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

• ChemBase ID: 3583
• Molecular Formular: C10H12ClN4O7P
• Molecular Mass: 366.651641
• Monoisotopic Mass: 366.01321305
• SMILES: O[C@H]1[C@H](COP(=O)(O)O)O[C@H]([C@@H]1O)n1cnc2c1ncnc2Cl
• Canonical SMILES: O[C@@H]1[C@@H](O)[C@@H](O[C@H]1n1cnc2c1ncnc2Cl)COP(=O)(O)O
• InChI: InChI=1S/C10H12ClN4O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,18,19,20)/t4-,6-,7+,10+/m0/s1
• InChIKey: ALOBOMYIOYNCBS-FCIPNVEPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2S,3R,4R,5R)-5-(6-chloro-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: [(2S,3R,4R,5R)-5-(6-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
• Synonyms: 6-Chloropurine Riboside, 5'-Monophosphate

Database IDs

• PubChem SID: 46506473; 160967021
• PubChem CID: 70789235; 46936839

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.2776111
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -3.595341
• LogD (pH = 7.4): -4.686346
• Log P: -2.7337902
• Molar Refractivity: 74.9207 cm^3
• Polarizability: 29.98918 Å^3
• Polar Surface Area: 160.05 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.89
• LOG S: -2.33
• Solubility (Water): 1.87e+00 g/l

DETAILS

DrugBank - DB03948

Drug information: experimental