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

• ChemBase ID: 159559
• Molecular Formular: C14H29N6O10P3
• Molecular Mass: 534.335543
• Monoisotopic Mass: 534.11580105
• SMILES: c1(ncnc2c1ncn2CCOCP(=O)(OP(=O)(O)OP(=O)(O)O)O)N.CCN(CC)CC
• Canonical SMILES: Nc1ncnc2c1ncn2CCOCP(=O)(OP(=O)(OP(=O)(O)O)O)O.CCN(CC)CC
• InChI: InChI=1S/C8H14N5O10P3.C6H15N/c9-7-6-8(11-3-10-7)13(4-12-6)1-2-21-5-24(14,15)22-26(19,20)23-25(16,17)18;1-4-7(5-2)6-3/h3-4H,1-2,5H2,(H,14,15)(H,19,20)(H2,9,10,11)(H2,16,17,18);4-6H2,1-3H3
• InChIKey: CMMZUURGSBCDLQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162253694
• PubChem CID: 71313032

CALCULATED PROPERTIES

• Acid pKa: 1.014567
• H Acceptors: 12
• H Donor: 5
• LogD (pH = 5.5): -8.737608
• LogD (pH = 7.4): -9.220071
• Log P: -5.043409
• Molar Refractivity: 84.862 cm^3
• Polarizability: 33.494354 Å^3
• Polar Surface Area: 229.44 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A247512

A labelled 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)