2-[3-(3,4-dimethoxyphenyl)prop-2-enamido]benzoic acid

• ChemBase ID: 178829
• Molecular Formular: C18H17NO5
• Molecular Mass: 327.33128
• Monoisotopic Mass: 327.11067265
• SMILES: c1ccc(c(c1)C(=O)O)NC(=O)/C=C/c1ccc(c(c1)OC)OC
• Canonical SMILES: COc1cc(/C=C/C(=O)Nc2ccccc2C(=O)O)ccc1OC
• InChI: InChI=1S/C18H17NO5/c1-23-15-9-7-12(11-16(15)24-2)8-10-17(20)19-14-6-4-3-5-13(14)18(21)22/h3-11H,1-2H3,(H,19,20)(H,21,22)
• InChIKey: NZHGWWWHIYHZNX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[3-(3,4-dimethoxyphenyl)prop-2-enamido]benzoic acid
• IUPAC Traditional name: tranilast
• Synonyms: 2-[[3-(3,4-Dimethoxyphenyl)-1-oxo-2-propen-1-yl]amino]benzoic Acid; 2-(3,4-Dimethoxycinnamoylamino)benzoic Acid; N-(3,4-Dimethoxycinnamoyl)-anthranilic acid; N-(3',4'-Dimethoxycinnamoyl)anthranilic Acid; Rizaben; Tranpro; Tranilast

Database IDs

• CAS Number: 53902-12-8
• PubChem SID: 164234739
• PubChem CID: 5527

CALCULATED PROPERTIES

• Acid pKa: 3.5528402
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.6218046
• LogD (pH = 7.4): 0.20370603
• Log P: 3.5626285
• Molar Refractivity: 91.5198 cm^3
• Polarizability: 33.853416 Å^3
• Polar Surface Area: 84.86 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Pale Green Solid
• Melting Point: 206-208°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - T714570

Antiallergic drug, used to treat bronchial asthma, allergic rhinitis and atopic dermatitis.

REFERENCES

• Shiota, N., et al.: Brit. J. Pharmacol., 159, 626 (2010)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2010)
• Kawabata, Y., et al.: Eur. J. Pharm. Sci., 39, 256 (2010)