#METABOLOMICS WORKBENCH torichristian_20220406_090827 DATATRACK_ID:3176 STUDY_ID:ST002174 ANALYSIS_ID:AN003562 PROJECT_ID:PR001383 VERSION 1 CREATED_ON May 24, 2022, 9:00 am #PROJECT PR:PROJECT_TITLE Identifying a tryptophan derivative in hydrogen peroxide-treated cell culture PR:PROJECT_TITLE medium PR:PROJECT_SUMMARY Reactive oxygen species (ROS) are by-products of metabolism of oxygen and they PR:PROJECT_SUMMARY play an important role in normal homeostasis and cell signaling, as well as in PR:PROJECT_SUMMARY the initiation of diseases including cancer when their production is PR:PROJECT_SUMMARY upregulated. Thus, it is imperative to understand the cellular and molecular PR:PROJECT_SUMMARY basis by which ROS impact on various biological and pathological processes. PR:PROJECT_SUMMARY Here, we identified 2-oxindole, a tryptophan derivative, was a major catabolic PR:PROJECT_SUMMARY product in hydrogen peroxide-treated cell culture medium. We used 2-oxindole to PR:PROJECT_SUMMARY study its role in regulating AhR signaling and tryptophan metabolic pathways. We PR:PROJECT_SUMMARY found that 2-oxindole significantly increased the activity of AhR, leading to PR:PROJECT_SUMMARY enhanced expression of its downstream targets including cytochrome P450 genes. PR:INSTITUTE NYU Langone Health PR:DEPARTMENT Department of Biochemistry and Molecular Pharmacology PR:LABORATORY Dai PR:LAST_NAME Choi PR:FIRST_NAME Byeong Hyeok PR:ADDRESS 341 East 25 Street New York, NY 10010 PR:EMAIL ByeongHyeok.Choi@nyulangone.org PR:PHONE 212-263-5521 PR:FUNDING_SOURCE NCI/US Public Service Award PR:CONTRIBUTORS Metabolomics Core Resource Laboratory #STUDY ST:STUDY_TITLE Identifying a tryptophan derivative in hydrogen peroxide-treated cell culture ST:STUDY_TITLE medium ST:STUDY_SUMMARY Reactive oxygen species (ROS) are by-products of metabolism of oxygen and they ST:STUDY_SUMMARY play an important role in normal homeostasis and cell signaling, as well as in ST:STUDY_SUMMARY the initiation of diseases including cancer when their production is ST:STUDY_SUMMARY upregulated. Thus, it is imperative to understand the cellular and molecular ST:STUDY_SUMMARY basis by which ROS impact on various biological and pathological processes. ST:STUDY_SUMMARY Here, we identified 2-oxindole, a tryptophan derivative, was a major catabolic ST:STUDY_SUMMARY product in hydrogen peroxide-treated cell culture medium. We used 2-oxindole to ST:STUDY_SUMMARY study its role in regulating AhR signaling and tryptophan metabolic pathways. We ST:STUDY_SUMMARY found that 2-oxindole significantly increased the activity of AhR, leading to ST:STUDY_SUMMARY enhanced expression of its downstream targets including cytochrome P450 genes. ST:INSTITUTE NYU Langone Health ST:DEPARTMENT Department of Biochemistry and Molecular Pharmacology ST:LABORATORY Dai ST:LAST_NAME Choi ST:FIRST_NAME Byeong Hyeok ST:ADDRESS 341 East 25 Street New York, NY 10010 ST:EMAIL ByeongHyeok.Choi@nyulangone.org ST:PHONE 2122635521 #SUBJECT SU:SUBJECT_TYPE Other abiotic sample #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 - 19 NT 13C 1 Group:VEH RAW_FILE_NAME=S16179.raw SUBJECT_SAMPLE_FACTORS - 19 NT 13C 2 Group:VEH RAW_FILE_NAME=S16180.raw SUBJECT_SAMPLE_FACTORS - 19 NT 13C 3 Group:VEH RAW_FILE_NAME=S16181.raw SUBJECT_SAMPLE_FACTORS - 19 +DON 13C 1 Group:+DON RAW_FILE_NAME=S16182.raw SUBJECT_SAMPLE_FACTORS - 19 +DON 13C 2 Group:+DON RAW_FILE_NAME=S16183.raw SUBJECT_SAMPLE_FACTORS - 19 +DON 13C 3 Group:+DON RAW_FILE_NAME=S16184.raw SUBJECT_SAMPLE_FACTORS - 19 NT 15N 1 Group:NT RAW_FILE_NAME=S16185.raw SUBJECT_SAMPLE_FACTORS - 19 NT 15N 2 Group:NT RAW_FILE_NAME=S16186.raw SUBJECT_SAMPLE_FACTORS - 19 NT 15N 3 Group:NT RAW_FILE_NAME=S16187.raw SUBJECT_SAMPLE_FACTORS - 19 +DON 15N 1 Group:DON RAW_FILE_NAME=S16188.raw SUBJECT_SAMPLE_FACTORS - 19 +DON 15N 2 Group:DON RAW_FILE_NAME=S16189.raw SUBJECT_SAMPLE_FACTORS - 19 +DON 15N 3 Group:DON RAW_FILE_NAME=S16190.raw #COLLECTION CO:COLLECTION_SUMMARY Treatment and sample collection summary Dulbecco’s Modified Eagle’s Medium CO:COLLECTION_SUMMARY (DMEM, Corning, NY) supplemented with 10% fetal bovine serum (Atlanta CO:COLLECTION_SUMMARY biologicals) were treated with or without 0.2 mM hydrogen peroxide for 30 min in CO:COLLECTION_SUMMARY room temperature in triplicate. After incubation samples were immediately frozen CO:COLLECTION_SUMMARY in -80C. CO:SAMPLE_TYPE Media #TREATMENT TR:TREATMENT_SUMMARY Dulbecco’s Modified Eagle’s Medium (DMEM, Corning, NY) supplemented with 10% TR:TREATMENT_SUMMARY fetal bovine serum (Atlanta biologicals) were treated with or without 0.2 mM TR:TREATMENT_SUMMARY hydrogen peroxide for 30 min in room temperature in triplicate. After incubation TR:TREATMENT_SUMMARY samples were immediately frozen in -80C. #SAMPLEPREP SP:SAMPLEPREP_SUMMARY Samples were extracted with methanol and in house cocktail of amino acids, SP:SAMPLEPREP_SUMMARY acting as an internal standards. Samples were then homogenized and spun down, SP:SAMPLEPREP_SUMMARY and supernatant was dried down. Dried down samples were reconstituted and SP:SAMPLEPREP_SUMMARY transferred to LCMS vials, then injected on LCMS at 2ul per sample SP:SAMPLEPREP_PROTOCOL_ID 0.01.12.12 SP:PROCESSING_STORAGE_CONDITIONS 4℃ SP:EXTRACTION_METHOD E.01 SP:EXTRACT_CONCENTRATION_DILUTION 9X SP:EXTRACT_STORAGE -80℃ SP:SAMPLE_RESUSPENSION 50uL SP:SAMPLE_SPIKING 500nM #CHROMATOGRAPHY CH:CHROMATOGRAPHY_SUMMARY SeQuant ZIC-pHILIC 5um polymer, 150x2.1mm - Part No. 15046000001 Buffer A: 10mM CH:CHROMATOGRAPHY_SUMMARY ammonium carbonate in water, LCMS Grade Buffer B: Acetonitrile, LCMS Grade Rear CH:CHROMATOGRAPHY_SUMMARY Wash: 10% methanol in water, LCMS Grade Wash Buffer: water, LCMS Grade Injection CH:CHROMATOGRAPHY_SUMMARY Volume: 2uL CH:CHROMATOGRAPHY_TYPE HILIC CH:INSTRUMENT_NAME Ulitmate 3000 CH:COLUMN_NAME SeQuant ZIC-pHILIC 5um polymer, 150x2.1mm CH:FLOW_RATE 0.100ml/min CH:COLUMN_TEMPERATURE 25 CH:METHODS_FILENAME L12 CH:SOLVENT_A Buffer A: 10mM ammonium carbonate in water, LCMS Grade CH:SOLVENT_B Buffer B: Acetonitrile, LCMS Grade CH:COLUMN_PRESSURE 1800 CH:INJECTION_TEMPERATURE 4 