2-cyano-3-(3,4-dihydroxyphenyl)-N-phenylprop-2-enamide

• ChemBase ID: 153635
• Molecular Formular: C16H12N2O3
• Molecular Mass: 280.27808
• Monoisotopic Mass: 280.08479225
• SMILES: c1ccc(cc1)NC(=O)/C(=C\c1ccc(c(c1)O)O)/C#N
• Canonical SMILES: N#C/C(=C/c1ccc(c(c1)O)O)/C(=O)Nc1ccccc1
• InChI: InChI=1S/C16H12N2O3/c17-10-12(8-11-6-7-14(19)15(20)9-11)16(21)18-13-4-2-1-3-5-13/h1-9,19-20H,(H,18,21)
• InChIKey: HKHOVJYOELRGMV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-cyano-3-(3,4-dihydroxyphenyl)-N-phenylprop-2-enamide
• IUPAC Traditional name: 2-cyano-3-(3,4-dihydroxyphenyl)-N-phenylprop-2-enamide
• Synonyms: N-Phenyl-3,4-dihydroxybenzylidenecyanoacetamide; Tyrphostin B48; Tyrphostin AG 494

Database IDs

• MDL Number: MFCD00209863
• PubChem SID: 162247774; 24278033
• PubChem CID: 5353387

CALCULATED PROPERTIES

• Acid pKa: 8.429044
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.7746084
• LogD (pH = 7.4): 2.736556
• Log P: 2.7751162
• Molar Refractivity: 80.3526 cm^3
• Polarizability: 29.368826 Å^3
• Polar Surface Area: 93.35 Å^2
• Rotatable Bonds: 3
• 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

Pharmacology Properties

• Gene Information: human ... EGFR(1956), ERBB2(2064)mouse ... Egfr(13649), Pdgfrb(18596)

Product Information

• Purity: ≥98%
• Empirical Formula (Hill Notation): C16H12N2O3

DETAILS

Sigma Aldrich - T4318

Biochem/physiol Actions
Inhibitor of EGF-receptor phosphorylation