CHEBI:134125 - (R)-NADHX

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ChEBI Name (R)-NADHX
ChEBI ID CHEBI:134125
Definition A tetrahydronicotinamide adenine dinucleotide obtained by formal stereo- and regioselective hydration across the 5,6-double bond in the nicotinyl ring of NADH, with the hydroxy group located at position 6, having (R)-configuration.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Julian Brandl
Supplier Information ZINC000038148193
Download Molfile XML SDF
Formula C21H31N7O15P2
Net Charge 0
Average Mass 683.457
Monoisotopic Mass 683.13534
InChI InChI=1S/C21H31N7O15P2/c22-17-12-19(25-6-24-17)28(7-26-12)21-16(33)14(31)10(42-21)5-40-45(37,38)43-44(35,36)39-4-9-13(30)15(32)20(41-9)27-3-8(18(23)34)1-2-11(27)29/h3,6-7,9-11,13-16,20-21,29-33H,1-2,4-5H2,(H2,23,34)(H,35,36)(H,37,38)(H2,22,24,25)/t9-,10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
InChIKey IDBZKGQRLBFUFQ-MTKBYBFRSA-N
SMILES N1(C2=C(C(=NC=N2)N)N=C1)[C@@H]3O[C@H](COP(OP(OC[C@H]4O[C@@H](N5C=C(CC[C@H]5O)C(=O)N)[C@@H]([C@@H]4O)O)(=O)O)(=O)O)[C@H]([C@H]3O)O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): fundamental metabolite
Any metabolite produced by all living cells.
(via NAD )
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 (R)-NADHX (CHEBI:134125) has functional parent NADH (CHEBI:16908)
(R)-NADHX (CHEBI:134125) is a hemiaminal (CHEBI:73080)
(R)-NADHX (CHEBI:134125) is a tetrahydronicotinamide adenine dinucleotide (CHEBI:26916)
(R)-NADHX (CHEBI:134125) is conjugate acid of (R)-NADHX(2−) (CHEBI:64075)
Incoming (R)-NADHX(2−) (CHEBI:64075) is conjugate base of (R)-NADHX (CHEBI:134125)
IUPAC Name
adenosine 5'-(3-{5-[(2R)-5-carbamoyl-2-hydroxy-3,4-dihydropyridin-1-yl]-5-deoxy-β-D-ribofuranosyl} dihydrogen diphosphate)
Synonyms Sources
(6R)-6-hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide ChEBI
(6R)-6β-hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide KEGG COMPOUND
(R)-NADH-hydrate KEGG COMPOUND
Manual Xrefs Databases
C20482 KEGG COMPOUND
CPD0-2472 MetaCyc
View more database links
Registry Number Type Source
25808108 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
21994945 PubMed citation SUBMITTER
24706747 PubMed citation Europe PMC
Last Modified
13 December 2016