NADH

Description

NADH is a reduced redox cofactor generated primarily by glycolysis and the tricarboxylic acid (TCA) cycle, and under aerobic conditions it is consumed by the electron transport chain to drive ATP synthesis via oxidative phosphorylation. Modulation of the intracellular NADH/NAD⁺ ratio in Escherichia coli can improve the production of metabolites that require distinct redox states for optimal synthesis, such as 2,3-butanediol, isobutanol [356] and butyrate [353]. Accumulation of NADH can be achieved by partial or complete inactivation of the electron transport chain [356].

Chemical Formula:

C₂₁H₂₇N₇O₁₄P₂

Molecular Weight:

663.43 Daltons

Monoisotopic Mass:

665.1247716966999 Daltons

SMILES:

C1(=C(CC=CN1C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5))C(N)=O)

InChI:

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)/p-2/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1

InChIKey:

BOPGDPNILDQYTO-NNYOXOHSSA-L

Synonyms

NADH₂
NADH2
dihydrodiphosphopyridine nucleotide
diphosphopyridine nucleotide reduced
dihydronicotinamide adenine dinucleotide
nicotinamide adenine dinucleotide reduced
NAD-reduced
NADH+H+
DPNH
β-NADH

Databases

MetaCyc: NADH

RefMet: NADH

BiGG: nadh

MetaboLights: MTBLC57945

HMDB: HMDB01487

ChemSpider: 10239197

ChEBI: 57945 16908

PubChem (CID): 21604869 439153

CAS: 58-68-4

KEGG: C00004

PDB-CCD: NAI

3DMET: B01127

NIKKAJI: J213.546I

Seed: cpd00004

MetaNetX: MNXM10

PupChem (SID): 3306

KNApSAcK: C00019343

CHEMBL: CHEMBL1234616