deucravacitinib   Click here for help

GtoPdb Ligand ID: 10432

Synonyms: BMS-986165 | BMS986165 | compound 11 [PMID: 31318208} | Tyk2-IN-4
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Deucravacitinib (BMS-986165) is a selective, orally active, allosteric inhibitor of the Janus kinase family enzyme, tyrosine kinase 2 (TYK2) [2,4]. The deuteromethyl amide group confers selectivity by virtue of binding to a pocket in the TYK2 JH2 pseudokinase domain.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 3
Rotatable bonds 9
Topological polar surface area 135.95
Molecular weight 422.18
XLogP 1.16
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CNC(=O)c1nnc(cc1Nc1cccc(c1OC)c1ncn(n1)C)NC(=O)C1CC1
Isomeric SMILES COc1c(cccc1c1ncn(n1)C)Nc1cc(nnc1C(=O)NC([2H])([2H])[2H])NC(=O)C1CC1
InChI InChI=1S/C20H22N8O3/c1-21-20(30)16-14(9-15(25-26-16)24-19(29)11-7-8-11)23-13-6-4-5-12(17(13)31-3)18-22-10-28(2)27-18/h4-6,9-11H,7-8H2,1-3H3,(H,21,30)(H2,23,24,25,29)/i1D3
InChI Key BZZKEPGENYLQSC-FIBGUPNXSA-N
Immunopharmacology Comments
BMS-986165 achieves its selectivity by targeting the JH2 pseudokinase domain of TYK2 rather than its orthosteric ATP binding domain [4]. It is the first pseudokinase-directed therapeutic to reach clinical evaluation as an oral treatment for autoimmune diseases. It has exhibited efficacy in several murine models of autoimmune disease and is reported to block signalling and functional responses in human cells that are known to drive autoimmune pathology (e.g.Th17, Th1, B cells, and myeloid cells) [1].