397PathwayDoxorubicin Metabolism PathwayDoxorubicin is an anthracycline antibiotic used as a cancer chemotherapy drug. The major metabolic route of doxorubicin metabolism is two-electron reduction to doxorubicinol. A second route is one-electron reduction resulting in a doxorubicin-semiquinone, which can be undertaken by NADH dehydrogenases in the sarcoplasmic reticulum or mitochondrion, or nitric oxide synthases, NADPH dehydrogenase, or xanthine oxidase. Reactive oxygen species are formed when the semiquinone is re-oxidized back to doxorubicin. The reactive oxygen species are thought by some to be responsible for the drug's effects and cardiotoxicity, and can be deactivated by glutathione peroxidase, catalase, and superoxide dismutase. A third and minor metabolic route involves deglycosidation and results in the formation of doxirubicinol hydroxyaglycone. Approximately 50% of doxorubicin is eliminated unchanged from the body.Drug MetabolismPW000626CenterPathwayVisualizationContext73930003000#000099PathwayVisualization369397Doxorubicin PathwayDoxorubicin is an anthracycline antibiotic used as a cancer chemotherapy drug. The major metabolic route of doxorubicin metabolism is two-electron reduction to doxorubicinol. A second route is one-electron reduction resulting in a doxorubicin-semiquinone, which can be undertaken by NADH dehydrogenases in the sarcoplasmic reticulum or mitochondrion, or nitric oxide synthases, NADPH dehydrogenase, or xanthine oxidase. Reactive oxygen species are formed when the semiquinone is re-oxidized back to doxorubicin. The reactive oxygen species are thought by some to be responsible for the drug's effects and cardiotoxicity, and can be deactivated by glutathione peroxidase, catalase, and superoxide dismutase. A third and minor metabolic route involves deglycosidation and results in the formation of doxirubicinol hydroxyaglycone. Approximately 50% of doxorubicin is eliminated unchanged from the body.Drug11783[PharmgKB](http://www.pharmgkb.org/pathway/PA165292177)397Pathway195519442138Mordente A, Meucci E, Silvestrini A, Martorana GE, Giardina B: New developments in anthracycline-induced cardiotoxicity. Curr Med Chem. 2009;16(13):1656-72.397Pathway19562555273Minotti G: Reactions of adriamycin with microsomal iron and lipids. Free Radic Res Commun. 1989;7(3-6):143-8.397Pathway19572850270Thornalley PJ, Bannister WH, Bannister JV: Reduction of oxygen by NADH/NADH dehydrogenase in the presence of adriamycin. Free Radic Res Commun. 1986;2(3):163-71.397Pathway19589618942Nohl H, Gille L, Staniek K: The exogenous NADH dehydrogenase of heart mitochondria is the key enzyme responsible for selective cardiotoxicity of anthracyclines. Z Naturforsch C. 1998 Mar-Apr;53(3-4):279-85.397Pathway19599333325Vasquez-Vivar J, Martasek P, Hogg N, Masters BS, Pritchard KA Jr, Kalyanaraman B: Endothelial nitric oxide synthase-dependent superoxide generation from adriamycin. Biochemistry. 1997 Sep 23;36(38):11293-7. doi: 10.1021/bi971475e.397Pathway196015054088Fogli S, Nieri P, Breschi MC: The role of nitric oxide in anthracycline toxicity and prospects for pharmacologic prevention of cardiac damage. FASEB J. 2004 Apr;18(6):664-75. doi: 10.1096/fj.03-0724rev.397Pathway196112688675Pawlowska J, Tarasiuk J, Wolf CR, Paine MJ, Borowski E: Differential ability of cytostatics from anthraquinone group to generate free radicals in three enzymatic systems: NADH dehydrogenase, NADPH cytochrome P450 reductase, and xanthine oxidase. Oncol Res. 2003;13(5):245-52.397Pathway19621911046Gustafson DL, Swanson JD, Pritsos CA: Role of xanthine oxidase in the potentiation of doxorubicin-induced cardiotoxicity by mitomycin C. Cancer Commun. 1991 Sep;3(9):299-304.397Pathway19639576481Minotti G, Recalcati S, Mordente A, Liberi G, Calafiore AM, Mancuso C, Preziosi P, Cairo G: The secondary alcohol metabolite of doxorubicin irreversibly inactivates aconitase/iron regulatory protein-1 in cytosolic fractions from human myocardium. FASEB J. 1998 May;12(7):541-52.397Pathway196412751786Miyamoto Y, Koh YH, Park YS, Fujiwara N, Sakiyama H, Misonou Y, Ookawara T, Suzuki K, Honke K, Taniguchi N: Oxidative stress caused by inactivation of glutathione peroxidase and adaptive responses. Biol Chem. 2003 Apr;384(4):567-74. doi: 10.1515/BC.2003.064.397Pathway196510813659Licata S, Saponiero A, Mordente A, Minotti G: Doxorubicin metabolism and toxicity in human myocardium: role of cytoplasmic deglycosidation and carbonyl reduction. Chem Res Toxicol. 2000 May;13(5):414-20.397Pathway1CellCL:00000005HepatocyteCL:00001824Cardiomyocyte CL:00007463NeuronCL:00005407Epithelial CellCL:00000662Platelet CL:00002338Beta cellCL:00006391Homo sapiens9606EukaryoteHuman3Escherichia coli562Prokaryote12Mus musculus10090EukaryoteMouse5Bos taurus9913EukaryoteCattle17Rattus norvegicus10116EukaryoteRat24Solanum lycopersicum4081EukaryoteTomato18Saccharomyces cerevisiae4932EukaryoteYeast21Xenopus laevis8355EukaryoteAfrican clawed frog6Caenorhabditis elegans6239EukaryoteRoundworm4Arabidopsis thaliana3702EukaryoteThale cress49Bathymodiolus platifrons220390EukaryoteDeep sea mussel10Drosophila melanogaster7227EukaryoteFruit fly23Pseudomonas aeruginosa287Prokaryote60Nitzschia sp.0001EukaryoteNitzschia42Bacteria2ProkaryoteBacteria19Schizosaccharomyces pombe4896Eukaryote25Escherichia coli (strain K12)83333Prokaryote29Saccharomyces cerevisiae (strain ATCC 204508 / S288c)559292EukaryoteBaker's yeast11Extracellular SpaceGO:00056155CytoplasmGO:00057372MitochondrionGO:00057396LysosomeGO:00057644PeroxisomeGO:00057773Mitochondrial MatrixGO:000575912Mitochondrial Inner MembraneGO:000574316Lysosomal LumenGO:004320213Endoplasmic ReticulumGO:00057831CytosolGO:000582910Cell MembraneGO:000588624Mitochondrial Intermembrane SpaceGO:00057587Endoplasmic Reticulum MembraneGO:000578914Mitochondrial Outer MembraneGO:000574120Endoplasmic Reticulum LumenGO:000578831Periplasmic SpaceGO:000562035ChloroplastGO:000950734Plant-Type VacuoleGO:000032539Mitochondrial membraneGO:003196618Melanosome MembraneGO:003316225Golgi apparatusGO:000579421SynapseGO:004520215NucleusGO:000563436MembraneGO:001602053Endoplasmic Reticulum BodyGO:001016840PeriplasmGO:004259727Peroxisome MembraneGO:000577832Inner MembraneGO:007025819sarcoplasmic reticulumGO:00165298Smooth Endoplasmic Reticulum GO:000579038Apical cell membraneGO:00163241LiverBTO:00007597294Adrenal MedullaBTO:000004971825IntestineBTO:000064828StomachBTO:0001307155267Nervous SystemBTO:00014848Blood VesselBTO:0001102741111HeartBTO:000056273102Endothelium BTO:000039318PancreasBTO:00009885cardiocyteBTO:000153915111PW_BS0000158511PW_BS0000083211PW_BS0000039611PW_BS0000095411PW_BS0000054311PW_BS000004171211PW_BS0000172811611PW_BS000028181311PW_BS0000182111PW_BS00000214101PW_BS000014422411PW_BS00004229111PW_BS00002949711PW_BS0000495811411PW_BS000058221411PW_BS000022261115PW_BS0000263612011PW_BS000036311511PW_BS00003113121PW_BS000013101711PW_BS0000106131PW_BS000006103331PW_BS0001031021231PW_BS0001021115121PW_BS000111126651PW_BS00012612711651PW_BS0001271181171PW_BS0001181553241PW_BS00015515612241PW_BS0001561613181PW_BS00016116212181PW_BS00016211PW_BS0000011783211PW_BS00017817912211PW_BS000179107313PW_BS0001071632181PW_BS000163205561PW_BS0000242137181PW_BS000024222341PW_BS0000242231241PW_BS000024224241PW_BS0000242164181PW_BS0000242156181PW_BS0000242111018PW_BS0000242253541PW_BS0000242491341PW_BS000024151141PW_BS0001512273441PW_BS000024226441PW_BS0000242916491PW_BS0000242924491PW_BS0000243016101PW_BS000024302116101PW_BS0000243183123PW_BS00002429341PW_BS0000241333121PW_BS00013313412121PW_BS0001341136121PW_BS0001131122121PW_BS0001121151012PW_BS0001153344121PW_BS0000281321121PW_BS000132337116121PW_BS00002832914121PW_BS00002834524121PW_BS0000283317121PW_BS0000283361121PW_BS0000283583912PW_BS0000283683601PW_BS00002836912601PW_BS0000281192171PW_BS000119406351PW_BS0001153841251PW_BS000100408451PW_BS000115407251PW_BS000115405105PW_BS000115122551PW_BS000122124151PW_BS000124429151PW_BS0001154182451PW_BS0001153821451PW_BS000100383751PW_BS0001001203171PW_BS00012012112171PW_BS0001213744171PW_BS0000534436171PW_BS0001153761017PW_BS0000531355171PW_BS000135448116171PW_BS0001154641171PW_BS00011545424171PW_BS00011539914171PW_BS0001133987171PW_BS0001134793101PW_BS00011548012101PW_BS0001154824101PW_BS0001154812101PW_BS0001152