3-{3-[(1,3-benzothiazol-2-ylsulfanyl)methyl]-4-hydroxy-5-methoxyphenyl}-2-cyanoprop-2-enamide

• ChemBase ID: 155596
• Molecular Formular: C19H15N3O3S2
• Molecular Mass: 397.4707
• Monoisotopic Mass: 397.05548336
• SMILES: COc1cc(cc(c1O)CSc1nc2ccccc2s1)/C=C(/C#N)\C(=O)N
• Canonical SMILES: N#C/C(=C/c1cc(CSc2nc3c(s2)cccc3)c(c(c1)OC)O)/C(=O)N
• InChI: InChI=1S/C19H15N3O3S2/c1-25-15-8-11(6-12(9-20)18(21)24)7-13(17(15)23)10-26-19-22-14-4-2-3-5-16(14)27-19/h2-8,23H,10H2,1H3,(H2,21,24)
• InChIKey: KXDONFLNGBQLTN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{3-[(1,3-benzothiazol-2-ylsulfanyl)methyl]-4-hydroxy-5-methoxyphenyl}-2-cyanoprop-2-enamide
• IUPAC Traditional name: 3-{3-[(1,3-benzothiazol-2-ylsulfanyl)methyl]-4-hydroxy-5-methoxyphenyl}-2-cyanoprop-2-enamide
• Synonyms: 5-[(Benzothiazol-2-yl)thiomethyl]-4-hydroxy-3-methoxybenzylidenecyanoacetamide; Tyrphostin C15; Tyrphostin AG 825

Database IDs

• CAS Number: 149092-50-2
• MDL Number: MFCD01074971
• PubChem SID: 162249734
• PubChem CID: 5353392

CALCULATED PROPERTIES

• Acid pKa: 8.5408125
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.7528958
• LogD (pH = 7.4): 3.7346663
• Log P: 3.753154
• Molar Refractivity: 106.3445 cm^3
• Polarizability: 41.504044 Å^3
• Polar Surface Area: 109.23 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble; methanol: 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: ~95%
• Empirical Formula (Hill Notation): C19H15N3O3S2

DETAILS

Sigma Aldrich - T5443

Biochem/physiol Actions
EGF receptor tyrosine kinase inhibitor, inactive against IGF-1 Receptor.