2-amino-9-[(2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyloxolan-2-yl]-6,9-dihydro-3H-purin-6-one

• ChemBase ID: 173751
• Molecular Formular: C11H15N5O5
• Molecular Mass: 297.2673
• Monoisotopic Mass: 297.10731861
• SMILES: n1c([nH]c2c(c1=O)ncn2[C@H]1[C@@](C([C@H](O1)CO)O)(O)C)N
• Canonical SMILES: OC[C@H]1O[C@H]([C@](C1O)(C)O)n1cnc2c1[nH]c(N)nc2=O
• InChI: InChI=1S/C11H15N5O5/c1-11(20)6(18)4(2-17)21-9(11)16-3-13-5-7(16)14-10(12)15-8(5)19/h3-4,6,9,17-18,20H,2H2,1H3,(H3,12,14,15,19)/t4-,6?,9-,11-/m1/s1
• InChIKey: NVKAMPJSWMHVDK-YEIDMZCRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyloxolan-2-yl]-6,9-dihydro-3H-purin-6-one
• IUPAC Traditional name: 2-amino-9-[(2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyloxolan-2-yl]-3H-purin-6-one
• Synonyms: 2'-C-Methylguanosine; 2'-C-β-Methyl Guanosine

Database IDs

• CAS Number: 374750-30-8
• PubChem SID: 164229661
• PubChem CID: 46782257

CALCULATED PROPERTIES

• Acid pKa: 7.981665
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -1.9100292
• LogD (pH = 7.4): -2.0036309
• Log P: -1.9080307
• Molar Refractivity: 68.8259 cm^3
• Polarizability: 26.3186 Å^3
• Polar Surface Area: 155.22 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M311820

2’-C-β-Methyl Guanosine is an anti-HCV agent. 2’-C-β-Methyl Guanosine is an intermediate in the synthesis of novel double prodrug INX-08189, a new clinical candidate for hepatitis C virus.

REFERENCES

• Pudlo, J., et al.: J. Med. Chem., 33, 1984 (1990)
• Takamizawa, A., et al.: J. Virol., 65, 1105 (1990)
• Dhanak, D., et al.: J. Biol. Chem., 277, 38322 (1990)