CH:INTERNAL_STANDARD ISTD (500nM amino acid cocktail) #ANALYSIS AN:ANALYSIS_TYPE MS AN:LABORATORY_NAME Metabolomics Core Resource Laboratory AN:OPERATOR_NAME Tori Rodrick AN:SOFTWARE_VERSION Xcalibur AN:ACQUISITION_DATE 8/24/2021 #MS MS:INSTRUMENT_NAME Thermo Q Exactive Orbitrap MS:INSTRUMENT_TYPE Triple quadrupole MS:MS_TYPE ESI MS:ION_MODE UNSPECIFIED MS:MS_COMMENTS M.13 Polar metabolites (pHILIC Hybrid). #MS_METABOLITE_DATA MS_METABOLITE_DATA:UNITS N/L MS_METABOLITE_DATA_START Samples 19 NT 13C 1 19 NT 13C 2 19 NT 13C 3 19 +DON 13C 1 19 +DON 13C 2 19 +DON 13C 3 19 NT 15N 1 19 NT 15N 2 19 NT 15N 3 19 +DON 15N 1 19 +DON 15N 2 19 +DON 15N 3 Factors Group:VEH Group:VEH Group:VEH Group:+DON Group:+DON Group:+DON Group:NT Group:NT Group:NT Group:DON Group:DON Group:DON 1-Methylnicotinamide - - 75254 115066 133132 177275 - 79054 - 127388 81938 - 2,3-Diphosphoglyceric acid - - - - - - - - - - - - 3-Hydroxybutyric acid - - - - - - - - - - - - 3-Phosphoglyceric acid - 16703 - - - - 253994 220213 - - - 28491 4,5-Dihydroorotic acid 18417 41087 32431 - - - - 55377 32835 - - - 4-Hydroxyproline 553468 711376 874622 278863 273890 215954 1145807 580216 601140 201204 401977 453766 5'-Methylthioadenosine 1627406 2762719 2126504 350566 651234 2006565 563278 277408 652685 379281 460310 1157802 5-Phosphoribosylamine - - - - - - - - - - - - 6-Phosphogluconic acid - - - - - - - - - - - - Acetoacetic acid - - - - - - - - - - - - Acetyl-CoA - - - - - - - 10519 - - - - Acetylcysteine 31989 38485 27245 49374 62671 73815 84192 60093 52068 17279 68422 73805 Adenine 6816201 11022569 5662713 1623460 3771650 4527343 2615867 1865545 1582122 2568473 5297785 4765224 Adenosine 10280982 25925034 5953598 5744020 27479956 26488952 15076647 3891646 1759514 4149446 14832680 34460224 Adenosine diphosphate ribose 90238 61435 93126 185284 437100 359053 96358 96351 54123 - 152779 444710 Adenosine monophosphate 1504149 2864510 1544946 654978 262315 351226 477965 881993 389842 - 224905 280409 Adenosine triphosphate - - - - - - - - - - - - Adenylsuccinic acid - - - - - - - - - - - - ADP - 90262 - - - - 50438 46087 - - - 43187 Allantoin 22085 22662 32344 164041 28177 52063 58787 22703 34777 35804 77418 59452 Aminoadipic acid - - - - - - - - - - - - Argininosuccinic acid - - - - - - 28858 26093 26469 - - 16471 Beta-Alanine - - - - - - - - - 326778 298729 - Betaine 7838222 7641372 7779132 21957112 32826932 41478952 10045224 7499725 9103739 12696412 22558274 26816526 Butyrylcarnitine 1403282 1668342 1745593 140945 243337 401903 2090290 1844790 2068265 92639 259665 306870 Carbamoyl phosphate - - - - - - - - - - - - Carnosine - - - 137402 83515 95633 - - - 69867 108315 78739 CDP - - - - - - 13749 17411 - - - - Choline - - - - 97349960 110752976 39968724 572580 424393 - 128679504 15066387 cis-Aconitic acid 152817 224788 146276 112570 - 153102 1095491 1049868 790343 - 159649 460602 Citric acid - 216483 53871 53319 - 91598 2866260 2265293 205812 - 104886 501627 Citrulline 341349 375502 298051 752624 625086 678726 443263 332349 360876 573840 1110757 571474 Creatine 