5-(hydroxymethyl)-N-[4-(trifluoromethyl)(2H4)phenyl]-1,2-oxazole-4-carboxamide

• ChemBase ID: 170701
• Molecular Formular: C12H9F3N2O3
• Molecular Mass: 286.2066696
• Monoisotopic Mass: 286.05652682
• SMILES: c1noc(c1C(=O)Nc1ccc(cc1)C(F)(F)F)CO
• Canonical SMILES: OCc1oncc1C(=O)Nc1ccc(cc1)C(F)(F)F
• InChI: InChI=1S/C12H9F3N2O3/c13-12(14,15)7-1-3-8(4-2-7)17-11(19)9-5-16-20-10(9)6-18/h1-5,18H,6H2,(H,17,19)
• InChIKey: PDBLFERZFMEGMZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(hydroxymethyl)-N-[4-(trifluoromethyl)(^2H₄)phenyl]-1,2-oxazole-4-carboxamide
• IUPAC Traditional name: 5-(hydroxymethyl)-N-[4-(trifluoromethyl)(^2H₄)phenyl]-1,2-oxazole-4-carboxamide
• Synonyms: 5-(Hydroxymethyl)-N-[4-(trifluoromethyl)phenyl]-4-isoxazolecarboxamide-d4; 5-Hydroxy Leflunomide-d4 (Metabolite M2)

Database IDs

• PubChem SID: 164226611
• PubChem CID: 71749090

CALCULATED PROPERTIES

• Acid pKa: 10.014507
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.4601632
• LogD (pH = 7.4): 1.4591746
• Log P: 1.4601759
• Molar Refractivity: 65.7006 cm^3
• Polarizability: 22.801188 Å^3
• Polar Surface Area: 75.36 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H943762

Labelled 5-Hydroxy Leflunomide is a metabolite of Leflunomide (L322750).

REFERENCES

• Chan, E.C. et al.: Drug Metab. Lett., 1, 299 (2007)
• Chan, E.C.Y. et al.: Rap. Comm. Mass Spec., 23, 384 (2007)