1-[(2R,4R,5R)-5-{[({[(2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1λ5-pyridin-1-ylium

• ChemBase ID: 175102
• Molecular Formular: C21H27N7O14P2
• Molecular Mass: 663.425102
• Monoisotopic Mass: 663.10912184
• SMILES: [C@H]1(C([C@@H](O[C@@H]1COP(=O)(OP(=O)(OC[C@@H]1[C@@H](C([C@@H](O1)n1c2c(nc1)c(ncn2)N)O)O)O)[O-])[n+]1cc(ccc1)C(=O)N)O)O
• Canonical SMILES: O[C@H]1[C@@H](COP(=O)(OP(=O)(OC[C@H]2O[C@H](C([C@H]2O)O)n2cnc3c2ncnc3N)O)[O-])O[C@H](C1O)[n+]1cccc(c1)C(=O)N
• InChI: InChI=1S/C21H27N7O14P2/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/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/t10-,11-,13+,14+,15?,16?,20-,21-/m1/s1
• InChIKey: BAWFJGJZGIEFAR-CZORXLPDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,4R,5R)-5-{[({[(2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1λ^5-pyridin-1-ylium
• IUPAC Traditional name: 1-[(2R,4R,5R)-5-[({[(2R,3R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl phosphonato}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1λ^5-pyridin-1-ylium
• Synonyms: Adenosine 5'-(Trihydrogen Diphosphate), P'→5'-Ester with 3-(Aminocarbonyl)-1-β-D-ribofuranosylpyridinium Hydroxide Inner Salt Hydrate; Adenine-nicotinamide Dinucleotide Hydrate; CO-I Hydrate; Codehydrase I Hydrate; Codehydrogenase I Hydrate; Coenzyme I Hydrate; Cozymase I Hydrate; DPN Hydrate; Diphosphopyridine Nucleotide Hydrate; Enzopride Hydrate; NAD Hydrate; NAD+ Hydrate; NSC 20272 Hydrate; Nadide Hydrate; Nicotinamide-adenine Dinucleotide Hydrate; Oxidized diphosphopyridine Nucleotide Hydrate; β-Diphosphopyridine Nucleotide Hydrate; β-NAD Hydrate; β-NAD+ Hydrate; β-Nicotinamide Adenine Dinucleotide Hydrate

Database IDs

• PubChem SID: 164231012
• PubChem CID: 71751003

CALCULATED PROPERTIES

• Acid pKa: 1.8569882
• H Acceptors: 15
• H Donor: 7
• LogD (pH = 5.5): -11.140584
• LogD (pH = 7.4): -11.40719
• Log P: -10.609851
• Molar Refractivity: 140.8752 cm^3
• Polarizability: 56.19417 Å^3
• Polar Surface Area: 321.09 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - N407775

β-Nicotinamide Adenine Dinucleotide is a coeznyme consisting of an adenine base and a nicotinamide base connected by a pair of bridging phosphate group. β-Nicotinamide Adenine Dinucleotide acts as a coenzyme in redox reactions, as a donor of ADP-ribose mo

REFERENCES

• Dudev, T. et al.: J. Am. Chem. Soc., 132, 16533 (2010)
• Kerbey, A. et al.: Biochem. J., 154, 327 (2010)
• Lahiri, S.D. et al.: ACS Chem. Biol., 7, 571 (2010)