tapinarof   Click here for help

GtoPdb Ligand ID: 9686

Synonyms: GSK-2894512 | GSK2894512 [2] | WB-1001 | WBI 1001 | WBI-1001
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Tapinarof (GSK2894512) is an aryl hydrocarbon receptor (AhR) agonist [2]. It is a natural product derived from bacteria that exist symbiotically with entomopathogenic nematodes. AhR was identified as the primary molecular target based on phenotypic screening using the DiscoveRx BioMAP Diversity Plus System and confirmed using AhR knockout mice.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 0
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 40.46
Molecular weight 254.13
XLogP 5.04
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CC(c1c(O)cc(cc1O)C=Cc1ccccc1)C
Isomeric SMILES CC(c1c(O)cc(cc1O)/C=C/c1ccccc1)C
InChI InChI=1S/C17H18O2/c1-12(2)17-15(18)10-14(11-16(17)19)9-8-13-6-4-3-5-7-13/h3-12,18-19H,1-2H3/b9-8+
InChI Key ZISJNXNHJRQYJO-CMDGGOBGSA-N
Bioactivity Comments
Tapinarof inhibits proinflammatory cytokine expression in vitro and exhibits anti-inflammatory effects in vivo [2].
Selectivity at other protein targets
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Aryl hydrocarbon receptor Primary target of this compound Hs Agonist Agonist 6.7 – 7.0 pKd - 2
pKd 6.7 – 7.0 (Kd 2x10-7 – 1x10-7 M) [2]
Description: Direct binding of tapinarof to the AhR-ARNT heterodimer by fluorescence assay.