chlorobenzylidene)-4-hydroxy-3-(methylthio)-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carbohydrazide; ΔMass: 120.2707 Da] 139110702.9 145238.9977 407234.887
[Similar to: N4-Acetylcytidine; ΔMass: 127.0282 Da] 93765.21746 6470334.73 17697533.25
[Similar to: N4-Acetylcytidine; ΔMass: 128.0123 Da] 108182.0285 79935.7704 20965216.49
[Similar to: Pyridoxamine; ΔMass: -18.0095 Da] 1489195.783 9912274.055 147887.3019
[Similar to: S-Lactoylglutathione; ΔMass: 51.9888 Da] 82279.9459 89427.86984 390082595.6
[Similar to: S-Lactoylglutathione; ΔMass: 52.9728 Da] 74886.02663 42359.54456 370091566.5
[Similar to: S-Lactoylglutathione; ΔMass: 53.9569 Da] 67009.70144 49513.51145 10919869.39
[Similar to: SSR504734; ΔMass: 124.0210 Da] 17749522.38 4020957.085 45320.18126
[Similar to: Threonine; ΔMass: -162.8571 Da] 4262248.335 85964807.91 178390.2567
[Similar to: Threonine; ΔMass: -179.0789 Da] 60432.75647 45326.29388 26344774.47
[Similar to: Threonine; ΔMass: -180.0629 Da] 80827.61568 448935.9608 377716623.9
[Similar to: Threonine; ΔMass: -180.8291 Da] 1412775.372 61509833.11 235176.2829
[Similar to: Threonine; ΔMass: -181.0458 Da] 72084.83028 53263.52741 4484628.325
[Similar to: Threonine; ΔMass: -72.0200 Da] 368896.313 1422774.349 26639274.44
[Similar to: Uracil; ΔMass: -176.0656 Da] 104483.622 93429.01165 16657748.66
1-(beta-D-Ribofuranosyl)-1,2-dihydropyrimidine 35034.90177 114165.7271 6659161.034
1-[5-(2,3,4-Trihydroxybutyl)-2-pyrazinyl]-1,2,3,4-butanetetrol 105073.7353 2065587.428 634325882.7
2,3,4,5,6,7-Hexahydroxyheptanoic acid 617892.7008 395414191 718715994.1
3-(3,4-dihydroxyphenyl)lactamide 26412.72795 3311067.718 12356.56919
3,4-Dihydroxy-5-(1,2,3-trihydroxypropyl)dihydro-2(3H)-furanone 1523433.459 1119066.461 18927665.92
4-Hydroxyprolylthreonine 510156.2404 3457825.832 17715469.14
4-Oxoproline 1603103.271 84775188.31 47794515.49
6-deoxyinosine 5'-phosphate 70875.86718 61958.45485 21362590.9
AC-benzyl 6454952.694 1029803.466 334603.3165
Bisphenol S 19436822.08 2513059.403 2556635.851
Bluensidine 136569.0882 101840.7823 7114171.782
D-(-)-Glutamine 252689.6501 262898.8427 1704079020
D-(-)-Glutamine (2) 88179.06901 1809381.556 76076651.08
D-(+)-Glucose 3528143.011 628428000.7 1145309760
D-Glucono-delta-lactone 199728.8439 13343796.53 58988883.81
Dinoterb 20312.00758 22922.68007 9389437.505
DL-Arginine 403963.821 293616.7443 778072378.7
DL-Arginine (2) 168693.019 126524.5837 55938900.97
DL-Glutamine 76189.16393 47931.64732 17099749.17
Ethylene glycol tetraacetic acid 13557.39738 32755.92506 8310556.495
Fenson 24443433.45 2012210.391 2944473.254
Galactosamine 391041.2314 15027349.12 234719463.2
Gluconic acid 4072601.333 10947594.08 49636292.09
Gluconic acid (2) 1565414.121 5146194.945 47293213.5
L-(-)-Malic acid 692182.0606 116901561.6 739222.8033
L-Aspartic acid 364455.4919 279213.8128 476247407.1
L-Aspartic acid (2) 147065.7769 162552.0329 465071040.1
