CHEBI:16474 - NADPH

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name NADPH
ChEBI ID CHEBI:16474
Definition The reduced form of NADP+; used in anabolic reactions, such as lipid and nucleic acid synthesis, which require NADPH as a reducing agent.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:44286, CHEBI:7425, CHEBI:13399, CHEBI:13400, CHEBI:21904
Supplier Information ZINC000008215411
Download Molfile XML SDF
Formula C21H30N7O17P3
Net Charge 0
Average Mass 745.42116
Monoisotopic Mass 745.09110
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
InChIKey ACFIXJIJDZMPPO-NNYOXOHSSA-N
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)n2cnc3c(N)ncnc23)[C@@H](O)[C@H]1O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Roles Classification
Biological Role(s): cofactor
An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group).
fundamental metabolite
Any metabolite produced by all living cells.
coenzyme
A low-molecular-weight, non-protein organic compound participating in enzymatic reactions as dissociable acceptor or donor of chemical groups or electrons.
(via NAD(P) )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing NADPH (CHEBI:16474) has role cofactor (CHEBI:23357)
NADPH (CHEBI:16474) has role fundamental metabolite (CHEBI:78675)
NADPH (CHEBI:16474) is a NAD(P)H (CHEBI:13392)
NADPH (CHEBI:16474) is a NADP (CHEBI:25523)
NADPH (CHEBI:16474) is conjugate acid of NADPH(4−) (CHEBI:57783)
Incoming (R)-NADPHX (CHEBI:64085) has functional parent NADPH (CHEBI:16474)
(S)-NADPHX (CHEBI:64084) has functional parent NADPH (CHEBI:16474)
NADPH(4−) (CHEBI:57783) is conjugate base of NADPH (CHEBI:16474)
IUPAC Name
2'-O-phosphonoadenosine 5'-{3-[1-(3-carbamoyl-1,4-dihydropyridin-1-yl)-1,4-anhydro-D-ribitol-5-yl] dihydrogen diphosphate}
Synonyms Sources
dihydronicotinamide-adenine dinucleotide phosphate ChemIDplus
NADPH KEGG COMPOUND
NADPH DIHYDRO-NICOTINAMIDE-ADENINE-DINUCLEOTIDE PHOSPHATE PDBeChem
Reduced nicotinamide adenine dinucleotide phosphate KEGG COMPOUND
reduced nicotinamide-adenine dinucleotide phosphate CBN
TPNH KEGG COMPOUND
Manual Xrefs Databases
C00005 KEGG COMPOUND
C00019545 KNApSAcK
ECMDB04111 ECMDB
HMDB0000221 HMDB
MOL000028 COMe
NDP PDBeChem
YMDB00426 YMDB
View more database links
Registry Numbers Types Sources
53-57-6 CAS Registry Number ChemIDplus
77911 Beilstein Registry Number Beilstein
Citations Waiting for Citations
Last Modified
15 July 2020