disodium [(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,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphonate

• ChemBase ID: 174902
• Molecular Formular: C21H27N7Na2O14P2
• Molecular Mass: 714.36791619
• Monoisotopic Mass: 714.10543459
• SMILES: C([C@@H]1[C@@H](O)[C@@H](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+]
• 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)O)n1cnc2c1ncnc2N)[O-])[O-].[Na+].[Na+]
• InChI: InChI=1S/C21H29N7O14P2.2Na/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);;/q;2*+1/p-2/t10-,11-,13-,14-,15-,16-,20-,21-;;/m1../s1/i5+1,10+1,13+1,15+1,20+1
• InChIKey: QRGNQKGQENGQSE-HWOSKCHSSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium [(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,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphonate
• IUPAC Traditional name: disodium [(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,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxyphosphonate
• Synonyms: Adenosine 5'-(Trihydrogen diphosphate) P'→5'-ester 1,4-Dihydro-1-β-D-ribofuranosylnicotinamide-13C5 Sodium Salt; 1,4-Dihydronicotinamide-13C5 Adenine Dinucleotide Disodium; Codehydrase I-13C5 Reduced; Codehydrogenase I-13C5 Reduced; Coenzyme I-13C5 Reduced; Cozymase I-13C5 Reduced; DPNH-13C5; Dihydrocodehydrogenase I-13C5; Dihydrocozymase-13C5 Disodium; Dihydronicotinamide-13C5 Adenine Dinucleotide Disodium; ENADA-13C5; N 8129-13C5; NADH-13C5; NADH2-13C5; Reduced Codehydrogenase I-13C5; Reduced Diphosphopyridine-13C5 Nucleotide; Reduced Ncotinamide-13C5 Adenine Diphosphate; β-DPNH-13C5 Disodium Salt; β-NADH-13C5 Disodium Salt

Database IDs

• PubChem SID: 164230812
• PubChem CID: 71750885

CALCULATED PROPERTIES

• Acid pKa: -5.4450006
• H Acceptors: 16
• H Donor: 6
• LogD (pH = 5.5): -8.287103
• LogD (pH = 7.4): -8.577429
• Log P: -6.6937027
• Molar Refractivity: 140.7563 cm^3
• Polarizability: 56.47071 Å^3
• Polar Surface Area: 323.28 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - N201482

Labelled β-NADH (N201480). One of the biologically active forms of nicotinic acid. Serves as a coenzyme of hydrogenases and dehydrogenases. NAD usually acts as a hydrogen acceptor, forming NADH which then serves as a hydrogen donor in the respiratory chai

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)