rebastinib   Click here for help

GtoPdb Ligand ID: 9173

Synonyms: DCC 2036 | DCC-2036 | DP-1919
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Rebastinib (DCC-2036) is an investigational orally administered kinase inhibitor, with activity against FLT3-ITD, TIE2, KDR, LYN, BCR-ABL and TRKA kinases. Yes1 inhibition is reported in [6]. This compound has been termed a switch-control inhibitor as it binds to residues Arg386/Glu282 which ABL1 uses to switch between inactive and active conformations [1,3]. Rebastinib inhibits native and phosphphorylated ABL by inducing a type II inactive conformation [1].
It is one of the compounds claimed in patent WO2008046003 [7] and subsequent related patent applications. Rebastinib appears to be Example 1, whilst acknowledging the limitations and complexities applied in compound naming and structure provision in the patent document.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 122.54
Molecular weight 553.22
XLogP 4.03
No. Lipinski's rules broken 0
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Canonical SMILES CNC(=O)c1nccc(c1)Oc1ccc(c(c1)F)NC(=O)Nc1cc(nn1c1ccc2c(c1)cccn2)C(C)(C)C
Isomeric SMILES CNC(=O)c1nccc(c1)Oc1ccc(c(c1)F)NC(=O)Nc1cc(nn1c1ccc2c(c1)cccn2)C(C)(C)C
InChI InChI=1S/C30H28FN7O3/c1-30(2,3)26-17-27(38(37-26)19-7-9-23-18(14-19)6-5-12-33-23)36-29(40)35-24-10-8-20(15-22(24)31)41-21-11-13-34-25(16-21)28(39)32-4/h5-17H,1-4H3,(H,32,39)(H2,35,36,40)
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Molecular structure representations generated using Open Babel