{[2-(6-amino-9H-purin-9-yl)(2H4)ethoxy]methyl}phosphonic acid

• ChemBase ID: 159557
• Molecular Formular: C8H12N5O4P
• Molecular Mass: 273.185741
• Monoisotopic Mass: 273.06269052
• SMILES: c1(ncnc2c1ncn2CCOCP(=O)(O)O)N
• Canonical SMILES: Nc1ncnc2c1ncn2CCOCP(=O)(O)O
• InChI: InChI=1S/C8H12N5O4P/c9-7-6-8(11-3-10-7)13(4-12-6)1-2-17-5-18(14,15)16/h3-4H,1-2,5H2,(H2,9,10,11)(H2,14,15,16)
• InChIKey: SUPKOOSCJHTBAH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[2-(6-amino-9H-purin-9-yl)(^2H₄)ethoxy]methyl}phosphonic acid
• IUPAC Traditional name: [2-(6-aminopurin-9-yl)(^2H₄)ethoxy]methylphosphonic acid
• Synonyms: P-[[2-(6-Amino-9H-purin-9-yl-d4)ethoxy]methyl]phosphonic Acid; 9-(2-Phosphonylmethoxyethyl)adenine-d4; [[2-(6-Amino-9H-purin-9-yl)ethoxy]methyl]phosponic Acid-d4; GS 0393-d4; PMEA-d4; Adefovir-d4

Database IDs

• PubChem SID: 162253692
• PubChem CID: 45038088

CALCULATED PROPERTIES

• Acid pKa: 1.3507168
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -3.9661872
• LogD (pH = 7.4): -3.9595268
• Log P: -4.54001
• Molar Refractivity: 63.1162 cm^3
• Polarizability: 23.977556 Å^3
• Polar Surface Area: 136.38 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Hot Water
• Apperance: White Solid
• Melting Point: >250°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - A247502

Labelled Adefovir, which is used as an antiviral.

REFERENCES

• Cundy, K.C., et al.: Antimicrob. Ag. Chemother., 39, 2401 (1995)
• Naesens, L. et al.: Antiviral Chem. Chemother., 8, 1 (1995)
• Kahn, J., et al.: J. Am. Med. Assoc., 282, 2305 (1995)