4-chloro-N-(2-{[5-(trifluoromethyl)pyridin-2-yl]sulfonyl}ethyl)benzamide

• ChemBase ID: 154589
• Molecular Formular: C15H12ClF3N2O3S
• Molecular Mass: 392.7805896
• Monoisotopic Mass: 392.02092559
• SMILES: c1cc(ccc1C(=O)NCCS(=O)(=O)c1ccc(cn1)C(F)(F)F)Cl
• Canonical SMILES: Clc1ccc(cc1)C(=O)NCCS(=O)(=O)c1ccc(cn1)C(F)(F)F
• InChI: InChI=1S/C15H12ClF3N2O3S/c16-12-4-1-10(2-5-12)14(22)20-7-8-25(23,24)13-6-3-11(9-21-13)15(17,18)19/h1-6,9H,7-8H2,(H,20,22)
• InChIKey: JFUIMTGOQCQTPF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-chloro-N-(2-{[5-(trifluoromethyl)pyridin-2-yl]sulfonyl}ethyl)benzamide
• IUPAC Traditional name: 4-chloro-N-{2-[5-(trifluoromethyl)pyridin-2-ylsulfonyl]ethyl}benzamide
• Synonyms: GSK3787; 4-Chloro-N-(2-{[5-trifluoromethyl)-2-pyridyl]sulfonyl}ethyl)benzamide; GSK3787

Database IDs

• CAS Number: 188591-46-0
• MDL Number: MFCD00099612
• PubChem SID: 162248727
• PubChem CID: 2800647

CALCULATED PROPERTIES

• Acid pKa: 14.732527
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.700459
• LogD (pH = 7.4): 2.700459
• Log P: 2.700459
• Molar Refractivity: 86.5642 cm^3
• Polarizability: 32.91177 Å^3
• Polar Surface Area: 76.13 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL
• Apperance: white to off-white powder

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: PPAR

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C15H12ClF3N2O3S

DETAILS

Sigma Aldrich - G7423

Biochem/physiol Actions
GSK3787 is an orally available selective irreversible Peroxisome Proliferator-Activated Receptor δ (PPARδ) antagonist (pIC50=6.6) with no measurable affinity for hPPARR or hPPARγ (pIC50<5). It acts by covalently modifying Cys249 within the ligand binding pocket, and has been shown to antagonize the induction of PPARδ-regulated target genes in skeletal muscle cells.