280278016 372881216 380261312 128704632 158693072 271911616 237451328 302649536 303910336 116641936 175368480 121951560 Creatinine 1754678 1421412 1760326 7134943 2118264 3068754 2613846 1914436 2383172 2923640 4746795 2616413 Cyclic AMP 14976 30899 13640 - - 12443 14785 - - - - - Cytidine 71714 138651 68967 186174 318332 414420 858562 402986 253212 173946 319064 344895 Cytidine monophosphate - 24868 - 32201 73830 127452 47343 47459 53429 - 50997 84414 Cytidine triphosphate - - - - - - - - - - - - Cytosine - - - - - - - - - - - - D-2-Hydroxyglutaric acid 795627 998997 771711 607757 1153825 1378968 4490232 5307756 5599480 1013261 3296686 4605436 D-Glucose 631874 313017 373860 2246042 689771 1694100 1222137 567055 1292970 2714355 2905295 1430038 D-Glyceraldehyde 3-phosphate 17093 344640 137959 - - 35496 784269 845654 39009 - - 65059 Dihydrofolic acid - - - - - - - - - - - - Dihydroxyacetone phosphate - 43959 26754 - - 28390 737723 581811 - - - 62199 D-Ribose 5-phosphate 74264 144685 88486 59789 89388 153066 257331 180885 106673 - 43252 194656 D-Sedoheptulose 7-phosphate 42977 97822 83588 - - 64686 162371 150271 78526 - - 86565 dTDP - - - - - - - - - - - - FAD - 12178 11554 - 12349 18722 11410 - - - - - Folic acid 61739 56400 55753 83748 90033 199650 304684 113177 130922 69129 261486 423626 Fructose 1,6-bisphosphate - - - - - - - - - - - - Fructose 6-phosphate 211642 248020 263922 233165 151473 798530 854551 839875 348444 - 144376 553902 Fumaric acid 351752 462956 413598 120490 173878 307675 2788542 2764236 2693962 105861 387928 994190 Glucose 6-phosphate 56979 124246 171990 54143 238351 113176 492516 496494 223862 - 140636 286276 Glutathione 454022 534240 1149510 - - - 4270637 26522858 861881 - 90964 - Glycerol 3-phosphate 4483794 6206809 6347296 354108 692640 995257 4054906 4315289 3734571 - 462231 905584 Glycine 15163700 16855448 16686242 8507090 13708776 18991054 17247416 14269748 16577966 8816242 14898328 15746782 Guanidoacetic acid 92132256 103093304 99893472 27634582 55933884 80565200 98441288 85305016 99545256 24306964 47590936 50506288 Guanine - 308475 - - 138601 207958 8851084 - - - 196826 170581 Guanosine 209614 378658 204056 180260 378247 615583 395927 248654 198660 182479 546046 594871 Guanosine diphosphate - - - - - - - - - - - - Guanosine monophosphate - 38310 - - - 26589 - - - - - 24038 Guanosine triphosphate - - - - - - - - - - - - Homocysteine - - - - - - - - - - - - Hypotaurine 1190214 1699762 1634619 151997 398693 686461 1670356 1740619 1823376 121237 221796 247070 Hypoxanthine 4252699 4444437 4499863 1368489 3808579 7242992 9197617 7540654 5124569 512880 3927324 3863015 Inosine 1630174 1747165 1759688 488811 1408756 2772335 3733191 2971168 1985286 198281 1432448 1418430 Inosinic acid - 22215 - - - - - - - - - - L-Acetylcarnitine 3685467 4298164 4237716 1258579 2929379 4273613 4204620 3174403 3826216 724675 1674697 2096978 L-Alanine 53013576 66890224 69137272 9620951 14830542 23128796 31899998 34595324 35443300 7285824 12175459 8036542 L-Arginine - 33684648 - 39750628 - 51781740 56682900 