L-Glutamic acid 20942420.78 1860818.323 7500495918
L-Histidine 103174.4911 81644.21257 71158955.36
MFCD00037215 22486.27512 130696.1291 33595517.12
Midodrine 5142940.189 63962.90147 11244.72468
N-(3-Carboxy-3-hydroxypropyl)-4-[(carboxymethyl)amino]homoserine 58986.03273 67994.08367 39710253.03
N-(4-Amino-1-carboxybutyl)glutamic acid 25746.25009 26128.73052 11039273.79
N-Acetyl-DL-glutamic acid 64164.42301 10291216.61 26937.02965
N-Acetylneuraminic acid 147443.0336 799110.1127 183786604.8
neuraminic acid 36769.2801 5762179.774 126284.027
N-hexadecanoylsphinganine 29288334.06 110656.1614 167881.9188
N-Methyl-<scp>D</scp>-aspartic acid 71662.74167 68809.91406 39710253.03
Orotidine 35254.80068 8313332.247 30795374.93
shinorine 10235015.58 534090.617 580146.4383
Trabodenoson 25996.0409 354740.7964 6464568.01
Υ-Aminobutyric acid (GABA) 878396.9767 73580.40888 428733204
MS_METABOLITE_DATA_END
#METABOLITES
METABOLITES_START
metabolite_name Formula Molecular Weight Retention times [min]
(±)-Ibotenic acid C5 H6 N2 O4 158.03334 1.976
(1R,2R,3S,5R,7R)-2-Acetamido-7-(1,2-dihydroxyethyl)-3-hydroxy-6,8-dioxabicyclo[3.2.1]octane-5-carboxylic acid C11 H17 N O8 291.09521 3.506
(1R,2R,3S,5R,7R)-2-Acetamido-7-(1,2-dihydroxyethyl)-3-hydroxy-6,8-dioxabicyclo[3.2.1]octane-5-carboxylic acid (2) C11 H17 N O8 291.09526 2.613
(2S)-2-({[(3S,4S,5R)-2,3,4-Trihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]methyl}amino)propanoic acid (non-preferred name) C9 H17 N O7 251.09995 1.954
(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 281.11064 1.996
[Similar to: (2-{[(1S,11aS)-7-(1,3-Benzodioxol-5-yl)-5,11-dioxo-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-1-yl]amino}-2-oxoethoxy)acetic acid; ΔMass: 305.0813 Da] 162.05153 1.923
[Similar to: (2-{[(1S,11aS)-7-(1,3-Benzodioxol-5-yl)-5,11-dioxo-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-1-yl]amino}-2-oxoethoxy)acetic acid; ΔMass: 306.0654 Da] 161.06751 1.954
[Similar to: (2-{[7-(2-Fluorophenyl)-5,11-dioxo-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-1-yl]amino}-2-oxoethoxy)acetic acid; ΔMass: 106.0721 Da] C11 H9 N7 O6 335.06151 1.945
[Similar to: (2-{[7-(2-Fluorophenyl)-5,11-dioxo-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-1-yl]amino}-2-oxoethoxy)acetic acid; ΔMass: 278.0869 Da] 163.04671 1.929
[Similar to: (3R,4R,6R)-6-{[4-(1-Hydroxycyclopentyl)-1H-1,2,3-triazol-1-yl]methyl}-N-(2-methoxybenzyl)quinuclidine-3-carboxamide; ΔMass: 301.1805 Da] 138.07787 2.211
[Similar to: (4S,6S)-N-(Cyclopropylmethyl)-6-isobutyl-1-[(1-methyl-1H-imidazol-2-yl)methyl]-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indole-4-carboxamide; ΔMass: 142.1527 Da] C6 H16 N9 O2 P 277.11577 2.425
[Similar to: (4S,6S)-N-(Cyclopropylmethyl)-6-isobutyl-1-[(1-methyl-1H-imidazol-2-yl)methyl]-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indole-4-carboxamide; ΔMass: 247.1849 Da] 172.08362 2.111
