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

• ChemBase ID: 179422
• Molecular Formular: C14H23ClN6O5
• Molecular Mass: 390.82262
• Monoisotopic Mass: 390.14184555
• SMILES: c1(=O)[nH]c(nc2c1ncn2COC(COC(=O)[C@H](C(C)C)N)CO)N.Cl
• Canonical SMILES: OCC(OCn1cnc2c1nc(N)[nH]c2=O)COC(=O)[C@H](C(C)C)N.Cl
• InChI: InChI=1S/C14H22N6O5.ClH/c1-7(2)9(15)13(23)24-4-8(3-21)25-6-20-5-17-10-11(20)18-14(16)19-12(10)22;/h5,7-9,21H,3-4,6,15H2,1-2H3,(H3,16,18,19,22);1H/t8?,9-;/m0./s1
• InChIKey: ZORWARFPXPVJLW-MTFPJWTKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)methoxy]-3-hydroxypropyl (2S)-2-amino-3-methylbutanoate hydrochloride
• IUPAC Traditional name: 2-[(2-amino-6-oxo-1H-purin-9-yl)methoxy]-3-hydroxypropyl (2S)-2-amino-3-methylbutanoate hydrochloride
• Synonyms: 2-[(2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]-3-hydroxypropyl Ester L-Valine Hydrochloride; RS 079070-194; Ro 107-9070/194; Valcyte; (S)-Valganciclovir Hydrochloride; Valganciclovir Hydrochloride

Database IDs

• CAS Number: 175865-59-5
• PubChem SID: 164235332
• PubChem CID: 110632

CALCULATED PROPERTIES

• Acid pKa: 10.160725
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -3.152424
• LogD (pH = 7.4): -1.5484567
• Log P: -1.2066475
• Molar Refractivity: 87.03 cm^3
• Polarizability: 33.330784 Å^3
• Polar Surface Area: 167.08 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White Solid
• Melting Point: 162-164°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - V092000

A pro-drug of Ganciclovir. Used in treatment of retro-virus.

REFERENCES

• Acosta, E., et al.: Clin. Pharmacol. Ther., 81, 867 (2007)
• Nassetta, L., et al.: J. Antimicrob. Chemother., 63, 862 (2007)