{[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid

• ChemBase ID: 4037
• Molecular Formular: C10H14N5O7P
• Molecular Mass: 347.221221
• Monoisotopic Mass: 347.06308444
• SMILES: Nc1nc(=O)c2c([nH]1)n(cn2)[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1
• Canonical SMILES: O[C@H]1C[C@@H](O[C@@H]1COP(=O)(O)O)n1cnc2c1[nH]c(N)nc2=O
• InChI: InChI=1S/C10H14N5O7P/c11-10-13-8-7(9(17)14-10)12-3-15(8)6-1-4(16)5(22-6)2-21-23(18,19)20/h3-6,16H,1-2H2,(H2,18,19,20)(H3,11,13,14,17)/t4-,5+,6+/m0/s1
• InChIKey: LTFMZDNNPPEQNG-KVQBGUIXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: deoxyguanylate
• Synonyms: 2'-Deoxyguanosine-5'-Monophosphate

Database IDs

• CAS Number: 902-04-5
• PubChem SID: 160967472; 46507156
• PubChem CID: 65059

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.2167609
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -3.8532805
• LogD (pH = 7.4): -5.0308766
• Log P: -2.7661393
• Molar Refractivity: 73.5499 cm^3
• Polarizability: 28.379108 Å^3
• Polar Surface Area: 181.52 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.92
• LOG S: -2.11
• Solubility (Water): 2.67e+00 g/l

DETAILS

DrugBank - DB04457

Drug information: experimental