N-[4-chloro-3-(trifluoromethyl)phenyl]-3-oxobutanamide

• ChemBase ID: 154610
• Molecular Formular: C11H9ClF3NO2
• Molecular Mass: 279.6428696
• Monoisotopic Mass: 279.02739087
• SMILES: CC(=O)CC(=O)Nc1ccc(c(c1)C(F)(F)F)Cl
• Canonical SMILES: O=C(Nc1ccc(c(c1)C(F)(F)F)Cl)CC(=O)C
• InChI: InChI=1S/C11H9ClF3NO2/c1-6(17)4-10(18)16-7-2-3-9(12)8(5-7)11(13,14)15/h2-3,5H,4H2,1H3,(H,16,18)
• InChIKey: GNYIJZMBLZXJEJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[4-chloro-3-(trifluoromethyl)phenyl]-3-oxobutanamide
• IUPAC Traditional name: N-[4-chloro-3-(trifluoromethyl)phenyl]-3-oxobutanamide
• Synonyms: N-[4-chloro-3-(trifluoromethyl)phenyl]-3-oxobutanamide; N-[4-Chloro-3-(trifluoromethyl)phenyl]-3-oxobutanamide; Fasentin

Database IDs

• CAS Number: 392721-37-8
• MDL Number: MFCD01001285
• PubChem SID: 162248748
• PubChem CID: 879520

CALCULATED PROPERTIES

• Acid pKa: 10.585191
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.9146998
• LogD (pH = 7.4): 2.9144201
• Log P: 2.9147034
• Molar Refractivity: 61.5947 cm^3
• Polarizability: 22.213797 Å^3
• Polar Surface Area: 46.17 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: white to off-white powder
• Hydrophobicity(logP): 2.739

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC); 95%
• Empirical Formula (Hill Notation): C11H9ClF3NO2

DETAILS

Sigma Aldrich - F5557

Biochem/physiol Actions
Fasentin is a novel inhibitor of glucose uptake, GluT1 inhibitor. Fasentin is a novel inhibitor of glucose uptake that sensitizes cells to FAS-induced cell death. Fasentin selectively sensitized to death ligands, but did not decrease FLIP expression. It alters expression of genes associated with nutrient and glucose deprivation. Fasentin interacted with a unique site in the intracellular channel of the glucose transport protein GLUT1.