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

• ChemBase ID: 174765
• Molecular Formular: C16H26N5O7P
• Molecular Mass: 431.380701
• Monoisotopic Mass: 431.15698483
• SMILES: n1cnc2c(c1N)ncn2C[C@H](OCP(=O)(OCOC(=O)OC(C)C)OCC)C
• Canonical SMILES: CCOP(=O)(CO[C@@H](Cn1cnc2c1ncnc2N)C)OCOC(=O)OC(C)C
• InChI: InChI=1S/C16H26N5O7P/c1-5-26-29(23,27-9-24-16(22)28-11(2)3)10-25-12(4)6-21-8-20-13-14(17)18-7-19-15(13)21/h7-8,11-12H,5-6,9-10H2,1-4H3,(H2,17,18,19)/t12-,29?/m1/s1
• InChIKey: JBEJTHIFJKPVQX-ICTCQJIBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl {[(propan-2-yloxy)carbonyl]oxy}methyl {[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methanephosphonate
• IUPAC Traditional name: ethyl [(isopropoxycarbonyl)oxy]methyl {[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxy}methanephosphonate
• Synonyms: (8R)-9-(6-Amino-9H-purin-9-yl)-5-ethoxy-8-methyl-2,4,7-trioxa-5-phosphanonanoic Acid Methyl 1-Methylethyl Ester 5-Oxide; Tenofovir Ethyl Monoisoproxil; [Isopropylcarbonyloxymethyl-(Ethoxy)-[(R)-9-(2-phosphonomethoxy)]propyl Adenine; Mono-POC Ethyl Tenofovir (Mixture of Diastereomers)

Database IDs

• PubChem SID: 164230675
• PubChem CID: 71750816

CALCULATED PROPERTIES

• Acid pKa: 18.587572
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 1.510785
• LogD (pH = 7.4): 1.6596148
• Log P: 1.6618917
• Molar Refractivity: 102.2925 cm^3
• Polarizability: 40.5712 Å^3
• Polar Surface Area: 149.91 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Water
• Apperance: Colorless Thick Oil

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M566985

Tenofovir (T018500) impurity.

REFERENCES

• Shaw, J.-P., et al.: Pharm. Res., 14, 1824 (1997)
• Wyles, D., et al.: Clin Infect. Dis., 40, 174 (1997)