LFM-A13

Ligand id: 9262

Name: LFM-A13

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 73.12
Molecular weight 357.9
XLogP 3.17
No. Lipinski's rules broken 0

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
IUPAC Name
(Z)-2-cyano-N-(2,5-dibromophenyl)-3-hydroxybut-2-enamide
Synonyms
α-cyano-beta-hydroxy-β-methyl-N-(2, 5-dibromophenyl)propenamide | alpha-cyano-beta-hydroxy-beta-methyl-N-(2, 5-dibromophenyl)propenamide
Database Links
PubChem CID 54676905
Search Google for chemical match using the InChIKey UVSVTDVJQAJIFG-VURMDHGXSA-N
Search Google for chemicals with the same backbone UVSVTDVJQAJIFG
Search UniChem for chemical match using the InChIKey UVSVTDVJQAJIFG-VURMDHGXSA-N
Search UniChem for chemicals with the same backbone UVSVTDVJQAJIFG
Comments
LFM-A13 is a potent, cell-permeable, reversible, substrate competitive, and specific inhibitor of Bruton's tyrosine kinase (BTK) [1]. It was the first reported BTK-selective tyrosine kinase inhibitor and the first anti-leukemic agent targeting BTK. Investigated preclinically for B-cell non-Hodgkin's lymphoma [5-6].
Structurally LFM-A13 is an analogue of a metaboliote of the antirheumatic drug leflunomide. The Mahajan et al. article also reports a three-dimensional homology model suggesting an energetically favorable position of LFM-A13 docked within BTK's catalytic site [1].