resatorvid   Click here for help

GtoPdb Ligand ID: 9036

Synonyms: TAK-242 | TAK242
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Resatorvid (TAK242) was first identified as an inhibitor of inflammatory mediator production in LPS treated mouse macrophages [2]. Subsequent work found that this action was attributable to the compound's activity as a Toll-like receptor 4 (TLR4) antagonist [1].
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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

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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 5
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 80.85
Molecular weight 361.06
XLogP 3.11
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 CCOC(=O)C1=CCCCC1S(=O)(=O)Nc1ccc(cc1Cl)F
Isomeric SMILES CCOC(=O)C1=CCCC[C@H]1S(=O)(=O)Nc1ccc(cc1Cl)F
InChI InChI=1S/C15H17ClFNO4S/c1-2-22-15(19)11-5-3-4-6-14(11)23(20,21)18-13-8-7-10(17)9-12(13)16/h5,7-9,14,18H,2-4,6H2,1H3/t14-/m1/s1
InChI Key LEEIJTHMHDMWLJ-CQSZACIVSA-N
Bioactivity Comments
In vitro, resatorvid inhibits cytokine production in human PBMCs without antagonizing the binding of LPS to the CD14/TLR4/MD-2 complex [1]. Resatorvid inhibits cytokine production from mouse RAW264.7 cells stimulated with various TLR4 agonists, but not TRL2, -3 or -9 agonists, confirming it as a selective TLR4 antagonist [1]. The Ii et al. paper [1] does not provide binding assay-derived data quantifying TLR4-resatorvid antagonism, all confirmatory work involved measuring inhibition of agonist-induced cytokine expression or secretion. We have tagged TLR4 as the primary molecular target for resatorvid based on this study.
Selectivity at catalytic receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
TLR4 Primary target of this compound Hs Antagonist Antagonist - - - 1
⤷ [1]