propan-2-yl N-{9-[(2R)-2-{[bis(benzyloxy)phosphoryl]methoxy}propyl]-9H-purin-6-yl}carbamate

• ChemBase ID: 178156
• Molecular Formular: C27H32N5O6P
• Molecular Mass: 553.546641
• Monoisotopic Mass: 553.2090204
• SMILES: n1cnc2c(c1NC(=O)OC(C)C)ncn2C[C@H](OCP(=O)(OCc1ccccc1)OCc1ccccc1)C
• Canonical SMILES: C[C@H](Cn1cnc2c1ncnc2NC(=O)OC(C)C)OCP(=O)(OCc1ccccc1)OCc1ccccc1
• InChI: InChI=1S/C27H32N5O6P/c1-20(2)38-27(33)31-25-24-26(29-17-28-25)32(18-30-24)14-21(3)35-19-39(34,36-15-22-10-6-4-7-11-22)37-16-23-12-8-5-9-13-23/h4-13,17-18,20-21H,14-16,19H2,1-3H3,(H,28,29,31,33)/t21-/m1/s1
• InChIKey: BOCUFFJMDAIOMR-OAQYLSRUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: propan-2-yl N-{9-[(2R)-2-{[bis(benzyloxy)phosphoryl]methoxy}propyl]-9H-purin-6-yl}carbamate
• IUPAC Traditional name: isopropyl N-{9-[(2R)-2-[(dibenzyloxyphosphoryl)methoxy]propyl]purin-6-yl}carbamate
• Synonyms: [[(1R)-2(6-Isopropylaminocarbamate-9H-purin-9-yl)-1-methylethoxy]methyl]phosphonic Acid Dibenzyl Ester; Tenofovir Dibenzyloxy Isopropyl Carbamate

Database IDs

• PubChem SID: 164234066
• PubChem CID: 71752363

CALCULATED PROPERTIES

• Acid pKa: 12.402625
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 4.894862
• LogD (pH = 7.4): 4.90117
• Log P: 4.901255
• Molar Refractivity: 146.6784 cm^3
• Polarizability: 57.017498 Å^3
• Polar Surface Area: 126.69 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Brown Gum

DETAILS

Toronto Research Chemicals - T018545

Protected Tenofovir (T018500). Acyclic phosphonate nucleotide analogue; reverse transcriptase inhibitor. Used as an anti-HIV agent. Antiviral.

REFERENCES

• Shaw, J.-P., et al.: Pharm. Res., 14, 1824 (1997)
• Wyles, D., et al.: Clin Infect. Dis., 40, 174 (1997)
• Peng, J., et al.: J. Clin. Pharmacol., 46, 265 (1997)
• Seminari, E., et al.: J. Antimicrob. Chemother., 60, 831 (2007)