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

• ChemBase ID: 153639
• Molecular Formular: C20H20N2O3
• Molecular Mass: 336.3844
• Monoisotopic Mass: 336.14739251
• SMILES: c1ccc(cc1)CCCCNC(=O)/C(=C\c1ccc(c(c1)O)O)/C#N
• Canonical SMILES: N#C/C(=C/c1ccc(c(c1)O)O)/C(=O)NCCCCc1ccccc1
• InChI: InChI=1S/C20H20N2O3/c21-14-17(12-16-9-10-18(23)19(24)13-16)20(25)22-11-5-4-8-15-6-2-1-3-7-15/h1-3,6-7,9-10,12-13,23-24H,4-5,8,11H2,(H,22,25)
• InChIKey: GWCNJMUSWLTSCW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-cyano-3-(3,4-dihydroxyphenyl)-N-(4-phenylbutyl)prop-2-enamide
• IUPAC Traditional name: 2-cyano-3-(3,4-dihydroxyphenyl)-N-(4-phenylbutyl)prop-2-enamide
• Synonyms: N-(4-Phenylbutyl)-3,4-dihydroxybenzylidenecyanoacetamide; Tyrphostin B56; Tyrphostin AG 556

Database IDs

• CAS Number: 133550-41-1
• MDL Number: MFCD00209860
• PubChem SID: 162247778
• PubChem CID: 5353391

CALCULATED PROPERTIES

• Acid pKa: 8.400118
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 3.6592793
• LogD (pH = 7.4): 3.6189044
• Log P: 3.6598194
• Molar Refractivity: 97.3638 cm^3
• Polarizability: 36.665863 Å^3
• Polar Surface Area: 93.35 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: 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

Product Information

• Purity: ≥98%
• Potency: >500 μM IC50 (EGFR activity); 1.1 μM IC50 (HER1-2 kinase activity)
• Empirical Formula (Hill Notation): C20H20N2O3

DETAILS

Sigma Aldrich - T4943

Biochem/physiol Actions
Highly selective EGFR protein tyrosine kinase inhibitor.