3-[(2S,3R,4R,5S)-5-({[(S)-({[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-5-carbamoylpyridin-1-ium

• ChemBase ID: 2726
• Molecular Formular: C21H27N7O14P2
• Molecular Mass: 663.425102
• Monoisotopic Mass: 663.10912184
• SMILES: NC(=O)c1c[nH+]cc(c1)[C@@H]1O[C@@H](COP(=O)([O-])O[P@](=O)(O)OC[C@@H]2O[C@H]([C@H](O)[C@H]2O)n2cnc3c2ncnc3N)[C@H](O)[C@H]1O
• Canonical SMILES: O[C@H]1[C@H](COP(=O)(O[P@@](=O)(OC[C@@H]2O[C@H]([C@@H]([C@H]2O)O)n2cnc3c2ncnc3N)O)[O-])O[C@H]([C@@H]1O)c1c[nH+]cc(c1)C(=O)N
• InChI: InChI=1S/C21H27N7O14P2/c22-18-12-20(26-6-25-18)28(7-27-12)21-16(32)14(30)11(41-21)5-39-44(36,37)42-43(34,35)38-4-10-13(29)15(31)17(40-10)8-1-9(19(23)33)3-24-2-8/h1-3,6-7,10-11,13-17,21,29-32H,4-5H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,25,26)/t10-,11-,13-,14-,15+,16+,17-,21+/m0/s1
• InChIKey: UINNILASBHZOTM-NYTQINMXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(2S,3R,4R,5S)-5-({[(S)-({[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-5-carbamoylpyridin-1-ium
• IUPAC Traditional name: 3-[(2S,3R,4R,5S)-5-({[(S)-([(2S,3R,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl phosphonato)]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-5-carbamoylpyridin-1-ium
• Synonyms: 5-Beta-D-Ribofuranosylnicotinamide Adenine Dinucleotide

Database IDs

• PubChem SID: 46506222; 160966175
• PubChem CID: 46936557

CALCULATED PROPERTIES

JChem

• Acid pKa: -7.028098
• H Acceptors: 15
• H Donor: 8
• LogD (pH = 5.5): -8.689731
• LogD (pH = 7.4): -9.0070095
• Log P: -7.2471027
• Molar Refractivity: 141.4347 cm^3
• Polarizability: 56.191696 Å^3
• Polar Surface Area: 331.35 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.38
• LOG S: -2.52
• Solubility (Water): 2.16e+00 g/l

DETAILS

DrugBank - DB03020

Drug information: experimental