2-[(2-amino-6-hydroxy-9H-purin-9-yl)methoxy]ethyl (2R)-2-amino-3-methylbutanoate hydrochloride

• ChemBase ID: 179411
• Molecular Formular: C13H21ClN6O4
• Molecular Mass: 360.79664
• Monoisotopic Mass: 360.13128086
• SMILES: Cl.n1c(nc2c(c1O)ncn2COCCOC(=O)[C@@H](C(C)C)N)N
• Canonical SMILES: CC([C@H](C(=O)OCCOCn1cnc2c1nc(N)nc2O)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-;/m1./s1
• InChIKey: ZCDDBUOENGJMLV-DDWIOCJRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2-amino-6-hydroxy-9H-purin-9-yl)methoxy]ethyl (2R)-2-amino-3-methylbutanoate hydrochloride
• IUPAC Traditional name: 2-[(2-amino-6-hydroxypurin-9-yl)methoxy]ethyl (2R)-2-amino-3-methylbutanoate hydrochloride
• Synonyms: D-Valine 2-[(2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl Ester Hydrochloride; Acyclovir D-Valinate Hydrochloride; D-VACV Hydrochloride; D-Valacyclovir Hydrochloride

Database IDs

• CAS Number: 124832-28-6
• PubChem SID: 164235321
• PubChem CID: 71752897

CALCULATED PROPERTIES

• Acid pKa: 11.584642
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -1.5314903
• LogD (pH = 7.4): 0.072709
• Log P: 0.4141625
• Molar Refractivity: 81.5689 cm^3
• Polarizability: 31.769855 Å^3
• Polar Surface Area: 151.4 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - V084995

Acyclovir (A192400) impurity. The D-Valine ester prodrug of Acyclovir.

REFERENCES

• Beauchamp, L.M., et al.: Antiviral Chem. Chemother., 3, 157 (1992)