975101PW_BS00002448924101PW_BS0001152991101PW_BS00002448414101PW_BS000115501361PW_BS0001153911261PW_BS000112502461PW_BS000115207661PW_BS000024206261PW_BS000024209106PW_BS0000245062461PW_BS000115388161PW_BS0001123891461PW_BS000112101531PW_BS0001011601181PW_BS000160204111PW_BS000020331811PW_BS000033541315PW_BS000054432511PW_BS0000432441011PW_BS00002460251PW_BS00006046114PW_BS0000467028511PW_BS00007072513PW_BS000072612517PW_BS0000613772113PW_BS00003793252011PW_BS00009327151PW_BS000027711PW_BS000007971521PW_BS000097100521PW_BS000100943PW_BS000094105113PW_BS000105110231PW_BS0001101231751PW_BS0001231251351PW_BS00012513013121PW_BS0001301141112PW_BS00011412915121PW_BS00012910813PW_BS000108140103PW_BS00014014315191PW_BS0001431465191PW_BS000146951721PW_BS0000951471241PW_BS0001471572241PW_BS00015715924PW_BS00015916611PW_BS0001661802211PW_BS00018015284PW_BS000152117131PW_BS000117188118PW_BS00002421425181PW_BS0000241985181PW_BS00002421013181PW_BS00002421217181PW_BS0000241901118PW_BS00002417018PW_BS0001702771218PW_BS0000241644PW_BS0001642811251PW_BS0000242851041PW_BS0000242863641PW_BS0000242875341PW_BS00002465111PW_BS0000652905491PW_BS00002429817101PW_BS00002430013101PW_BS0000242941141PW_BS0000243081011PW_BS000024315123PW_BS0000243221231PW_BS000024253541PW_BS00002433217121PW_BS0000283331212PW_BS00002834141121PW_BS00002834318121PW_BS00002834713125PW_BS0000283522512PW_BS00002835325127PW_BS00002835625121PW_BS000028360410121PW_BS0000283702601PW_BS000028228361PW_BS000024390761PW_BS000112232403PW_BS000024412125PW_BS000115409115PW_BS0001154151851PW_BS0001154141551PW_BS0001154251355PW_BS0001154192551PW_BS00011543441051PW_BS000115436255PW_BS0001154461217PW_BS0001151371117PW_BS00013744717171PW_BS00011513613171PW_BS00013645118171PW_BS00011545015171PW_BS00011546013175PW_BS00011545525171PW_BS000115469410171PW_BS0001154712517PW_BS00011547225177PW_BS0001154831110PW_BS0001154781010PW_BS00011548718101PW_BS00011549025101PW_BS0001154957101PW_BS000115208116PW_BS0000245041861PW_BS0001155072561PW_BS00011551541061PW_BS0001153951361PW_BS0001135131761PW_BS00011516212PW_BS0000163211515PW_BS000032397113PW_BS000039592711PW_BS0000596618518PW_BS0000665181PW_BS000051231511PW_BS000023918511PW_BS000091892PW_BS0000891041431PW_BS00010419914181PW_BS0000242171518PW_BS00002421815181PW_BS000024350114121PW_BS00002812815121PW_BS0001283511512PW_BS00002833527121PW_BS000028184121PW_BS000024109323PW_BS00010943311451PW_BS0001154101551PW_BS0001154222751PW_BS000115435155PW_BS000115468114171PW_BS00011544415171PW_BS00011537527171PW_BS0000534701517PW_BS00011548515101PW_BS00011549127101PW_BS0001154991510PW_BS0001155161561PW_BS0001155082761PW_BS000115517156PW_BS000115471914PW_BS000047241529PW_BS00002425715291PW_BS00002430412PW_BS00002431323PW_BS0000243551914PW_BS00003514117191PW_BS000141111811PW_BS00001178811PW_BS0000785311015PW_BS0000539911025PW_BS000099230381PW_BS0000249432DoxorubicinHMDB0015132Doxorubicin is only found in individuals that have used or taken this drug. It is antineoplastic antibiotic obtained from Streptomyces peucetius. It is a hydroxy derivative of daunorubicin. [PubChem]Doxorubicin has antimitotic and cytotoxic activity through a number of proposed mechanisms of action: Doxorubicin forms complexes with DNA by intercalation between base pairs, and it inhibits topoisomerase II activity by stabilizing the DNA-topoisomerase II complex, preventing the religation portion of the ligation-religation reaction that topoisomerase II catalyzes.23214-92-8C01661317032874829400DB00997COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@](O)(C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(=O)CO)C(O)=C1C2=OC27H29NO11InChI=1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,17-,22+,27-/m0/s1AOJJSUZBOXZQNB-TZSSRYMLSA-N(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione543.5193543.174060775-2.676doxorubicin01Doxorubicina [inn-spanish];Doxorubicine [inn-french];Doxorubicinum [inn-latin];(1s,3s)-3-glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranoside;(8s-cis)-10-((3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione;14-hydroxydaunomycin;14-hydroxydaunorubicine;Adriamycin;Doxorubicine;Doxorubicinum;(1s,3s)-3-glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-a-l-lyxo-hexopyranoside;(1s,3s)-3-glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-α-l-lyxo-hexopyranoside;(8s-cis)-10-((3-amino-2,3,6-trideoxy-a-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione;(8s-cis)-10-((3-amino-2,3,6-trideoxy-α-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedionePW_C009432Doxor398115398284061340618Doxorubicine hydroxyaglyconeHMDB0061231Adriamycinone, also known as 4-dox-done or doxorubicinone, belongs to the class of organic compounds known as tetracenequinones. These are polyaromatic hydrocarbon derivatives containing a tetracyclic cycle made up of four linearly fused benzene rings, one of which bears two ketone groups at position 1 and 4. Adriamycinone is slightly soluble (in water) and a very weakly acidic compound (based on its pKa).7240165332COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@](O)(C[C@@H]3O)C(=O)CO)C(O)=C1C2=OC21H18O9InChI=1S/C21H18O9/c1-30-11-4-2-3-8-14(11)20(28)16-15(17(8)25)18(26)9-5-21(29,12(24)7-22)6-10(23)13(9)19(16)27/h2-4,10,22-23,26-27,29H,5-7H2,1H3/t10-,21-/m0/s1IBZGBXXTIGCACK-CWKPULSASA-N(8S,10S)-6,8,10,11-tetrahydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione414.3622414.095082174-2.555(8S,10S)-6,8,10,11-tetrahydroxy-8-(2-hydroxyacetyl)-1-methoxy-9,10-dihydro-7H-tetracene-5,12-dione00DBMET01078PW_C040618DH14000840619Doxorubicinol hydroxyaglyconeHMDB0061232SCHEMBL14713045 belongs to the class of organic compounds known as tetracenequinones. These are polyaromatic hydrocarbon derivatives containing a tetracyclic cycle made up of four linearly fused benzene rings, one of which bears two ketone groups at position 1 and 4. SCHEMBL14713045 is slightly soluble (in water) and a very weakly acidic compound (based on its pKa).104769888652398COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@](O)(C[C@@H]3O)C(O)CO)C(O)=C1C2=OC21H20O9InChI=1S/C21H20O9/c1-30-11-4-2-3-8-14(11)20(28)16-15(17(8)25)18(26)9-5-21(29,12(24)7-22)6-10(23)13(9)19(16)27/h2-4,10,12,22-24,26-27,29H,5-7H2,1H3/t10-,12?,21-/m0/s1CGVVIRBOJFDFBH-PTIJRGHASA-N(8S,10S)-8-(1,2-dihydroxyethyl)-6,8,10,11-tetrahydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione416.3781416.110732238-2.376(8S,10S)-8-(1,2-dihydroxyethyl)-6,8,10,11-tetrahydroxy-1-methoxy-9,10-dihydro-7H-tetracene-5,12-dione00DBMET01079PW_C040619DH24001840617Doxorubicinol deoxaglyconeHMDB00612067-Deoxydoxorubicinolone, also known as aglycone C, belongs to the class of organic compounds known as tetracenequinones. These are polyaromatic hydrocarbon derivatives containing a tetracyclic cycle made up of four linearly fused benzene rings, one of which bears two ketone groups at position 1 and 4. 7-Deoxydoxorubicinolone is considered to be a practically insoluble (in water) and relatively neutral molecule.4503881323935799COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@](O)(CC3)C(O)CO)C(O)=C1C2=OC21H20O8InChI=1S/C21H20O8/c1-29-12-4-2-3-10-14(12)20(27)16-15(18(10)25)19(26)11-7-21(28,13(23)8-22)6-5-9(11)17(16)24/h2-4,13,22-24,26,28H,5-8H2,1H3/t13?,21-/m1/s1IGJIPNOEJDYNRR-QUXALOBESA-N(8R)-8-(1,2-dihydroxyethyl)-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione400.3787400.115817616-2.875(8R)-8-(1,2-dihydroxyethyl)-6,8,11-trihydroxy-1-methoxy-9,10-dihydro-7H-tetracene-5,12-dione00DBMET00847PW_C040617DDeo40028964FADHMDB0001248FAD, also known as flavitan or adeflavin, belongs to the class of organic compounds known as flavin nucleotides. These are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions. FAD is a drug which is used to treat eye diseases caused by vitamin b2 deficiency, such as keratitis and blepharitis. FAD is slightly soluble (in water) and a moderately acidic compound (based on its pKa). FAD has been found in human liver and muscle tissues, and has also been detected in multiple biofluids, such as feces and blood. Within the cell, FAD is primarily located in the cytoplasm, mitochondria, endoplasmic reticulum and peroxisome. FAD exists in all living organisms, ranging from bacteria to humans. In humans, FAD is involved in the risedronate action pathway, the ibandronate