1.0 2016-09-30 22:26:57 UTC 2020-05-21 16:29:28 UTC BMDB0000221 BMDB00221 NADPH Dihydronicotinamide-adenine dinucleotide phosphate NADPH dihydro-nicotinamide-adenine-dinucleotide phosphATE Reduced nicotinamide adenine dinucleotide phosphate Reduced nicotinamide-adenine dinucleotide phosphate TPNH Dihydronicotinamide-adenine dinucleotide phosphoric acid NADPH dihydro-nicotinamide-adenine-dinucleotide phosphoric acid Reduced nicotinamide adenine dinucleotide phosphoric acid Reduced nicotinamide-adenine dinucleotide phosphoric acid Coenzyme II Nicotinamide-adenine dinucleotide phosphate Nucleotide, triphosphopyridine Triphosphopyridine nucleotide Dinucleotide phosphate, nicotinamide-adenine NADP Nicotinamide adenine dinucleotide phosphate Phosphate, nicotinamide-adenine dinucleotide Nadph dihydro-nicotinamide-adenine-dinucleotidephosphoric acid NADPH Nicotinamide-adenine dinucleotide phosphate, reduced Reduced triphosphopyridine nucleotide Triphosphopyridine nucleotide, reduced beta-NADPH beta-Nicotinamide-adenine-dinucleotide-phosphoric acid beta-TPNH β-NADPH β-Nicotinamide-adenine-dinucleotide-phosphoric acid β-TPNH C21H30N7O17P3 745.4209 745.091102105 {[(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2R,3S,4R,5R)-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 acid nadph 53-57-6 NC(=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=C2N=CN=C3N)[C@@H](O)[C@H]1O InChI=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-/m1/s1 ACFIXJIJDZMPPO-NNYOXOHSSA-N belongs to the class of organic compounds known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage. Organic compounds Nucleosides, nucleotides, and analogues (5'->5')-dinucleotides (5'->5')-dinucleotides 6-aminopurines Aminopyrimidines and derivatives Azacyclic compounds Carboximidic acids Dihydropyridinecarboxylic acids and derivatives Enamines Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Imidolactams Monoalkyl phosphates Monosaccharide phosphates N-substituted imidazoles N-substituted nicotinamides Nicotinamide nucleotides Organic oxides Organic pyrophosphates Organopnictogen compounds Oxacyclic compounds Pentose phosphates Primary amines Purine nucleotide sugars Purine ribonucleoside 2',5'-bisphosphates Purine ribonucleoside diphosphates Secondary alcohols Tetrahydrofurans (5'->5')-dinucleotide 6-aminopurine Alcohol Alkyl phosphate Amine Aminopyrimidine Aromatic heteropolycyclic compound Azacycle Azole Carboximidic acid Carboximidic acid derivative Dihydropyridine Dihydropyridinecarboxylic acid derivative Enamine Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Hydropyridine Imidazole Imidazopyrimidine Imidolactam Monoalkyl phosphate Monosaccharide Monosaccharide phosphate N-glycosyl compound N-substituted imidazole N-substituted nicotinamide Nicotinamide-nucleotide Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organic pyrophosphate Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Pentose phosphate