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Compound Detail

CHEMBL4643134

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CCn1nnc2c(C)c([C@@H](CC(=O)O)c3ccc4c(c3)CN(C(=O)c3c(C)c(C)cc(C)c3C)CC4)ccc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4643134
Phase Preclinical
Structure Type MOL
InChI Key LOIDURPHCVSHLE-MHZLTWQESA-N
4
Targets
6
Activities
2
Assay Types
13
PK Parameters
16
Publications
0
Known Names

Molecular Properties

524.7
MW (Da)
5.80
ALogP
5
HBA
1
HBD
88.3
PSA (Ų)
0.34
QED
2
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C32H36N4O3
MW 524.67
Aromatic Rings 4
Heavy Atoms 39
NP-Likeness -0.92

Activity Summary

EC50 4 meas. best 8.04
Kd 2 meas. best 9.15

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Kelch-like ECH-associated protein 1
CHEMBL2069156
 Kd 9.15 9.15 0.7 2
Nuclear factor erythroid 2-related factor 2
CHEMBL1075094
 EC50 8.04 7.24 9.2 2
Astrocyte
CHEMBL614871
 EC50 7.29 7.29 51.0 1
Keap1/Nrf2
CHEMBL3038498
 EC50 6.44 6.44 360.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2720.0 ng.hr.mL-1 Rattus norvegicus
AUC 2510.0 ng.hr.mL-1 Rattus norvegicus
CL 6.16 mL.min-1.kg-1 Rattus norvegicus
Cmax 6700.0 nM Mus musculus
Cmax 1825.91 nM Rattus norvegicus
F 20.0 % Rattus norvegicus
Fu 0.0211 - Mus musculus
Fu 0.00708 - Homo sapiens
Fu 0.00568 - Rattus norvegicus
Fu 0.00505 - Mus musculus
Ka 8.8 10'5/M/s Homo sapiens
T1/2 3.77 hr Rattus norvegicus
Tmax 0.92 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Kelch-like ECH-associated protein 1 Kd = 0.7 nM 9.15 Binding affinity to Keap1 (unknown origin) by SPR assay 31898999
Kelch-like ECH-associated protein 1 Kd = 0.7 nM 9.15 Binding affinity to Keap1 kelch domain (unknown origin) by surface plasmon reson... 36263945
Nuclear factor erythroid 2-related factor 2 EC50 = 9.2 nM 8.04 Activation of Nrf2 in human spinal cord astrocytes assessed as increase in gluta... 31898999
Astrocyte EC50 = 51.0 nM 7.29 Neuroprotective activity against sodium arsenite-induced oxidative stress in hum... 31898999
Nuclear factor erythroid 2-related factor 2 EC50 = 360.0 nM 6.44 Induction of Nrf2 nuclear translocation in human U2OS cells 31898999
Keap1/Nrf2 EC50 = 360.0 nM 6.44 Inhibition of Keap1-Nrf2 (unknown origin) protein-protein interaction assessed i... 32902980

Literature References

PubMed DOI Target Context # Activities
31898999 10.1016/j.bmcl.2019.126852 ADMET 17
31898999 10.1016/j.bmcl.2019.126852 Nuclear factor erythroid 2-related factor 2 6
31898999 10.1016/j.bmcl.2019.126852 KEAP1/NRF2 6
31898999 10.1016/j.bmcl.2019.126852 Kelch-like ECH-associated protein 1 3
31898999 10.1016/j.bmcl.2019.126852 No relevant target 2
31898999 10.1016/j.bmcl.2019.126852 Voltage-gated inwardly rectifying potassium channel KCNH2 1
31898999 10.1016/j.bmcl.2019.126852 Cytochrome P450 1A2 1
31898999 10.1016/j.bmcl.2019.126852 Cytochrome P450 2B6 1
31898999 10.1016/j.bmcl.2019.126852 Cytochrome P450 2C19 1
31898999 10.1016/j.bmcl.2019.126852 Cytochrome P450 2C8 1
31898999 10.1016/j.bmcl.2019.126852 Cytochrome P450 2C9 1
31898999 10.1016/j.bmcl.2019.126852 Cytochrome P450 2D6 1
31898999 10.1016/j.bmcl.2019.126852 Cytochrome P450 3A4 1
31898999 10.1016/j.bmcl.2019.126852 Astrocyte 1
32902980 10.1021/acs.jmedchem.0c01116 Keap1/Nrf2 1
36263945 10.1021/acs.jmedchem.2c00830 Kelch-like ECH-associated protein 1 1

Data from ChEMBL 36 via Core Engine