action pathway, the valine, leucine and isoleucine degradation pathway, and the pyrimidine metabolism pathway. FAD is also involved in several metabolic disorders, some of which include the oncogenic action OF L-2-hydroxyglutarate in hydroxygluaricaciduria pathway, gaba-transaminase deficiency, 4-hydroxybutyric aciduria/succinic semialdehyde dehydrogenase deficiency, and the saccharopinuria/hyperlysinemia II pathway. FAD is a condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972).146-14-5C0001664397516238FAD559059DB03147CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)CO[P@](O)(=O)O[P@@](O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC3=C1N=CN=C3N)C1=NC(=O)NC(=O)C1=N2C27H33N9O15P2InChI=1S/C27H33N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1VWWQXMAJTJZDQX-UYBVJOGSSA-N{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid785.5497785.157134455-2.279flavine-adenine dinucleotide0-3FDB0225111h-purin-6-amine flavin dinucleotide;1h-purin-6-amine flavine dinucleotide;Adenine-flavin dinucleotide;Adenine-flavine dinucleotide;Adenine-riboflavin dinuceotide;Adenine-riboflavin dinucleotide;Adenine-riboflavine dinucleotide;Fad;Flamitajin b;Flanin f;Flavin adenine dinucleotide;Flavin adenine dinucleotide oxidized;Flavin-adenine dinucleotide;Flavine adenosine diphosphate;Flavine-adenine dinucleotide;Flavitan;Flaziren;Isoalloxazine-adenine dinucleotide;Riboflavin 5'-adenosine diphosphate;Riboflavin-adenine dinucleotide;Riboflavine-adenine dinucleotide;AdeflavinPW_C000964FAD99911451868192321642531762828825188402118814148942161229162249213358253622372326460236468831474113475810488165268103528510253351115496126551112756131186030155605415660821616116162639016475178649917966661077039163717520573212137465222748722390762241181821611887215118992111229622512328249124431511251922712595226127102911272029213029301130413024362331877080293771261337715213477501113775071127751811577541334776151327772633778054329783753457893033179222336792723588001236880034369807141191199584061199993841200514081201074071204324051204531221204901241212784291212984181214173821214893831227481201227761211228023741228234431230663761230871351231664481238494641238684541239763991240473981253484791253784801254294821254744811256972971259794891261072991262774841268915011269203911269685021269872071270112061273102091274325061276023881278403891170Flavin MononucleotideHMDB0001520Flavin mononucleotide (FMN), or riboflavin-5?-phosphate, is a biomolecule produced from riboflavin (vitamin B2) by the enzyme riboflavin kinase and functions as prosthetic group of various oxidoreductases including NADH dehydrogenase as well as cofactor in biological blue-light photo receptors. During the catalytic cycle, the reversible interconversion of oxidized (FMN), semiquinone (FMNH) and reduced (FMNH2) forms occurs in the various oxidoreductases. FMN is a stronger oxidizing agent than NAD and is particularly useful because it can take part in both one- and two-electron transfers. Flavin mononucleotide is also used as an orange-red food colour additive. It is the principal form in which riboflavin is found in cells and tissues.146-17-8C0006164397617621FMN559060DB03247CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(O)=O)C1=NC(=O)NC(=O)C1=N2C17H21N4O9PInChI=1S/C17H21N4O9P/c1-7-3-9-10(4-8(7)2)21(15-13(18-9)16(25)20-17(26)19-15)5-11(22)14(24)12(23)6-30-31(27,28)29/h3-4,11-12,14,22-24H,5-6H2,1-2H3,(H,20,25,26)(H2,27,28,29)/t11-,12+,14-/m0/s1FVTCRASFADXXNN-SCRDCRAPSA-N{[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}phosphonic acid456.3438456.104614802-2.836riboflavin 5'-phosphate0-3FDB001984Fmn;Flanin;Flavine mononucleotide;Flavol;Riboflavin;Riboflavin 5'-monophosphate;Riboflavin 5'-phosphate;Riboflavin mononucleotide;Riboflavin monophosphate;Riboflavin phosphate;Riboflavin-5'-phosphate na;Riboflavin-5-phosphate;Riboflavine 5'-monophosphate;Riboflavine 5'-phosphate;Riboflavine dihydrogen phosphate;Riboflavine monophosphate;Riboflavine phosphate;Riboflavine-5'-phosphate;Vitamin b2 phosphate;Flavin mononucleotide;Riboflavin 5'-(dihydrogen phosphate)PW_C001170FlvnMnt53981190141692249613157721011190021112313225775191157759011178730132120433405120454122121929124123067376123088135124482118125698297126104299127190205127312209127686388405582Fe-2SHMDB0061344Bis(λ²-iron(2+) ion) disulfane tetrasulfanide belongs to the class of inorganic compounds known as transition metal sulfides. These are inorganic compounds containing a sulfur atom of an oxidation state of -2, in which the heaviest atom bonded to the oxygen is a transition metal.S[Fe]1(S)S[Fe](S)(S)S1Fe2H4S6InChI=1S/2Fe.4H2S.2S/h;;4*1H2;;/q2*+2;;;;;;/p-4TUVRTRPESCSNGS-UHFFFAOYSA-Jbis(lambda2-iron(2+) ion) disulfane tetrasulfanide308.112307.7336085340bis(lambda2-iron(2+) ion) disulfane tetrasulfanide02PW_C0405582Fe2S374224012842571743893462654754314829948372850564549712655121277046160130303011304230277715113777273377837713478386132792071121178111331215864071217951241225673841226644061231524431231674481241441191243461181251401211252391201261892991267154801267964791276803881283063911283945011491MolybdopterinHMDB0002206Molybdenum cofactor is a cofactor required for the activity of enzymes such as sulfite oxidase, xanthine oxidoreductase, and aldehyde oxidase. It is a coordination complex formed between molybdopterin (which, despite the name, does not contain molybdenum) and an oxide of molybdenum. Molybdopterins, in turn, are synthesized from guanosine triphosphate. Molybdenum cofactor functions directly in ethylbenzene dehydrogenase, glyceraldehyde-3-phosphate ferredoxin oxidoreductase, and respiratory arsenate reductase. In animals and plants these enzymes use molybdenum bound at the active site in a tricyclic molybdenum cofactor. All molybdenum-using enzymes so far identified in nature use this cofactor The simplest structure of molybdopterin contains a pyranopterin coordinated to molybdenum. The pyranopterin structure is a fused ring system containing a pyran fused to pterin. In addition, the pyran ring is substituted with two thiols and an alkyl phosphate. In molybdopterin, the thiols coordinate to molybdenum. In some cases, the alkyl phosphate group is replaced by an alkyl diphosphate nucleotide. -- Wikipedia.73508-07-3C059242330423721437CPD0-18824883416NC1=NC2=C(NC3C(N2)OC(COP(O)(O)=O)C2=C3S[Mo](=O)(=O)S2)C(=O)N1C10H12MoN5O8PS2InChI=1S/C10H14N5O6PS2.Mo.2O/c11-10-14-7-4(8(16)15-10)12-3-6(24)5(23)2(21-9(3)13-7)1-20-22(17,18)19;;;/h2-3,9,12,23-24H,1H2,(H2,17,18,19)(H4,11,13,14,15,16);;;/q;+2;;/p-2HDAJUGGARUFROU-UHFFFAOYSA-Lmolybdenum(2+) ion 8-[(hydrogen phosphonooxy)methyl]-2-imino-6,7-disulfanyl-1H,2H,5H,5aH,8H,9aH,10H-pyrano[3,2-g]pteridin-4-olate dihydrate521.27522.891898123-2.747molybdenum(2+) ion 8-[(hydrogen phosphonooxy)methyl]-2-imino-6,7-disulfanyl-1H,5H,5aH,8H,9aH,10H-pyrano[3,2-g]pteridin-4-olate dihydrate0-2FDB022906Moco;Molybdenum cofactor;Molybdenum enzyme molybdenum cofactor;Molybdoenzyme molybdenum-containing cofactor;Nitrate reductase molybdenum cofactor;Pterin molybdenum cofactorPW_C001491mlyBdpn1684817042391826395329438834627547533148309483828549812655131271203815113031301130433027771611377728337783851327920611212158540712179412412315344312316844812414311912434511812610829912767938840616Doxorubicin-semiquinoneHMDB0060822Doxorubicin-semiquinone is a metabolite of doxorubicin. Doxorubicin is a drug used in cancer chemotherapy. It is an anthracycline antibiotic, closely related to the natural product daunomycin, and like all anthracyclines, it works by intercalating DNA. Doxorubicin is commonly used in the treatment of a wide range of cancers, including hematological malignancies, many types of carcinoma, and soft tissue sarcomas. Doxorubicin's most serious adverse effect is life-threatening heart damage. (Wikipedia)COC1=CC=CC2=C1C(O)C1=C(C2O)C(O)=C2CC(O)(CC(OC3CC(N)C(O)C(C)O3)C2=C1O)C(=O)COC27H33NO11InChI=1S/C27H33NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22-23,25,29,31-36H,6-9,28H2,1-2H3WHLRWGKIZVSENZ-UHFFFAOYSA-N1-{4-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-2,5,6,11,12-pentahydroxy-7-methoxy-1,2,3,4,6,11-hexahydrotetracen-2-yl}-2-hydroxyethan-1-one547.557547.205360887-2.5281-{4-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-2,5,6,11,12-pentahydroxy-7-methoxy-3,4,6,11-tetrahydro-1H-tetracen-2-yl}-2-hydroxyethanone01DBMET00846PW_C040616DorbSqm40528406431420WaterHMDB0002111Water