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

• ChemBase ID: 178155
• Molecular Formular: C13H20N5O6P
• Molecular Mass: 373.301561
• Monoisotopic Mass: 373.11512002
• SMILES: n1cnc2c(c1NC(=O)OC(C)C)ncn2C[C@H](OCP(=O)(O)O)C
• Canonical SMILES: C[C@H](Cn1cnc2c1ncnc2NC(=O)OC(C)C)OCP(=O)(O)O
• InChI: InChI=1S/C13H20N5O6P/c1-8(2)24-13(19)17-11-10-12(15-5-14-11)18(6-16-10)4-9(3)23-7-25(20,21)22/h5-6,8-9H,4,7H2,1-3H3,(H2,20,21,22)(H,14,15,17,19)/t9-/m1/s1
• InChIKey: HKTHVGLNIJWELG-SECBINFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ({[(2R)-1-(6-{[(propan-2-yloxy)carbonyl]amino}-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphonic acid
• IUPAC Traditional name: {[(2R)-1-{6-[(isopropoxycarbonyl)amino]purin-9-yl}propan-2-yl]oxy}methylphosphonic acid
• Synonyms: [[(1R)-2(6-Isopropylaminocarbamate-9H-purin-9-yl)-1-methylethoxy]methyl]phosphonic Acid; Tenofovir Isopropyl Carbamate

Database IDs

• PubChem SID: 164234065
• PubChem CID: 71752362

CALCULATED PROPERTIES

• Acid pKa: 1.3486452
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -1.9524239
• LogD (pH = 7.4): -2.0687382
• Log P: -1.9189184
• Molar Refractivity: 88.4886 cm^3
• Polarizability: 33.89107 Å^3
• Polar Surface Area: 148.69 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-white Solid

DETAILS

Toronto Research Chemicals - T018535

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 (1997)