masitinib   Click here for help

GtoPdb Ligand ID: 5656

Synonyms: AB-1010 | AB1010 | Masican® (proposed trade name)
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Using the trade name Masivet, this compound has been used for several years to treat mast cell tumours in dogs [6]. It is a receptor tyrosine kinase (RTK) inhibitor, with inhibitory activity at the cKIT, platelet derived growth factor receptor (PDGFR) and fibroblast growth factor receptor (FGFR) RTKs [4].

SARS-CoV-2: Using X-ray crystallography, masitinib has been shown to bind (non-covalently) into the catalytic site of the SARS-CoV-2 3CL protease (Mpro) [3], which corresponds with detection of in vitro Mpro inhibitory activity. It does not bind to the other viral protease PLpro.
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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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Click here for structure editor
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 7
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 101.63
Molecular weight 498.22
XLogP 3.41
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 CN1CCN(CC1)Cc1ccc(cc1)C(=O)Nc1ccc(c(c1)Nc1scc(n1)c1cccnc1)C
Isomeric SMILES CN1CCN(CC1)Cc1ccc(cc1)C(=O)Nc1ccc(c(c1)Nc1scc(n1)c1cccnc1)C
InChI InChI=1S/C28H30N6OS/c1-20-5-10-24(16-25(20)31-28-32-26(19-36-28)23-4-3-11-29-17-23)30-27(35)22-8-6-21(7-9-22)18-34-14-12-33(2)13-15-34/h3-11,16-17,19H,12-15,18H2,1-2H3,(H,30,35)(H,31,32)
InChI Key WJEOLQLKVOPQFV-UHFFFAOYSA-N

Large-scale screening data

DiscoveRx KINOMEscan® screen Click here for help
A screen of 72 inhibitors against 456 human kinases. Quantitative data were derived using DiscoveRx KINOMEscan® platform.
http://www.discoverx.com/services/drug-discovery-development-services/kinase-profiling/kinomescan
Reference: 2,9
Key to terms and symbols Click column headers to sort
Target Name in screen Sp. Type Action Value Parameter
ABL proto-oncogene 1, non-receptor tyrosine kinase ABL1-nonphosphorylated Hs Inhibitor Inhibition 8.7 pKd
ABL proto-oncogene 1, non-receptor tyrosine kinase ABL1(Q252H)-phosphorylated Hs Inhibitor Inhibition 8.3 pKd
KIT proto-oncogene, receptor tyrosine kinase KIT(V559D,V654A) Hs Inhibitor Inhibition 8.3 pKd
KIT proto-oncogene, receptor tyrosine kinase KIT(V559D) Hs Inhibitor Inhibition 8.2 pKd
ABL proto-oncogene 1, non-receptor tyrosine kinase ABL1(Q252H)-nonphosphorylated Hs Inhibitor Inhibition 8.2 pKd
colony stimulating factor 1 receptor CSF1R Hs Inhibitor Inhibition 8.1 pKd
KIT proto-oncogene, receptor tyrosine kinase KIT(L576P) Hs Inhibitor Inhibition 8.1 pKd
ABL proto-oncogene 1, non-receptor tyrosine kinase ABL1(F317I)-nonphosphorylated Hs Inhibitor Inhibition 8.1 pKd
KIT proto-oncogene, receptor tyrosine kinase KIT Hs Inhibitor Inhibition 8.1 pKd
platelet derived growth factor receptor beta PDGFRB Hs Inhibitor Inhibition 8.1 pKd
Displaying the top 10 targets  View all targets in screen »
EMD Millipore KinaseProfilerTM screen/Reaction Biology Kinase HotspotSM screen Click here for help
A screen profiling 158 kinase inhibitors (Calbiochem Protein Kinase Inhibitor Library I and II, catalogue numbers 539744 and 539745) for their inhibitory activity at 1µM and 10µM against 234 human recombinant kinases using the EMD Millipore KinaseProfilerTM service.

A screen profiling the inhibitory activity of 178 commercially available kinase inhibitors at 0.5µM against a panel of 300 recombinant protein kinases using the Reaction Biology Corporation Kinase HotspotSM platform.

http://www.millipore.com/techpublications/tech1/pf3036
http://www.reactionbiology.com/webapps/main/pages/kinase.aspx

Reference: 1,5
Key to terms and symbols Click column headers to sort
Target Name in screen Sp. Type Action % Activity remaining at 0.5µM % Activity remaining at 1µM % Activity remaining at 10µM
platelet derived growth factor receptor alpha PDGFRα/PDGFRa Hs Inhibitor Inhibition 1.6
LCK proto-oncogene, Src family tyrosine kinase Lck/LCK Hs Inhibitor Inhibition 7.6
colony stimulating factor 1 receptor Fms/FMS Hs Inhibitor Inhibition 8.4
LYN proto-oncogene, Src family tyrosine kinase Lyn/LYN Hs Inhibitor Inhibition 16.2
platelet derived growth factor receptor beta PDGFRβ/PDGFRb Hs Inhibitor Inhibition 17.3
LYN proto-oncogene, Src family tyrosine kinase nd/LYN B Hs Inhibitor Inhibition 18.7
fyn related Src family tyrosine kinase PTK5/FRK(PTK5) Hs Inhibitor Inhibition 25.8
discoidin domain receptor tyrosine kinase 2 DDR2/DDR2 Hs Inhibitor Inhibition 36.4
FYN proto-oncogene, Src family tyrosine kinase Fyn/FYN Hs Inhibitor Inhibition 37.3
KIT proto-oncogene, receptor tyrosine kinase cKit/c-Kit Hs Inhibitor Inhibition 41.3
Displaying the top 10 targets  View all targets in screen »