is a chemical substance that is essential to all known forms of life. It appears colorless to the naked eye in small quantities, though it is actually slightly blue in color. It covers 71% of Earth's surface. Current estimates suggest that there are 1.4 billion cubic kilometers (330 million m3) of it available on Earth, and it exists in many forms. It appears mostly in the oceans (saltwater) and polar ice caps, but it is also present as clouds, rain water, rivers, freshwater aquifers, lakes, and sea ice. Water in these bodies perpetually moves through a cycle of evaporation, precipitation, and runoff to the sea. Clean water is essential to human life. In many parts of the world, it is in short supply. From a biological standpoint, water has many distinct properties that are critical for the proliferation of life that set it apart from other substances. It carries out this role by allowing organic compounds to react in ways that ultimately allow replication. All known forms of life depend on water. Water is vital both as a solvent in which many of the body's solutes dissolve and as an essential part of many metabolic processes within the body. Metabolism is the sum total of anabolism and catabolism. In anabolism, water is removed from molecules (through energy requiring enzymatic chemical reactions) in order to grow larger molecules (e.g. starches, triglycerides and proteins for storage of fuels and information). In catabolism, water is used to break bonds in order to generate smaller molecules (e.g. glucose, fatty acids and amino acids to be used for fuels for energy use or other purposes). Water is thus essential and central to these metabolic processes. Water is also central to photosynthesis and respiration. Photosynthetic cells use the sun's energy to split off water's hydrogen from oxygen. Hydrogen is combined with CO2 (absorbed from air or water) to form glucose and release oxygen. All living cells use such fuels and oxidize the hydrogen and carbon to capture the sun's energy and reform water and CO2 in the process (cellular respiration). Water is also central to acid-base neutrality and enzyme function. An acid, a hydrogen ion (H+, that is, a proton) donor, can be neutralized by a base, a proton acceptor such as hydroxide ion (OH-) to form water. Water is considered to be neutral, with a pH (the negative log of the hydrogen ion concentration) of 7. Acids have pH values less than 7 while bases have values greater than 7. Stomach acid (HCl) is useful to digestion. However, its corrosive effect on the esophagus during reflux can temporarily be neutralized by ingestion of a base such as aluminum hydroxide to produce the neutral molecules water and the salt aluminum chloride. Human biochemistry that involves enzymes usually performs optimally around a biologically neutral pH of 7.4. (Wikipedia).7732-18-5C0000196215377937OH2OInChI=1S/H2O/h1H2XLYOFNOQVPJJNP-UHFFFAOYSA-Nwater18.015318.0105646861water00FDB013390Dihydrogen oxide;Steam;[oh2];Acqua;Agua;Aqua;Bound water;Dihydridooxygen;Eau;H2o;Hoh;Hydrogen hydroxide;WasserPW_C001420H2O5589491095139415131621448113526156242865210691207703382318838210943113774914655415904320182425322226786027274627781728052931437031647236346145983647273749419350302751567519597521410052279452361035297105531911153431135355112540211054701235483125549212655071275534130553711455411295591135560811856221085691657591405778101584114358531465877107589095591014759401516032155605915760871616123163613315962151621816664771786507180660015267131176840188688816071622057181207719320672112117228213723821472432157295198735021673882107401212746722274922247500190758817082012258237226841416292652611850277119221641201128112213285122502861226428712327249125202271263265126932901270529112715292130072981301930013025301130373021326122313327294153403084232731542695318436913227691429377019253771021327713113377215134773783317739733277471333775161157753633477628336777223377775934177816343779823477807132978235352782423537827035679113360800143688003937080591228806561199383038394794384110557390110639391115844398119879232119915122119963406120008407120046408120113124120365412120430405120438409120606415120794414121158425121240429121351121121381419121607434122118382122384436122753120122797374122804443123012446123064376123072137123131447123142136123162448123231451123384450123730460123810464123940455124165469124670399124938471124945472125305297125353479125386481125424482125480299125682483125707478125745487126054490126238495126273484126764480126896501126963502127017388127177208127199209127227504127506507127576515127836389128082395128176513414Adenosine triphosphateHMDB0000538Adenosine triphosphate (ATP) is a nucleotide consisting of a purine base (adenine) attached to the first carbon atom of ribose (a pentose sugar). Three phosphate groups are esterified at the fifth carbon atom of the ribose. ATP is incorporated into nucleic acids by polymerases in the processes of DNA replication and transcription. ATP contributes to cellular energy charge and participates in overall energy balance, maintaining cellular homeostasis. ATP can act as an extracellular signaling molecule via interactions with specific purinergic receptors to mediate a wide variety of processes as diverse as neurotransmission, inflammation, apoptosis, and bone remodelling. Extracellular ATP and its metabolite adenosine have also been shown to exert a variety of effects on nearly every cell type in human skin, and ATP seems to play a direct role in triggering skin inflammatory, regenerative, and fibrotic responses to mechanical injury, an indirect role in melanocyte proliferation and apoptosis, and a complex role in Langerhans cell-directed adaptive immunity. During exercise, intracellular homeostasis depends on the matching of adenosine triphosphate (ATP) supply and ATP demand. Metabolites play a useful role in communicating the extent of ATP demand to the metabolic supply pathways. Effects as different as proliferation or differentiation, chemotaxis, release of cytokines or lysosomal constituents, and generation of reactive oxygen or nitrogen species are elicited upon stimulation of blood cells with extracellular ATP. The increased concentration of adenosine triphosphate (ATP) in erythrocytes from patients with chronic renal failure (CRF) has been observed in many studies but the mechanism leading to these abnormalities still is controversial. (PMID: 15490415, 15129319, 14707763, 14696970, 11157473).56-65-5C00002595715422ATP5742DB00171NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1OC10H16N5O13P3InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1ZKHQWZAMYRWXGA-KQYNXXCUSA-N({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid507.181506.995745159-2.057adenosine triphosphate0-3FDB0218135'-(tetrahydrogen triphosphate) adenosine;5'-atp;Atp;Adenosine 5'-triphosphate;Adenosine 5'-triphosphorate;Adenosine 5'-triphosphoric acid;Adenosine triphosphate;Adenylpyrophosphorate;Adenylpyrophosphoric acid;Adephos;Adetol;Adynol;Atipi;Atriphos;Cardenosine;Fosfobion;Glucobasin;Myotriphos;Phosphobion;Striadyne;Triadenyl;Triphosphaden;Triphosphoric acid adenosine ester;Adenosine-5'-triphosphate;H4atp;Adenosine triphosphoric acid;Adenosine-5'-triphosphoric acidPW_C000414ATP922146082661641422478137333279959343997632105182112102146492156142160582405592434272726462812293029663163723616613617514399234474314768914864545032895035265155752059752151005250104529110153131115346112539010354061175430118544312055421295556132556913356031355621108584614358541465876107589714759241516048155610916162301666493178683918868701606976199715720571842067209210722521372292117298198730221673902177408218743216374812227499190818622511847277119031701201028112039164121782851257822612691290132642231532730842326315426213224269431877028253772181347723332977468333776323367803733278041350781681287821435178240353784113357849411578850130788653317891933480028368800461848067411985629194826124113234941132823881162801091199141221199924061201544071202453821203624121212464291213921231213974331214714081219744101220651251220793831220834051224024221224444351229193991230094461238164641239514471239564681240293741245274441246161361246303981246343761249434721249723751250114701253042971253714791253922991255154811255954841261234851262203001262344951262404781265474911265964991269135011271233891277315161277813951277963901278012091281195081281675171104PhosphateHMDB0001429Phosphate