5-chloro-2-methoxy-N-(2-phenylethyl)benzamide

• ChemBase ID: 164389
• Molecular Formular: C16H16ClNO2
• Molecular Mass: 289.75674
• Monoisotopic Mass: 289.08695644
• SMILES: c1cc(c(cc1Cl)C(=O)NCCc1ccccc1)OC
• Canonical SMILES: COc1ccc(cc1C(=O)NCCc1ccccc1)Cl
• InChI: InChI=1S/C16H16ClNO2/c1-20-15-8-7-13(17)11-14(15)16(19)18-10-9-12-5-3-2-4-6-12/h2-8,11H,9-10H2,1H3,(H,18,19)
• InChIKey: MTPTUMXFGUUUSZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-chloro-2-methoxy-N-(2-phenylethyl)benzamide
• IUPAC Traditional name: 5-chloro-2-methoxy-N-(2-phenylethyl)benzamide
• Synonyms: 5-Chloro-N-phenethyl-o-anisamide; N-Phenethyl-5-chloro-2-methoxybenzamide; 5-Chloro-2-methoxy-N-(2-phenylethyl)benzamide

Database IDs

• CAS Number: 33924-49-1
• PubChem SID: 162258524
• PubChem CID: 118575

CALCULATED PROPERTIES

• Acid pKa: 13.717768
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.5070698
• LogD (pH = 7.4): 3.5070698
• Log P: 3.5070698
• Molar Refractivity: 80.6687 cm^3
• Polarizability: 30.815405 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C368785

5-Chloro-2-methoxy-N-(2-phenylethyl)benzamide is a metabolite of the antidiabetic, Glyburide (G598350).

REFERENCES

• Tiller, P.R. et al.: J. Chrom. A, 794, 15 (1998)
• Yuriev, E. et al .: Eur. J. Med. Chem., 39, 835 (1998)