[Similar to: 2-Methoxy-N-{2-[1-(2-naphthyl)-1H-1,2,3,4-tetraazol-5-yl]vinyl}-5-(trifluoromethyl)aniline; ΔMass: 43.0187 Da] C18 H16 N4 O5 368.11199 1.938
[Similar to: 2-Methoxy-N-{2-[1-(2-naphthyl)-1H-1,2,3,4-tetraazol-5-yl]vinyl}-5-(trifluoromethyl)aniline; ΔMass: 43.2561 Da] C7 H4 N2 O6 P4 S 367.87461 1.817
[Similar to: 2-Methoxy-N-{2-[1-(2-naphthyl)-1H-1,2,3,4-tetraazol-5-yl]vinyl}-5-(trifluoromethyl)aniline; ΔMass: 44.0152 Da] 367.11548 1.944
[Similar to: 4-Guanidinobutyric acid; ΔMass: 43.0549 Da] 102.03026 1.936
[Similar to: 4-Oxoproline; ΔMass: -0.9228 Da] 129.96544 2.072
[Similar to: 4-Oxoproline; ΔMass: -0.9825 Da] 130.02513 1.934
[Similar to: 4-Oxoproline; ΔMass: -67.9864 Da] C5 H14 N O P3 197.02904 3.595
[Similar to: Argininosuccinic acid; ΔMass: 158.0342 Da] 132.08842 1.859
[Similar to: Argininosuccinic acid; ΔMass: 158.1592 Da] 131.96345 1.816
[Similar to: Argininosuccinic acid; ΔMass: 159.1223 Da] C H2 N5 O P 131.00029 1.928
[Similar to: D-(-)-Glutamine; ΔMass: -71.9041 Da] C5 H3 N2 O6 P 217.9732 2.41
[Similar to: DL-Arginine; ΔMass: 0.1561 Da] C5 H5 O P3 173.95553 1.865
[Similar to: DL-Arginine; ΔMass: 1.0828 Da] 173.02889 1.812
[Similar to: DL-Homoserine ; ΔMass: -161.0380 Da] C7 H18 N6 O2 P2 280.0962 2.016
[Similar to: DL-Malic acid; ΔMass: 0.9854 Da] 133.03612 2.417
[Similar to: Guanidinosuccinic acid; ΔMass: 43.0073 Da] 132.05203 1.841
[Similar to: L-(-)-Malic acid; ΔMass: -156.0032 Da] C6 H6 N6 O8 290.02473 2.414
[Similar to: L-Glutamic acid; ΔMass: 0.0481 Da] 147.00505 1.924
[Similar to: L-Glutamic acid; ΔMass: -147.0028 Da] C6 H10 N6 O8 294.05597 1.942
[Similar to: L-Glutamic acid; ΔMass: -161.0684 Da] C11 H20 N2 O8 308.12158 1.994
[Similar to: L-Glutamic acid; ΔMass: -168.0507 Da] C7 H17 N5 O9 315.10383 1.904
[Similar to: L-Glutamic acid; ΔMass: -168.6796 Da] 315.73276 1.836
[Similar to: L-Glutamic acid; ΔMass: -169.0348 Da] C8 H20 N4 O5 S2 316.08793 1.954
[Similar to: L-Glutamic acid; ΔMass: -184.6535 Da] 331.70662 1.84
[Similar to: L-Glutamic acid; ΔMass: -250.1156 Da] C10 H23 N9 O8 397.1688 1.908
[Similar to: L-Glutamic acid; ΔMass: -251.0997 Da] C17 H27 N4 O3 P S 398.15289 1.955
[Similar to: L-Histidine; ΔMass: -0.8350 Da] 155.90452 2.019
[Similar to: Microcystin LF; ΔMass: 855.5507 Da] 129.96539 1.824
[Similar to: N-(2,3-Dihydro-1,4-benzodioxin-6-yl)-1,2-dimethyl-1H-imidazole-4-sulfonamide; ΔMass: 122.9789 Da] 186.09943 2.525
[Similar to: N-1-({2-[4-(Dimethylamino)benzoyl]hydrazino}carbothioyl)-2-methylbut-2-enamide; ΔMass: 118.1227 Da] C4 H13 O3 P3 202.00801 2.417
[Similar to: N'1-(2-Chlorobenzylidene)-4-hydroxy-3-(methylthio)-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carbohydrazide; ΔMass: 120.2707 Da] 259.77129 1.845
[Similar to: N4-Acetylcytidine; ΔMass: 127.0282 Da] 158.06785 1.871
[Similar to: N4-Acetylcytidine; ΔMass: 128.0123 Da] 157.08381 1.856
[Similar to: Pyridoxamine; ΔMass: -18.0095 Da] 186.09936 2.213
[Similar to: S-Lactoylglutathione; ΔMass: 51.9888 Da] C11 H21 N O10 327.11613 1.925