Pentose-5-phosphate Phosphoric acid ester Primary amine Purine Purine nucleotide sugar Purine ribonucleoside 2',5'-bisphosphate Purine ribonucleoside bisphosphate Purine ribonucleoside diphosphate Pyrimidine Secondary alcohol Tetrahydrofuran Aromatic heteropolycyclic compounds NAD(P)H NADP Solid logp -1.13 ALOGPS logs -2.14 ALOGPS logp -6.4 ChemAxon pka_strongest_acidic 0.66 ChemAxon pka_strongest_basic 4 ChemAxon iupac {[(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2R,3S,4R,5R)-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 acid ChemAxon average_mass 745.4209 ChemAxon mono_mass 745.091102105 ChemAxon smiles NC(=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=C2N=CN=C3N)[C@@H](O)[C@H]1O ChemAxon formula C21H30N7O17P3 ChemAxon inchi InChI=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-/m1/s1 ChemAxon inchikey ACFIXJIJDZMPPO-NNYOXOHSSA-N ChemAxon polar_surface_area 364.15 ChemAxon refractivity 153.87 ChemAxon polarizability 63.54 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 18 ChemAxon donor_count 9 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon number_of_rings 5 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Androgen and Estrogen Metabolism SMP0087251 Androstenedione Metabolism SMP0087271 Arachidonic Acid Metabolism SMP0087220 Arginine and Proline Metabolism SMP0087178 beta-Alanine Metabolism SMP0087180 Bile Acid Biosynthesis SMP0087236 Estrone Metabolism SMP0087272 Ethanol Degradation SMP0087192 Fatty Acid Elongation in Mitochondria SMP0087194 Folate Metabolism SMP0087196 Fructose and Mannose Degradation SMP0087197 Glutamate Metabolism SMP0087169 Glutathione Metabolism SMP0087167 Glycerolipid Metabolism SMP0087230 Histidine Metabolism SMP0087219 LPS and Citrate Signaling and Inflammation SMP0120946 Lysine Degradation SMP0087203 Nicotinate and Nicotinamide Metabolism SMP0087241 Pterine Biosynthesis SMP0087250 Purine Metabolism SMP0087239 Pyrimidine Metabolism SMP0087247 Pyruvate Metabolism SMP0087231 Retinol Metabolism SMP0087260 Sphingolipid Metabolism SMP0087244 Steroid Biosynthesis SMP0087233 Steroidogenesis SMP0087238 Transfer of Acetyl Groups into Mitochondria SMP0087254 Tryptophan Metabolism SMP0087237 Tyrosine Metabolism SMP0087235 Ubiquinone Biosynthesis SMP0087215 Vitamin K Metabolism SMP0087227 Warburg Effect SMP0087270 Specdb::NmrTwoD 2058 Specdb::MsMs 26093 Specdb::MsMs 26094 Specdb::MsMs 26095 Specdb::MsMs 32651 Specdb::MsMs 32652 Specdb::MsMs 32653 Specdb::MsMs 1448529 Specdb::MsMs 1448530 Specdb::MsMs 1448531 Specdb::MsMs 1471351 Specdb::MsMs 1471352 Specdb::MsMs 1471353 Specdb::MsMs 1471354 Specdb::MsMs 1471355 Specdb::MsMs 1471356 Specdb::MsMs 1471357 Specdb::MsMs 1471358 Specdb::MsMs 1471359 Specdb::MsMs 1471360 Specdb::MsMs 1471361 Specdb::MsMs 2451598 Specdb::MsMs 2451599 Specdb::MsMs 2451600 Specdb::MsMs 2487927 Specdb::MsMs 2487928 Specdb::CMs 773267 Specdb::CMs 773268 Specdb::CMs 773269 Specdb::CMs 773270 