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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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
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
4-[4-(4-fluorophenyl)-2-(4-methanesulfinylphenyl)-1H-imidazol-5-yl]pyridine
Synonyms Click here for help
PB 203580 | RWJ 64809 | SB-203580
Database Links Click here for help
CAS Registry No. 152121-47-6
ChEMBL Ligand CHEMBL10
GtoPdb PubChem SID 178101952
PubChem CID 176155
Search Google for chemical match using the InChIKey CDMGBJANTYXAIV-UHFFFAOYSA-N
Search Google for chemicals with the same backbone CDMGBJANTYXAIV
SynPHARM 78583 (in complex with mitogen-activated protein kinase 14)
UniChem Compound Search for chemical match using the InChIKey CDMGBJANTYXAIV-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey CDMGBJANTYXAIV-UHFFFAOYSA-N
Wikipedia SB_203580

Product suppliers

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Tocris
SB 203580 (links to external site)
Cat. No. 1202