2-cyano-N-(2,5-dibromophenyl)-3-hydroxybut-2-enamide

• ChemBase ID: 154914
• Molecular Formular: C11H8Br2N2O2
• Molecular Mass: 360.00142
• Monoisotopic Mass: 357.89525151
• SMILES: C/C(=C(\C#N)/C(=O)Nc1cc(ccc1Br)Br)/O
• Canonical SMILES: C/C(=C(/C(=O)Nc1cc(Br)ccc1Br)\C#N)/O
• InChI: InChI=1S/C11H8Br2N2O2/c1-6(16)8(5-14)11(17)15-10-4-7(12)2-3-9(10)13/h2-4,16H,1H3,(H,15,17)
• InChIKey: UVSVTDVJQAJIFG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-cyano-N-(2,5-dibromophenyl)-3-hydroxybut-2-enamide
• IUPAC Traditional name: 2-cyano-N-(2,5-dibromophenyl)-3-hydroxybut-2-enamide
• Synonyms: α-Cyano-β-hydroxy-β-methyl-N-(2,5-dibromophenyl)propenamide; (2Z)-2-Cyano-N-(2,5-dibromophenyl)-3-hydroxy-2-butenamide; a-Cyano-b-hydroxy-b-methyl-N-(2,5-dibromophenyl)propenamide; LFM-A13

Database IDs

• CAS Number: 244240-24-2
• MDL Number: MFCD09878279
• PubChem SID: 162249052
• PubChem CID: 54676905

CALCULATED PROPERTIES

• Acid pKa: 5.3892603
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.4387848
• LogD (pH = 7.4): 0.79653144
• Log P: 2.7985399
• Molar Refractivity: 73.6647 cm^3
• Polarizability: 26.901913 Å^3
• Polar Surface Area: 73.12 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥19 mg/mL
• Apperance: white to tan powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C11H8Br2N2O2

DETAILS

Sigma Aldrich - L6920

Biochem/physiol Actions
LFM-A13 is an inhibitor of the nonreceptor tyrosine kinase Bruton′s tyrosine kinase (Btk), a new molecular target for treatment of B-cell lymphoma and autoimmune disorders. LFMA13 inhibited recombinant BTK with an IC50 value of 2.5microM with 100-fold lower inhibitory activity against a number of other protein kinases including JAK1, JAK2, EGFR, IRK, IKK, and CDK1, 2 and 3, as well as several other related kinases