2-cyano-3-(3,4-dihydroxyphenyl)-N-[(1S)-1-phenylethyl]prop-2-enamide

• ChemBase ID: 155746
• Molecular Formular: C18H16N2O3
• Molecular Mass: 308.33124
• Monoisotopic Mass: 308.11609238
• SMILES: C[C@@H](c1ccccc1)NC(=O)/C(=C\c1ccc(c(c1)O)O)/C#N
• Canonical SMILES: N#C/C(=C/c1ccc(c(c1)O)O)/C(=O)N[C@H](c1ccccc1)C
• InChI: InChI=1S/C18H16N2O3/c1-12(14-5-3-2-4-6-14)20-18(23)15(11-19)9-13-7-8-16(21)17(22)10-13/h2-10,12,21-22H,1H3,(H,20,23)/t12-/m0/s1
• InChIKey: UMGQVUWXNOJOSJ-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-cyano-3-(3,4-dihydroxyphenyl)-N-[(1S)-1-phenylethyl]prop-2-enamide
• IUPAC Traditional name: 2-cyano-3-(3,4-dihydroxyphenyl)-N-[(1S)-1-phenylethyl]prop-2-enamide
• Synonyms: (+)-(S)-N-(α-Methylbenzyl)-3,4-dihydroxybenzylidenecyanoacetamide; Tyrphostin B50; Tyrphostin AG 835

Database IDs

• CAS Number: 133550-37-5
• MDL Number: MFCD00209855
• PubChem SID: 24278745; 162249884
• PubChem CID: 56845663

CALCULATED PROPERTIES

• Acid pKa: 7.994606
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.8973103
• LogD (pH = 7.4): 2.8056426
• Log P: 2.8985958
• Molar Refractivity: 87.8256 cm^3
• Polarizability: 33.056805 Å^3
• Polar Surface Area: 93.35 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO or ethanol: soluble

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... MST1R(4486), PTK2(5747), PTK6(5753), PTK7(5754), TWF1(5756), TXK(7294)

Product Information

• Purity: ≥98%
• Potency: IC50 (860 nanomolar for the inhibition of EGFR-kinase activity.)
• Empirical Formula (Hill Notation): C18H16N2O3

DETAILS

Sigma Aldrich - T5568

Biochem/physiol Actions
Protein tyrosine kinase inhibitor.