(3S)-1-[(2R,3R,4R,5S)-5-{[({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-4-oxo-3,4-dihydro-1λ?-pyridin-1-ylium

• ChemBase ID: 1527
• Molecular Formular: C21H28N7O18P3
• Molecular Mass: 759.404403
• Monoisotopic Mass: 759.07036698
• SMILES: NC(=O)[C@H]1C=[N+](C=CC1=O)[C@@H]1O[C@@H](COP(=O)([O-])O[P@](=O)(O)OC[C@@H]2O[C@H]([C@H](OP(=O)(O)O)[C@H]2O)n2cnc3c2ncnc3N)[C@H](O)[C@H]1O
• Canonical SMILES: O[C@@H]1[C@@H](O)[C@@H](O[C@H]1[N+]1=C[C@@H](C(=O)C=C1)C(=O)N)COP(=O)(O[P@@](=O)(OC[C@@H]1O[C@H]([C@@H]([C@H]1O)OP(=O)(O)O)n1cnc2c1ncnc2N)O)[O-]
• InChI: InChI=1S/C21H28N7O18P3/c22-17-12-19(25-6-24-17)28(7-26-12)21-16(45-47(34,35)36)14(31)11(44-21)5-42-49(39,40)46-48(37,38)41-4-10-13(30)15(32)20(43-10)27-2-1-9(29)8(3-27)18(23)33/h1-3,6-8,10-11,13-16,20-21,30-32H,4-5H2,(H7-,22,23,24,25,33,34,35,36,37,38,39,40)/t8-,10-,11-,13-,14-,15+,16+,20+,21+/m0/s1
• InChIKey: PIXSDSMVQQICPA-KOGMLKCQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-1-[(2R,3R,4R,5S)-5-{[({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-4-oxo-3,4-dihydro-1λ?-pyridin-1-ylium
• IUPAC Traditional name: (3S)-1-[(2R,3R,4R,5S)-5-[({[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl phosphonato}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-4-oxo-3H-1λ?-pyridin-1-ylium
• Synonyms: 4-Oxo-Nicotinamide-Adenine Dinucleotide Phosphate

Database IDs

• PubChem SID: 160964984; 46505149
• PubChem CID: 70789207

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.6620108
• H Acceptors: 18
• H Donor: 8
• LogD (pH = 5.5): -10.662375
• LogD (pH = 7.4): -12.342666
• Log P: -9.995952
• Molar Refractivity: 163.7701 cm^3
• Polarizability: 61.50111 Å^3
• Polar Surface Area: 383.82 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.06
• LOG S: -2.08
• Solubility (Water): 6.74e+00 g/l

DETAILS

DrugBank - DB01753

Drug information: experimental