bardoxolone   Click here for help

GtoPdb Ligand ID: 2717

Synonyms: CDDO | RTA-401
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Bardoxolone was a Phase 3 NF-κB signaling inhibitor [2]. Although the recommended INN for this compound is bardoxolone, it is administered as bardoxolone methyl which has ChEMBL ID CHEMBL1762621. Bardoxolone can be described as a KEAP1 antagonist, as it antigonises KEAP1 interaction with the Nrf2 transription factor [1]. As this action releases Nrf2 from the inhibitory effect of the protein-protein interaction, it can also be described as a functional Nrf2 activator.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 95.23
Molecular weight 491.3
XLogP 6.3
No. Lipinski's rules broken 1
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Canonical SMILES N#CC1=CC2(C)C(C(C1=O)(C)C)CCC1(C2=CC(=O)C2C1(C)CCC1(C2CC(C)(C)CC1)C(=O)O)C
Isomeric SMILES N#CC1=C[C@@]2(C)[C@H](C(C1=O)(C)C)CC[C@@]1(C2=CC(=O)[C@H]2[C@@]1(C)CC[C@@]1([C@H]2CC(C)(C)CC1)C(=O)O)C
InChI InChI=1S/C31H41NO4/c1-26(2)10-12-31(25(35)36)13-11-30(7)23(19(31)16-26)20(33)14-22-28(5)15-18(17-32)24(34)27(3,4)21(28)8-9-29(22,30)6/h14-15,19,21,23H,8-13,16H2,1-7H3,(H,35,36)/t19-,21-,23-,28-,29+,30+,31-/m0/s1
Immunopharmacology Comments
Inhibitors of the KEAP1-Nrf2 protein-protein interaction (or functional Nrf2 activators as they are also known) have reported anti-inflammatory and cytoprotective effects. This mechanism is exemplifird by the approval of dimethyl fumarate for multiple sclerosis.