2-[(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)methoxy]-3-hydroxypropyl acetate

• ChemBase ID: 169575
• Molecular Formular: C11H15N5O5
• Molecular Mass: 297.2673
• Monoisotopic Mass: 297.10731861
• SMILES: [nH]1c(nc2c(c1=O)ncn2COC(COC(=O)C)CO)N
• Canonical SMILES: OCC(OCn1cnc2c1nc(N)[nH]c2=O)COC(=O)C
• InChI: InChI=1S/C11H15N5O5/c1-6(18)20-3-7(2-17)21-5-16-4-13-8-9(16)14-11(12)15-10(8)19/h4,7,17H,2-3,5H2,1H3,(H3,12,14,15,19)
• InChIKey: YKLKCCHLLFMWQE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)methoxy]-3-hydroxypropyl acetate
• IUPAC Traditional name: 2-[(2-amino-6-oxo-1H-purin-9-yl)methoxy]-3-hydroxypropyl acetate
• Synonyms: 9-[[2-(Acetyloxy)-1-(hydroxymethyl)ethoxy]methyl]-2-amino-1,9-dihydro- 6H-Purin-6-one; Ganciclovir Mono-O-acetate

Database IDs

• CAS Number: 88110-89-8
• PubChem SID: 162263707
• PubChem CID: 492440

CALCULATED PROPERTIES

• Acid pKa: 10.159822
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -1.7388391
• LogD (pH = 7.4): -1.7394438
• Log P: -1.738777
• Molar Refractivity: 70.1808 cm^3
• Polarizability: 26.36257 Å^3
• Polar Surface Area: 141.06 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; Dimethylformamide; Methanol
• Apperance: White Solid
• Melting Point: 194-197°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - G235010

Ganciclovir derivative.

REFERENCES

• Albers, E., et al.: J. Pharm. Sci., 81, 756 (1992)
• Dias, C., et al.: J. Pharm. Sci., 91, 6607 (1992)
• Macha, S., et al.: Drug Metab. Dispos., 30, 670 (1992)