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].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

RA839 is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
InChI Key BVYWIQHJXAEJOD-IBGZPJMESA-N
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).