NAI

1,4-DIHYDRONICOTINAMIDE ADENINE DINUCLEOTIDE

Created: 1999-12-13
Last modified:  2024-09-27

Help

Find related ligands:

Chemical Details

Formal Charge0
Atom Count73
Chiral Atom Count10
Bond Count77
Aromatic Bond Count10
2D diagram of NAI
Toggle HydrogenToggle Labels

Chemical Component Summary

Name1,4-DIHYDRONICOTINAMIDE ADENINE DINUCLEOTIDE
SynonymsNADH
Systematic Name (OpenEye OEToolkits)[[(2R,3S,4R,5R)-5-(3-aminocarbonyl-4H-pyridin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl] [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methyl hydrogen phosphate
FormulaC21 H29 N7 O14 P2
Molecular Weight665.441
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESCACTVS3.341NC(=O)C1=CN(C=CC1)[CH]2O[CH](CO[P](O)(=O)O[P](O)(=O)OC[CH]3O[CH]([CH](O)[CH]3O)n4cnc5c(N)ncnc45)[CH](O)[CH]2O
SMILESOpenEye OEToolkits1.5.0c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COP(=O)(O)OP(=O)(O)OCC4C(C(C(O4)N5C=CCC(=C5)C(=O)N)O)O)O)O)N
Canonical SMILESCACTVS3.341 NC(=O)C1=CN(C=CC1)[C@@H]2O[C@H](CO[P@@](O)(=O)O[P@](O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)n4cnc5c(N)ncnc45)[C@@H](O)[C@H]2O
Canonical SMILESOpenEye OEToolkits1.5.0 c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO[P@](=O)(O)O[P@@](=O)(O)OC[C@@H]4[C@H]([C@H]([C@@H](O4)N5C=CCC(=C5)C(=O)N)O)O)O)O)N
InChIInChI1.03 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)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
InChIKeyInChI1.03 BOPGDPNILDQYTO-NNYOXOHSSA-N

Drug Info: DrugBank

DrugBank IDDB00157 
NameNADH
Groups
  • nutraceutical
  • approved
DescriptionNADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH, a coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). It forms NADP with the addition of a phosphate group to the 2' position of the adenosyl nucleotide through an ester linkage. (Dorland, 27th ed)
Synonyms
  • Nicotinamide-adenine dinucleotide, reduced
  • Nicotinamide adenine dinucleotide (reduced)
  • Reduced nicotinamide adenine diphosphate
  • 1,4-dihydronicotinamide adenine dinucleotide
  • DPNH
Brand Names
  • Amladex
  • Genicin Vita-Q
  • Xyzbac
  • EnBrace HR
  • Mebolic
IndicationSome evidence suggests that NADH might be useful in treating Parkinson's disease, chronic fatigue syndrome, Alzheimer's disease and cardiovascular disease.
Categories
  • Adenine Nucleotides
  • Coenzymes
  • Dietary Supplements
  • Enzymes and Coenzymes
  • Heterocyclic Compounds, Fused-Ring
CAS number58-68-4

Drug Targets

NameTarget SequencePharmacological ActionActions
UDP-glucose 6-dehydrogenaseMFEIKKICCIGAGYVGGPTCSVIAHMCPEIRVTVVDVNESRINAWNSPTL...unknown
Alcohol dehydrogenase 1AMSTAGKVIKCKAAVLWELKKPFSIEEVEVAPPKAHEVRIKMVAVGICGTD...unknown
Sorbitol dehydrogenaseMAAAAKPNNLSLVVHGPGDLRLENYPIPEPGPNEVLLRMHSVGICGSDVH...unknown
Alcohol dehydrogenase 4MGTKGKVIKCKAAIAWEAGKPLCIEEVEVAPPKAHEVRIQIIATSLCHTD...unknown
Alcohol dehydrogenase 1CMSTAGKVIKCKAAVLWELKKPFSIEEVEVAPPKAHEVRIKMVAAGICRSD...unknown
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 439153
ChEBI CHEBI:16908