32539852 37839184 43095156 55307960 68930560 L-Asparagine 4151112 3882609 4805518 1208813 3044970 2893212 - - - - - - L-Aspartic acid 4698386 5229554 5342695 2167952 3006138 4635444 15218922 14218617 15951043 3186673 9110588 10030000 L-Carnitine 6610110 6893648 7110006 4351368 8354844 15321950 9007999 6849848 8500165 4039988 9287232 10356434 L-Cystathionine 53610 194053 162102 - - - 118969 125702 83006 - - 22366 L-Cysteine - - - - - - - - - - - - L-Cystine - - - 90749 42040 127072 - - - 258361 377720 817378 L-Glutamic acid 9411872 11283354 10968184 9689792 10829047 13134197 56496736 60894164 67915096 34193180 57598512 47924600 L-Glutamine 5385116 6038293 5906636 50072068 8281308 12055641 13671962 11544841 11071612 8372764 11019563 11473502 L-Histidine 43598928 44160492 44658432 32091490 35987172 55282984 89435192 56142124 65789580 43088140 83755336 87185312 L-Isoleucine 122976216 110308400 120700360 71495888 111820184 160702128 195030192 125190568 165774592 113752872 198770160 233978384 L-Kynurenine 2461734 2212893 2498136 877222 2109799 3675793 5622546 3419615 4641154 2359060 5086955 6411168 L-Lactic acid 32870632 30479248 36005512 7441272 6955268 11171552 93855488 51894292 68163192 10513494 17159988 19009282 L-Leucine 130266664 117303568 122334072 75384848 112143280 171864528 203006704 128592680 171249440 120935968 203182848 252420080 L-Lysine 15245039 16286602 11512247 17766012 11490066 27978834 35938788 18014222 20478206 17866918 29661070 44112044 L-Malic acid 5135600 7166162 6563284 2182823 2558814 5127050 38173212 39269320 34594772 1154273 5540368 16313300 L-Methionine 43324876 41609364 43901924 24536708 36848524 55181812 62952800 44970188 58335568 34010252 61471148 76212648 L-Phenylalanine 126585160 117274912 124047896 66401564 106164456 173570800 222640480 150274240 192308336 110660632 201805776 261712416 L-Proline 53750172 69479544 64007360 39576500 56619604 91591344 158068368 150679056 161887808 77392952 142958128 149085760 L-Serine 21240808 23300312 24112808 9913722 15093106 21745766 22461306 19985142 21808554 10343734 19303172 24138384 L-Threonine 14477016 17348656 18486894 5370885 17733876 20694296 35381520 19429282 20880828 8454703 15168020 25568048 L-Tryptophan 7456000 6534721 7534966 5564449 8117979 13414392 16306852 9715182 12509640 9073860 18262760 23313564 L-Tyrosine 56496100 54384364 59652676 31254682 45694440 73206608 104670896 68307920 87281608 57561952 95902048 116258696 L-Valine 90652808 84090888 86873336 56991876 82120496 124117736 151718096 104612688 132693848 88851680 150932192 178035328 N6-Acetyl-L-lysine - - - - - 109188 - - - - - - N-Acetylglutamic acid - - - - 40245 36843 106877 95632 107418 37289 72040 76759 N-Acetylglutamine - - - - - - - - - - - - N-Acetyl-L-alanine 280621 428520 395210 58414 795519 621104 911865 184846 834736 666280 2529028 2165574 N-Acetyl-L-methionine 99066 122708 115848 18637 47187 63636 143728 133493 144684 20158 43714 48058 N-Acetyl-L-phenylalanine - - - - 259031 278907 - - - - - - N-Acetylornithine 113428 112181 110017 258604 103240 164614 257227 