{[(2S,3R,4R,5R)-5-(2-amino-7H-purin-7-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

• ChemBase ID: 2487
• Molecular Formular: C10H14N5O7P
• Molecular Mass: 347.221221
• Monoisotopic Mass: 347.06308444
• SMILES: Nc1ncc2n(cnc2n1)[C@@H]1O[C@@H](COP(=O)(O)O)[C@H](O)[C@H]1O
• Canonical SMILES: O[C@@H]1[C@@H](O)[C@@H](O[C@H]1n1cnc2c1cnc(n2)N)COP(=O)(O)O
• InChI: InChI=1S/C10H14N5O7P/c11-10-12-1-4-8(14-10)13-3-15(4)9-7(17)6(16)5(22-9)2-21-23(18,19)20/h1,3,5-7,9,16-17H,2H2,(H2,11,12,14)(H2,18,19,20)/t5-,6-,7+,9+/m0/s1
• InChIKey: UDRQVOJQMHZSIM-XZMZPDFPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2S,3R,4R,5R)-5-(2-amino-7H-purin-7-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: [(2S,3R,4R,5R)-5-(2-aminopurin-7-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
• Synonyms: 7-Alpha-D-Ribofuranosyl-2-Aminopurine-5'-Phosphate

Database IDs

• PubChem SID: 160965937; 46506157
• PubChem CID: 46936483

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.2254494
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -4.6894875
• LogD (pH = 7.4): -5.7044797
• Log P: -4.713435
• Molar Refractivity: 75.3212 cm^3
• Polarizability: 29.09255 Å^3
• Polar Surface Area: 186.07 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.98
• LOG S: -2.03
• Solubility (Water): 3.26e+00 g/l

DETAILS

DrugBank - DB02770

Drug information: experimental