{[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}({[(2,2-dimethylpropanoyl)oxy]methoxy})phosphinic acid

• ChemBase ID: 159562
• Molecular Formular: C14H22N5O6P
• Molecular Mass: 387.328141
• Monoisotopic Mass: 387.13077008
• SMILES: c1(ncnc2c1ncn2CCOCP(=O)(O)OCOC(=O)C(C)(C)C)N
• Canonical SMILES: O=C(C(C)(C)C)OCOP(=O)(COCCn1cnc2c1ncnc2N)O
• InChI: InChI=1S/C14H22N5O6P/c1-14(2,3)13(20)24-8-25-26(21,22)9-23-5-4-19-7-18-10-11(15)16-6-17-12(10)19/h6-7H,4-5,8-9H2,1-3H3,(H,21,22)(H2,15,16,17)
• InChIKey: MYHVYLHIHRHSDC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}({[(2,2-dimethylpropanoyl)oxy]methoxy})phosphinic acid
• IUPAC Traditional name: [2-(6-aminopurin-9-yl)ethoxy]methyl[(2,2-dimethylpropanoyl)oxy]methoxyphosphinic acid
• Synonyms: Mono-POM Adefovir; Mono(pivaloyloxymethyl) Adefovir; 2,2-Dimethylpropanoic Acid [[[[2-(6-amino-9H-purin-9-yl)ethoxy]methyl]hydroxyphosphinyl]oxy]methyl Ester; Adefovir Monopivoxil

Database IDs

• CAS Number: 142341-05-7
• PubChem SID: 162253697
• PubChem CID: 10362748

CALCULATED PROPERTIES

• Acid pKa: 0.8233316
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -1.6721966
• LogD (pH = 7.4): -1.5457315
• Log P: -2.3566334
• Molar Refractivity: 91.5542 cm^3
• Polarizability: 35.943733 Å^3
• Polar Surface Area: 151.68 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A247525

The monoester metabolite of the adefovir prodrug Adefovir Dipivoxil (A280465).

REFERENCES

• Shaw, J.-P. et al.: Drug Metab. Dispos., 25, 362 (1997)
• Annaert, P. et al.: Pharmac. res., 15, 1168 (1997)
• Annaert, P. et al.: J. Pharmac. Sci., 89, 1054 (1997)