147782 189746 114741 249287 320857 N-Acetylserine 2814505 3726018 3710239 421884 1026306 1403558 3120054 3200768 3567495 471252 928534 1013832 NAD 1515550 2174683 1905039 300906 364545 1048731 457032 511435 429030 - 374991 336904 NADH 144825 208087 170784 - - 38709 11599 13417 44831 - - - NADP - 13216 - - - - 15518 11805 - - - - NADPH - - - - - - - - - - - - Niacinamide 83913392 71400720 92669416 83300528 165834192 175123456 256174976 223060992 203672512 74068904 211265664 252823680 Nicotinic acid - - - - - - - - - - - - O-Phosphoethanolamine - - - 74551 66864 242160 - - - - - 351717 Ornithine 2776734 3156078 2323027 3203676 1945521 4808218 6853920 4083339 3756571 2965654 4962243 7430484 Orotic acid - 26835 - - - - 89601 54749 56295 - - - Orotidylic acid - - - - - 15193 - - - - - - Oxidized glutathione 403016 217081 - - - - 3984092 1522928 3951873 - 242599 711322 Oxoadipic acid - 56041 - - - - - - - - - - Oxoglutaric acid 301862 456339 371954 180884 238906 303703 6198706 4693736 4270862 932872 2185006 2524212 Palmitic acid 10235076 12173226 27537780 33519324 33728960 21377810 41747636 32055270 20737492 5293155 26162030 19979222 Pantothenic acid 12783097 12706163 13387352 6115150 8410749 12723107 28264314 18210752 22052672 12519488 21747884 25379612 Phenol - - - - 2190109 2511168 - - - - - - Phosphocreatine 1217606 1656701 1653073 511258 824151 1735315 2042024 1944359 2019338 - 517708 1424283 Phosphoenolpyruvic acid - 188449 124603 - - 118130 840290 628399 192446 - 84369 126399 Phosphoribosyl pyrophosphate - - - - - - - - - - - - Phosphorylcholine 1176475904 1299928192 1262987776 427093056 690023680 973493376 1411326720 1285212032 1415810048 - 604781632 914511360 Phosphoserine - 15513 - - - - 96345 56171 - - - 15337 Pipecolic acid - - - - - - - - - - - 119865 Propionylcarnitine 258826 288140 319986 100891 143863 289878 785426 481086 553028 74850 171876 209326 Pyruvic acid 359590 536025 280244 208572 203467 149248 669128 227387 319851 398069 554383 775342 Ribose 1-phosphate 59091 109549 77560 40707 61031 106946 175116 147583 75720 - 25489 118738 Saccharopine - - - - - - - - - - - - S-Adenosylhomocysteine 58632 67807 133738 - - 21949 38794 33118 32157 - - - S-Adenosylmethionine 1651344 2695079 2057337 402557 449155 1366478 985221 792603 468070 - 531883 1252942 Sarcosine 3197714 3949228 3941094 854744 1523954 2130235 4043406 4085608 4159710 1689944 1896893 1530099 Succinic acid - 647202 - - 931042 823190 3115668 2998269 4003606 1043063 1625075 1855276 Taurine 30955318 35872372 36702044 4450372 8593851 12933810 32744536 27991790 39822360 5074655 7706667 7344633 Thymidine - - - - - - - - - - - - Uracil - - - 43417 109622 185100 83700 57565 49074 40224 112464 142679 Ureidopropionic acid 1146882 1379422 1434561 312241 575684 859760 65793 60193 59298 - 58651 - Ureidosuccinic acid 173013 512337 437079 - - 55213 879725 915579 819055 - 27110 37984 Uric acid - - - - - - - - - - - - Uridine 39475 54880 39940 214346 627214 963341 492422 284292 301860 251051 737415 879012 Uridine 5'-diphosphate 51864 79141 73371 146240 333280 