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
Click here for structure editor
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
References
1. Bissonnette R, Bolduc C, Maari C, Nigen S, Webster JM, Tang L, Lyle M. (2012)
Efficacy and safety of topical WBI-1001 in patients with mild to moderate psoriasis: results from a randomized double-blind placebo-controlled, phase II trial.
J Eur Acad Dermatol Venereol, 26 (12): 1516-21. [PMID:22077962]
2. Smith SH, Jayawickreme C, Rickard DJ, Nicodeme E, Bui T, Simmons C, Coquery CM, Neil J, Pryor WM, Mayhew D et al.. (2017)
Tapinarof Is a Natural AhR Agonist that Resolves Skin Inflammation in Mice and Humans.
J. Invest. Dermatol., 137 (10): 2110-2119. [PMID:28595996]