[(2S,3aR,4R,6R,6aR)-4-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-6-(hydroxymethyl)-tetrahydro-2H-furo[3,4-d][1,3]dioxol-2-yl]phosphonic acid

• ChemBase ID: 4305
• Molecular Formular: C11H14N5O8P
• Molecular Mass: 375.231321
• Monoisotopic Mass: 375.05799906
• SMILES: Nc1nc(=O)c2c([nH]1)n(cn2)[C@@H]1O[C@H](CO)[C@H]2O[C@@H](O[C@@H]12)P(=O)(O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@H]2[C@@H]1O[C@@H](O2)P(=O)(O)O)n1cnc2c1[nH]c(N)nc2=O
• InChI: InChI=1S/C11H14N5O8P/c12-10-14-7-4(8(18)15-10)13-2-16(7)9-6-5(3(1-17)22-9)23-11(24-6)25(19,20)21/h2-3,5-6,9,11,17H,1H2,(H2,19,20,21)(H3,12,14,15,18)/t3-,5-,6-,9-,11+/m1/s1
• InChIKey: GKAPYWCOOQBBHV-KXSYMAMXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2S,3aR,4R,6R,6aR)-4-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-6-(hydroxymethyl)-tetrahydro-2H-furo[3,4-d][1,3]dioxol-2-yl]phosphonic acid
• IUPAC Traditional name: (2S,3aR,4R,6R,6aR)-4-(2-amino-6-oxo-3H-purin-9-yl)-6-(hydroxymethyl)-tetrahydro-2H-furo[3,4-d][1,3]dioxol-2-ylphosphonic acid
• Synonyms: GUANOSINE-2',3'-O-METHYLIDENEPHOSPHONATE

Database IDs

• PubChem SID: 46505178; 160967737
• PubChem CID: 5327014

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.79888105
• H Acceptors: 12
• H Donor: 5
• LogD (pH = 5.5): -3.5734913
• LogD (pH = 7.4): -3.951477
• Log P: -2.9777687
• Molar Refractivity: 77.5089 cm^3
• Polarizability: 30.276566 Å^3
• Polar Surface Area: 190.75 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.85
• LOG S: -2.03
• Solubility (Water): 3.53e+00 g/l

DETAILS

DrugBank - DB04757

Drug information: experimental