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

• ChemBase ID: 1742
• Molecular Formular: C16H25N5O13P2
• Molecular Mass: 557.342922
• Monoisotopic Mass: 557.09240915
• SMILES: Nc1ncnc2c1ncn2[C@@H]1O[C@@H](CO[P@](=O)(O)C[P@@](=O)(O)OC[C@H]2O[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H]1O
• Canonical SMILES: O[C@H]1[C@H](CO[P@@](=O)(C[P@](=O)(OC[C@H]2O[C@@H]([C@H]([C@@H]2O)O)O)O)O)O[C@H]([C@@H]1O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C16H25N5O13P2/c17-13-8-14(19-3-18-13)21(4-20-8)15-11(24)9(22)6(33-15)1-31-35(27,28)5-36(29,30)32-2-7-10(23)12(25)16(26)34-7/h3-4,6-7,9-12,15-16,22-26H,1-2,5H2,(H,27,28)(H,29,30)(H2,17,18,19)/t6-,7+,9-,10+,11+,12-,15+,16-/m0/s1
• InChIKey: ZPZRETFSCSWNDT-VXLWFBCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[(2R,3S,4S,5S)-3,4,5-trihydroxyoxolan-2-yl]methoxy})phosphoryl]methyl})phosphinic acid
• IUPAC Traditional name: @ampcpr
• Synonyms: alpha-beta methylene adp-ribose; ADV; AMPCPR

Database IDs

• PubChem SID: 160965198; 46508105
• PubChem CID: 46936273

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.80344886
• H Acceptors: 15
• H Donor: 8
• LogD (pH = 5.5): -9.50277
• LogD (pH = 7.4): -9.443228
• Log P: -8.492279
• Molar Refractivity: 113.477 cm^3
• Polarizability: 46.311176 Å^3
• Polar Surface Area: 282.29 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.02
• LOG S: -2.12
• Solubility (Water): 4.24e+00 g/l

DETAILS

DrugBank - DB01975

Drug information: experimental