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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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)
InChI Key WVXNSAVVKYZVOE-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
4-[4-[(5-tert-butyl-2-quinolin-6-ylpyrazol-3-yl)carbamoylamino]-3-fluorophenoxy]-N-methylpyridine-2-carboxamide
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
Search Google for chemical match using the InChIKey WVXNSAVVKYZVOE-UHFFFAOYSA-N
Search Google for chemicals with the same backbone WVXNSAVVKYZVOE
Search PubMed clinical trials rebastinib
Search PubMed titles rebastinib
Search PubMed titles/abstracts rebastinib
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