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Compound Detail

CHEMBL3237245

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COc1ccc(S(=O)(=O)N(CC(=O)O)c2ccc(N(CC(=O)O)S(=O)(=O)c3ccc(OC)cc3)c3ccccc23)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3237245
Phase Preclinical
Structure Type MOL
InChI Key KWSIQJUNYMMCTB-UHFFFAOYSA-N
2
Targets
32
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

614.6
MW (Da)
3.42
ALogP
8
HBA
2
HBD
167.8
PSA (Ų)
0.24
QED
1
Ro5 Violations
12
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C28H26N2O10S2
MW 614.65
Aromatic Rings 4
Heavy Atoms 42
NP-Likeness -0.66

Activity Summary

IC50 20 meas. best 8.43
Kd 6 meas. best 8.45
Ki 4 meas. best 9.0
EC50 2 meas. best 7.54

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Keap1/Nrf2
CHEMBL3038498
 Ki 9.0 8.52 1.0 3
Kelch-like ECH-associated protein 1
CHEMBL2069156
 Kd 8.45 7.67 3.6 5
Keap1/Nrf2
CHEMBL3038498
 IC50 8.43 7.4557 3.7 14
Kelch-like ECH-associated protein 1
CHEMBL2069156
 Ki 8.21 8.21 6.1 1
Kelch-like ECH-associated protein 1
CHEMBL2069156
 IC50 8.11 7.4283 7.7 6
Keap1/Nrf2
CHEMBL3038498
 Kd 7.7 7.7 20.0 1
Kelch-like ECH-associated protein 1
CHEMBL2069156
 EC50 7.54 6.385 28.6 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Keap1/Nrf2 Ki = 1.0 nM 9.0 Inhibition of Keap1-Nrf2 protein-protein interaction (unknown origin) assessed a... 38159482
Keap1/Nrf2 Ki = 2.3 nM 8.64 Inhibition of Keap1-Nrf2 protein-protein interaction (unknown origin) preincubat... 36989811
Kelch-like ECH-associated protein 1 Kd = 3.59 nM 8.45 Binding affinity to biotinylated Keap1 DC domain (unknown origin) by biolayer in... 24512214
Keap1/Nrf2 IC50 = 3.7 nM 8.43 Inhibition of human Keap1 KELCH domain (321 to 609 residues) expressed in Escher... 38043492
Kelch-like ECH-associated protein 1 Kd = 5.16 nM 8.29 Binding affinity to human KEAP1 by SPR direct binding assay 32668381
Kelch-like ECH-associated protein 1 Ki = 6.1 nM 8.21 Inhibition of Cys5-LDEETGEFL-NH2 binding to recombinant human KEAP1 Kelch domain... 31411465
Keap1/Nrf2 IC50 = 7.5 nM 8.12 Inhibition of Keap1-Nrf2 protein-protein interaction (unknown origin) preincubat... 36989811
Kelch-like ECH-associated protein 1 IC50 = 7.7 nM 8.11 Inhibition of human KEAP1 incubated for 60 mins by TR-FRET assay 32668381
Keap1/Nrf2 Ki = 12.0 nM 7.92 Inhibition of Keap1-Nrf2 protein-protein interaction (unknown origin) assessed a... 38159482
Kelch-like ECH-associated protein 1 Kd = 20.0 nM 7.7 Binding affinity to Keap1 Kelch domain (unknown origin) by surface plasmon reson... 30122040
Keap1/Nrf2 Kd = 20.0 nM 7.7 Inhibition of Keap1-Nrf2 (unknown origin) protein-protein interaction by SPR ass... 35549469
Kelch-like ECH-associated protein 1 IC50 = 20.0 nM 7.7 Binding affinity to the Keap1 (321 to 609 residues) (unknown origin) expressed i... 26363505
Kelch-like ECH-associated protein 1 IC50 = 24.0 nM 7.62 Inhibition of KEAP1 (unknown origin) 36490325
Keap1/Nrf2 IC50 = 24.1 nM 7.62 Inhibition of recombinant human KEAP1 Kelch domain (321 to 609 residues) express... 34252790
Keap1/Nrf2 IC50 = 24.0 nM 7.62 Inhibition of Keap1-NRF2 interaction (unknown origin) expressed in Escherichia c... 26363505
Keap1/Nrf2 IC50 = 25.0 nM 7.6 Inhibition of Keap1 Kelch domain (unknown origin) /Nrf2 (unknown origin) interac... 30122040
Kelch-like ECH-associated protein 1 IC50 = 28.6 nM 7.54 Inhibition of FITC-9mer Nrf2 peptide interaction with human recombinant Keap1 Ke... 32902980
Keap1/Nrf2 IC50 = 28.5 nM 7.54 Inhibition of His-tagged Keap1 kelch domain/Nrf2 (unknown origin) protein-protei... 35462166
Keap1/Nrf2 IC50 = 28.6 nM 7.54 Inhibition of Keap1-Nrf2 (unknown origin) protein-protein interaction expressed ... 35549469
Keap1/Nrf2 IC50 = 28.5 nM 7.54 Inhibition of Keap1-Nrf2 protein-protein interaction (unknown origin) by TR-FRET... 38159482

Literature References

PubMed DOI Target Context # Activities
24512214 10.1021/jm5000529 Kelch-like ECH-associated protein 1 18
30122040 10.1021/acs.jmedchem.8b01133 Salmonella typhimurium 9
38159482 10.1016/j.ejmech.2023.116104 Keap1/Nrf2 8
31411465 10.1021/acs.jmedchem.9b00723 Kelch-like ECH-associated protein 1 7
34252790 10.1016/j.bmc.2021.116300 Keap1/Nrf2 6
30122040 10.1021/acs.jmedchem.8b01133 Keap1/Nrf2 6
35462166 10.1016/j.ejmech.2022.114380 Keap1/Nrf2 5
26258437 10.1021/acs.jmedchem.5b00185 Keap1/Nrf2 4
36989811 10.1016/j.ejmech.2023.115302 Keap1/Nrf2 3
32046917 10.1016/j.bmc.2020.115343 Kelch-like ECH-associated protein 1 3
35549469 10.1021/acs.jmedchem.2c00457 No relevant target 3
35462166 10.1016/j.ejmech.2022.114380 No relevant target 2
35549469 10.1021/acs.jmedchem.2c00457 Unchecked 2
26363505 10.1016/j.ejmech.2015.08.049 Nuclear factor erythroid 2-related factor 2 2
35549469 10.1021/acs.jmedchem.2c00457 Keap1/Nrf2 2
30122040 10.1021/acs.jmedchem.8b01133 No relevant target 2
30122040 10.1021/acs.jmedchem.8b01133 ADMET 2
26258437 10.1021/acs.jmedchem.5b00185 No relevant target 2
32668381 10.1016/j.ejmech.2020.112532 Kelch-like ECH-associated protein 1 2
24512214 10.1021/jm5000529 No relevant target 2

Data from ChEMBL 36 via Core Engine