Compound Detail

CHEMBL1762621

BARDOXOLONE METHYL

🧪 Phase III

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🧪 Phase III

COC(=O)[C@]12CCC(C)(C)C[C@H]1[C@H]1C(=O)C=C3[C@@]4(C)C=C(C#N)C(=O)C(C)(C)[C@@H]4CC[C@@]3(C)[C@]1(C)CC2

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL1762621
Name	BARDOXOLONE METHYL
Phase	Phase III
Structure Type	MOL
InChI Key	WPTTVJLTNAWYAO-KPOXMGGZSA-N

Known Names

Bardoxolone methyl Bardoxolone methyl ester CDDO-Me CDDO-METHYL ESTER NSC 713200 NSC-713200 RTA 402 Rta-402 RTA402

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

505.7

MW (Da)

6.38

ALogP

HBA

HBD

84.2

PSA (Å²)

0.39

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Single Enantiomer

Flags

Natural Product

USAN Stem	-olone
USAN Year	2008

Extended Properties

Molecular Formula	C32H43NO4
MW	505.70
Aromatic Rings	0
Heavy Atoms	37
NP-Likeness	2.23

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Peroxisome proliferator-activated receptor gamma antagonist	ANTAGONIST	Peroxisome proliferator-activated receptor gamma	✓	✓
Inhibitor of nuclear factor kappa B kinase beta subunit inhibitor	INHIBITOR	Inhibitor of nuclear factor kappa-B kinase subunit beta	✓	✓
Keap1/Nrf2 inhibitor	INHIBITOR	Keap1/Nrf2	✓	✓

Indications

Diabetic Nephropathies Hypertension, Pulmonary Hypertension, Pulmonary Polycystic Kidney, Autosomal Dominant Melanoma Nephritis, Hereditary Renal Insufficiency, Chronic Severe Acute Respiratory Syndrome Hematologic Neoplasms Liver Diseases Neoplasms Pancreatic Neoplasms