is a salt of phosphoric acid. In organic chemistry, a phosphate, or organophosphate, is an ester of phosphoric acid. Organic phosphates are important in biochemistry, biogeochemistry and ecology. Phosphate (Pi) is an essential component of life. In biological systems, phosphorus is found as a free phosphate ion in solution and is called inorganic phosphate, to distinguish it from phosphates bound in various phosphate esters. Inorganic phosphate is generally denoted Pi and at physiological (neutral) pH primarily consists of a mixture of HPO<sup>2-</sup><sub>4</sub> and H<sub>2</sub>PO<sup>-</sup><sub>4</sub> ions. phosphates are most commonly found in the form of adenosine phosphates, (AMP, ADP and ATP) and in DNA and RNA and can be released by the hydrolysis of ATP or ADP. Similar reactions exist for the other nucleoside diphosphates and triphosphates. Phosphoanhydride bonds in ADP and ATP, or other nucleoside diphosphates and triphosphates, contain high amounts of energy which give them their vital role in all living organisms. Phosphate must be actively transported into cells against its electrochemical gradient. In vertebrates, two unrelated families of Na+-dependent Pi transporters carry out this task. Remarkably, the two families transport different Pi species: whereas type II Na+/Pi cotransporters (SCL34) prefer divalent HPO4(2), type III Na+/Pi cotransporters (SLC20) transport monovalent H2PO4. The SCL34 family comprises both electrogenic and electroneutral members that are expressed in various epithelia and other polarized cells. Through regulated activity in apical membranes of the gut and kidney, they maintain body Pi homeostasis, and in salivary and mammary glands, liver, and testes they play a role in modulating the Pi content of luminal fluids. Phosphate levels in the blood play an important role in hormone signaling and in bone homeostasis. In classical endocrine regulation, low serum phosphate induces the renal production of the seco-steroid hormone 1,25-dihydroxyvitamin D3 (1,25(OH)2D3).This active metabolite of vitamin D acts to restore circulating mineral (i.e. phosphate and calcium) levels by increasing absorption in the intestine, reabsorption in the kidney, and mobilization of calcium and phosphate from bone. Thus, chronic renal failure is associated with hyperparathyroidism, which in turn contributes to osteomalacia (softening of the bones). Another complication of chronic renal failure is hyperphosphatemia (low levels of phosphate in the blood). Hyperphosphatemia (excess levels of phosphate in the blood) is a prevalent condition in kidney dialysis patients and is associated with increased risk of mortality. Hypophosphatemia (hungry bone syndrome) has been associated to postoperative electrolyte aberrations and after parathyroidectomy. (PMID: 17581921, 11169009, 11039261, 9159312, 17625581)Fibroblast growth factor 23 (FGF-23) has recently been recognized as a key mediator of phosphate homeostasis, its most notable effect being promotion of phosphate excretion. FGF-23 was discovered to be involved in diseases such as autosomal dominant hypophosphatemic rickets, X-linked hypophosphatemia, and tumor-induced osteomalacia in which phosphate wasting was coupled to inappropriately low levels of 1,25(OH)2D3. FGF-23 is regulated by dietary phosphate in humans. In particular it was found that phosphate restriction decreased FGF-23, and phosphate loading increased FGF-23.14265-44-2C00009106118367CPD-85871032[O-]P([O-])([O-])=OO4PInChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)/p-3NBIIXXVUZAFLBC-UHFFFAOYSA-Kphosphoric acid94.971494.953423phosphoric acid0-2DBMET00532FDB022617Nfb orthophosphate;O-phosphoric acid;Ortho-phosphate;Orthophosphate (po43-);Orthophosphate(3-);Phosphate;Phosphate (po43-);Phosphate anion(3-);Phosphate ion (po43-);Phosphate ion(3-);Phosphate trianion;Phosphate(3-);Phosphoric acid ion(3-);Pi;[po4](3-);Orthophosphate;Phosphate ion;Po4(3-);Phosphoric acid;Orthophosphoric acid;Phosphoric acid ionPW_C001104Pi24484881458181883129803176314176749250010272947273746312929316672363661385123424922447531503127515875207975216100531711153511125381103544712055431295573133560513556251085693658481435855146591114759411516040155610016162941076487178669110167141176842188688916071612057189206721221173061987389210740221274361637475222819622582582271011824110134257117481321176111511773213119041701192716412014281127282901326322334819174225530442350315424353184369232277018253771942937721713477940336779661307804833278057329782453537866933180022368892793089383138394796384110558390110640391113235941158453981162061091199824061200691221206994071210571241212161251212684291213521211214091231214233821218524051233041191236211181237861361238384641239684471239813991244053761249484721253624791254462971257744811259542991262214781265943001266042981267234841269045011274133881277832091281663951281775131283153891034Adenosine diphosphateHMDB0001341Adenosine diphosphate, abbreviated ADP, is a nucleotide. It is an ester of pyrophosphoric acid with the nucleotide adenine. ADP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase adenine. ADP is the product of ATP dephosphorylation by ATPases. ADP is converted back to ATP by ATP synthases.58-64-0C00008602216761ADP5800NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1OC10H15N5O10P2InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1XTWYTFMLZFPYCI-KQYNXXCUSA-N[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid427.2011427.029414749-2.126adenosine-diphosphate0-2FDB021817Adp;Adenosindiphosphorsaeure;Adenosine 5'-pyrophosphate;Adenosine diphosphate;Adenosine pyrophosphate;Adenosine-5'-diphosphate;Adenosine-5-diphosphate;Adenosine-diphosphate;5'-adenylphosphoric acid;Adenosine 5'-diphosphate;H3adp;5'-adenylphosphate;Adenosine 5'-diphosphoric acid;Adenosine-5'-diphosphoric acidPW_C001034ADP234134841522482138015963159783106114151821901492104182113102161582408592435272728472736462855293165723635614400234476314770915036265157752089752171005315111534911253921035446120554412955721335624108574111757641015849143585614658781075899147592615160501556111161623116664951786700946841188687216071592057187206720821072262137231211730019873032167391217741021874331637483222818722511851277119051701201328112180285132622231532930842328315423983134262232242696318770292537708713277216134773063297747233377663336780393327804335078170128782153517824435378414335784951157870533178849130789203348003036880622118806511358067611994827124113283388116204109119944122119994406120156407120318382120366412121248429121394123121399433121472408121899383121976410122064125122085405122405422122445435122973399123013446123818464123953447123958468124030374124452398124529444124615136124636376124947472124975375125012470125334297125373479125492299125517481125645484126125485126219300126235495126242478126550491126597499126915501127733516127780395127797390127803209128122508128168517128313389146NADPHHMDB0000221Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.).53-57-6C000052283351216474NADPH17215925NC(=O)C1=CN(C=CC1)[C@H]1O[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](OP(O)(O)=O)[C@H]2O)N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1OC21H30N7O17P3InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m0/s1ACFIXJIJDZMPPO-NCHANQSKSA-N{[(2S,3S,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2S,3R,4S,5S)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid745.4209745.091102105-2.149[(2S,3S,4S,5S)-2-(6-aminopurin-9-yl)-5-{[({[(2S,3R,4S,5S)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid0-4FDB0219092'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-d-ribofuranosylnicotinamide;2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-d-ribofuranosyl-3-pyridinecarboxamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide;Dihydrocodehydrogenase ii;Dihydronicotinamide adenine dinucleotide phosphate;Dihydronicotinamide adenine dinucleotide-p;Dihydrotriphosphopyridine nucleotide reduced;Nadp-reduced;Nadph;Nicotinamide-adenine-dinucleotide-phosphorate;Nicotinamide-adenine-dinucleotide-phosphoric