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Compound Detail

CHEMBL1242297

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Cc1cc(-c2ccc(/C=C3\S/C(=N\c4ccc(Cl)c(C(=O)O)c4)NC3=O)o2)c([N+](=O)[O-])cc1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1242297
Phase Preclinical
Structure Type MOL
InChI Key RTHRCOIONCZINZ-JMIUGGIZSA-N
4
Targets
9
Activities
1
Assay Types
0
PK Parameters
10
Publications
0
Known Names

Molecular Properties

497.9
MW (Da)
5.71
ALogP
7
HBA
2
HBD
135.0
PSA (Ų)
0.26
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H16ClN3O6S
MW 497.92
Aromatic Rings 3
Heavy Atoms 34
NP-Likeness -1.62

Activity Summary

EC50 9 meas. best 6.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1
CHEMBL2111345
 EC50 6.52 6.52 300.0 2
AMPK alpha2/beta1/gamma1
CHEMBL3038455
 EC50 6.52 6.52 300.0 1
5'-AMP-activated protein kinase catalytic subunit alpha-1
CHEMBL4045
 EC50 5.1 5.0675 8000.0 4
5'-AMP-activated protein kinase catalytic subunit alpha-2
CHEMBL2116
 EC50 4.92 4.92 12000.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
AMPK alpha2/beta1/gamma1 EC50 = 300.0 nM 6.52 Activation of recombinant AMPK alpha2beta1gamma1 (unknown origin) after 2 hrs by... 24900695
AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1 EC50 = 300.0 nM 6.52 Activation of human recombinant AMPK alpha1/beta1/gamma1 expressed in Escherichi... 27727125
AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1 EC50 = 300.0 nM 6.52 Activation of recombinant human AMPK alpha1/beta1/gamma1expressed in Escherichia... 29211480
5'-AMP-activated protein kinase catalytic subunit alpha-1 EC50 = 8000.0 nM 5.1 Activation of human recombinant AMPK alpha1 subunit 25122135
5'-AMP-activated protein kinase catalytic subunit alpha-1 EC50 = 8000.0 nM 5.1 Activation of human recombinant AMPK alpha1 (1 to 394 residues) expressed in Esc... 27727125
5'-AMP-activated protein kinase catalytic subunit alpha-1 EC50 = 9000.0 nM 5.05 Activation of human AMPK alpha1 (1 to 394) expressed in African green monkey COS... 24900695
5'-AMP-activated protein kinase catalytic subunit alpha-1 EC50 = 9600.0 nM 5.02 Activation of recombinant AMPK alpha1 (1 to 394) (unknown origin) after 2 hrs by... 24900695
5'-AMP-activated protein kinase catalytic subunit alpha-2 EC50 = 12000.0 nM 4.92 Activation of human AMPK alpha2 (1 to 398) expressed in African green monkey COS... 24900695
5'-AMP-activated protein kinase catalytic subunit alpha-2 EC50 = 12000.0 nM 4.92 Activation of human recombinant AMPK alpha2 expressed in Escherichia coli BL21-C... 27727125

Literature References

PubMed DOI Target Context # Activities
20154666 10.1038/nchembio.318 Unchecked 3
24900695 10.1021/ml400028q AMPK alpha2/beta1/gamma1 2
24900695 10.1021/ml400028q 5'-AMP-activated protein kinase catalytic subunit alpha-1 2
24900695 10.1021/ml400028q 5'-AMP-activated protein kinase catalytic subunit alpha-2 1
- 10.6019/CHEMBL3301361 No relevant target 1
25122135 10.1021/jm401994c 5'-AMP-activated protein kinase catalytic subunit alpha-1 1
27727125 10.1016/j.bmcl.2016.09.065 AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1 1
27727125 10.1016/j.bmcl.2016.09.065 5'-AMP-activated protein kinase catalytic subunit alpha-2 1
27727125 10.1016/j.bmcl.2016.09.065 5'-AMP-activated protein kinase catalytic subunit alpha-1 1
29211480 10.1021/acs.jmedchem.7b01019 AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1 1

Data from ChEMBL 36 via Core Engine