2-hydroxy-4-(trifluoromethyl)(1,2,3,4,5,6-13C6)benzoic acid

• ChemBase ID: 166141
• Molecular Formular: C8H5F3O3
• Molecular Mass: 212.07463863
• Monoisotopic Mass: 212.03920771
• SMILES: [13cH]1[13cH][13c]([13cH][13c]([13c]1C(=O)O)O)C(F)(F)F
• Canonical SMILES: OC(=O)[13c]1[13cH][13cH][13c]([13cH][13c]1O)C(F)(F)F
• InChI: InChI=1S/C8H5F3O3/c9-8(10,11)4-1-2-5(7(13)14)6(12)3-4/h1-3,12H,(H,13,14)/i1+1,2+1,3+1,4+1,5+1,6+1
• InChIKey: XMLFPUBZFSJWCN-IDEBNGHGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-4-(trifluoromethyl)(1,2,3,4,5,6-^1^3C₆)benzoic acid
• IUPAC Traditional name: 2-hydroxy-4-(trifluoromethyl)(1,2,3,4,5,6-^1^3C₆)benzoic acid
• Synonyms: 2-Hydroxy-4-(trifluoromethyl)benzoic Acid-13C6; α,α,α-Trifluoro-2,4-cresotic Acid-13C6; 4-(Trifluoromethyl)salicylic Acid-13C6; 4-Trifluoromethyl-2-hydroxybenzoic Acid-13C6; Desacetyl Triflusal-13C6

Database IDs

• PubChem SID: 162260274
• PubChem CID: 71315582

CALCULATED PROPERTIES

• Acid pKa: 2.7575486
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.17756708
• LogD (pH = 7.4): -0.6421133
• Log P: 2.8551118
• Molar Refractivity: 41.2688 cm^3
• Polarizability: 14.765727 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D288767

The active labelled metabolite of Triflusal; inhibits cardiac hypertrophy in vitro and in vivo by blocking the NF-κB signaling pathway.

REFERENCES

• Bayon, Y., et al.: Br. J. Pharmacol., 126, 1359 (1999)
• Cabrero, A., et al.: Diabetes, 50, 1883 (1999)
• Cabrero, A., et al.: J. Biol. Chem., 277, 10100 (1999)
• Culebras, A., et al.: Neurology, 62, 1073 (1999)