{[(2R,3S,5R)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2R,4S,5R)-5-[(4S)-3-carbamoyl-1,4-dihydro(4-2H1)pyridin-1-yl]-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid

• ChemBase ID: 174904
• Molecular Formular: C21H30N7O17P3
• Molecular Mass: 745.420883
• Monoisotopic Mass: 745.09110243
• SMILES: C([C@@H]1C(O)[C@H](OP(=O)(O)O)[C@@H](O1)n1c2c(nc1)c(ncn2)N)OP(=O)(OP(=O)(OC[C@@H]1C([C@@H]([C@@H](O1)N1C=C(CC=C1)C(=O)N)O)O)O)O
• Canonical SMILES: O[C@H]1C(O)[C@H](O[C@H]1N1C=CCC(=C1)C(=O)N)COP(=O)(OP(=O)(OC[C@H]1O[C@H]([C@H](C1O)OP(=O)(O)O)n1cnc2c1ncnc2N)O)O
• InChI: InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13?,14?,15+,16+,20-,21-/m1/s1
• InChIKey: ACFIXJIJDZMPPO-WWRWIPRPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3S,5R)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2R,4S,5R)-5-[(4S)-3-carbamoyl-1,4-dihydro(4-^2H₁)pyridin-1-yl]-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
• IUPAC Traditional name: [(2R,3S,5R)-2-(6-aminopurin-9-yl)-5-{[({[(2R,4S,5R)-5-[(4S)-3-carbamoyl(4-^2H₁)-4H-pyridin-1-yl]-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid
• Synonyms: Adenosine 5'-(trihydrogen diphosphate) 2'-(Dihydrogen Phosphate) P'-5'-Ester with (4S)-1,4-Dihydro-1-β-d-ribofuranosyl-3-pyridine-4-d-carboxamide; Dihydro-codehydrogenase II-d; β-NADPH-d; β-Nicotinamide-adenine-dinucleotide-phosphoric Acid-d; β-TPNH-d; Triphosphopyridine Nucleotide-d Reduced; β-NADPH-D

Database IDs

• CAS Number: 74784-45-5
• PubChem SID: 164230814
• PubChem CID: 71750887

CALCULATED PROPERTIES

• Acid pKa: 0.6552744
• H Acceptors: 18
• H Donor: 9
• LogD (pH = 5.5): -10.989815
• LogD (pH = 7.4): -12.689332
• Log P: -6.4180613
• Molar Refractivity: 153.8726 cm^3
• Polarizability: 61.29122 Å^3
• Polar Surface Area: 364.15 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - N201502

One of the biologically active forms of nicotinic acid. Differs from NAD by an additional phosphate group at the 2’-position of the adenosine moiety. Serves as a coenzyme of hydrogenases and dehydrogenases. Present in living cells primarily in the reduced

REFERENCES

• Bartlett, G.R., et al.: J. Biol. Chem., 234, 449 (1959)
• Dixon, M., et al.: Science, 132, 1548 (1959)
• Heyes, D., et al.: Biochemistry, 43, 8265 (1959)
• Dietzek, B., et al.: Chem. Phys. Chem., 7, 1727 (1959)