Specdb::CMs 773271 Specdb::CMs 773272 Specdb::CMs 773273 Specdb::CMs 773274 Specdb::CMs 773275 Specdb::CMs 773276 Specdb::CMs 773277 Specdb::CMs 773278 Specdb::CMs 773279 Specdb::CMs 773280 Specdb::CMs 773281 Specdb::CMs 773282 Specdb::CMs 773283 Specdb::CMs 773284 Specdb::CMs 773285 Specdb::CMs 773286 Specdb::CMs 773287 Specdb::CMs 773288 Specdb::CMs 773289 Specdb::CMs 773290 Specdb::CMs 773291 Specdb::NmrOneD 4888 Specdb::NmrOneD 4889 Specdb::NmrOneD 4890 Specdb::NmrOneD 4891 All Tissues Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 5884 C00005 16474 5673 FDB021909 DB02338 NADPH Nicotinamide adenine dinucleotide phosphate C00019545 3691 Seelbach, Karsten; Riebel, Bettina; Hummel, Werner; Kula, Maria-Regina; Tishkov, Vladimir I.; Egorov, Alexey M.; Wandrey, Christian; Kragl, Udo. A novel, efficient regenerating method of NADPH using a new formate dehydrogenase. Tetrahedron Letters (1996), 37(9), 1377-80. BMDBP00014 Lanosterol 14-alpha demethylase Q4PJW3 CYP51A1 Enzyme BMDBP00016 Cytochrome P450 3A28 P79102 CYP3A28 Enzyme BMDBP00022 Nitric oxide synthase, endothelial P29473 NOS3 Enzyme BMDBP00024 Prostacyclin synthase Q29626 PTGIS Enzyme BMDBP00053 Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CYP11A1 Enzyme BMDBP00062 Cytochrome P450 2E1 O18963 CYP2E1 Enzyme BMDBP00069 Nitric oxide synthase, inducible Q27995 NOS2 Enzyme BMDBP00071 3-ketodihydrosphingosine reductase Q2KIJ5 KDSR Enzyme BMDBP00116 Dehydrogenase/reductase SDR family member 4 Q8SPU8 DHRS4 Enzyme BMDBP00118 Monofunctional C1-tetrahydrofolate synthase, mitochondrial Q0VCR7 MTHFD1L Enzyme BMDBP00119 Dimethylaniline monooxygenase [N-oxide-forming] 3 Q8HYJ9 FMO3 Enzyme BMDBP00261 Squalene synthase Q32KR6 FDFT1 Enzyme BMDBP00356 6-phosphogluconate dehydrogenase, decarboxylating Q3ZCI4 PGD Enzyme BMDBP00368 Fatty acid synthase Q71SP7 FASN Enzyme BMDBP00379 Sepiapterin reductase Q17QK8 SPR Enzyme BMDBP00383 Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q148L6 DHDH Enzyme BMDBP00432 GMP reductase 2 Q32L93 GMPR2 Enzyme BMDBP00448 Isocitrate dehydrogenase [NADP], mitochondrial Q04467 IDH2 Enzyme BMDBP00501 Thioredoxin reductase 2, mitochondrial Q9N2I8 TXNRD2 Enzyme BMDBP00516 Isocitrate dehydrogenase [NADP] cytoplasmic Q9XSG3 IDH1 Enzyme BMDBP00540 Thioredoxin reductase 1, cytoplasmic O62768 TXNRD1 Enzyme BMDBP00585 Flavin reductase (NADPH) P52556 BLVRB Enzyme BMDBP00594 L-xylulose reductase Q1JP75 DCXR Enzyme BMDBP00597 Dihydropteridine reductase Q3T0Z7 QDPR Enzyme BMDBP00601 Retinal dehydrogenase 1 P48644 ALDH1A1 Enzyme BMDBP00602 Carbonyl reductase [NADPH] 1 Q3SZD7 CBR1 Enzyme BMDBP00620 Malate dehydrogenase, cytoplasmic Q3T145 MDH1 Enzyme BMDBP00630 Corticosteroid 11-beta-dehydrogenase isozyme 2 O77667 HSD11B2 Enzyme BMDBP00631 Alpha-aminoadipic semialdehyde synthase, mitochondrial A8E657 AASS Enzyme BMDBP00689 Dihydropyrimidine dehydrogenase [NADP(+)] Q28007 DPYD Enzyme BMDBP00713 Retinol dehydrogenase 8 Q9N126 