{[(2R,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]methyl}phosphonic acid

• ChemBase ID: 4303
• Molecular Formular: C12H16N5O8P
• Molecular Mass: 389.257901
• Monoisotopic Mass: 389.07364913
• SMILES: Nc1nc(=O)c2c([nH]1)n(cn2)[C@@H]1O[C@H](CO)[C@H]2O[C@@H](CP(=O)(O)O)O[C@@H]12
• Canonical SMILES: OC[C@H]1O[C@H]([C@H]2[C@@H]1O[C@H](O2)CP(=O)(O)O)n1cnc2c1[nH]c(N)nc2=O
• InChI: InChI=1S/C12H16N5O8P/c13-12-15-9-6(10(19)16-12)14-3-17(9)11-8-7(4(1-18)23-11)24-5(25-8)2-26(20,21)22/h3-5,7-8,11,18H,1-2H2,(H2,20,21,22)(H3,13,15,16,19)/t4-,5-,7-,8-,11-/m1/s1
• InChIKey: HYAPEMYRVFIHDJ-QWEIRQIHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,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]methyl}phosphonic acid
• IUPAC Traditional name: [(2R,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-yl]methylphosphonic acid
• Synonyms: GUANOSINE-2',3'-O-ETHYLIDENEPHOSPHONATE

Database IDs

• PubChem SID: 46506626; 160967735
• PubChem CID: 5327012

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.6701496
• H Acceptors: 12
• H Donor: 5
• LogD (pH = 5.5): -4.551626
• LogD (pH = 7.4): -4.7212696
• Log P: -3.3028119
• Molar Refractivity: 81.7915 cm^3
• Polarizability: 32.06751 Å^3
• Polar Surface Area: 190.75 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.02
• LOG S: -2.05
• Solubility (Water): 3.45e+00 g/l

DETAILS

DrugBank - DB04754

Drug information: experimental