(2R)-2-(3-benzoylphenyl)propanoic acid

• ChemBase ID: 172092
• Molecular Formular: C16H14O3
• Molecular Mass: 254.28056
• Monoisotopic Mass: 254.09429431
• SMILES: c1cccc(c1)C(=O)c1cccc(c1)[C@@H](C)C(=O)O
• Canonical SMILES: OC(=O)[C@@H](c1cccc(c1)C(=O)c1ccccc1)C
• InChI: InChI=1S/C16H14O3/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-11H,1H3,(H,18,19)/t11-/m1/s1
• InChIKey: DKYWVDODHFEZIM-LLVKDONJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-(3-benzoylphenyl)propanoic acid
• IUPAC Traditional name: ketoprofen
• Synonyms: (αR)-3-Benzoyl-α-methylbenzeneacetic Acid; (-)-2-(3-Benzoylphenyl)propionic Acid; (-)-3-Benzoyl-α-methylbenzeneacetic Acid; (-)-Ketoprofen; (2R)-2-(3-Benzoylphenyl)propionic Acid; (R)-2-(3-Benzoylphenyl)propionic Acid; (R)-3-Benzoyl-α-methylphenylacetic Acid; (R)-Ketoprophen; (R)-(-)-Ketoprofen

Database IDs

• CAS Number: 56105-81-8
• PubChem SID: 164228002
• PubChem CID: 180540

CALCULATED PROPERTIES

• Acid pKa: 3.882609
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.9908713
• LogD (pH = 7.4): 0.39084414
• Log P: 3.6133335
• Molar Refractivity: 72.5156 cm^3
• Polarizability: 28.005615 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 69-72°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - K200806

Anti-inflammatory; analgesic.

REFERENCES

• Ueno, K., et al.: J. Med. Chem., 19, 941 (1976)
• Liversidge, G.G., Anal. Profiles Drug Subs., 10, 443 (1976)
• Jamali, F., et al.: Clin. Pharmacokinet., 19, 197 (1976)