2-amino-9-[(2,3-dihydroxypropoxy)methyl]-6,9-dihydro-1H-purin-6-one

• ChemBase ID: 171802
• Molecular Formular: C9H13N5O4
• Molecular Mass: 255.23062
• Monoisotopic Mass: 255.09675392
• SMILES: c1(=O)[nH]c(nc2c1ncn2COCC(CO)O)N
• Canonical SMILES: OCC(COCn1cnc2c1nc(N)[nH]c2=O)O
• InChI: InChI=1S/C9H13N5O4/c10-9-12-7-6(8(17)13-9)11-3-14(7)4-18-2-5(16)1-15/h3,5,15-16H,1-2,4H2,(H3,10,12,13,17)
• InChIKey: YMJRISBBXAOKCD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(2,3-dihydroxypropoxy)methyl]-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 2-amino-9-[(2,3-dihydroxypropoxy)methyl]-1H-purin-6-one
• Synonyms: Isoganciclovir; Iso Ganciclovir; 2-Amino-9-[(2,3-dihydroxypropoxy)methyl]-1,9-dihydro-6H-purin-6-one

Database IDs

• CAS Number: 86357-09-7
• PubChem SID: 164227712
• PubChem CID: 122343

CALCULATED PROPERTIES

• Acid pKa: 10.1596985
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -2.1799798
• LogD (pH = 7.4): -2.180569
• Log P: -2.1799026
• Molar Refractivity: 61.0293 cm^3
• Polarizability: 22.506752 Å^3
• Polar Surface Area: 134.99 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - I818750

An impurity of the anti-viral Gangiclovir (G235000) and Valganclovir (V092000) used in enzymatic phosphorylation studies of antiherpetic agents.

REFERENCES

• Karkas, J.D. et al.: J. Med. Chem., 29, 842 (1986)