BARDOXOLONE METHYL

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Synonyms
Status
Molecule Category UNKNOWN
UNII CEG1Q6OGU1
EPA CompTox DTXSID5048764

Structure

InChI Key WPTTVJLTNAWYAO-KPOXMGGZSA-N
Smiles 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
InChI
InChI=1S/C32H43NO4/c1-27(2)11-13-32(26(36)37-8)14-12-31(7)24(20(32)17-27)21(34)15-23-29(5)16-19(18-33)25(35)28(3,4)22(29)9-10-30(23,31)6/h15-16,20,22,24H,9-14,17H2,1-8H3/t20-,22-,24-,29-,30+,31+,32-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C32H43NO4
Molecular Weight 505.7
AlogP 6.38
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 1.0
Polar Surface Area 84.23
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 37.0

Bioactivity

Mechanism of Action Action Reference
Inhibitor of nuclear factor kappa B kinase beta subunit inhibitor INHIBITOR PubMed PubMed
Protein: Inhibitor of nuclear factor kappa B kinase beta subunit
Description: Inhibitor of nuclear factor kappa-B kinase subunit beta
Organism : Homo sapiens
O14920 ENSG00000104365
Protein: Peroxisome proliferator-activated receptor gamma
Description: Peroxisome proliferator-activated receptor gamma
Organism : Homo sapiens
P37231 ENSG00000132170
Protein: Keap1/Nrf2
Description: Kelch-like ECH-associated protein 1
Organism : Homo sapiens
Q14145 ENSG00000079999
Protein: Keap1/Nrf2
Description: Nuclear factor erythroid 2-related factor 2
Organism : Homo sapiens
Q16236 ENSG00000116044
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Protease Cysteine protease Cysteine protease CA clan Cysteine protease C19 family
- 14080 - - -
Transcription factor
60 2380 - - -
Assay Description Organism Bioactivity Reference
Inhibitory activity against production of nitric oxide induced by interferon-gamma in mouse macrophages Mus musculus 0.1 nM
Inhibitory activity against production of nitric oxide induced by interferon gamma in mouse macrophages Mus musculus 0.11 nM
Inhibition of nitric oxide (NO) production induced by interferon-gamma (IFN-gamma) in mouse macrophages Mus musculus 0.1 nM
Inhibitory concentration against proliferation of MCF-7 (ER Positive) breast cancer cells Homo sapiens 50.0 nM
Antiinflammatory activity in CD-1 mouse Macrophage assessed as inhibition of IFN-gamma induced NO production after 48 hrs by Griess reaction Mus musculus 0.2 nM
Antiproliferative activity against human HCT8 cells assessed as inhibition of cell proliferation after 72 hrs by MTT assay Homo sapiens 399.0 nM
Antiproliferative activity against 5-FU resistant human HCT8 cells assessed as inhibition of cell proliferation after 72 hrs by MTT assay Homo sapiens 363.0 nM
Antiproliferative activity against human CCD-841-CoN cells assessed as inhibition of cell proliferation after 72 hrs by MTT assay Homo sapiens 316.0 nM
Antitumor activity against FU-resistant human HCT8 cells xenografted in nude BALB/c mouse assessed as reduction in tumor weight at 59.4 umol/kg administered as via oral gavage daily for 21 days Homo sapiens 58.4 %
Inhibition of human ERG expressed in CHO cells at 200 uM at -80 mV holding potential by patch clamp assay relative to control Homo sapiens 45.72 %
Activation of Nrf2 (unknown origin) expressed in human HaCaT-ARE-luc cells after 6 hrs by luciferase reporter gene assay Homo sapiens 60.0 nM
Antiproliferative activity against human HCT116 cells after 72 hrs by SRB assay Homo sapiens 0.25 nM
Antiproliferative activity against human HT-29 cells after 72 hrs by SRB assay Homo sapiens 280.0 nM
Antiproliferative activity against human HCT8 cells after 72 hrs by SRB assay Homo sapiens 290.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 0.8 %
Activation of Keap1/Cul3/Nrf2 in human BEAS2B cells assessed as increase in NQO1 levels measured after 48 hrs Homo sapiens 8.71 nM
Antiproliferative activity against human A549 cells assessed as inhibition of cell growth incubated for 48 hrs by MTT assay Homo sapiens 520.0 nM
Antiproliferative activity against human MCF7 cells assessed as inhibition of cell growth incubated for 48 hrs by MTT assay Homo sapiens 850.0 nM
Antiproliferative activity against human HOS cells assessed as inhibition of cell growth incubated for 48 hrs by MTT assay Homo sapiens 660.0 nM
Antiproliferative activity against human HepG2 cells assessed as inhibition of cell growth incubated for 48 hrs by MTT assay Homo sapiens 520.0 nM
Cytotoxicity against human A549 cells assessed as reduction in cell viability incubated for 48 hrs by MTT assay Homo sapiens 360.0 nM
Cytotoxicity against human MCF7 cells assessed as reduction in cell viability incubated for 48 hrs by MTT assay Homo sapiens 350.0 nM
Cytotoxicity against human HepG2 cells assessed as reduction in cell viability incubated for 48 hrs by MTT assay Homo sapiens 260.0 nM
Inhibition of mouse GOAT expressed in HEK293FT cells co-expressing pre-proghrelin assessed as reduction in ghrelin octanoylation incubated for 24 hrs by ELISA Mus musculus 35.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 8.39 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.26 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.26 %

Related Entries

Cross References

Resources Reference
ChEMBL CHEMBL1762621
DrugBank DB05983
FDA SRS CEG1Q6OGU1
Guide to Pharmacology 3443
PubChem 400769
SureChEMBL SCHEMBL12521530
ZINC ZINC000003982151
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