({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)(methoxy)phosphinic acid

• ChemBase ID: 178147
• Molecular Formular: C10H16N5O4P
• Molecular Mass: 301.238901
• Monoisotopic Mass: 301.09399065
• SMILES: n1cnc2c(c1N)ncn2C[C@H](OCP(=O)(O)OC)C
• Canonical SMILES: COP(=O)(CO[C@@H](Cn1cnc2c1ncnc2N)C)O
• InChI: InChI=1S/C10H16N5O4P/c1-7(19-6-20(16,17)18-2)3-15-5-14-8-9(11)12-4-13-10(8)15/h4-5,7H,3,6H2,1-2H3,(H,16,17)(H2,11,12,13)/t7-/m1/s1
• InChIKey: QNIIFMBLEIMHIO-SSDOTTSWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)(methoxy)phosphinic acid
• IUPAC Traditional name: {[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxy}methyl(methoxy)phosphinic acid
• Synonyms: (±)-[[2-(6-Amino-9H-purin-9-yl)-1-methylethoxy]methyl]-phosphonic Acid Monomethyl Ester; Tenofovir Monomethyl Ester

Database IDs

• CAS Number: 123155-85-1
• PubChem SID: 164234057
• PubChem CID: 71752358

CALCULATED PROPERTIES

• Acid pKa: 1.4960687
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -3.0038395
• LogD (pH = 7.4): -2.8840501
• Log P: -3.529965
• Molar Refractivity: 72.0173 cm^3
• Polarizability: 27.76222 Å^3
• Polar Surface Area: 125.38 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Light Yellow Solid

DETAILS

Toronto Research Chemicals - T018495

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 (1997)