3-(acetyloxy)-2-[(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)methoxy]propyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanoate

• ChemBase ID: 159175
• Molecular Formular: C24H30N6O8
• Molecular Mass: 530.5304
• Monoisotopic Mass: 530.21251195
• SMILES: c1(=O)[nH]c(nc2c1ncn2COC(COC(=O)[C@H](C(C)C)NC(=O)OCc1ccccc1)COC(=O)C)N
• Canonical SMILES: O=C(N[C@H](C(=O)OCC(OCn1cnc2c1nc(N)[nH]c2=O)COC(=O)C)C(C)C)OCc1ccccc1
• InChI: InChI=1S/C24H30N6O8/c1-14(2)18(27-24(34)37-9-16-7-5-4-6-8-16)22(33)36-11-17(10-35-15(3)31)38-13-30-12-26-19-20(30)28-23(25)29-21(19)32/h4-8,12,14,17-18H,9-11,13H2,1-3H3,(H,27,34)(H3,25,28,29,32)/t17?,18-/m0/s1
• InChIKey: MPEPPXVLNHJWMG-ZVAWYAOSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(acetyloxy)-2-[(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)methoxy]propyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanoate
• IUPAC Traditional name: 3-(acetyloxy)-2-[(2-amino-6-oxo-1H-purin-9-yl)methoxy]propyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanoate
• Synonyms: N-[(Phenylmethoxy)carbonyl]-L-valine 3-(Acetyloxy)-2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]propyl Ester; O-Acetyl N-Benzyloxycarbonyl Valganciclovir

Database IDs

• CAS Number: 194159-22-3
• PubChem SID: 162253310
• PubChem CID: 9871653

CALCULATED PROPERTIES

• Acid pKa: 10.159027
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 1.397038
• LogD (pH = 7.4): 1.3964205
• Log P: 1.3970888
• Molar Refractivity: 131.8615 cm^3
• Polarizability: 50.82502 Å^3
• Polar Surface Area: 185.46 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A171090

Protected Valganciclovir, a pro-drug of ganciclovir.

REFERENCES

• Martin, J., et al.: J. Pharm. Sci., 76,180 (1987)