Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL1093059

BARDOXOLONE
🧪 Phase II
Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
🧪 Phase II
CC1(C)CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](C(=O)C=C4[C@@]5(C)C=C(C#N)C(=O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1093059
Name BARDOXOLONE
Phase Phase II
Structure Type MOL
InChI Key TXGZJQLMVSIZEI-UQMAOPSPSA-N

Known Names

Bardoxolona Bardoxolone CDDO RTA 401 RTA-401 RTA401
9
Targets
20
Activities
3
Assay Types
0
PK Parameters
20
Publications
6
Known Names

Molecular Properties

491.7
MW (Da)
6.29
ALogP
4
HBA
1
HBD
95.2
PSA (Ų)
0.46
QED
1
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -olone
USAN Year 2009

Extended Properties

Molecular Formula C31H41NO4
MW 491.67
Aromatic Rings 0
Heavy Atoms 36
NP-Likeness 2.31

Activity Summary

IC50 17 meas. best 9.7
EC50 2 meas. best 6.8
Kd 1 meas. best 4.31

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mus musculus
CHEMBL375
 IC50 9.7 9.492 0.2 5
Nitric oxide synthase, inducible
CHEMBL4481
 IC50 9.7 9.7 0.2 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 9.4 9.0233 0.4 3
RAW264.7
CHEMBL612557
 IC50 7.96 7.765 11.0 4
RAW
CHEMBL614631
 IC50 7.7 7.7 20.0 2
Nitric oxide synthase, inducible
CHEMBL3464
 IC50 7.64 7.64 23.0 1
MCF7
CHEMBL387
 EC50 6.8 6.8 160.0 1
MCF7
CHEMBL387
 IC50 6.8 6.8 160.0 1
HT-29
CHEMBL384
 EC50 5.89 5.89 1300.0 1
Kelch-like ECH-associated protein 1
CHEMBL2069156
 Kd 4.31 4.31 48720.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mus musculus IC50 = 0.2 nM 9.7 Inhibitory activity against production of nitric oxide induced by interferon-gam... 10617085
Mus musculus IC50 = 0.2 nM 9.7 Inhibition of nitric oxide (NO) production induced by interferon-gamma (IFN-gamm... 11063620
Nitric oxide synthase, inducible IC50 = 0.2 nM 9.7 Inhibition of inducible nitric oxide synthase in activated macrophages 15837296
Mus musculus IC50 = 0.4 nM 9.4 Compound was evaluated for inhibitory activity against production of nitric oxid... 9873608
NON-PROTEIN TARGET IC50 = 0.4 nM 9.4 Antiinflammatory activity in mouse macrophages assessed as inhibition of IFN-gam... 23837912
Mus musculus IC50 = 0.44 nM 9.36 Inhibitory activity against production of nitric oxide induced by interferon gam... 11909709
Mus musculus IC50 = 0.5 nM 9.3 Inhibitory activity against nitric oxide production induced by interferon-gamma ... 12383005
NON-PROTEIN TARGET IC50 = 0.5 nM 9.3 Antiinflammatory activity in CD-1 mouse Macrophage assessed as inhibition of IFN... 21361338
NON-PROTEIN TARGET IC50 = 4.3 nM 8.37 Antiinflammatory activity in CD-1 mouse Macrophage assessed as inhibition of IFN... 21361338
RAW264.7 IC50 = 11.0 nM 7.96 Inhibition of NO production in INFgamma-stimulated mouse RAW264.7 cells measured... 21441026
RAW264.7 IC50 = 16.5 nM 7.78 Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of IFNg... 22533790
RAW264.7 IC50 = 17.0 nM 7.77 Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of IFN-... 21361338
RAW IC50 = 20.0 nM 7.7 Inhibition of interferon gamma-stimulated NO production in RAW 264.7 cells after... 17367124
RAW IC50 = 20.0 nM 7.7 Inhibition of nitric oxide production in IFN-gamma stimulated RAW 264.7 cells 16996735
Nitric oxide synthase, inducible IC50 = 23.0 nM 7.64 Inhibition of iNOS in LPS-stimulated mouse RAW264.7 cells assessed as inhibition... 25965897
RAW264.7 IC50 = 28.3 nM 7.55 Antiinflammatory activity against IFN-gamma-stimulated mouse RAW264.7 cells asse... 20188548
MCF7 IC50 = 160.0 nM 6.8 Inhibitory concentration against proliferation of MCF-7 (ER Positive) breast can... 15369396
MCF7 EC50 = 160.0 nM 6.8 Cytotoxicity against human MCF7 cells assessed as inhibition of cell proliferati... 26177446
HT-29 EC50 = 1300.0 nM 5.89 Anti-necroptotic activity in human HT-29 cells assessed as inhibition of TNFalph... 33248849
Kelch-like ECH-associated protein 1 Kd = 48720.0 nM 4.31 Binding affinity to Keap1 (unknown origin) assessed as dissociation constant inc... 37386884

Literature References

PubMed DOI Target Context # Activities
37386884 10.1021/acs.jmedchem.3c00822 Mus musculus 13
37386884 10.1021/acs.jmedchem.3c00822 ADMET 11
33248849 10.1016/j.ejmech.2020.113030 HT-29 9
37386884 10.1021/acs.jmedchem.3c00822 AML12 7
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
21361338 10.1021/jm101445p NON-PROTEIN TARGET 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
17367124 10.1021/jm070141c Heme oxygenase 1 2
20188548 10.1016/j.bmcl.2010.02.007 ADMET 1
21441026 10.1016/j.bmcl.2011.03.018 NAD(P)H dehydrogenase [quinone] 1 1
21441026 10.1016/j.bmcl.2011.03.018 RAW264.7 1
20188548 10.1016/j.bmcl.2010.02.007 Heme oxygenase 1 1
20188548 10.1016/j.bmcl.2010.02.007 Liver 1
20188548 10.1016/j.bmcl.2010.02.007 Lung 1
16996735 10.1016/j.bmcl.2006.09.012 RAW 1
15369396 10.1021/jm049727e MCF7 1
11063620 10.1021/jm0002230 Mus musculus 1
9873608 10.1016/s0960-894x(98)00479-x Mus musculus 1
10617085 10.1016/s0960-894x(99)00623-x Mus musculus 1

Data from ChEMBL 36 via Core Engine