3-carbamoyl-1-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-{3H-imidazo[2,1-f]purin-3-yl}oxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-1λ5-pyridin-1-ylium

• ChemBase ID: 175095
• Molecular Formular: C23H27N7O14P2
• Molecular Mass: 687.446502
• Monoisotopic Mass: 687.10912184
• SMILES: O=C(N)c1ccc[n+](c1)[C@@H]1O[C@@H]([C@@H](O)[C@H]1O)COP(=O)([O-])OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c2ncn2ccnc32)[C@H](O)[C@@H]1O
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(OC[C@H]2O[C@H]([C@@H]([C@@H]2O)O)[n+]2cccc(c2)C(=O)N)[O-])O)O[C@H]([C@@H]1O)n1cnc2c1ncn1c2ncc1
• InChI: InChI=1S/C23H27N7O14P2/c24-19(35)11-2-1-4-28(6-11)22-17(33)15(31)12(42-22)7-40-45(36,37)44-46(38,39)41-8-13-16(32)18(34)23(43-13)30-10-26-14-20-25-3-5-29(20)9-27-21(14)30/h1-6,9-10,12-13,15-18,22-23,31-34H,7-8H2,(H3-,24,35,36,37,38,39)/t12-,13-,15-,16-,17-,18-,22-,23-/m1/s1
• InChIKey: JCDBQDNBEQHDHK-BSLNIGMPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-carbamoyl-1-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-{3H-imidazo[2,1-f]purin-3-yl}oxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-1λ^5-pyridin-1-ylium
• IUPAC Traditional name: 3-carbamoyl-1-[(2R,3R,4S,5R)-5-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-{imidazo[2,1-f]purin-3-yl}oxolan-2-yl]methoxy(hydroxy)phosphoryl phosphonato}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-1λ^5-pyridin-1-ylium
• Synonyms: 3-(Aminocarbonyl)-1-[5-O-[hydroxy(phosphonooxy)phosphinyl]-β-D-ribofuranosyl]pyridinium Inner Salt P'5'-Ester with 3-β-D-Ribofuranosyl-3H-imidazo[2,1-i]purine; 1,N6-Ethenonicotinamide Adenine Dinucleotide; ε-NAD; Nicotinamide 1,N6-Ethenoadenine Dinucleotide

Database IDs

• CAS Number: 38806-38-1
• PubChem SID: 164231005
• PubChem CID: 170119

CALCULATED PROPERTIES

• Acid pKa: 1.8613118
• H Acceptors: 14
• H Donor: 6
• LogD (pH = 5.5): -11.328179
• LogD (pH = 7.4): -11.659365
• Log P: -10.198208
• Molar Refractivity: 147.2714 cm^3
• Polarizability: 58.869633 Å^3
• Polar Surface Area: 299.48 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - N407735

A fluorescent analog of Nicotinamide Adenine Dinucleotide as a coenzyme for glutamate dehydrogenase.

REFERENCES

• Gafni, A., et al.: Biochemistry, 20, 6041 (1981)
• Creedon, K., et al.: J. Biol. Chem., 269, 16364 (1981)
• Seley, K., et al.: Bioorg. Med. Chem., 6, 797 (1981)