SB203580   Click here for help

GtoPdb Ligand ID: 5269

Synonyms: PB 203580 | RWJ 64809 | SB-203580
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: SB203580 inhibits p38 MAPK enzymes, with some selectivity for p38α. The compound has been used to dissect the p38 signalling pathway and to determine the binding mode and differentiate functions between the four p38 MAP kinase homologues [4,6]. The hydrochloride salt is water-soluble.
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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

SB203580 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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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 3
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 77.85
Molecular weight 377.1
XLogP 3.75
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 Fc1ccc(cc1)c1nc([nH]c1c1ccncc1)c1ccc(cc1)S(=O)C
Isomeric SMILES Fc1ccc(cc1)c1nc([nH]c1c1ccncc1)c1ccc(cc1)S(=O)C
InChI InChI=1S/C21H16FN3OS/c1-27(26)18-8-4-16(5-9-18)21-24-19(14-2-6-17(22)7-3-14)20(25-21)15-10-12-23-13-11-15/h2-13H,1H3,(H,24,25)
InChI Key CDMGBJANTYXAIV-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: 2,7
Key to terms and symbols Click column headers to sort
Target Name in screen Sp. Type Action Value Parameter
mitogen-activated protein kinase 14 p38-alpha Hs Inhibitor Inhibition 7.9 pKd
cyclin G associated kinase GAK Hs Inhibitor Inhibition 7.7 pKd
receptor interacting serine/threonine kinase 2 RIPK2 Hs Inhibitor Inhibition 7.6 pKd
nemo like kinase NLK Hs Inhibitor Inhibition 7.6 pKd
mitogen-activated protein kinase 10 JNK3 Hs Inhibitor Inhibition 7.5 pKd
casein kinase 1 delta CSNK1D Hs Inhibitor Inhibition 7.4 pKd
mitogen-activated protein kinase 11 p38-beta Hs Inhibitor Inhibition 7.2 pKd
casein kinase 1 alpha 1 CSNK1A1 Hs Inhibitor Inhibition 7.1 pKd
casein kinase 1 epsilon CSNK1E Hs Inhibitor Inhibition 7.0 pKd
mitogen-activated protein kinase 9 JNK2 Hs Inhibitor Inhibition 6.9 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
casein kinase 1 delta CK1δ/CK1d Hs Inhibitor Inhibition 13.9 11.0 5.0
mitogen-activated protein kinase 14 SAPK2a/P38a(MAPK14) Hs Inhibitor Inhibition 22.8 5.0 2.0
casein kinase 1 epsilon nd/CK1epsilon Hs Inhibitor Inhibition 31.0
Raf-1 proto-oncogene, serine/threonine kinase c-RAF/RAF1 Hs Inhibitor Inhibition 41.1 17.0 3.0
A-Raf proto-oncogene, serine/threonine kinase nd/ARAF Hs Inhibitor Inhibition 42.7
receptor interacting serine/threonine kinase 2 RIPK2/RIPK2 Hs Inhibitor Inhibition 49.1 24.0 21.0
nemo like kinase NLK/NLK Hs Inhibitor Inhibition 53.8 62.0 24.0
protein tyrosine kinase 6 BRK/BRK Hs Inhibitor Inhibition 54.2 59.0 7.0
EPH receptor A6 nd/EPHA6 Hs Inhibitor Inhibition 57.2
TXK tyrosine kinase Txk/TXK Hs Inhibitor Inhibition 63.9 77.0 42.0
Displaying the top 10 targets  View all targets in screen »