2-cyano-3-{3-ethoxy-4-hydroxy-5-[(phenylsulfanyl)methyl]phenyl}prop-2-enamide

• ChemBase ID: 154406
• Molecular Formular: C19H18N2O3S
• Molecular Mass: 354.42282
• Monoisotopic Mass: 354.10381345
• SMILES: CCOc1cc(cc(c1O)CSc1ccccc1)/C=C(/C#N)\C(=O)N
• Canonical SMILES: CCOc1cc(/C=C(\C(=O)N)/C#N)cc(c1O)CSc1ccccc1
• InChI: InChI=1S/C19H18N2O3S/c1-2-24-17-10-13(8-14(11-20)19(21)23)9-15(18(17)22)12-25-16-6-4-3-5-7-16/h3-10,22H,2,12H2,1H3,(H2,21,23)
• InChIKey: YKLMGKWXBLSKPK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-cyano-3-{3-ethoxy-4-hydroxy-5-[(phenylsulfanyl)methyl]phenyl}prop-2-enamide
• IUPAC Traditional name: 2-cyano-3-{3-ethoxy-4-hydroxy-5-[(phenylsulfanyl)methyl]phenyl}prop-2-enamide
• Synonyms: ST638; α-Cyano-(3-ethoxy-4-hydroxy-5-phenylthiomethyl)cinnamide

Database IDs

• CAS Number: 107761-24-0
• MDL Number: MFCD00236446
• PubChem SID: 162248545
• PubChem CID: 5353962

CALCULATED PROPERTIES

• Acid pKa: 8.585801
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.2851923
• LogD (pH = 7.4): 3.2629564
• Log P: 3.285486
• Molar Refractivity: 100.5491 cm^3
• Polarizability: 38.01422 Å^3
• Polar Surface Area: 96.34 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble19 mg/mL
• Apperance: yellow solid
• Melting Point: 134-135.5 °C

Safety Information

• RTECS: UC6316200
• German water hazard class: 3
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H18N2O3S

DETAILS

Sigma Aldrich - S1195

Biochem/physiol Actions
Protein tyrosine kinase inhibitor (IC50 = 370 nM). Also inhibits HGF-induced MAP kinase activation in hepatocytes and inhibits phospholipase D activity in human neutrophils.
Packaging
Light sensitive and packaged under nitrogen.