582151 164815 166971 182988 45426 299424 485064 Uridine 5'-monophosphate 76470 134702 97174 218629 243911 646253 240055 360168 163586 126878 276941 395226 Uridine diphosphate glucose 129115 346776 253024 395611 955869 5031902 1733620 1900844 479692 100380 868857 3939373 Uridine diphosphate-N-acetylglucosamine 135745 137000 137223 100700 232244 330985 308463 324406 350399 87483 325211 366901 Uridine triphosphate - - - - - - - - - - - - Valerylcarnitine 696556 815824 872879 56094 95224 144999 472565 699599 901118 30071 90633 120158 Xanthine - - - 246131 63466 79384 52699 - - 58449 97308 96674 Xanthosine - - - - - - - - - - - - Xanthylic acid - - 12518 - - - - - - - - - MS_METABOLITE_DATA_END #METABOLITES METABOLITES_START metabolite_name 1-Methylnicotinamide 2,3-Diphosphoglyceric acid 3-Hydroxybutyric acid 3-Phosphoglyceric acid 4,5-Dihydroorotic acid 4-Hydroxyproline 5'-Methylthioadenosine 5-Phosphoribosylamine 6-Phosphogluconic acid Acetoacetic acid Acetyl-CoA Acetylcysteine Adenine Adenosine Adenosine diphosphate ribose Adenosine monophosphate Adenosine triphosphate Adenylsuccinic acid ADP Allantoin Aminoadipic acid Argininosuccinic acid Beta-Alanine Betaine Butyrylcarnitine Carbamoyl phosphate Carnosine CDP Choline cis-Aconitic acid Citric acid Citrulline Creatine Creatinine Cyclic AMP Cytidine Cytidine monophosphate Cytidine triphosphate Cytosine D-2-Hydroxyglutaric acid D-Glucose D-Glyceraldehyde 3-phosphate Dihydrofolic acid Dihydroxyacetone phosphate D-Ribose 5-phosphate D-Sedoheptulose 7-phosphate dTDP FAD Folic acid Fructose 1,6-bisphosphate Fructose 6-phosphate Fumaric acid Glucose 6-phosphate Glutathione Glycerol 3-phosphate Glycine Guanidoacetic acid Guanine Guanosine Guanosine diphosphate Guanosine monophosphate Guanosine triphosphate Homocysteine Hypotaurine Hypoxanthine Inosine Inosinic acid L-Acetylcarnitine L-Alanine L-Arginine L-Asparagine L-Aspartic acid L-Carnitine L-Cystathionine L-Cysteine L-Cystine L-Glutamic acid L-Glutamine L-Histidine L-Isoleucine L-Kynurenine L-Lactic acid L-Leucine L-Lysine L-Malic acid L-Methionine L-Phenylalanine L-Proline L-Serine L-Threonine L-Tryptophan L-Tyrosine L-Valine N6-Acetyl-L-lysine N-Acetylglutamic acid N-Acetylglutamine N-Acetyl-L-alanine N-Acetyl-L-methionine N-Acetyl-L-phenylalanine N-Acetylornithine N-Acetylserine NAD NADH NADP NADPH Niacinamide Nicotinic acid O-Phosphoethanolamine Ornithine Orotic acid Orotidylic acid Oxidized glutathione Oxoadipic acid Oxoglutaric acid Palmitic acid Pantothenic acid Phenol Phosphocreatine Phosphoenolpyruvic acid Phosphoribosyl pyrophosphate Phosphorylcholine Phosphoserine Pipecolic acid Propionylcarnitine Pyruvic acid Ribose 1-phosphate Saccharopine S-Adenosylhomocysteine S-Adenosylmethionine Sarcosine Succinic acid Taurine Thymidine Uracil Ureidopropionic acid Ureidosuccinic acid Uric acid Uridine Uridine 5'-diphosphate Uridine 5'-monophosphate Uridine diphosphate glucose Uridine diphosphate-N-acetylglucosamine Uridine triphosphate Valerylcarnitine Xanthine Xanthosine Xanthylic acid METABOLITES_END #END