{[(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2S,3R,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid

• ChemBase ID: 2081
• Molecular Formular: C21H30N7O17P3
• Molecular Mass: 745.420883
• Monoisotopic Mass: 745.09110243
• SMILES: NC(=O)C1=CN(C=CC1)[C@@H]1O[C@@H](CO[P@@](=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]1N1C=CCC(=C1)C(=O)N)CO[P@](=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/C21H30N7O17P3/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)/t10-,11-,13-,14-,15+,16+,20+,21+/m0/s1
• InChIKey: ACFIXJIJDZMPPO-XCSFTKGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2S,3R,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
• IUPAC Traditional name: [(2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-5-{[({[(2S,3R,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid
• Synonyms: Nadph Dihydro-Nicotinamide-Adenine-Dinucleotidephosphate

Database IDs

• PubChem SID: 46508520; 160965535
• PubChem CID: 5702548

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.65010667
• H Acceptors: 18
• H Donor: 9
• LogD (pH = 5.5): -10.961866
• LogD (pH = 7.4): -12.689183
• Log P: -7.4556303
• Molar Refractivity: 153.8726 cm^3
• Polarizability: 61.29122 Å^3
• Polar Surface Area: 364.15 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.13
• LOG S: -2.14
• Solubility (Water): 5.45e+00 g/l

DETAILS

DrugBank - DB02338

Drug information: experimental