N-[(2S)-3-{4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl}-2-({4-oxo-4-[4-(trifluoromethyl)phenyl]but-2-en-2-yl}amino)propyl]propanamide

• ChemBase ID: 154327
• Molecular Formular: C35H36F3N3O4
• Molecular Mass: 619.6732496
• Monoisotopic Mass: 619.26579131
• SMILES: CCC(=O)NC[C@H](Cc1ccc(cc1)OCCc1c(oc(n1)c1ccccc1)C)N/C(=C/C(=O)c1ccc(cc1)C(F)(F)F)/C
• Canonical SMILES: CCC(=O)NC[C@H](Cc1ccc(cc1)OCCc1nc(oc1C)c1ccccc1)N/C(=C/C(=O)c1ccc(cc1)C(F)(F)F)/C
• InChI: InChI=1S/C35H36F3N3O4/c1-4-33(43)39-22-29(40-23(2)20-32(42)26-12-14-28(15-13-26)35(36,37)38)21-25-10-16-30(17-11-25)44-19-18-31-24(3)45-34(41-31)27-8-6-5-7-9-27/h5-17,20,29,40H,4,18-19,21-22H2,1-3H3,(H,39,43)/t29-/m0/s1
• InChIKey: TYEFSRMOUXWTDN-LJAQVGFWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S)-3-{4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl}-2-({4-oxo-4-[4-(trifluoromethyl)phenyl]but-2-en-2-yl}amino)propyl]propanamide
• IUPAC Traditional name: N-[(2S)-3-{4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl}-2-({4-oxo-4-[4-(trifluoromethyl)phenyl]but-2-en-2-yl}amino)propyl]propanamide
• Synonyms: N-((2S)-2-(((1Z)-1-Methyl-3-oxo-3-(4-(trifluoromethyl)phenyl)prop-1-enyl)amino)-3-(4-(2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy)phenyl)propyl)propanamide; GW6471

Database IDs

• CAS Number: 880635-03-0
• MDL Number: MFCD07784503
• PubChem SID: 24724489; 162248466
• PubChem CID: 71311842

CALCULATED PROPERTIES

• Acid pKa: 15.414248
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 6.248316
• LogD (pH = 7.4): 6.288632
• Log P: 6.2891707
• Molar Refractivity: 178.5831 cm^3
• Polarizability: 63.330585 Å^3
• Polar Surface Area: 93.46 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: off-white to light yellow solid

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C35H36F3N3O4

DETAILS

Sigma Aldrich - G5045

Biochem/physiol Actions
GW6471 is a PPARα antagonist, which completely inhibits GW409544-induced activation of PPARα with an IC50 = 0.24 μM. GW6471 induces a PPARα conformation that interacts efficiently with co-repressors.