RA839   Click here for help

GtoPdb Ligand ID: 10487

Synonyms: compound 7 [PMID: 31411465] | RA-839
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: RA839 is a small molecule that noncovalently interacts with KEAP1 and acts as a selective activator of Nrf2-mediated gene transcription [2]. RA839-induced activation of the Nrf2/ARE pathway is reported to produce an anti-rotaviral effect, via inhibition of rotavirus propagation, in vitro [1].
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 6
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 95.09
Molecular weight 452.18
XLogP 5.19
No. Lipinski's rules broken 1
Click here for help
Canonical SMILES OC(=O)C1CCN(C1)c1ccc(c2c1cccc2)NS(=O)(=O)c1c(C)c(C)cc(c1C)C
Isomeric SMILES OC(=O)[C@H]1CCN(C1)c1ccc(c2c1cccc2)NS(=O)(=O)c1c(C)c(C)cc(c1C)C
InChI InChI=1S/C25H28N2O4S/c1-15-13-16(2)18(4)24(17(15)3)32(30,31)26-22-9-10-23(21-8-6-5-7-20(21)22)27-12-11-19(14-27)25(28)29/h5-10,13,19,26H,11-12,14H2,1-4H3,(H,28,29)/t19-/m0/s1
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
kelch like ECH-associated protein 1 Hs None Binding 5.2 pKd - 2
pKd 5.2 (Kd 6x10-6 M) [2]
Description: Binding affinity determined by ITC, between KEAP1 kelch domain and RA839.
kelch like ECH-associated protein 1 Hs None Binding ~6.8 pIC50 - 2
pIC50 ~6.8 (IC50 ~1.4x10-7 M) [2]
Description: Inhibition constant determined using fluorescence polarization to monitor the interaction of human KEAP1 kelch domain (amino acids Ala321–Thr609) to a fluorescently labeled human Nrf2 peptide (Alexa633-AFFAQLQLDEETGEFL).