{[(2S,3R,4R,5R)-5-(2-amino-7-methyl-6-oxo-6,7,8,9-tetrahydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

• ChemBase ID: 3870
• Molecular Formular: C11H18N5O8P
• Molecular Mass: 379.263081
• Monoisotopic Mass: 379.08929919
• SMILES: CN1CN([C@@H]2O[C@@H](COP(=O)(O)O)[C@H](O)[C@H]2O)c2c1c(=O)[nH]c(N)n2
• Canonical SMILES: O[C@@H]1[C@@H](O)[C@@H](O[C@H]1N1CN(c2c1nc(N)[nH]c2=O)C)COP(=O)(O)O
• InChI: InChI=1S/C11H18N5O8P/c1-15-3-16(8-5(15)9(19)14-11(12)13-8)10-7(18)6(17)4(24-10)2-23-25(20,21)22/h4,6-7,10,17-18H,2-3H2,1H3,(H2,20,21,22)(H3,12,13,14,19)/t4-,6-,7+,10+/m0/s1
• InChIKey: ZMWJGXGSWZFZPJ-FCIPNVEPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2S,3R,4R,5R)-5-(2-amino-7-methyl-6-oxo-6,7,8,9-tetrahydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: [(2S,3R,4R,5R)-5-(2-amino-7-methyl-6-oxo-1,8-dihydropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
• Synonyms: 7n-Methyl-8-Hydroguanosine-5'-Monophosphate

Database IDs

• PubChem SID: 160967307; 46506194
• PubChem CID: 46936935

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.2159674
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -4.1881814
• LogD (pH = 7.4): -6.0108995
• Log P: -2.9308531
• Molar Refractivity: 90.261 cm^3
• Polarizability: 31.322613 Å^3
• Polar Surface Area: 190.41 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.94
• LOG S: -1.63
• Solubility (Water): 8.92e+00 g/l

DETAILS

DrugBank - DB04259

Drug information: experimental