[({[({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid; triethylamine

• ChemBase ID: 178154
• Molecular Formular: C15H31N6O10P3
• Molecular Mass: 548.362123
• Monoisotopic Mass: 548.13145111
• SMILES: N(CC)(CC)CC.n1cnc2c(c1N)ncn2C[C@H](OCP(=O)(OP(=O)(O)OP(=O)(O)O)O)C
• Canonical SMILES: C[C@H](Cn1cnc2c1ncnc2N)OCP(=O)(OP(=O)(OP(=O)(O)O)O)O.CCN(CC)CC
• InChI: InChI=1S/C9H16N5O10P3.C6H15N/c1-6(2-14-4-13-7-8(10)11-3-12-9(7)14)22-5-25(15,16)23-27(20,21)24-26(17,18)19;1-4-7(5-2)6-3/h3-4,6H,2,5H2,1H3,(H,15,16)(H,20,21)(H2,10,11,12)(H2,17,18,19);4-6H2,1-3H3/t6-;/m1./s1
• InChIKey: SHPQIISMXAPZDX-FYZOBXCZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [({[({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid; triethylamine
• IUPAC Traditional name: [({[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxy}methyl(hydroxy)phosphoryl)oxy(hydroxy)phosphoryl]oxyphosphonic acid; triethylamine
• Synonyms: Diphosphoric Acid Triethylamine Salt , Anhydride with [[(1R)-2-(6-Amino-9H-purin-9-yl)-1-methylethoxy]methyl]phosphonic Acid Triethylamine Salt; PMPApp Triethylamine Salt; Tenofovir Diphosphate Triethylamine Salt (mixture of diastereomers)

Database IDs

• PubChem SID: 164234064
• PubChem CID: 71752361

CALCULATED PROPERTIES

• Acid pKa: 1.0145234
• H Acceptors: 12
• H Donor: 5
• LogD (pH = 5.5): -8.3267975
• LogD (pH = 7.4): -8.80957
• Log P: -4.632901
• Molar Refractivity: 89.2808 cm^3
• Polarizability: 35.20654 Å^3
• Polar Surface Area: 229.44 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off-White Low Melting Solid
• Melting Point: 43-45°C

Safety Information

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

DETAILS

Toronto Research Chemicals - T018525

A metabolite of Tenofovir (T018500).

REFERENCES

• Hazra, R., et al.: Antimicrob. Agents Chemother., 48, 124 (2004)
• Piketty, C., et al.: Antivir. Ther., 11, 213 (2004)
• Molto, J., et al.: Ther. Drug Monit., 29, 648 (2004)