acid;Reduced codehydrase ii;Reduced coenzyme ii;Reduced cozymase ii;Reduced triphosphopyridine nucleotide;Triphosphopyridine nucleotide reduced;B-nadph;B-nicotinamide-adenine-dinucleotide-phosphorate;B-nicotinamide-adenine-dinucleotide-phosphoric acid;Beta-nadph;Beta-nicotinamide-adenine-dinucleotide-phosphorate;Beta-nicotinamide-adenine-dinucleotide-phosphoric acid;Nicotinamide adenine dinucleotide phosphate - reducedPW_C000146NADPH1858190377810796582118837216092916154946873147931447971453101115789108597214761281596271356779117706818871031637154205720516073152137345210755921275911708194225821915184212241181219811893211120062221215016412245286125962261264824942343315437463227691129377166132773853317739433277460130775041127751111577623336807121191131649412010540712042540512045212212061612312114112512127542912140212412148338312305937612308613512324144712371213612384646412396111812404139812547248112569629712621429912652949512700920612757238812810139022645DoxorubicinolHMDB0041884Doxorubicinol, also known as adriamycinol or doxol, belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage. Doxorubicinol is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Doxorubicinol has been found in human liver and kidney tissues, and has also been detected in multiple biofluids, such as urine and blood. Within the cell, doxorubicinol is primarily located in the cytoplasm. In humans, doxorubicinol is involved in the doxorubicin metabolism pathway. Doxorubicinol belongs to the family of Anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.54193-28-18397075768COC1=CC=CC2=C1C(=O)C1=C(C(O)=C3C[C@](O)(C[C@H](O[C@H]4C[C@H](N)[C@H](O)[C@H](C)O4)C3=C1O)[C@@H](O)CO)C2=OC27H31NO11InChI=1S/C27H31NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15-17,22,29-31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,16-,17-,22+,27-/m0/s1NKZRZOVSJNSBFR-FEMMEMONSA-N(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-[(1S)-1,2-dihydroxyethyl]-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione545.5351545.189710839-2.567(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-[(1S)-1,2-dihydroxyethyl]-6,8,11-trihydroxy-1-methoxy-9,10-dihydro-7H-tetracene-5,12-dione01DBMET00647PW_C022645Dorubol39928495431143NADPHMDB0000217Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5-phosphate (NMN) coupled by pyrophosphate linkage to the 5-phosphate adenosine 2,5-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.) Hydrogen carrier in biochemical redox systems. In the hexose monophosphoric acid system it is reduced to Dihydrocoenzyme II and reoxidation in the presence of flavoproteins (Dictionary of Organic Compounds).53-59-8C00006588618009NAD(P)5675NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1OC21H29N7O17P3InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1XJLXINKUBYWONI-NNYOXOHSSA-O1-[(2R,3R,4S,5R)-5-[({[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium744.4129744.083277073-2.2791-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium1-3FDB021908Adenine-nicotinamide dinucleotide phosphate;Codehydrase ii;Codehydrogenase ii;Coenzyme ii;Cozymase ii;Nad phosphate;Nadp;Nadp+;Nicotinamide adenine dinucleotide phosphate;Nicotinamide-adenine dinucleotide phosphate;Tpn;Triphosphopyridine nucleotide;B-nadp;B-nicotinamide adenine dinucleotide phosphate;B-tpn;Beta-nadp;Beta-nicotinamide adenine dinucleotide phosphate;Beta-tpn;Oxidized nicotinamide-adenine dinucleotide phosphate;B-nicotinamide adenine dinucleotide phosphoric acid;Beta-nicotinamide adenine dinucleotide phosphoric acid;β-nicotinamide adenine dinucleotide phosphate;β-nicotinamide adenine dinucleotide phosphoric acidPW_C000143NADP18381913768578010824188392161129161749468531479614480114530811157901086017147613215962733567781177069188710516371522057206160731721373462107562212758917081972258220151841922411811198118972111200822212152164122492861259722612650249423443154374532276913293771641327738433177396332774611307751511577624336778143347787011280713119113165941201064071204294051204501221206044081206181231211421251212774291214011241214853831230633761230841351232293741232434471237131361238484641239601181240433981254734811256942971257434821262152991265284951270102061272255021275703881281003901144NADHHMDB0001487NADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH, A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). It forms NADP with the addition of a phosphate group to the 2' position of the adenosyl nucleotide through an ester linkage.(Dorland, 27th ed).58-68-4C0000443915316908NADH388299DB00157NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1OC21H29N7O14P2InChI=1S/C21H29N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1BOPGDPNILDQYTO-NNYOXOHSSA-N[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid665.441665.124771695-2.358NADH0-2FDB0226491,4-dihydronicotinamide adenine dinucleotide;Dpnh;Dihydrocodehydrogenase i;Dihydrocozymase;Dihydronicotinamide adenine dinucleotide;Dihydronicotinamide mononucleotide;Enada;Nadh;Nadh2;Reduced codehydrogenase i;Reduced diphosphopyridine nucleotide;Reduced nicotinamide adenine diphosphate;Reduced nicotinamide-adenine dinucleotide;B-dpnh;B-nadh;Beta-dpnh;Beta-nadh;Nicotinamide adenine dinucleotide (reduced);Reduced nicotinamide adenine dinucleotidePW_C001144NADH14341533490864810111521275514695422304927811728362931099480618481218482128490464959315169955240103533211153581125466123547912555931355698100573710858291415915147594515160271556079161638716472178677111768931607011188709916371722057195206746222282442268360225908622411809198118212161232024913003298130153001325522342403322426183157710713277123133772081347737133177651336776683347770033277707130779171137798634780009368806911199382212411054938811285494115838118119955406120172407120378122120986408121162425121244126121693429121818383122616384122745120123127447123138136123551374123734460123814443124242464124371398125189121125345479125531481125762297125808299125926482126516495126767480126888501127385502128090390128362391128429395721NADHMDB0000902NAD (or Nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be converted to ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it by cellular respiration. (wikipedia). Nicotinamide adenine dinucleotide is a A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed).53-84-9C00003589315846NAD5682NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1OC21H28N7O14P2InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1BAWFJGJZGIEFAR-NNYOXOHSSA-O1-[(2R,3R,4S,5R)-5-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium664.433664.116946663-2.5981-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium1-1FDB0223093-carbamoyl-1-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;3-carbamoyl-1-beta-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;Adenine-nicotinamide dinucleotide;Co-i;Codehydrase i;Codehydrogenase i;Coenzyme i;Cozymase;Cozymase i;Diphosphopyridine nucleotide;Diphosphopyridine nucleotide oxidized;Endopride;Nad trihydrate;Nad-oxidized;Nicotinamide adenine dinucleotide;Nicotinamide adenine dinucleotide oxidized;Nicotinamide dinucleotide;Nicotineamide adenine dinucleotide;Oxidized diphosphopyridine nucleotide;Pyridine nucleotide diphosphate;[(3s,2r,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3s,2r,4r,5r)-5-(3-carbamoylpyridyl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxyphosphoryl) hydrogen phosphate;[adenylate-32-p]-nad;Beta-diphosphopyridine nucleotide;Beta-nad;Beta-nicotinamide adenine dinucleotide;Beta-nicotinamide adenine dinucleotide trihydrate;Dpn;Nad;Nad+;Nadide;B-nad;β-nadPW_C000721NAD140415033538651101114211344312735146654222949277917283529310794807184813184819284902649603151679552381035334111536011254691235482125559013556101185696100573810858271415912147594215160241556072157607616163851646917867721176890160701218870971637174205719720674051987459222824122683592259085224118192161232224913006298130183001325622342404322426193157710413277120133772091347737033177650336776673347770233277709130779151137798334778406356800063688069011993825124110552388112750166112853941199291221199524061201714071208344191209844081211594251212421261212594291218173831226143841227421201231304471231411361234194551235493741237314601238124431238294641243703981251871211253192971253424791255304811258062991258254901259244821265154951267654801268855011272785071273835021280893901283603911284283951799HemeHMDB0003178Heme