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Compound Detail

CHEMBL2402207

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COc1ccc(S(=O)(=O)Nc2ccc(NS(=O)(=O)c3ccc(OC)cc3)c3ccccc23)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2402207
Phase Preclinical
Structure Type MOL
InChI Key XLLVCULLOGKYOO-UHFFFAOYSA-N
4
Targets
18
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

498.6
MW (Da)
4.46
ALogP
6
HBA
2
HBD
110.8
PSA (Ų)
0.37
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C24H22N2O6S2
MW 498.58
Aromatic Rings 4
Heavy Atoms 34
NP-Likeness -0.77

Activity Summary

IC50 8 meas. best 6.04
Kd 5 meas. best 6.43
EC50 4 meas. best 5.84
Ki 1 meas. best 6.6

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Kelch-like ECH-associated protein 1
CHEMBL2069156
 Ki 6.6 6.6 250.0 1
Kelch-like ECH-associated protein 1
CHEMBL2069156
 Kd 6.43 6.0675 370.0 4
Keap1-p62
CHEMBL4106129
 IC50 6.04 6.04 910.0 1
Keap1/Nrf2
CHEMBL3038498
 IC50 6.03 5.96 940.0 4
Kelch-like ECH-associated protein 1
CHEMBL2069156
 EC50 5.84 5.54 1460.0 2
Kelch-like ECH-associated protein 1
CHEMBL2069156
 IC50 5.8 5.7133 1600.0 3
Keap1/Nrf2
CHEMBL3038498
 Kd 5.77 5.77 1700.0 1
Keap1/Nrf2
CHEMBL3038498
 EC50 5.57 5.57 2700.0 1
Nuclear factor erythroid 2-related factor 2
CHEMBL1075094
 EC50 5.0 5.0 10000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Kelch-like ECH-associated protein 1 Ki = 250.0 nM 6.6 Inhibition of Cys5-LDEETGEFL-NH2 binding to recombinant human KEAP1 Kelch domain... 31411465
Kelch-like ECH-associated protein 1 Kd = 370.0 nM 6.43 Binding affinity to recombinant human KEAP1 Kelch domain (321 to 609 residues) e... 31411465
Kelch-like ECH-associated protein 1 Kd = 500.0 nM 6.3 Binding affinity to Keap1 (unknown origin) by SPR assay 31898999
Keap1-p62 IC50 = 910.0 nM 6.04 Inhibition of recombinant GST-His-tagged Keap1-DC domain (321 to 609 residues) (... 27839920
Keap1/Nrf2 IC50 = 940.0 nM 6.03 Inhibition of Keap1-NRF2 interaction (unknown origin) expressed in Escherichia c... 26363505
Keap1/Nrf2 IC50 = 940.0 nM 6.03 Inhibition of Keap1 Kelch domain (unknown origin) /Nrf2 (unknown origin) interac... 30122040
Keap1/Nrf2 IC50 = 940.0 nM 6.03 Inhibition of Keap1-Nrf2 (unknown origin) protein-protein interaction expressed ... 35549469
Kelch-like ECH-associated protein 1 EC50 = 1460.0 nM 5.84 Displacement of FITC-LDEETGEFL-NH2 from Keap1 Kelch domain (unknown origin) afte... 24512214
Kelch-like ECH-associated protein 1 IC50 = 1600.0 nM 5.8 Binding affinity to His-tagged Keap1 DC domain (321 to 609 residues) (unknown or... 29037947
Kelch-like ECH-associated protein 1 IC50 = 1700.0 nM 5.77 Binding affinity to the Keap1 (321 to 609 residues) (unknown origin) expressed i... 26363505
Keap1/Nrf2 Kd = 1700.0 nM 5.77 Inhibition of Keap1-Nrf2 (unknown origin) protein-protein interaction by SPR ass... 35549469
Kelch-like ECH-associated protein 1 Kd = 1700.0 nM 5.77 Binding affinity to Keap1 Kelch domain (unknown origin) by surface plasmon reson... 30122040
Kelch-like ECH-associated protein 1 Kd = 1690.0 nM 5.77 Binding affinity to biotinylated Keap1 DC domain (unknown origin) by biolayer in... 24512214
Keap1/Nrf2 IC50 = 1800.0 nM 5.75 Inhibition of recombinant GST-His-tagged Keap1-DC domain (321 to 609 residues) (... 27839920
Kelch-like ECH-associated protein 1 IC50 = 2700.0 nM 5.57 Displacement of MR121-Nrf2 from human N-terminal His-tagged Kelch-DC domain of K... 23647822
Keap1/Nrf2 EC50 = 2700.0 nM 5.57 Inhibition of Keap1 (unknown origin) interaction to Nrf2 26348784
Kelch-like ECH-associated protein 1 EC50 = 5800.0 nM 5.24 Binding affinity to recombinant human KEAP1 Kelch domain (321 to 609 residues) e... 31411465
Nuclear factor erythroid 2-related factor 2 EC50 = 10000.0 nM 5.0 Induction of Nrf2 nuclear translocation in human U2OS cells 31898999

Literature References

PubMed DOI Target Context # Activities
31411465 10.1021/acs.jmedchem.9b00723 Kelch-like ECH-associated protein 1 7
23647822 10.1016/j.bmc.2013.04.019 Kelch-like ECH-associated protein 1 3
23647822 10.1016/j.bmc.2013.04.019 Nuclear factor erythroid 2-related factor 2 3
35549469 10.1021/acs.jmedchem.2c00457 Keap1/Nrf2 2
30122040 10.1021/acs.jmedchem.8b01133 ADMET 2
26653613 10.1016/j.bmcl.2015.11.082 Keap1/Nrf2 2
26363505 10.1016/j.ejmech.2015.08.049 Nuclear factor erythroid 2-related factor 2 2
24512214 10.1021/jm5000529 Kelch-like ECH-associated protein 1 2
24417449 10.1021/jm4017174 Nuclear factor erythroid 2-related factor 2 2
26363505 10.1016/j.ejmech.2015.08.049 Kelch-like ECH-associated protein 1 1
26363505 10.1016/j.ejmech.2015.08.049 Keap1/Nrf2 1
26348784 10.1021/acs.jmedchem.5b00602 Keap1/Nrf2 1
27839920 10.1016/j.bmcl.2016.10.083 Keap1-p62 1
27839920 10.1016/j.bmcl.2016.10.083 Keap1/Nrf2 1
27839920 10.1016/j.bmcl.2016.10.083 Unchecked 1
29037947 10.1016/j.bmcl.2017.10.008 Kelch-like ECH-associated protein 1 1
29037947 10.1016/j.bmcl.2017.10.008 Liver 1
30122040 10.1021/acs.jmedchem.8b01133 Kelch-like ECH-associated protein 1 1
30122040 10.1021/acs.jmedchem.8b01133 Keap1/Nrf2 1
30122040 10.1021/acs.jmedchem.8b01133 No relevant target 1

Data from ChEMBL 36 via Core Engine