2-{[4-chloro(2H4)phenyl]formamido}-3-(2-oxo-1,2-dihydroquinolin-4-yl)propanoic acid

• ChemBase ID: 177386
• Molecular Formular: C19H15ClN2O4
• Molecular Mass: 370.7864
• Monoisotopic Mass: 370.07203465
• SMILES: c1(c2c([nH]c(=O)c1)cccc2)CC(NC(=O)c1ccc(cc1)Cl)C(=O)O
• Canonical SMILES: Clc1ccc(cc1)C(=O)NC(C(=O)O)Cc1cc(=O)[nH]c2c1cccc2
• InChI: InChI=1S/C19H15ClN2O4/c20-13-7-5-11(6-8-13)18(24)22-16(19(25)26)9-12-10-17(23)21-15-4-2-1-3-14(12)15/h1-8,10,16H,9H2,(H,21,23)(H,22,24)(H,25,26)
• InChIKey: ALLWOAVDORUJLA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[4-chloro(^2H₄)phenyl]formamido}-3-(2-oxo-1,2-dihydroquinolin-4-yl)propanoic acid
• IUPAC Traditional name: 2-{[4-chloro(^2H₄)phenyl]formamido}-3-(2-oxo-1H-quinolin-4-yl)propanoic acid
• Synonyms: α-[(4-Chlorobenzoyl-d4)-amino]-1,2-dihydro-2-oxo-4-quinolinepropanoic Acid; OPC-12759-d4; Mucosta-d4; Proamipide-d4; Rebamipide-d4

Database IDs

• PubChem SID: 164233296
• PubChem CID: 57369397

CALCULATED PROPERTIES

• Acid pKa: 3.518527
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 0.7906722
• LogD (pH = 7.4): -0.6052261
• Log P: 2.7645504
• Molar Refractivity: 98.4974 cm^3
• Polarizability: 36.550293 Å^3
• Polar Surface Area: 95.5 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-White Solid
• Melting Point: 290-294°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - R139002

Labelled Rebamipide, which shows antiulcer activity in rats.

REFERENCES

• Uchida, M., et al.: Chem. Pharm. Bull., 33, 3775 (1985)
• Yamasaki, K., et al.: Eur. J. Pharmacol., 142, 23 (1985)