is the color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins. A heme or haem is a prosthetic group that consists of an iron atom contained in the center of a large heterocyclic organic ring called a porphyrin. Not all porphyrins contain iron, but a substantial fraction of porphyrin-containing metalloproteins have heme as their prosthetic subunit; these are known as hemoproteins.14875-96-8C0003217627HEME_A24604415DB02577CC1=C(CCC(O)=O)C2=CC3=[N+]4C(=CC5=C(C)C(C=C)=C6C=C7C(C)=C(C=C)C8=[N+]7[Fe--]4(N2C1=C8)N56)C(C)=C3CCC(O)=OC34H32FeN4O4InChI=1S/C34H34N4O4.Fe/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;/h7-8,13-16H,1-2,9-12H2,3-6H3,(H4,35,36,37,38,39,40,41,42);/q;+2/p-2/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;KABFMIBPWCXCRK-RGGAHWMASA-L4,20-bis(2-carboxyethyl)-10,15-diethenyl-5,9,14,19-tetramethyl-2lambda5,22,23lambda5,25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2,4,6,8,10,12,14,16(23),17,19,21(24)-undecaene-2,23-bis(ylium)-1,1-diuide616.487616.177297665-5.4824,20-bis(2-carboxyethyl)-10,15-diethenyl-5,9,14,19-tetramethyl-2lambda5,22,23lambda5,25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2,4,6,8,10,12,14,16(23),17,19,21(24)-undecaene-2,23-bis(ylium)-1,1-diuide0-2FDB016272(protoporphyrinato)iron;Ferroheme;Ferroheme b;Ferroprotoheme;Ferroprotoporphyrin;Ferroprotoporphyrin ix;Ferrous protoheme;Ferrous protoheme ix;Haem;Hem;Heme;Iron protoporphyrin;Iron protoporphyrin ix;Iron(ii) protoporphyrin ix;Protoferroheme;Protohaem;Protoheme;Protoheme ix;Reduced hematinPW_C001799Heme24716308103248608276651244313544914133619631828062929389323811336726342114373444043314823285170955472123548512555171295830141624678628316597151704416070601617326213118351981189821112065164130092981302130042278177691529376931249773511117736413077367331773983327751711577629336778133347838013378602132789631127993213412043140512060340812095540712108538312165842912174612412191012212257040612269138412306537612313344712314413612322837412352111912365039812421646412429711812446313512514212012527712112574248212589648112619629912649929712651249512671847912682748012722450212735720612763238812807020512808339512808639012830950112843439119TetrahydrobiopterinHMDB0000027Tetrahydrobiopterin or BH4 is a cofactor in the synthesis of nitric oxide. In fact it is used by all three human nitric-oxide synthases (NOS) eNOS, nNOS, and iNOS as well as the enzyme glyceryl-ether monooxygenase. It is also essential in the conversion of phenylalanine to tyrosine by the enzyme phenylalanine-4-hydroxylase; the conversion of tyrosine to L-dopa by the enzyme tyrosine hydroxylase; and conversion of tryptophan to 5-hydroxytryptophan via tryptophan hydroxylase. Specifically, tetrahydrobiopterin is a cofactor for tryptophan 5-hydroxylase 1, tyrosine 3-monooxygenase, and phenylalanine hydroxylase all of which are essential for the formation of the neurotransmitters dopamine, noradrenaline and adrenaline. Tetrahydrobiopterin has been proposed to be involved in promotion of neurotransmitter release in the brain and the regulation of human melanogenesis. A defect in BH4 production and/or a defect in the enzyme dihydropteridine reductase (DHPR) causes phenylketonuria type IV, as well as dopa-responsive dystonias. BH4 is also implicated in Parkinson's disease, Alzheimer's disease and depression. Tetrahydrobiopterin is present in probably every cell or tissue of higher animals. On the other hand, most bacteria, fungi and plants do not synthesize tetrahydrobiopterin. -- Wikipedia.17528-72-2C00272112515372TETRA-H-BIOPTERIN1093DB00360CC(O)C(O)C1CNC2=C(N1)C(=O)N=C(N)N2C9H15N5O3InChI=1S/C9H15N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17)FNKQXYHWGSIFBK-UHFFFAOYSA-N2-amino-6-(1,2-dihydroxypropyl)-1,4,5,6,7,8-hexahydropteridin-4-one241.2471241.117489371-2.046tetrahydrobiopterin00FDB021880(1r,2s)-(2-amino-3,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)-1,2-propandiol;2-amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1h)-5,6,7,8-tetrahydro-2-amino-6-(1,2-dihydroxypropyl)-4(1h)-pteridinone;2-amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(1h)-pteridinone;5,6,7,8-erythro-tetrahydrobiopterin;5,6,7,8-tetra-h-biopterin;5,6,7,8-tetrahydro-2-amino-6-(1,2-dihydroxypropyl)-4(1h)-pteridinone;5,6,7,8-tetrahydrobiopterin;L-erythro-2-amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3h)-pteridinon;Tetra-h-biopterin;Tetra-hydro-biopterin;Tetrahydrobiopterin;2-amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1h)-pteridinone;Bh4PW_C000019BH419572408584800144803144962311190121177520115786631321204344051216161241230683761241741181264932991275853882111Solute carrier family 22 member 16Q86VW1High affinity carnitine transporter; the uptake is partially sodium-ion dependent. Thought to mediate the L-carnitine secretion mechanism from testis epididymal epithelium into the lumen which is involved in the maturation of spermatozoa. Also transports organic cations such as tetraethylammonium (TEA) and doxorubicin. The uptake of TEA is inhibited by various organic cations. The uptake of doxorubicin is sodium-independentHMDBP02811SLC22A166q22.1|6q21-q22.1AB05579811543NAD(P)H dehydrogenase [quinone] 1P15559The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinons involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
HMDBP01689NQO116q22.1J0393411.6.5.216132940048468931178NADPH--cytochrome P450 reductaseP16435This enzyme is required for electron transfer from NADP to cytochrome P450 in microsomes. It can also provide electron transfer to heme oxygenase and cytochrome B5.
HMDBP00183POR7q11.2AC00633011.6.2.440058176Xanthine dehydrogenase/oxidaseP47989Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
HMDBP00181XDH2p23.1U3948711.17.1.4; 1.17.3.262928187253748240038483194964311787Multidrug resistance protein 1P08183Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cellsHMDBP02101ABCB17q21.12M2942513.6.3.442976144924535218991647Multidrug resistance-associated protein 1P33527Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o- glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiencyHMDBP01858ABCC116p13.1AF02283213079144919535209991531Canalicular multispecific organic anion transporter 1Q92887Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporterHMDBP01658ABCC210q24AJ245627131011484822301862ATP-binding cassette sub-family G member 2Q9UNQ0Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123HMDBP02257ABCG24q22AY33375613078144923535213991897RalA-binding protein 1Q15311Can activate specifically hydrolysis of GTP bound to RAC1 and CDC42, but not RALA. Mediates ATP-dependent transport of S-(2,4-dinitrophenyl)-glutathione (DNP-SG) and doxorubicin (DOX) and is the major ATP-dependent transporter of glutathione conjugates of electrophiles (GS-E) and DOX in erythrocytes. Can catalyze transport of glutathione conjugates and xenobiotics, and may contribute to the multidrug resistance phenomenon. Serves as a scaffold protein that brings together proteins forming an endocytotic complex during interphase and also with CDK1 to switch off endocytosis, One of its substrates would be EPN1/EpsinHMDBP02344RALBP118p11.3L425421321714852222880291872Carbonyl reductase [NADPH] 1P16152NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. Catalyzes the reduction of the antitumor anthracyclines doxorubicin and daunorubicin to the cardiotoxic compounds doxorubicinol and daunorubicinol. Can convert prostaglandin E2 to prostaglandin F2-alpha. Can bind glutathione, which explains its higher affinity for glutathione-conjugated substrates. Catalyzes the reduction of S-nitrosoglutathione.
HMDBP00075CBR121q22.13BC01564011.1.1.184; 1.1.1.197; 1.1.1.189136681954249553174Carbonyl reductase [NADPH] 3O75828Has low NADPH-dependent oxidoreductase activity towards 4-benzoylpyridine and menadione (in vitro).
HMDBP00077CBR321q22.2CR54170911.1.1.18439938495631353Aldo-keto reductase family 1 member C3P42330Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2. Functions as a bi-directional 3-alpha-, 17-beta- and 20-alpha HSD. Can interconvert active androgens, estrogens and progestins with their cognate inactive metabolites. Preferentially transforms androstenedione (4-dione) to testosterone.
