tetrasodium [(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxy(2,3,4,5-13C4)oxolan-2-yl](13C)methyl ({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxy)phosphonate

• ChemBase ID: 174905
• Molecular Formular: C21H26N7Na4O17P3
• Molecular Mass: 838.31147719
• Monoisotopic Mass: 838.03565361
• SMILES: C([C@@H]1[C@@H](O)[C@@H](OP(=O)([O-])[O-])[C@@H](O1)n1c2c(nc1)c(ncn2)N)OP(=O)(OP(=O)(O[13CH2][13C@@H]1[13C@H]([13C@H]([13C@@H](O1)N1C=C(CC=C1)C(=O)N)O)O)[O-])[O-].[Na+].[Na+].[Na+].[Na+]
• Canonical SMILES: O[13C@@H]1[13C@H](O)[13C@H](O[13C@H]1N1C=CCC(=C1)C(=O)N)[13CH2]OP(=O)(OP(=O)(OC[C@H]1O[C@H]([C@@H]([C@@H]1O)OP(=O)([O-])[O-])n1cnc2c1ncnc2N)[O-])[O-].[Na+].[Na+].[Na+].[Na+]
• InChI: InChI=1S/C21H30N7O17P3.4Na/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);;;;/q;4*+1/p-4/t10-,11-,13-,14-,15-,16-,20-,21-;;;;/m1..../s1/i5+1,10+1,13+1,15+1,20+1
• InChIKey: WYWWVJHQDVCHKF-WLDPAVLYSA-J

NAMES AND DATABASE IDS

Names

• IUPAC name: tetrasodium [(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxy(2,3,4,5-^1^3C₄)oxolan-2-yl](^1^3C)methyl ({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxy)phosphonate
• IUPAC Traditional name: tetrasodium [(2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxy(2,3,4,5-^1^3C₄)oxolan-2-yl](^1^3C)methyl {[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxyphosphonate
• Synonyms: 2'-(Dihydrogen Phosphate) 5'-(Trihydrogen Pyrophosphate)adenosine 5'5'-Ester 1,4-Dihydro-1-β-D-ribofuranosyl(nicotinamide-13C5) Tetrasodium Salt Hydrate; β-NADPH-13C5 Hydrate; 2′-NADPH-13C5 Hydrate; Coenzyme II-13C5 Reduced Tetrasodium Salt Hydrate; Triphosphopyridine-13C5 Nucleotide Reduced Tetrasodium Salt Hydrate; Dihydronicotinamide-13C5 Adenine Dinucleotide Phosphate Tetrasodium Salt Hydrate; β-NADPH-13C5 Tetrasodium Salt Hydrate

Database IDs

• PubChem SID: 164230815
• PubChem CID: 71750888

CALCULATED PROPERTIES

• Acid pKa: 0.6552744
• H Acceptors: 18
• H Donor: 5
• LogD (pH = 5.5): -10.989815
• LogD (pH = 7.4): -12.689332
• Log P: -6.4180613
• Molar Refractivity: 149.3858 cm^3
• Polarizability: 60.81711 Å^3
• Polar Surface Area: 375.47 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - N201503

Labelled NADPH (N201500). 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 cell

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)