[({[2-(6-amino-9H-purin-9-yl)(2H4)ethoxy]methyl}(hydroxy)phosphoryl)oxy]phosphonic acid; triethylamine

• ChemBase ID: 159561
• Molecular Formular: C14H28N6O7P2
• Molecular Mass: 454.355642
• Monoisotopic Mass: 454.14947053
• SMILES: c1(ncnc2c1ncn2CCOCP(=O)(O)OP(=O)(O)O)N.CCN(CC)CC
• Canonical SMILES: Nc1ncnc2c1ncn2CCOCP(=O)(OP(=O)(O)O)O.CCN(CC)CC
• InChI: InChI=1S/C8H13N5O7P2.C6H15N/c9-7-6-8(11-3-10-7)13(4-12-6)1-2-19-5-21(14,15)20-22(16,17)18;1-4-7(5-2)6-3/h3-4H,1-2,5H2,(H,14,15)(H2,9,10,11)(H2,16,17,18);4-6H2,1-3H3
• InChIKey: PRJUZHMINXEXPO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [({[2-(6-amino-9H-purin-9-yl)(^2H₄)ethoxy]methyl}(hydroxy)phosphoryl)oxy]phosphonic acid; triethylamine
• IUPAC Traditional name: triethylamine; {[2-(6-aminopurin-9-yl)(^2H₄)ethoxy]methyl(hydroxy)phosphoryl}oxyphosphonic acid
• Synonyms: P'-[[2-(6-Amino-9H-purin-9-yl)ethoxy-d4]methyl]isohypophosphoric Acid Triethylamine Salt; [[2-(6-Amino-9H-purin-9-yl)ethoxy-d4]methyl]isohypophosphoric Acid Triethylamine Salt; Adefovir-d4 Diphosphate Triethylamine Salt; ADV-DP-d4; Adefovir-d4 Phosphate Triethylamine Salt

Database IDs

• PubChem SID: 162253696
• PubChem CID: 71313035

CALCULATED PROPERTIES

• Acid pKa: 1.6540852
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -6.25354
• LogD (pH = 7.4): -6.6008143
• Log P: -4.2972565
• Molar Refractivity: 73.9891 cm^3
• Polarizability: 28.714045 Å^3
• Polar Surface Area: 182.91 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A247517

The labelled active metabolite of Adefovir (A247500).

REFERENCES

• Schultz, C., et al.: Bioorg. Med. Chem., 11, 885 (2003)
• Erion, M., et al.: J. Pharmacol. Exp. Ther., 312, 554 (2003)
• Lai, C., et al.: N. Engl. J. Med., 354, 1011 (2003)