tapinarof   

GtoPdb Ligand ID: 9686

Synonyms: GSK-2894512 | GSK2894512 [2] | WB-1001 | WBI 1001 | WBI-1001
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.
2D Structure
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Physico-chemical Properties
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
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
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Aryl hydrocarbon receptor 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.