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

• ChemBase ID: 1661
• Molecular Formular: C17H21N5O10P2
• Molecular Mass: 517.323662
• Monoisotopic Mass: 517.07636516
• SMILES: O[C@H]1[C@H](CO[P@@](=O)(O)OP(=O)(O)O)O[C@H]([C@@H]1O)n1cnc2c1ncnc2NCc1ccccc1
• Canonical SMILES: O[C@@H]1[C@@H](O)[C@@H](O[C@H]1n1cnc2c1ncnc2NCc1ccccc1)CO[P@](=O)(OP(=O)(O)O)O
• InChI: InChI=1S/C17H21N5O10P2/c23-13-11(7-30-34(28,29)32-33(25,26)27)31-17(14(13)24)22-9-21-12-15(19-8-20-16(12)22)18-6-10-4-2-1-3-5-10/h1-5,8-9,11,13-14,17,23-24H,6-7H2,(H,28,29)(H,18,19,20)(H2,25,26,27)/t11-,13-,14+,17+/m0/s1
• InChIKey: MRHGMAGSDAQUFH-HVOFVXBASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [({[(2S,3R,4R,5R)-5-[6-(benzylamino)-9H-purin-9-yl]-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
• IUPAC Traditional name: {[(2S,3R,4R,5R)-5-[6-(benzylamino)purin-9-yl]-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid
• Synonyms: N6-Benzyl Adenosine-5'-Diphosphate

Database IDs

• PubChem SID: 46507276; 160965118
• PubChem CID: 46936250

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.7004353
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -5.0621924
• LogD (pH = 7.4): -5.6547813
• Log P: -3.2328436
• Molar Refractivity: 115.0474 cm^3
• Polarizability: 44.974728 Å^3
• Polar Surface Area: 218.61 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.15
• LOG S: -2.37
• Solubility (Water): 2.23e+00 g/l

DETAILS

DrugBank - DB01893

Drug information: experimental