2-cyano-3-(3,4-dihydroxyphenyl)-N-(2-phenylethyl)prop-2-enamide

• ChemBase ID: 153833
• Molecular Formular: C18H16N2O3
• Molecular Mass: 308.33124
• Monoisotopic Mass: 308.11609238
• SMILES: c1ccc(cc1)CCNC(=O)/C(=C\c1ccc(c(c1)O)O)/C#N
• Canonical SMILES: N#C/C(=C/c1ccc(c(c1)O)O)/C(=O)NCCc1ccccc1
• InChI: InChI=1S/C18H16N2O3/c19-12-15(10-14-6-7-16(21)17(22)11-14)18(23)20-9-8-13-4-2-1-3-5-13/h1-7,10-11,21-22H,8-9H2,(H,20,23)
• InChIKey: ZZQHNBGRWRQWFI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-cyano-3-(3,4-dihydroxyphenyl)-N-(2-phenylethyl)prop-2-enamide
• IUPAC Traditional name: 2-cyano-3-(3,4-dihydroxyphenyl)-N-(2-phenylethyl)prop-2-enamide
• Synonyms: N-(2-Phenylethyl)-3,4-dihydroxybenzylidenecyanoacetamide; Tyrphostin B52; Tyrphostin AG 698

Database IDs

• MDL Number: MFCD00209864
• PubChem SID: 162247972; 24278743
• PubChem CID: 21971226

CALCULATED PROPERTIES

• Acid pKa: 8.385271
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.7701259
• LogD (pH = 7.4): 2.7285082
• Log P: 2.770682
• Molar Refractivity: 88.1618 cm^3
• Polarizability: 33.059265 Å^3
• Polar Surface Area: 93.35 Å^2
• Rotatable Bonds: 5
• 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 ... EGFR(1956), ERBB2(2064)

Product Information

• Purity: ≥98%
• Potency: IC50 (930 nanomolar for inhibition of EGFR-kinase activity.)
• Empirical Formula (Hill Notation): C18H16N2O3

DETAILS

Sigma Aldrich - T5193

Biochem/physiol Actions
EGFR protein tyrosine kinase inhibitor.