Activity Summary

IC50 50 meas. best 10.0

EC50 5 meas. best 8.06

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Mus musculus CHEMBL375	IC50	10.0	9.9867	0.1	3
NON-PROTEIN TARGET CHEMBL3879801	IC50	9.7	6.9425	0.2	4
HCT-116 CHEMBL394	IC50	9.6	7.84	0.2	2
Unchecked CHEMBL612545	EC50	8.06	8.06	8.7	1
Ghrelin O-acyltransferase CHEMBL1255134	IC50	7.46	7.46	35.0	1
MCF7 CHEMBL387	IC50	7.3	6.4375	50.0	4
Nuclear factor erythroid 2-related factor 2 CHEMBL1075094	EC50	7.22	7.22	60.0	1
SARS-CoV-2 CHEMBL4303835	EC50	6.7	6.62	200.0	2
HepG2 CHEMBL395	IC50	6.58	6.115	260.0	4
HT-29 CHEMBL384	IC50	6.55	6.55	280.0	1
HCT-8 CHEMBL613510	IC50	6.54	6.54	290.0	1
ADMET CHEMBL612558	IC50	6.5	6.175	316.0	2
A549 CHEMBL392	IC50	6.44	6.15	360.0	4
Unchecked CHEMBL612545	IC50	6.42	6.0067	377.4	3
L02 CHEMBL4296457	IC50	6.4	6.4	400.0	1
GES1 CHEMBL4296415	IC50	6.4	6.4	400.0	1
BGC-823 CHEMBL614526	IC50	6.3	6.3	500.0	2
MDA-MB-231 CHEMBL400	IC50	6.25	6.25	560.0	1
SGC-7901 CHEMBL614909	IC50	6.22	6.22	600.0	1
HOS CHEMBL614736	IC50	6.18	6.18	660.0	1
U2OS CHEMBL615023	IC50	6.13	6.13	740.0	1
NCI-N87 CHEMBL614197	IC50	6.1	6.1	800.0	1
MCF-10A CHEMBL614321	IC50	6.1	6.1	800.0	1
MGC-803 CHEMBL3706566	IC50	6.05	6.05	900.0	1
A549/TR CHEMBL4483226	IC50	5.77	5.77	1703.0	1
HEK293 CHEMBL614818	IC50	5.66	5.66	2200.0	1
Signal transducer and activator of transcription 3 CHEMBL4026	IC50	5.62	5.62	2380.0	1
RAW264.7 CHEMBL612557	IC50	5.4	5.4	4000.0	1
HT-29 CHEMBL384	EC50	5.36	5.36	4340.0	1
H9c2 CHEMBL614576	IC50	5.28	5.28	5200.0	1
Replicase polyprotein 1ab CHEMBL4523582	IC50	5.24	5.24	5810.0	1
Ghrelin O-acyltransferase CHEMBL3588729	IC50	5.22	4.93	6000.0	2
Ubiquitin carboxyl-terminal hydrolase 7 CHEMBL2157850	IC50	4.85	4.85	14080.0	1
Ubiquitin carboxyl-terminal hydrolase 2 CHEMBL1293227	IC50	4.66	4.66	22000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	2179.2	ng.hr.mL-1	Rattus norvegicus
AUC	2057.2	ng.hr.mL-1	Rattus norvegicus
CL	78.05	mL.min-1.kg-1	Rattus norvegicus
Cmax	9920.9	nM	Rattus norvegicus
T1/2	4.413	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Mus musculus	IC50	=	0.1	nM	10.0	Inhibitory activity against production of nitric oxide induced by interferon-gam...	10617085
Mus musculus	IC50	=	0.1	nM	10.0	Inhibition of nitric oxide (NO) production induced by interferon-gamma (IFN-gamm...	11063620
Mus musculus	IC50	=	0.11	nM	9.96	Inhibitory activity against production of nitric oxide induced by interferon gam...	11909709
NON-PROTEIN TARGET	IC50	=	0.2	nM	9.7	Antiinflammatory activity in CD-1 mouse Macrophage assessed as inhibition of IFN...	21361338
HCT-116	IC50	=	0.25	nM	9.6	Antiproliferative activity against human HCT116 cells after 72 hrs by SRB assay	30429953
Unchecked	EC50	=	8.71	nM	8.06	Activation of Keap1/Cul3/Nrf2 in human BEAS2B cells assessed as increase in NQO1...	30626555
Ghrelin O-acyltransferase	IC50	=	35.0	nM	7.46	Inhibition of mouse GOAT expressed in HEK293FT cells co-expressing pre-proghreli...	-
MCF7	IC50	=	50.0	nM	7.3	Inhibitory concentration against proliferation of MCF-7 (ER Positive) breast can...	15369396
Nuclear factor erythroid 2-related factor 2	EC50	=	60.0	nM	7.22	Activation of Nrf2 (unknown origin) expressed in human HaCaT-ARE-luc cells after...	28753294
SARS-CoV-2	EC50	=	200.0	nM	6.7	Antiviral activity against SARS-CoV-2 infected in human Calu-3 cells assessed as...	37659195
HepG2	IC50	=	260.0	nM	6.58	Cytotoxicity against human HepG2 cells assessed as reduction in cell viability i...	31051401
HT-29	IC50	=	280.0	nM	6.55	Antiproliferative activity against human HT-29 cells after 72 hrs by SRB assay	30429953
SARS-CoV-2	EC50	=	290.0	nM	6.54	Antiviral activity against SARS-CoV-2 infected in African green monkey Vero cell...	37659195
HCT-8	IC50	=	290.0	nM	6.54	Antiproliferative activity against human HCT8 cells after 72 hrs by SRB assay	30429953
ADMET	IC50	=	316.0	nM	6.5	Antiproliferative activity against human CCD-841-CoN cells assessed as inhibitio...	25675144
MCF7	IC50	=	350.0	nM	6.46	Cytotoxicity against human MCF7 cells assessed as reduction in cell viability in...	31051401
A549	IC50	=	360.0	nM	6.44	Cytotoxicity against human A549 cells assessed as reduction in cell viability in...	31051401
NON-PROTEIN TARGET	IC50	=	363.0	nM	6.44	Antiproliferative activity against 5-FU resistant human HCT8 cells assessed as i...	25675144
Unchecked	IC50	=	377.4	nM	6.42	Inhibition of Pseudomonas aeruginosa RuvA/RuvB protein complex helicase activity...	36155320
L02	IC50	=	400.0	nM	6.4	Cytotoxicity against human L02 cells assessed as inhibition of cell proliferatio...	39091011

Literature References

PubMed	DOI	Target Context	# Activities
25675144	10.1021/jm5019302	HCT-8	29
29501947	10.1016/j.ejmech.2018.02.062	A549/TR	22
28994286	10.1021/acs.jmedchem.7b00971	Mus musculus	19
25675144	10.1021/jm5019302	Mus musculus	13
39091011	10.1021/acs.jmedchem.4c01160	ADMET	12
28994286	10.1021/acs.jmedchem.7b00971	Inhibitor of nuclear factor kappa-B kinase subunit beta	8
39091011	10.1021/acs.jmedchem.4c01160	BGC-823	8
29377691	10.1021/acs.jmedchem.7b01153	Rattus norvegicus	6
28994286	10.1021/acs.jmedchem.7b00971	Kelch-like ECH-associated protein 1	6
26908173	10.1021/acs.jmedchem.5b01292	Kelch-like ECH-associated protein 1	6
28994286	10.1021/acs.jmedchem.7b00971	Rattus norvegicus	6
36155320	10.1016/j.bmc.2022.117022	Unchecked	6
27031670	10.1021/acs.jmedchem.6b00228	Keap1/Nrf2	6
28994286	10.1021/acs.jmedchem.7b00971	Unchecked	5
25675144	10.1021/jm5019302	NON-PROTEIN TARGET	5
29377691	10.1021/acs.jmedchem.7b01153	Lung	5
30429953	10.1021/acsmedchemlett.8b00345	Unchecked	4
31682434	10.1021/acs.jmedchem.9b01074	Keap1/Nrf2	4
28994286	10.1021/acs.jmedchem.7b00971	Voltage-gated inwardly rectifying potassium channel KCNH2	2
28994286	10.1021/acs.jmedchem.7b00971	No relevant target	2

Data from ChEMBL 36 via Core Engine