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)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
9685 rebastinib
Synonyms Click here for help
DCC 2036 | DCC-2036 | DP-1919
Database Links Click here for help
CAS Registry No. 1020172-07-9 (source: WHO INN record)
ChEMBL Ligand CHEMBL1738757
GtoPdb PubChem SID 315661256
PubChem CID 25066467
RCSB PDB Ligand 919
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SynPHARM 83605 (in complex with ABL proto-oncogene 1, non-receptor tyrosine kinase)
UniChem Compound Search for chemical match using the InChIKey WVXNSAVVKYZVOE-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey WVXNSAVVKYZVOE-UHFFFAOYSA-N