RDH8 Enzyme BMDBP00716 Retinol dehydrogenase 10 Q8HZT6 RDH10 Enzyme BMDBP00798 Aldo-keto reductase family 1 member B1 P16116 AKR1B1 Enzyme BMDBP00821 Dihydrofolate reductase P00376 DHFR Enzyme BMDBP00868 Flavin-containing monooxygenase Q0P566 FMO2 Enzyme BMDBP00869 Truncated flavin-containing monooxygenase 3 Q8HYK2 FMO3 Enzyme BMDBP00878 NADPH:adrenodoxin oxidoreductase, mitochondrial P08165 FDXR Enzyme BMDBP00880 Flavin-containing monooxygenase 3 Q8HYK1 FMO3 Enzyme BMDBP00882 Flavin-containing monooxygenase 3 Q8HYK4 FMO3 Enzyme BMDBP00891 Flavin-containing monooxygenase 3 Q8HYK3 FMO3 Enzyme BMDBP00893 NADPH--cytochrome P450 reductase Q3SYT8 POR Enzyme BMDBP00896 Flavin-containing monooxygenase 3 Q8HYK0 FMO3 Enzyme BMDBP00898 Thioredoxin reductase 3 Q9GKW9 trxr3 Enzyme BMDBP00910 7-dehydrocholesterol reductase Q5E9J5 DHCR7 Enzyme BMDBP00987 Aldo-keto reductase family 1 member A1 Q3ZCJ2 AKR1A1 Enzyme BMDBP00989 Aldehyde dehydrogenase family 3 member B1 Q1JPA0 ALDH3B1 Enzyme BMDBP00992 H6PD protein Q0P587 H6PD Enzyme BMDBP00993 Prostaglandin F synthase 1 P05980 Enzyme BMDBP00994 Fatty acyl-CoA reductase 2 Q0P5J1 FAR2 Enzyme BMDBP00995 Prostaglandin F synthase 2 P52897 Enzyme BMDBP00996 Delta(14)-sterol reductase TM7SF2 Q8WMV1 TM7SF2 Enzyme BMDBP00997 Glucose-6-phosphate dehydrogenase Q5EM56 Enzyme BMDBP00998 Similar to 6-phosphogluconate dehydrogenase Q862J6 Enzyme BMDBP00999 GMP reductase Q08DA2 GMPR Enzyme BMDBP01000 Enoyl-[acyl-carrier-protein] reductase, mitochondrial Q7YS70 MECR Enzyme BMDBP01001 NAD(P) transhydrogenase, mitochondrial P11024 NNT Enzyme BMDBP01014 Sterol-4-alpha-carboxylate 3-dehydrogenase, decarboxylating Q3ZBE9 NSDHL Enzyme BMDBP01022 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase P14893 HSD3B Enzyme BMDBP01029 Prostaglandin reductase 2 Q32L99 PTGR2 Enzyme BMDBP01286 Hydroxysteroid 11-beta-dehydrogenase 1-like protein Q6Q7D1 HSD11B1L Enzyme BMDBP01288 Retinol dehydrogenase 12 P59837 RDH12 Enzyme BMDBP01290 Dihydrodiol dehydrogenase 3 P52898 Enzyme BMDBP01333 EBP cholestenol delta-isomerase Q3ZBT8 EBP Enzyme BMDBP02110 24-dehydrocholesterol reductase A6QR14 DHCR24 Enzyme BMDBP02114 Dimethylaniline monooxygenase [N-oxide-forming] A6QLN7 FMO5 Enzyme BMDBP02119 Flavin-containing monooxygenase Q3SZW0 FMO3 Enzyme BMDBP02248 Ras-related C3 botulinum toxin substrate 2 Q9TU25 RAC2 Enzyme BMDBP02249 3-hydroxy-3-methylglutaryl-coenzyme A reductase A7Z064 HMGCR Enzyme BMDBP02250 Zeta-crystallin O97764 CRYZ Enzyme BMDBP02566 Malic enzyme B8YB77 ME1 Enzyme BMDBP02912 NAD(P)H dehydrogenase, quinone 1 Q3ZBH2 NQO1 Enzyme BMDBP02920 Methylsterol monooxygenase 1 A6H7G3 MSMO1 Enzyme BMDBP02921 HSD17B7 protein A4FUD2 HSD17B7 Enzyme BMDBP02922 Sterol-C5-desaturase Q3SYX8 SC5D Enzyme BMDBP02930 Kynurenine 3-monooxygenase E1BN59 KMO Enzyme BMDBP02970 Glucose-6-phosphate 1-dehydrogenase F1MMK2 G6PD Enzyme BMDBP03185 Tissue specific transplantation antigen P35B Q2KIT8 TSTA3 Enzyme