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.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
5-[(E)-2-phenylethenyl]-2-propan-2-ylbenzene-1,3-diol
International Nonproprietary Names Click here for help
INN number INN
10253 tapinarof
Synonyms Click here for help
GSK-2894512 | GSK2894512 [2] | WB-1001 | WBI 1001 | WBI-1001
Database Links Click here for help
CAS Registry No. 79338-84-4 (source: WHO INN record)
ChEMBL Ligand CHEMBL259571
GtoPdb PubChem SID 348353645
PubChem CID 6439522
Search Google for chemical match using the InChIKey ZISJNXNHJRQYJO-CMDGGOBGSA-N
Search Google for chemicals with the same backbone ZISJNXNHJRQYJO
Search PubMed clinical trials tapinarof
Search PubMed titles tapinarof
Search PubMed titles/abstracts tapinarof
Search UniChem for chemical match using the InChIKey ZISJNXNHJRQYJO-CMDGGOBGSA-N
Search UniChem for chemicals with the same backbone ZISJNXNHJRQYJO