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

• ChemBase ID: 70766
• Molecular Formular: C8H12N5O4P
• Molecular Mass: 273.185741
• Monoisotopic Mass: 273.06269052
• SMILES: C(OCCn1cnc2c1ncnc2N)P(=O)(O)O
• 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)ethoxy]methyl}phosphonic acid
• IUPAC Traditional name: adefovir
• Synonyms: ((2-(6-Amino-9H-purin-9-yl)ethoxy)-methyl)phosphonic acid; ((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)phosphonic acid; P-[[2-(6-Amino-9H-purin-9-yl)ethoxy]methyl]phosphonic Acid; 9-(2-Phosphonylmethoxyethyl)adenine; [[2-(6-Amino-9H-purin-9-yl)ethoxy]methyl]phosponic Acid; GS 0393; PMEA; Adefovir

Database IDs

• CAS Number: 106941-25-7
• MDL Number: MFCD00866943
• PubChem SID: 162036477
• PubChem CID: 60172

CALCULATED PROPERTIES

• Acid pKa: 1.3507211
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -3.9661891
• LogD (pH = 7.4): -3.959527
• Log P: -4.539991
• Molar Refractivity: 63.1162 cm^3
• Polarizability: 23.904772 Å^3
• Polar Surface Area: 136.38 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Hot Water
• Apperance: Pale Brown Solid
• Melting Point: >250°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT
• TSCA Listed: false

Product Information

• Purity: 95+%

DETAILS

Toronto Research Chemicals - A247500

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)