(2-{[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}-2-oxoethyl)phosphonic acid

• ChemBase ID: 2335
• Molecular Formular: C12H16N5O8P
• Molecular Mass: 389.257901
• Monoisotopic Mass: 389.07364913
• SMILES: Nc1ncnc2c1ncn2[C@@H]1O[C@@H](COC(=O)CP(=O)(O)O)[C@H](O)[C@H]1O
• Canonical SMILES: O=C(CP(=O)(O)O)OC[C@@H]1O[C@H]([C@@H]([C@H]1O)O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C12H16N5O8P/c13-10-7-11(15-3-14-10)17(4-16-7)12-9(20)8(19)5(25-12)1-24-6(18)2-26(21,22)23/h3-5,8-9,12,19-20H,1-2H2,(H2,13,14,15)(H2,21,22,23)/t5-,8-,9+,12+/m0/s1
• InChIKey: KJNLSEOJEFDELT-REFFQAGNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-{[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}-2-oxoethyl)phosphonic acid
• IUPAC Traditional name: @adenosine phosphonoacetic acid
• Synonyms: Adenosine Phosphonoacetic Acid

Database IDs

• PubChem SID: 160965786; 46507434
• PubChem CID: 46936436

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.6067387
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -5.568619
• LogD (pH = 7.4): -5.5779924
• Log P: -5.741308
• Molar Refractivity: 83.3374 cm^3
• Polarizability: 32.87671 Å^3
• Polar Surface Area: 203.14 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.61
• LOG S: -2.12
• Solubility (Water): 2.97e+00 g/l

DETAILS

DrugBank - DB02607

Drug information: experimental