DCLK1-IN-1   Click here for help

GtoPdb Ligand ID: 11114

Synonyms: compound 4 [PMID: 32251410]
PDB Ligand
Compound class: Synthetic organic
Comment: DCLK1-IN-1 is reported as a selective inhibitor of the serine/threonine kinases, doublecortin-like kinase 1 and 2 [1-2]. It was discovered using chemoproteomic profiling and structure-based design, and is an in vivo suitable tool for investigating and characterizing the physiological and pathophysiological roles of these kinases, particularly the role of DCLK1 in cancer and type II immunity in the gut (via epithelial tuft cells). DCLK1-IN-1 shares a chemical scaffold with LRRK2-IN-1 (an LRRK2 inhibitor) and XMD8-92 (an ERK5 inhibitor) which both exhibit off-target activity towards DCLK1. These latter tool compounds also inhibit the bromodomains of the oncology target BRD4. DCLK1-IN-1 was designed to reduce off-target effects and increase DCLK1 selectivity.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 80.45
Molecular weight 527.23
XLogP 6.41
No. Lipinski's rules broken 1
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Canonical SMILES COc1cc(ccc1Nc1ncc2c(n1)n(C)c1ccccc1c(=O)n2CC(F)(F)F)N1CCN(CC1)C
Isomeric SMILES COc1cc(ccc1Nc1ncc2c(n1)n(C)c1ccccc1c(=O)n2CC(F)(F)F)N1CCN(CC1)C
InChI InChI=1S/C26H28F3N7O2/c1-33-10-12-35(13-11-33)17-8-9-19(22(14-17)38-3)31-25-30-15-21-23(32-25)34(2)20-7-5-4-6-18(20)24(37)36(21)16-26(27,28)29/h4-9,14-15H,10-13,16H2,1-3H3,(H,30,31,32)
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Molecular structure representations generated using Open Babel