[Similar to: S-Lactoylglutathione; ΔMass: 52.9728 Da] C11 H22 N2 O9 326.13211 1.885
[Similar to: S-Lactoylglutathione; ΔMass: 53.9569 Da] C11 H23 N3 O8 325.14802 1.844
[Similar to: SSR504734; ΔMass: 124.0210 Da] C11 H16 N2 O6 272.10065 6.542
[Similar to: Threonine; ΔMass: -162.8571 Da] C6 H2 O9 S2 281.9153 1.81
[Similar to: Threonine; ΔMass: -179.0789 Da] C10 H22 N2 O8 298.13713 1.854
[Similar to: Threonine; ΔMass: -180.0629 Da] C10 H21 N O9 299.12119 1.889
[Similar to: Threonine; ΔMass: -180.8291 Da] C3 H5 N4 O P5 S 299.88734 1.818
[Similar to: Threonine; ΔMass: -181.0458 Da] C7 H12 N10 O4 300.10408 1.845
[Similar to: Threonine; ΔMass: -72.0200 Da] 191.07826 1.998
[Similar to: Uracil; ΔMass: -176.0656 Da] C16 H17 O3 P 288.09284 1.983
1-(beta-D-Ribofuranosyl)-1,2-dihydropyrimidine C9 H14 N2 O4 214.09469 3.086
1-[5-(2,3,4-Trihydroxybutyl)-2-pyrazinyl]-1,2,3,4-butanetetrol C12 H20 N2 O7 304.12694 3.09
2,3,4,5,6,7-Hexahydroxyheptanoic acid C7 H14 O8 226.06821 1.916
3-(3,4-dihydroxyphenyl)lactamide C9 H11 N O4 197.06785 8.838
3,4-Dihydroxy-5-(1,2,3-trihydroxypropyl)dihydro-2(3H)-furanone C7 H12 O7 208.05737 1.948
4-Hydroxyprolylthreonine C9 H16 N2 O5 232.10532 2.292
4-Oxoproline C5 H7 N O3 129.04115 3.595
6-deoxyinosine 5'-phosphate C10 H13 N4 O7 P 332.05276 1.963
AC-benzyl C11 H12 O3 192.07952 2.045
Bisphenol S C12 H10 O4 S 250.02955 12.231
Bluensidine C8 H16 N4 O6 264.10658 1.858
D-(-)-Glutamine C5 H10 N2 O3 146.06776 1.878
D-(-)-Glutamine (2) C5 H10 N2 O3 146.06779 2.08
D-(+)-Glucose C6 H12 O6 180.06239 1.913
D-Glucono-delta-lactone C6 H10 O6 178.04682 1.919
Dinoterb C10 H12 N2 O5 240.07166 2.515
DL-Arginine C6 H14 N4 O2 174.11054 1.857
DL-Arginine (2) C6 H14 N4 O2 174.11142 1.859
DL-Glutamine C5 H10 N2 O3 146.06895 1.876
Ethylene glycol tetraacetic acid C14 H24 N2 O10 380.14271 2.998
Fenson C12 H9 Cl O3 S 267.9959 15.934
Galactosamine C6 H13 N O5 179.07863 1.815
Gluconic acid C6 H12 O7 136.03593 1.951
Gluconic acid (2) C6 H12 O7 196.05729 1.941
L-(-)-Malic acid C4 H6 O5 134.0201 2.412
L-Aspartic acid C4 H7 N O4 73.01495 1.87
L-Aspartic acid (2) C4 H7 N O4 133.03603 1.873
L-Glutamic acid C5 H9 N O4 147.05178 1.932
L-Histidine C6 H9 N3 O2 155.06814 1.83
MFCD00037215 C8 H14 N2 O5 218.08957 2.515
Midodrine C12 H18 N2 O4 254.12626 8.065
N-(3-Carboxy-3-hydroxypropyl)-4-[(carboxymethyl)amino]homoserine C10 H18 N2 O8 294.10602 1.947
N-(4-Amino-1-carboxybutyl)glutamic acid C10 H18 N2 O6 262.11613 2.326
N-Acetyl-DL-glutamic acid C7 H11 N O5 189.0627 4.216
N-Acetylneuraminic acid C11 H19 N O9 309.10572 2.027
neuraminic acid C9 H17 N O8 267.09509 2.114
N-hexadecanoylsphinganine C34 H69 N O3 539.52716 1.826
N-Methyl-<scp>D</scp>-aspartic acid C5 H9 N O4 147.05297 1.936
Orotidine C10 H12 N2 O8 288.05907 2.073
shinorine C13 H20 N2 O8 332.12179 6.556
Trabodenoson C15 H20 N6 O6 380.1427 2.159
Υ-Aminobutyric acid (GABA) C4 H9 N O2 103.06166 1.931
METABOLITES_END
#END