SKF-86002   Click here for help

GtoPdb Ligand ID: 6040

Synonyms: SK&F 86002 | SKF 86002
PDB Ligand
Compound class: Synthetic organic
Comment: SKF-86002 is a potent inhibitor of p38 MAPK.
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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

SKF-86002 is commercially available from our sponsors

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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 2
Hydrogen bond donors 0
Rotatable bonds 2
Topological polar surface area 56.01
Molecular weight 297.07
XLogP 3.87
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES Fc1ccc(cc1)c1nc2n(c1c1ccncc1)CCS2
Isomeric SMILES Fc1ccc(cc1)c1nc2n(c1c1ccncc1)CCS2
InChI InChI=1S/C16H12FN3S/c17-13-3-1-11(2-4-13)14-15(12-5-7-18-8-6-12)20-9-10-21-16(20)19-14/h1-8H,9-10H2
InChI Key YOELZIQOLWZLQC-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Bioactivity Comments
Klüter et al (2010) [3] describe the development of a kinase binding assay, that produces enzyme assay results comparable with the classic HTRF (homogeneous time-resolved fluorescence) type assays typically used to screen kinase inhibitors. The HTRF assay is inherently selective for the detection of ATP-competitive (aka type I) kinase inhibitors. To overcome this problem, Klüter et al's novel assay was designed to screen for kinase inhibitors which bind outside of the ATP catalytic site (type II and III inhibitors) as these have improved selectivity and enhanced pharmacological properties compared to the type I inhibitors. Using this new assay, SKF-86002 has an IC50 of 820nM against p38 MAPK alpha (aka mitogen-activated protein kinase 14), compared to 110nM measured using an HTRF assay [3].
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
mitogen-activated protein kinase 14 Primary target of this compound Hs Inhibitor Inhibition 7.0 pIC50 - 3
⤷ pIC50 7.0 (IC50 1.1x10-7 M) [3]
Description: Measured using a classic homogeneous time-resolved fluorescence (HTRF) kinase assay