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

• ChemBase ID: 2512
• Molecular Formular: C11H16N5O6P
• Molecular Mass: 345.248401
• Monoisotopic Mass: 345.08381989
• SMILES: C[P@](=O)(O)OC[C@@H]1O[C@H]([C@H](O)[C@H]1O)n1cnc2c1ncnc2N
• Canonical SMILES: O[C@@H]1[C@@H](O)[C@@H](O[C@H]1n1cnc2c1ncnc2N)CO[P@@](=O)(O)C
• InChI: InChI=1S/C11H16N5O6P/c1-23(19,20)21-2-5-7(17)8(18)11(22-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H,19,20)(H2,12,13,14)/t5-,7-,8+,11+/m0/s1
• InChIKey: PXSSQXBLDTZHLF-WOIOKPISSA-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}(methyl)phosphinic acid
• IUPAC Traditional name: [(2S,3R,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(methyl)phosphinic acid
• Synonyms: Alpha-Methylene Adenosine Monophosphate

Database IDs

• PubChem SID: 46505912; 160965962
• PubChem CID: 46936495

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.3867539
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -4.713696
• LogD (pH = 7.4): -4.6494985
• Log P: -4.9088454
• Molar Refractivity: 76.5946 cm^3
• Polarizability: 30.344091 Å^3
• Polar Surface Area: 165.84 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.88
• LOG S: -2.04
• Solubility (Water): 3.16e+00 g/l

DETAILS

DrugBank - DB02798

Drug information: experimental