({[1-(6-amino-9H-purin-9-yl)(2H6)propan-2-yl]oxy}methyl)phosphonic acid

• ChemBase ID: 178148
• Molecular Formular: C9H14N5O4P
• Molecular Mass: 287.212321
• Monoisotopic Mass: 287.07834058
• SMILES: n1cnc2c(c1N)ncn2CC(OCP(=O)(O)O)C
• Canonical SMILES: CC(Cn1cnc2c1ncnc2N)OCP(=O)(O)O
• InChI: InChI=1S/C9H14N5O4P/c1-6(18-5-19(15,16)17)2-14-4-13-7-8(10)11-3-12-9(7)14/h3-4,6H,2,5H2,1H3,(H2,10,11,12)(H2,15,16,17)
• InChIKey: SGOIRFVFHAKUTI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ({[1-(6-amino-9H-purin-9-yl)(^2H₆)propan-2-yl]oxy}methyl)phosphonic acid
• IUPAC Traditional name: {[1-(6-aminopurin-9-yl)(^2H₆)propan-2-yl]oxy}methylphosphonic acid
• Synonyms: 2(6-Amino-9H-purin-9-yl)-1-methylethoxy]methyl]-d6-phosphonic Acid; 9-(2-Phosphonomethoxypropyl)adenine-d6; PMPA-d6; rac-GS-1278-d6; rac-Tenefovir-d6; rac Tenofovir-d6

Database IDs

• CAS Number: 1020719-94-1
• PubChem SID: 164234058
• PubChem CID: 45040468

CALCULATED PROPERTIES

• Acid pKa: 1.3504702
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -3.5553482
• LogD (pH = 7.4): -3.5490735
• Log P: -4.1293197
• Molar Refractivity: 67.535 cm^3
• Polarizability: 25.787909 Å^3
• Polar Surface Area: 136.38 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Warm DMSO; Warm Water
• Apperance: White to Off-White Solid
• Melting Point: 258-260°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T018502

A deuterated 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)