2-(2,3-dihydro-1H-indole-1-carbonyl)-3-(3,4-dihydroxyphenyl)prop-2-enenitrile

• ChemBase ID: 155737
• Molecular Formular: C18H14N2O3
• Molecular Mass: 306.31536
• Monoisotopic Mass: 306.10044232
• SMILES: c1ccc2c(c1)CCN2C(=O)/C(=C\c1ccc(c(c1)O)O)/C#N
• Canonical SMILES: N#C/C(=C/c1ccc(c(c1)O)O)/C(=O)N1CCc2c1cccc2
• InChI: InChI=1S/C18H14N2O3/c19-11-14(9-12-5-6-16(21)17(22)10-12)18(23)20-8-7-13-3-1-2-4-15(13)20/h1-6,9-10,21-22H,7-8H2
• InChIKey: MYKCTDWWIWGLHW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2,3-dihydro-1H-indole-1-carbonyl)-3-(3,4-dihydroxyphenyl)prop-2-enenitrile
• IUPAC Traditional name: 2-(2,3-dihydroindole-1-carbonyl)-3-(3,4-dihydroxyphenyl)prop-2-enenitrile
• Synonyms: N-(3′,4′-Dihydroxybenzylidenecyanoacetyl)indoline; Tyrphostin B66; Tyrphostin AG 528

Database IDs

• CAS Number: 133550-49-9
• MDL Number: MFCD01076474
• PubChem SID: 24278034; 162249875
• PubChem CID: 1838042

CALCULATED PROPERTIES

• Acid pKa: 8.428658
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.6785626
• LogD (pH = 7.4): 2.640478
• Log P: 2.6790707
• Molar Refractivity: 86.7781 cm^3
• Polarizability: 32.31867 Å^3
• Polar Surface Area: 84.56 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

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: ~90%
• Potency: IC50 (2.1 micromolar, HER1-2 kinase activity); IC50 (4.9 micromolar for EGFK kinase activity)
• Empirical Formula (Hill Notation): C18H14N2O3

DETAILS

Sigma Aldrich - T4568

Biochem/physiol Actions
EGFR protein tyrosine kinase inhibitor.