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Compound Detail

CHEMBL3393137

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COc1ccc(C(=O)C2CCN(C(=O)c3ccc(C(=O)NC4CCN(Cc5ccc(C#N)cc5)CC4)cn3)CC2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3393137
Phase Preclinical
Structure Type MOL
InChI Key JKGJLUCJLNJXKG-UHFFFAOYSA-N
7
Targets
11
Activities
2
Assay Types
12
PK Parameters
20
Publications
0
Known Names

Molecular Properties

565.7
MW (Da)
4.09
ALogP
7
HBA
1
HBD
115.6
PSA (Ų)
0.41
QED
1
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C33H35N5O4
MW 565.67
Aromatic Rings 3
Heavy Atoms 42
NP-Likeness -1.55

Activity Summary

IC50 6 meas. best 8.55
EC50 5 meas. best 7.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
AMP-activated protein kinase, AMPK
CHEMBL2096907
 IC50 8.55 8.55 2.8 1
AMP-activated protein kinase, AMPK
CHEMBL2096907
 EC50 7.52 7.2233 30.0 3
Unchecked
CHEMBL612545
 EC50 7.51 7.51 31.0 1
5'-AMP-activated protein kinase
CHEMBL4524004
 EC50 6.86 6.86 137.0 1
HepG2
CHEMBL395
 IC50 5.55 5.415 2817.0 2
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.33 5.33 4700.0 1
A549
CHEMBL392
 IC50 4.71 4.71 19500.0 1
L02
CHEMBL4296457
 IC50 4.59 4.59 25900.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 256.0 ng.hr.mL-1 Rattus norvegicus
AUC 1339.0 ng.hr/Kg Mus musculus
AUC 2429.0 ng.hr/Kg Mus musculus
AUC 1283.0 ng.hr/Kg Mus musculus
AUC 937.0 ng.hr/Kg Mus musculus
AUC 256.0 ng.hr.mL-1 Rattus norvegicus
CL 150.0 mL.min-1.kg-1 Rattus norvegicus
CL 150.0 mL.min-1.kg-1 Rattus norvegicus
F 46.0 % Rattus norvegicus
T1/2 1.183 hr Homo sapiens
T1/2 2.7 hr Rattus norvegicus
T1/2 1.177 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
AMP-activated protein kinase, AMPK IC50 = 2.82 nM 8.55 Activation of AMPK in human HepG2 cells assessed as reduction in mitochondrial A... 35973281
AMP-activated protein kinase, AMPK EC50 = 30.0 nM 7.52 Activation of AMPK in human HepG2 cells using ACC as substrate after 2 hrs 25122135
AMP-activated protein kinase, AMPK EC50 = 31.0 nM 7.51 Activation of AMPK in human HepG2 cells assessed as increase in ACC phosphorylat... 35973281
Unchecked EC50 = 31.0 nM 7.51 Activation of AMPK in human HepG2 cells incubated for 2 hrs 38079537
5'-AMP-activated protein kinase EC50 = 137.0 nM 6.86 Activation of AMPK in mouse C2C12 cells incubated for 2 hrs 38079537
AMP-activated protein kinase, AMPK EC50 = 230.0 nM 6.64 Activation of AMPK in human C2C12 cells using ACC as substrate after 2 hrs 25122135
HepG2 IC50 = 2817.0 nM 5.55 Inhibition of mitochondrial function in human HepG2 cells assessed as reduction ... 38079537
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 4700.0 nM 5.33 Inhibition of hERG 38079537
HepG2 IC50 = 5200.0 nM 5.28 Cytotoxicity against human HepG2 cells after 72 hrs by MTT assay 30001917
A549 IC50 = 19500.0 nM 4.71 Cytotoxicity against human A549 cells after 72 hrs by MTT assay 30001917
L02 IC50 = 25900.0 nM 4.59 Cytotoxicity against human L02 cells after 72 hrs by MTT assay 30001917

Literature References

PubMed DOI Target Context # Activities
35973281 10.1016/j.bmc.2022.116951 ADMET 14
35973281 10.1016/j.bmc.2022.116951 Mus musculus 4
38079537 10.1021/acs.jmedchem.3c01983 ADMET 3
38079537 10.1021/acs.jmedchem.3c01983 Cytochrome P450 3A4 2
32512485 10.1016/j.ejmech.2020.112466 Unchecked 2
35973281 10.1016/j.bmc.2022.116951 AMP-activated protein kinase, AMPK 2
35973281 10.1016/j.bmc.2022.116951 Cytochrome P450 3A4 2
25122135 10.1021/jm401994c AMP-activated protein kinase, AMPK 2
35973281 10.1016/j.bmc.2022.116951 Voltage-gated inwardly rectifying potassium channel KCNH2 1
38079537 10.1021/acs.jmedchem.3c01983 No relevant target 1
38079537 10.1021/acs.jmedchem.3c01983 HepG2 1
38079537 10.1021/acs.jmedchem.3c01983 5'-AMP-activated protein kinase 1
38079537 10.1021/acs.jmedchem.3c01983 Unchecked 1
38079537 10.1021/acs.jmedchem.3c01983 Voltage-gated inwardly rectifying potassium channel KCNH2 1
35973281 10.1016/j.bmc.2022.116951 NCI-H1299 1
35973281 10.1016/j.bmc.2022.116951 A549 1
30001917 10.1016/j.bmcl.2018.07.006 HepG2 1
30001917 10.1016/j.bmcl.2018.07.006 L02 1
30001917 10.1016/j.bmcl.2018.07.006 A549 1
30001917 10.1016/j.bmcl.2018.07.006 Unchecked 1

Data from ChEMBL 36 via Core Engine