2-[(2-acetamido-6-hydroxy-9H-purin-9-yl)methoxy]ethyl acetate

• ChemBase ID: 159063
• Molecular Formular: C12H15N5O5
• Molecular Mass: 309.278
• Monoisotopic Mass: 309.10731861
• SMILES: n1c(nc2c(c1O)ncn2COCCOC(=O)C)NC(=O)C
• Canonical SMILES: CC(=O)OCCOCn1cnc2c1nc(NC(=O)C)nc2O
• InChI: InChI=1S/C12H15N5O5/c1-7(18)14-12-15-10-9(11(20)16-12)13-5-17(10)6-21-3-4-22-8(2)19/h5H,3-4,6H2,1-2H3,(H2,14,15,16,18,20)
• InChIKey: VBHLKZHSCMQLTI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2-acetamido-6-hydroxy-9H-purin-9-yl)methoxy]ethyl acetate
• IUPAC Traditional name: 2-[(2-acetamido-6-hydroxypurin-9-yl)methoxy]ethyl acetate
• Synonyms: Diacetyl Acyclovir; N2-Acetyl-9-(2-acetoxyethoxymethyl)guanine; Acyclovir N,O-Diacetate; N-[9-[[2-(Acetyloxy)ethoxy]methyl]-6,9-dihydro-6-oxo-1H-purin-2-yl]acetamide; 9-[(2-Acetoxyethoxy)methyl]-N2-acetylguanine

Database IDs

• CAS Number: 75128-73-3
• PubChem SID: 162253198
• PubChem CID: 653052

CALCULATED PROPERTIES

• Acid pKa: 11.006982
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -0.051332906
• LogD (pH = 7.4): -0.051436186
• Log P: -0.05133081
• Molar Refractivity: 74.8823 cm^3
• Polarizability: 28.560118 Å^3
• Polar Surface Area: 128.46 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide
• Apperance: White Solid
• Melting Point: 189-190°C

DETAILS

Toronto Research Chemicals - A167995

An impurity of Acyclovir.

REFERENCES

• Laskin, O., et al.: Clin. Pharmacok., 8, 187 (1983)
• Grass, G., et al.: Pharm. Res., 5, 372 (1983)
• Mahony, W., et al.: J. Biol. Chem., 263, 9285 (1983)
• Merino, V., et al.: J. Pharm. Sci., 84, 777 (1983)