HMDBP00360AKR1C310p15-p14L4383611.-.-.-; 1.1.1.357; 1.1.1.112; 1.1.1.188; 1.1.1.239; 1.1.1.64; 1.3.1.20620213588495731486Alcohol dehydrogenase [NADP(+)]P14550Catalyzes the NADPH-dependent reduction of a variety of aromatic and aliphatic aldehydes to their corresponding alcohols. Catalyzes the reduction of mevaldate to mevalonic acid and of glyceraldehyde to glycerol. Has broad substrate specificity. In vitro substrates include succinic semialdehyde, 4-nitrobenzaldehyde, 1,2-naphthoquinone, methylglyoxal, and D-glucuronic acid. Plays a role in the activation of procarcinogens, such as polycyclic aromatic hydrocarbon trans-dihydrodiols, and in the metabolism of various xenobiotics and drugs, including the anthracyclines doxorubicin (DOX) and daunorubicin (DAUN).
HMDBP00507AKR1A11p33-p32BT00700311.1.1.234148376029495831872Nitric oxide synthase, endothelialP29474Produces nitric oxide (NO) which is implicated in vascular smooth muscle relaxation through a cGMP-mediated signal transduction pathway. NO mediates vascular endothelial growth factor (VEGF)-induced angiogenesis in coronary vessels and promotes blood clotting through the activation of platelets.
Isoform eNOS13C: Lacks eNOS activity, dominant-negative form that may down-regulate eNOS activity by forming heterodimers with isoform 1.
HMDBP00929NOS37q36L1070711.14.13.3940868496331115NADH dehydrogenase [ubiquinone] iron-sulfur protein 2, mitochondrialO75306Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
HMDBP00120NDUFS21q23AF05064011.6.5.3; 1.6.99.34053840653496510496817135NADH dehydrogenase [ubiquinone] iron-sulfur protein 3, mitochondrialO75489Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
HMDBP00140NDUFS311p11.11AK31380211.6.5.3; 1.6.99.34054840663496610496917175NADH dehydrogenase [ubiquinone] iron-sulfur protein 7, mitochondrialO75251Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
HMDBP00180NDUFS719p13.3BC00171511.6.5.3; 1.6.99.34055840673496710497017869Nitric oxide synthase, inducibleP35228Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such COX2.
HMDBP00926NOS217q11.2-q12U2014111.14.13.3940878871Nitric oxide synthase, brainP29475Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In the brain and peripheral nervous system, NO displays many properties of a neurotransmitter. Probably has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such SRR.
HMDBP00928NOS112q24.2-q24.31U1730811.14.13.3940888480214480414942Solute carrier family 22 member 161PW_P000942106721111440NAD(P)H dehydrogenase [quinone] 11PW_P000440463154322119641160729936NADPH--cytochrome P450 reductase1PW_P00093610611781377964137811701189Xanthine dehydrogenase/oxidase1PW_P000189207176285964139140558239214912738Multidrug resistance protein 11PW_P00073883317871759Multidrug resistance-associated protein 11PW_P00075985616471754Canalicular multispecific organic anion transporter 11PW_P00075484915311305714758ATP-binding cassette sub-family G member 21PW_P00075885518621765RalA-binding protein 11PW_P0007658621897381Carbonyl reductase [NADPH] 11PW_P000381403721928Carbonyl reductase [NADPH] 31PW_P0009281053741188Aldo-keto reductase family 1 member C31PW_P000188206353824Alcohol dehydrogenase [NADP(+)]1PW_P0008249484861937Nitric-oxide synthase, endothelial1PW_P0009371062872237917991380964138111701382191932NADH dehydrogenase [ubiquinone] iron-sulfur protein 2, mitochondrial1PW_P00093210571151933NADH dehydrogenase [ubiquinone] iron-sulfur protein 3, mitochondrial1PW_P00093310581351934NADH dehydrogenase [ubiquinone] iron-sulfur protein 7, mitochondrial1PW_P00093410591751938Nitric oxide synthase, inducible1PW_P0009381063869238317991384964138511701386191940Nitric-oxide synthase, brain1PW_P00094010658712387179913889641389117013901912036falsePW_R002036Right729694321Compoundfalse7297406181Compoundfalse2037falsePW_R002037Right7298406181Compoundfalse7299406191Compoundfalse2035falsePW_R002035Right729494321Compoundfalse7295406171Compoundfalse191418919154401.6.5.219169361.6.2.42073falsePW_R002073Right7385406161Compoundfalse738694321Compoundfalse2032falsePW_R002032Right728894321Compoundfalse88951461Compoundtrue7289226451Compoundfalse88961431Compoundtrue190138119029281.1.1.184190318819048241.1.1.22034falsePW_R002034Right729294321Compoundfalse889311441Compoundtrue7293406161Compoundfalse88947211Compoundtrue19069321907933190893419099371.14.13.3919109381.14.13.3919119401.14.13.39191218919134401.6.5.271PW_RCT000071Right421719432Compound131422711420Compound13142371414Compound131424719432Compound115425711104Compound131426711034Compound1317172PW_RCT000072Right427729432Compound131428721420Compound13142972414Compound131430729432Compound115431721104Compound131432721034Compound1317274PW_RCT000074Right439749432Compound131440741420Compound13144174414Compound131442749432Compound115443741104Compound131444741034Compound1317473PW_RCT000073Right433739432Compound131434731420Compound13143573414Compound131436739432Compound131437731104Compound131438731034Compound13173198PW_T00019823194321Compound158Right1569422013-09-12T13:16:37-06:002013-09-12T13:16:37-06:0014201PW_T00020123494321Compound83Both202PW_T000202235406161Compound38Both199PW_T00019923294321Compound815Right1577382013-09-12T13:46:58-06:002013-09-12T13:46:58-06:00141587592013-09-12T13:46:58-06:002013-09-12T13:46:58-06:00141597542013-09-12T13:46:58-06:002013-09-12T13:46:58-06:00141607582013-09-12T13:46:58-06:002013-09-12T13:46:58-06:00141617652013-09-12T13:46:58-06:002013-09-12T13:46:58-06:00148012943215157false9105510regular200190801394328157false91099010regular2001908014943283true56043510regular1001008048406188157false1660110510regular2001908049406198157false2100110510regular2001908050406178157false2105144510regular200190805296489false1705155510regular10025805396489false1730165510regular100258054117089false1850165510regular10035806196489false1730147010regular1002580624055889false1730141010regular100258063149189false1850147010regular100258164406168157false785264010regular200190817294323157false1855241010regular2001908174406163157false2320241010regular20019081764061683true0010regular100110818094328157true0010regular2001908181943215157false5099010regular20019081829432153true0010regular10010081839432153true0010regular10010081849432153true0010regular10010081859432153true0010regular1001001118114203149false52050010regular7878111824143142false60058010regular50301118311043146false59370510regular44431118410343143false52571110regular50301118514203149false60077510regular7878111864143142false53080010regular50301118711043146false59897010regular44431118810343143false53097610regular50301118914203149false600113510regular7878111904143142false530116010regular50301119111043146false598132510regular44431119210343143false530133610regular50301119314203149false600140010regular7878111944143142false530142510regular50301119511043146false598160510regular44431119610343143false530161610regular5030111971463162false132093510regular5030111982264531157false209574010regular200190111991433161false184080010regular50301120011443160false935172010regular5030112017213159false1170212510regular5030112021799319false980198510regular1002511203964319false1100191510regular10025112041170319false1100198510regular100351120519319false980191510regular1002511206964319false1200183010regular100251120740558319false1095181010regular10025112081491319false1195189010regular1002511209964319false925208510regular100251121011441060false1605174010regular5030112117211059false1605209510regular50301121211441760false1880234510regular5030112137211759false2455235010regular50303980211176false9353958subunitregular150704018154386false176015008subunitregular16080401917886false176015908subunitregular16080402617686false176014058subunitregular16080410717871476false3756008subunitregular15070410816471476false3758708subunitregular150704109153123076false37515008subunitregular150704110186276false37512308subunitregular150704111189722876false37510508subunitregular15070590472312false14558958subunitregular15070590574312false15109758subunitregular150705906353312false15908558subunitregular150705907486312false16459408subunitregular150705908872316false101019208subunitregular160805909176316false109518258subunitregular1608059101543316false90020208subunitregular160805911115102false167019608subunitregular150705912135102false158019008subunitregular150705913175102false167018408subunitregular150705914115172false200522378subunitregular150705915135172false212022878subunitregular150705916175172false223022378subunitregular1507032929423693964398033194403698400140181423805212102Cofactor33209363698400240191424805312103Cofactor1425805412104Cofactor33271893698400940261429806112114Cofactor1430806212115Cofactor1431806312116Cofactor340073836940854107340175936940864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