5-[(4-ethylphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one

• ChemBase ID: 154010
• Molecular Formular: C12H11NOS2
• Molecular Mass: 249.35184
• Monoisotopic Mass: 249.02820598
• SMILES: CCc1ccc(cc1)/C=C/1\C(=O)NC(=S)S1
• Canonical SMILES: CCc1ccc(cc1)/C=C\1/SC(=S)NC1=O
• InChI: InChI=1S/C12H11NOS2/c1-2-8-3-5-9(6-4-8)7-10-11(14)13-12(15)16-10/h3-7H,2H2,1H3,(H,13,14,15)
• InChIKey: SVXDHPADAXBMFB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(4-ethylphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one; (5E)-5-[(4-ethylphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
• IUPAC Traditional name: 5-[(4-ethylphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one; (5E)-5-[(4-ethylphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
• Synonyms: 5-[(4-Ethylphenyl)methylene]-2-thioxo-4-thiazolidinone; 10058-F4; 10058-F4

Database IDs

• CAS Number: 403811-55-2
• MDL Number: MFCD00758517
• PubChem SID: 162248149
• PubChem CID: 1271002

CALCULATED PROPERTIES

• Acid pKa: 7.4830008
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 3.693377
• LogD (pH = 7.4): 3.440381
• Log P: 3.6978185
• Molar Refractivity: 73.8541 cm^3
• Polarizability: 28.165894 Å^3
• Polar Surface Area: 29.1 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; H2O: <2 mg/mL
• Apperance: yellow solid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36-43
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H317-H319
• GHS Precautionary statements: P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: c-Myc

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C12H11NOS2

DETAILS

Sigma Aldrich - F3680

Biochem/physiol Actions
10058-F4 is a c-Myc inhibitor that induces cell-cycle arrest and apoptosis. It is a cell-permeable thiazolidinone that specificallly inhibits the c-Myc-Max interaction and prevents transactivation of c-Myc target gene expression. 10058-F4 inhibits tumor cell growth in a c-Myc-dependent manner both in vitro and in vivo (64 mM using c-Myc transfected Rat1a fibroblasts).