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Compound Detail

CHEMBL2381968

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O=C(O)[C@H]1CCCC[C@H]1C(=O)N1CCc2ccccc2[C@H]1CN1C(=O)c2ccccc2C1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2381968
Phase Preclinical
Structure Type MOL
InChI Key LNENLABLFGGAFF-BHIFYINESA-N
3
Targets
17
Activities
4
Assay Types
0
PK Parameters
16
Publications
0
Known Names

Molecular Properties

446.5
MW (Da)
3.30
ALogP
4
HBA
1
HBD
95.0
PSA (Ų)
0.73
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C26H26N2O5
MW 446.50
Aromatic Rings 2
Heavy Atoms 33
NP-Likeness -0.36

Activity Summary

IC50 8 meas. best 6.15
EC50 4 meas. best 5.64
Kd 4 meas. best 6.12
Ki 1 meas. best 6.25

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Kelch-like ECH-associated protein 1
CHEMBL2069156
 Ki 6.25 6.25 560.0 1
Keap1/Nrf2
CHEMBL3038498
 IC50 6.15 5.79 710.0 4
Kelch-like ECH-associated protein 1
CHEMBL2069156
 Kd 6.12 5.865 753.0 4
Kelch-like ECH-associated protein 1
CHEMBL2069156
 IC50 6.1 5.97 792.0 3
Keap1/Nrf2
CHEMBL3038498
 EC50 5.64 5.1033 2300.0 3
Unchecked
CHEMBL612545
 IC50 4.98 4.98 10400.0 1
Kelch-like ECH-associated protein 1
CHEMBL2069156
 EC50 4.58 4.58 26000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Kelch-like ECH-associated protein 1 Ki = 560.0 nM 6.25 Inhibition of Cys5-LDEETGEFL-NH2 binding to recombinant human KEAP1 Kelch domain... 31411465
Keap1/Nrf2 IC50 = 710.0 nM 6.15 Inhibition of Nrf2-Keap1 Kelch domain (unknown origin) protein-protein interacti... 37197451
Kelch-like ECH-associated protein 1 Kd = 753.0 nM 6.12 Binding affinity to human KEAP1 by SPR direct binding assay 32668381
Kelch-like ECH-associated protein 1 IC50 = 792.0 nM 6.1 Displacement of AF647-9-mer ETGE peptide from recombinant human biotinylated KEA... 32435379
Kelch-like ECH-associated protein 1 Kd = 1000.0 nM 6.0 Binding affinity to Keap1 kelch domain (unknown origin) by competitive SPR assay 23562243
Kelch-like ECH-associated protein 1 IC50 = 1100.0 nM 5.96 Inhibition of fluorescent labelled Nrf2 peptide ligand binding to human Keap1 (3... 30108745
Keap1/Nrf2 IC50 = 1400.0 nM 5.85 Inhibition of His-tagged human Keap1 Kelch domain /FITC-labelled-9mer Nrf2 (unkn... 38408347
Kelch-like ECH-associated protein 1 IC50 = 1400.0 nM 5.85 Inhibition of human KEAP1 incubated for 60 mins by TR-FRET assay 32668381
Kelch-like ECH-associated protein 1 Kd = 1900.0 nM 5.72 Binding affinity to KEAP1 interaction with Nrf2 (unknown origin) by SRP assay 32142281
Keap1/Nrf2 EC50 = 2300.0 nM 5.64 Inhibition of Keap1 (unknown origin) interaction to Nrf2 26348784
Keap1/Nrf2 IC50 = 2300.0 nM 5.64 Inhibition of Keap1 kelch domain (unknow origin)/Nrf2-ETGE peptide (unknown orig... 29750408
Kelch-like ECH-associated protein 1 Kd = 2400.0 nM 5.62 Binding affinity to recombinant human KEAP1 Kelch domain (321 to 609 residues) e... 31411465
Keap1/Nrf2 IC50 = 3000.0 nM 5.52 Inhibition of Keap1-Nrf2 (unknown origin) protein-protein interaction by fluores... 26258437
Unchecked IC50 = 10400.0 nM 4.98 Upregulation of HO-1 expression in human HRMC cells incubated for 18 hrs by ELIS... 37197451
Keap1/Nrf2 EC50 = 12000.0 nM 4.92 Inhibition of Keap1-Nrf2 interaction in human U2OS cells assessed as Nrf2 nuclea... 23562243
Keap1/Nrf2 EC50 = 18000.0 nM 4.75 Inhibition of Keap1-Nrf2 interaction in human HepG2 cells expressing ARE-bla ass... 23562243
Kelch-like ECH-associated protein 1 EC50 = 26000.0 nM 4.58 Binding affinity to recombinant human KEAP1 Kelch domain (321 to 609 residues) e... 31411465

Literature References

PubMed DOI Target Context # Activities
31411465 10.1021/acs.jmedchem.9b00723 Kelch-like ECH-associated protein 1 7
23562243 10.1016/j.bmcl.2013.03.013 No relevant target 4
29750408 10.1021/acs.jmedchem.8b00358 ADMET 3
23562243 10.1016/j.bmcl.2013.03.013 Keap1/Nrf2 2
32668381 10.1016/j.ejmech.2020.112532 Kelch-like ECH-associated protein 1 2
23562243 10.1016/j.bmcl.2013.03.013 Kelch-like ECH-associated protein 1 1
26258437 10.1021/acs.jmedchem.5b00185 Keap1/Nrf2 1
26348784 10.1021/acs.jmedchem.5b00602 Keap1/Nrf2 1
30108745 10.1039/C6MD00500D Kelch-like ECH-associated protein 1 1
29750408 10.1021/acs.jmedchem.8b00358 Keap1/Nrf2 1
31411465 10.1021/acs.jmedchem.9b00723 No relevant target 1
32435379 10.1021/acsmedchemlett.9b00594 Kelch-like ECH-associated protein 1 1
32142281 10.1021/acs.jmedchem.9b01451 Kelch-like ECH-associated protein 1 1
37197451 10.1021/acsmedchemlett.3c00067 Keap1/Nrf2 1
37197451 10.1021/acsmedchemlett.3c00067 Unchecked 1
38408347 10.1021/acs.jmedchem.3c02171 Keap1/Nrf2 1

Data from ChEMBL 36 via Core Engine