{[(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-({[hydroxy({[hydroxy({[(2R,3S,4S,5S)-3,4,5-trihydroxyoxolan-2-yl]methoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

• ChemBase ID: 4070
• Molecular Formular: C15H24N5O17P3
• Molecular Mass: 639.295643
• Monoisotopic Mass: 639.03800422
• SMILES: Nc1ncnc2c1ncn2[C@@H]1O[C@@H](CO[P@@](=O)(O)O[P@](=O)(O)OC[C@H]2O[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H]1OP(=O)(O)O
• Canonical SMILES: O[C@H]1[C@H](CO[P@](=O)(O[P@@](=O)(OC[C@H]2O[C@@H]([C@H]([C@@H]2O)O)O)O)O)O[C@H]([C@@H]1OP(=O)(O)O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C15H24N5O17P3/c16-12-7-13(18-3-17-12)20(4-19-7)14-11(36-38(25,26)27)9(22)6(34-14)2-33-40(30,31)37-39(28,29)32-1-5-8(21)10(23)15(24)35-5/h3-6,8-11,14-15,21-24H,1-2H2,(H,28,29)(H,30,31)(H2,16,17,18)(H2,25,26,27)/t5-,6+,8-,9+,10+,11-,14-,15+/m1/s1
• InChIKey: ICNHOLCERMYLRZ-FJUXWURESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-({[hydroxy({[hydroxy({[(2R,3S,4S,5S)-3,4,5-trihydroxyoxolan-2-yl]methoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
• IUPAC Traditional name: [(2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-4-hydroxy-5-({[hydroxy({hydroxy[(2R,3S,4S,5S)-3,4,5-trihydroxyoxolan-2-yl]methoxyphosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid
• Synonyms: 2'-Monophosphoadenosine-5'-Diphosphoribose

Database IDs

• PubChem SID: 46508839; 160967504
• PubChem CID: 46936990; 70789240

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.65010655
• H Acceptors: 17
• H Donor: 9
• LogD (pH = 5.5): -11.17305
• LogD (pH = 7.4): -12.900412
• Log P: -7.666814
• Molar Refractivity: 121.9962 cm^3
• Polarizability: 49.931973 Å^3
• Polar Surface Area: 338.05 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.28
• LOG S: -2.06
• Solubility (Water): 5.84e+00 g/l

DETAILS

DrugBank - DB04497

Drug information: experimental