2-[(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)methoxy](2H4)ethyl (2S)-2-amino-3-methylbutanoate hydrochloride

• ChemBase ID: 179413
• Molecular Formular: C13H21ClN6O4
• Molecular Mass: 360.79664
• Monoisotopic Mass: 360.13128086
• SMILES: Cl.[nH]1c(nc2c(c1=O)ncn2COCCOC(=O)[C@H](C(C)C)N)N
• Canonical SMILES: CC([C@@H](C(=O)OCCOCn1cnc2c1nc(N)[nH]c2=O)N)C.Cl
• InChI: InChI=1S/C13H20N6O4.ClH/c1-7(2)8(14)12(21)23-4-3-22-6-19-5-16-9-10(19)17-13(15)18-11(9)20;/h5,7-8H,3-4,6,14H2,1-2H3,(H3,15,17,18,20);1H/t8-;/m0./s1
• InChIKey: ZCDDBUOENGJMLV-QRPNPIFTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)methoxy](^2H₄)ethyl (2S)-2-amino-3-methylbutanoate hydrochloride
• IUPAC Traditional name: 2-[(2-amino-6-oxo-1H-purin-9-yl)methoxy](^2H₄)ethyl (2S)-2-amino-3-methylbutanoate hydrochloride
• Synonyms: L-Valine 2-[(2-Amino-1,6-dihydro-6-oxo-9H-purin-9yl)methoxy]ethyl Ester-d4, Hydrochlroride Salt, ValACV; Valacyclovir-d4, Hydrochloride

Database IDs

• PubChem SID: 164235323
• PubChem CID: 46783220

CALCULATED PROPERTIES

• Acid pKa: 10.160745
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -2.5221028
• LogD (pH = 7.4): -0.91812485
• Log P: -0.57631254
• Molar Refractivity: 81.0675 cm^3
• Polarizability: 30.825941 Å^3
• Polar Surface Area: 146.85 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 163-166°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - V085002

The Labelled L-Valine ester prodrug of Acyclovir.

REFERENCES

• Beauchamp, L.M., et al.: Antiviral Chem. Chemother., 3, 157 (1992)
• Weller, S., et al.: Clin. Pharmacol. Ther., 54, 595 (1992)
• Lowance, D., et al.: N. Engl. J. Med., 340, 1462 (1992)