{[(3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid

• ChemBase ID: 2190
• Molecular Formular: C9H12N5O6P
• Molecular Mass: 317.195241
• Monoisotopic Mass: 317.05251976
• SMILES: Nc1ncnc2c1ncn2[C@@H]1OC[C@@H](OP(=O)(O)O)[C@H]1O
• Canonical SMILES: O[C@@H]1[C@@H](CO[C@H]1n1cnc2c1ncnc2N)OP(=O)(O)O
• InChI: InChI=1S/C9H12N5O6P/c10-7-5-8(12-2-11-7)14(3-13-5)9-6(15)4(1-19-9)20-21(16,17)18/h2-4,6,9,15H,1H2,(H2,10,11,12)(H2,16,17,18)/t4-,6-,9-/m1/s1
• InChIKey: IJEJRDCFMFEDGL-NVMQTXNBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
• IUPAC Traditional name: [(3R,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxyoxolan-3-yl]oxyphosphonic acid
• Synonyms: 5-(6-Amino-9h-Purin-9-Yl)-4-Hydroxytetrahydrofuran-3-Yl Dihydrogen Phosphate

Database IDs

• PubChem SID: 160965643; 46507823
• PubChem CID: 46936389

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.829147
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -4.16838
• LogD (pH = 7.4): -5.449767
• Log P: -4.1773343
• Molar Refractivity: 68.106 cm^3
• Polarizability: 26.574593 Å^3
• Polar Surface Area: 165.84 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.94
• LOG S: -1.99
• Solubility (Water): 3.25e+00 g/l

DETAILS

DrugBank - DB02454

Drug information: experimental