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

• ChemBase ID: 153638
• Molecular Formular: C19H18N2O3
• Molecular Mass: 322.35782
• Monoisotopic Mass: 322.13174245
• SMILES: c1ccc(cc1)CCCNC(=O)/C(=C\c1ccc(c(c1)O)O)/C#N
• Canonical SMILES: N#C/C(=C/c1ccc(c(c1)O)O)/C(=O)NCCCc1ccccc1
• InChI: InChI=1S/C19H18N2O3/c20-13-16(11-15-8-9-17(22)18(23)12-15)19(24)21-10-4-7-14-5-2-1-3-6-14/h1-3,5-6,8-9,11-12,22-23H,4,7,10H2,(H,21,24)
• InChIKey: GSQOBTOAOGXIFL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-cyano-3-(3,4-dihydroxyphenyl)-N-(3-phenylpropyl)prop-2-enamide
• IUPAC Traditional name: 2-cyano-3-(3,4-dihydroxyphenyl)-N-(3-phenylpropyl)prop-2-enamide
• Synonyms: N-(3′-Phenylpropyl)-3,4-dihydroxybenzylidenecyanoacetamide; Tyrphostin B46; Tyrphostin AG 555

Database IDs

• CAS Number: 133550-34-2
• MDL Number: MFCD00209865
• PubChem SID: 162247777; 24278742
• PubChem CID: 5353390

CALCULATED PROPERTIES

• Acid pKa: 8.392876
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 3.2147026
• LogD (pH = 7.4): 3.1737254
• Log P: 3.2152507
• Molar Refractivity: 92.7628 cm^3
• Polarizability: 34.90017 Å^3
• Polar Surface Area: 93.35 Å^2
• Rotatable Bonds: 6
• 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 (700 nM)
• Empirical Formula (Hill Notation): C19H18N2O3

DETAILS

Sigma Aldrich - T4818

Biochem/physiol Actions
EGFR protein tyrosine kinase inhibitor.