NADPH (CHEBI:16474)

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CHEBI:16474 - NADPH

ChEBI ID	CHEBI:16474
ChEBI Name	NADPH
Stars
Definition	The reduced form of NADP+; used in anabolic reactions, such as lipid and nucleic acid synthesis, which require NADPH as a reducing agent.
Secondary ChEBI IDs	CHEBI:7425, CHEBI:13399, CHEBI:13400, CHEBI:21904, CHEBI:44286
Last Modified	15 July 2020
Downloads	Molfile

Formula	C21H30N7O17P3
Net Charge	0
Average Mass	745.425
Monoisotopic Mass	745.09110
SMILES	NC(=O)C1=CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](OP(=O)(O)O)[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1
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

Species of Metabolite	Component	Source	Comments
Escherichia coli (ncbitaxon:562)	-	PubMed (21988831)
Mus musculus (ncbitaxon:10090)	-	PubMed (19425150)	Source: BioModels - MODEL1507180067

Roles Classification

Biological Roles:

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.

ChEBI Ontology

Outgoing Relation(s)
	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 Relation(s)
	(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	Source
dihydronicotinamide-adenine dinucleotide phosphate	ChemIDplus
NADPH	KEGG COMPOUND
NADPH DIHYDRO-NICOTINAMIDE-ADENINE-DINUCLEOTIDE PHOSPHATE	PDBeChem
reduced nicotinamide-adenine dinucleotide phosphate	IUBMB
Reduced nicotinamide adenine dinucleotide phosphate	KEGG COMPOUND
TPNH	KEGG COMPOUND

Manual Xrefs	Databases
C00005	KEGG COMPOUND
C00019545	KNApSAcK
ECMDB04111	ECMDB
HMDB0000221	HMDB
NDP	PDBeChem
YMDB00426	YMDB

Registry Numbers	Sources
Beilstein:77911	Beilstein
CAS:53-57-6	ChemIDplus

Citations