2-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]benzoic acid

• ChemBase ID: 165814
• Molecular Formular: C17H15NO5
• Molecular Mass: 313.3047
• Monoisotopic Mass: 313.09502259
• SMILES: c1cc(c(cc1)NC(=O)/C=C/c1cc(c(cc1)O)OC)C(=O)O
• Canonical SMILES: COc1cc(/C=C/C(=O)Nc2ccccc2C(=O)O)ccc1O
• InChI: InChI=1S/C17H15NO5/c1-23-15-10-11(6-8-14(15)19)7-9-16(20)18-13-5-3-2-4-12(13)17(21)22/h2-10,19H,1H3,(H,18,20)(H,21,22)/b9-7+
• InChIKey: FSKJPXSYWQUVGO-VQHVLOKHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]benzoic acid
• IUPAC Traditional name: 2-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]benzoic acid
• Synonyms: 2-[[(2E)-3-(4-Hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl]amino]benzoic Acid; (E)-2-[[3-(4-Hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]amino]benzoic Acid; Avenanthramide 1f; Avenanthramide E; 4-Demethyl Tranilast

Database IDs

• CAS Number: 93755-77-2
• PubChem SID: 162259947
• PubChem CID: 10245047

CALCULATED PROPERTIES

• Acid pKa: 3.55284
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.4758929
• LogD (pH = 7.4): 0.056408852
• Log P: 3.4167345
• Molar Refractivity: 87.0375 cm^3
• Polarizability: 31.947914 Å^3
• Polar Surface Area: 95.86 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D231280

A metabolite of Tranilast (T714570).

REFERENCES

• Lacki, K., et al.: Biotechnol. Bioeng., 57, 694 (1998)
• Frankel, E., et al.: Sci. Food Agric., 80, 1925 (1998)
• Ward, G., et al.: J. Biol. Chem., 22, 18734 (1998)