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CHEBI:16908 - NADH

Default Structure
ChEBI IDCHEBI:16908
ChEBI NameNADH
Stars
DefinitionA coenzyme found in all living cells; consists of two nucleotides joined through their 5'-phosphate groups, with one nucleotide containing an adenine base and the other containing nicotinamide.
Secondary ChEBI IDsCHEBI:7423, CHEBI:13395, CHEBI:13396, CHEBI:21902, CHEBI:44216
Last Modified26 July 2019
DownloadsMolfile
FormulaC21H29N7O14P2
Net Charge0
Average Mass665.446
Monoisotopic Mass665.12477
SMILESNC(=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](O)[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1
InChIInChI=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/s1
InChIKeyBOPGDPNILDQYTO-NNYOXOHSSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
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.
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.
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)
NADH (CHEBI:16908) has role cofactor (CHEBI:23357)
NADH (CHEBI:16908) has role fundamental metabolite (CHEBI:78675)
NADH (CHEBI:16908) is a NAD (CHEBI:13389)
NADH (CHEBI:16908) is a NAD(P)H (CHEBI:13392)
NADH (CHEBI:16908) is conjugate acid of NADH(2−) (CHEBI:57945)
Incoming Relation(s)
(S)-NADHX (CHEBI:44236) has functional parent NADH (CHEBI:16908)
(4S)-4-(2-propylisonicotinoyl)nicotinamide adenine dinucleotide (CHEBI:44608) has functional parent NADH (CHEBI:16908)
(R)-NADHX (CHEBI:134125) has functional parent NADH (CHEBI:16908)
AcNADH (CHEBI:74521) has functional parent NADH (CHEBI:16908)
NADH(2−) (CHEBI:57945) is conjugate base of NADH (CHEBI:16908)
IUPAC Name 
adenosine 5'-{3-[1-(3-carbamoyl-1,4-dihydropyridin-1-yl)-1,4-anhydro-D-ribitol-5-yl] dihydrogen diphosphate}
Synonyms  Source
1,4-DIHYDRONICOTINAMIDE ADENINE DINUCLEOTIDEPDBeChem
DPNHKEGG COMPOUND
NADHKEGG COMPOUND
nicotinamide adenine dinucleotide (reduced)ChEBI
Reduced nicotinamide adenine dinucleotideKEGG COMPOUND
Manual XrefsDatabases
C00004KEGG COMPOUND
C00019343KNApSAcK
DB00157DrugBank
HMDB0001487HMDB
NAIPDBeChem
Nicotinamide_adenine_dinucleotideWikipedia
Registry NumbersSources
Gmelin:544241Gmelin
Reaxys:79324Reaxys
Beilstein:79324Beilstein
CAS:58-68-4KEGG COMPOUND
CAS:58-68-4ChemIDplus
Citations