Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:41:56 UTC
Update Date2024-04-30 19:42:01 UTC
Metabolite IDMMDBc0029795
Metabolite Identification
Common NameNADPH
DescriptionNicotinamide 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.)
Structure
Synonyms
ValueSource
2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-D-ribofuranosylnicotinamideHMDB
2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamideHMDB
Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamideHMDB
Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamideHMDB
b-NADPHHMDB
b-Nicotinamide-adenine-dinucleotide-phosphorateHMDB
b-Nicotinamide-adenine-dinucleotide-phosphoric acidHMDB
beta-NADPHHMDB
beta-Nicotinamide-adenine-dinucleotide-phosphorateHMDB
beta-Nicotinamide-adenine-dinucleotide-phosphoric acidHMDB
Dihydrocodehydrogenase IIHMDB
Dihydronicotinamide adenine dinucleotide phosphateHMDB
Dihydronicotinamide adenine dinucleotide-pHMDB
Dihydrotriphosphopyridine nucleotide reducedHMDB
NADP-reducedHMDB
Nicotinamide adenine dinucleotide phosphate - reducedHMDB
Nicotinamide-adenine-dinucleotide-phosphorateHMDB
Nicotinamide-adenine-dinucleotide-phosphoric acidHMDB
Reduced codehydrase IIHMDB
Reduced coenzyme IIHMDB
Reduced cozymase IIHMDB
Reduced triphosphopyridine nucleotideHMDB
Triphosphopyridine nucleotide reducedHMDB
Molecular FormulaC21H30N7O17P3
Average Mass745.4209
Monoisotopic Mass745.091102105
IUPAC Name{[(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 acid
Traditional Name[(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 acid
CAS Registry Number53-57-6
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=C(N)N=CN=C23)[C@H](O)[C@@H]1O
InChI Identifier
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-/m0/s1
InChI KeyACFIXJIJDZMPPO-NCHANQSKSA-N