4-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]butanoic acid

• ChemBase ID: 101576
• Molecular Formular: C12H11ClN2O3
• Molecular Mass: 266.68034
• Monoisotopic Mass: 266.0458199
• SMILES: n1c(noc1CCCC(=O)O)c1ccc(cc1)Cl
• Canonical SMILES: OC(=O)CCCc1onc(n1)c1ccc(cc1)Cl
• InChI: InChI=1S/C12H11ClN2O3/c13-9-6-4-8(5-7-9)12-14-10(18-15-12)2-1-3-11(16)17/h4-7H,1-3H2,(H,16,17)
• InChIKey: ROMPPAWVATWIKR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]butanoic acid
• IUPAC Traditional name: 4-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]butanoic acid
• Synonyms: 4-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]butanoic acid; 4-[3-(4-Chlorophenyl)-1,2,4-oxadiazol-5-yl]butanoic Acid; 3-(4-Chlorophenyl)-1,2,4-oxadiazole-5-butanoic Acid

Database IDs

• CAS Number: 439108-15-3
• MDL Number: MFCD00121620
• PubChem SID: 162087591
• PubChem CID: 731146

CALCULATED PROPERTIES

• Acid pKa: 4.275036
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.8909318
• LogD (pH = 7.4): 0.14161816
• Log P: 3.1391602
• Molar Refractivity: 76.825 cm^3
• Polarizability: 25.53679 Å^3
• Polar Surface Area: 76.22 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 108 - 110°C
• Hydrophobicity(logP): 2.219

Product Information

• Purity: 95%

DETAILS

Toronto Research Chemicals - C379573

An aldose reductase inhibitor.

REFERENCES

• Suzuki, L., et al.: Diabetes, 50, 851 (2001)
• Evans, J., et al.: Endocrine Rev., 23, 599 (2001)
• Mylari, B., et al.: J. Med. Chem., 46, 2283 (2001)
• Skyler, J., et al.: J. Med. Chem., 47, 4113 (2001)
• Stumvoll, M., et al.: Lancet, 365, 1333 (2001)