[({[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}(ethoxy)phosphoryl)oxy]methyl 2,2-dimethylpropanoate

• ChemBase ID: 174769
• Molecular Formular: C16H26N5O6P
• Molecular Mass: 415.381301
• Monoisotopic Mass: 415.16207021
• SMILES: c1(ncnc2c1ncn2CCOCP(=O)(OCC)OCOC(=O)C(C)(C)C)N
• Canonical SMILES: CCOP(=O)(COCCn1cnc2c1ncnc2N)OCOC(=O)C(C)(C)C
• InChI: InChI=1S/C16H26N5O6P/c1-5-26-28(23,27-10-25-15(22)16(2,3)4)11-24-7-6-21-9-20-12-13(17)18-8-19-14(12)21/h8-9H,5-7,10-11H2,1-4H3,(H2,17,18,19)
• InChIKey: NOZLVTCICOSPFI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [({[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}(ethoxy)phosphoryl)oxy]methyl 2,2-dimethylpropanoate
• IUPAC Traditional name: ({[2-(6-aminopurin-9-yl)ethoxy]methyl(ethoxy)phosphoryl}oxy)methyl 2,2-dimethylpropanoate
• Synonyms: Mono(pivaloyloxymethyl) Ethyl Adefovir; 2,2-Dimethylpropanoic Acid [[[[2-(6-amino-9H-purin-9-yl)ethoxy]methyl]ethoxyphosphinyl]oxy]methyl ester; Mono-POM Ethyl Adefovir

Database IDs

• CAS Number: 142341-04-6
• PubChem SID: 164230679
• PubChem CID: 10319663

CALCULATED PROPERTIES

• Acid pKa: 18.58806
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 1.5078375
• LogD (pH = 7.4): 1.6570752
• Log P: 1.6593595
• Molar Refractivity: 100.7851 cm^3
• Polarizability: 39.82097 Å^3
• Polar Surface Area: 140.68 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M567050

An analogue of the antiviral drug Adefovir (A247500) with a mono-POM ester protecting group.

REFERENCES

• Starrett, J.E. et al.: J. Med. Chem., 37, 1857 (1994)