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

• ChemBase ID: 179412
• Molecular Formular: C13H20N6O4
• Molecular Mass: 324.3357
• Monoisotopic Mass: 324.15460315
• SMILES: c12c(ncn2COCCOC(=O)[C@@H](N)C(C)C)c(=O)[nH]c(n1)N
• Canonical SMILES: CC([C@@H](C(=O)OCCOCn1cnc2c1nc(N)[nH]c2=O)N)C
• InChI: InChI=1S/C13H20N6O4/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)/t8-/m0/s1
• InChIKey: HDOVUKNUBWVHOX-QMMMGPOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate
• IUPAC Traditional name: valacyclovir
• Synonyms: L-Valine 2-[(2-Amino-1,6-dihydro-6-oxo-9H-purin-9yl)methoxy]ethyl Ester Hydrochlroride Salt; 256U; 256U87 Hydrochloride; BW 256; BW 256U87; Valaciclovir Hydrochloride; Valtrex; Zelitrex; L-Valacyclovir Hydrochloride

Database IDs

• CAS Number: 124832-27-5
• PubChem SID: 164235322
• PubChem CID: 60773

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: 30.825937 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: 170-172°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - V085000

Acyclovir (A192400) impurity. The 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)