LFM-A13   Click here for help

GtoPdb Ligand ID: 9262

Synonyms: α-cyano-beta-hydroxy-β-methyl-N-(2, 5-dibromophenyl)propenamide | alpha-cyano-beta-hydroxy-beta-methyl-N-(2, 5-dibromophenyl)propenamide
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: 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 metabolite 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].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 73.12
Molecular weight 357.9
XLogP 3.13
No. Lipinski's rules broken 0
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Canonical SMILES CC(=C(C(=O)Nc1cc(Br)ccc1Br)C#N)O
Isomeric 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)/b8-6-
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
Synonyms Click here for help
α-cyano-beta-hydroxy-β-methyl-N-(2, 5-dibromophenyl)propenamide | alpha-cyano-beta-hydroxy-beta-methyl-N-(2, 5-dibromophenyl)propenamide
Database Links Click here for help
GtoPdb PubChem SID 315661337
PubChem CID 54676905
Search Google for chemical match using the InChIKey UVSVTDVJQAJIFG-VURMDHGXSA-N
Search Google for chemicals with the same backbone UVSVTDVJQAJIFG
UniChem Compound Search for chemical match using the InChIKey UVSVTDVJQAJIFG-VURMDHGXSA-N
UniChem Connectivity Search for chemical match using the InChIKey UVSVTDVJQAJIFG-VURMDHGXSA-N

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LFM-A13 (links to external site)
Cat. No. 1300