2-{5-[(4-bromophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl}-3-methylbutanoic acid

• ChemBase ID: 154199
• Molecular Formular: C15H14BrNO3S2
• Molecular Mass: 400.31056
• Monoisotopic Mass: 398.95984731
• SMILES: CC(C)C(C(=O)O)N1C(=O)/C(=C/c2ccc(cc2)Br)/SC1=S
• Canonical SMILES: CC(C(N1C(=S)S/C(=C\c2ccc(cc2)Br)/C1=O)C(=O)O)C
• InChI: InChI=1S/C15H14BrNO3S2/c1-8(2)12(14(19)20)17-13(18)11(22-15(17)21)7-9-3-5-10(16)6-4-9/h3-8,12H,1-2H3,(H,19,20)
• InChIKey: COHIEJLWRGREHV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{5-[(4-bromophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl}-3-methylbutanoic acid
• IUPAC Traditional name: 2-{5-[(4-bromophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl}-3-methylbutanoic acid
• Synonyms: 5-(p-Bromobenzylidine)-α-isopropyl-4-oxo-2-thioxo-3-thiozolidineacetic acid; BH3I-1

Database IDs

• CAS Number: 300817-68-9
• MDL Number: MFCD03453544
• PubChem SID: 162248338
• PubChem CID: 5720188

CALCULATED PROPERTIES

• Acid pKa: 3.7354531
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.9019468
• LogD (pH = 7.4): 1.3756595
• Log P: 4.6665
• Molar Refractivity: 96.3055 cm^3
• Polarizability: 37.051514 Å^3
• Polar Surface Area: 57.61 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble >10 mg/mL; H2O: insoluble
• Apperance: powder, yellow

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C15H14BrNS2O3

DETAILS

Sigma Aldrich - B8809

Biochem/physiol Actions
BH3I-1is a synthetic cell permeable Bcl-xL antagonist; apoptosis inducer.