Compound Detail

CHEMBL4082745

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Cc1ccc(Oc2nc3cc(-c4ccc(-c5ccccc5)cc4)c(Cl)cc3[nH]2)cc1C(=O)O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL4082745
Phase	Preclinical
Structure Type	MOL
InChI Key	FIKQZQDYGXAUHC-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

454.9

MW (Da)

7.35

ALogP

HBA

HBD

75.2

PSA (Å²)

0.29

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C27H19ClN2O3
MW	454.91
Aromatic Rings	5
Heavy Atoms	33
NP-Likeness	-0.65

Activity Summary

EC50 14 meas. best 8.1

IC50 2 meas. best 5.75

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	8.1	8.1	8.0	1
AMPK alpha2/beta1/gamma1 CHEMBL3038455	EC50	8.1	8.1	8.0	1
Unchecked CHEMBL612545	EC50	8.1	8.1	8.0	1
AMPK alpha1/beta1/gamma3 CHEMBL3038452	EC50	7.72	7.72	19.0	1
AMPK alpha1/beta1/gamma2 CHEMBL3038451	EC50	7.68	7.68	21.0	1
5'-AMP-activated protein kinase catalytic subunit alpha-2/beta-1/gamma-2 CHEMBL3885504	EC50	7.66	7.66	22.0	1
AMP-activated protein kinase alpha-2/beta-2/gamma-2 CHEMBL4106158	EC50	7.64	7.64	23.0	1
AMP-activated protein kinase alpha-2/beta-1/gamma-3 CHEMBL4106159	EC50	7.58	7.58	26.0	1
AMPK alpha2/beta2/gamma3 CHEMBL3038457	EC50	7.46	7.46	35.0	1
AMPK alpha2/beta2/gamma1 CHEMBL3038456	EC50	7.41	7.41	39.0	1
AMPK alpha1/beta2/gamma1 CHEMBL3038453	EC50	7.4	7.4	40.0	1
Prkaa1/Prkab2/Prkag1 CHEMBL4523617	EC50	7.4	7.4	40.0	1
AMP-activated protein kinase alpha-1/beta-2/gamma-2 CHEMBL4106163	EC50	6.93	6.93	118.0	1
Transcription factor Dp-2 CHEMBL4105986	IC50	5.75	5.75	1800.0	1
AMP-activated protein kinase alpha-1/beta-2/gamma-3 CHEMBL4106162	EC50	5.54	5.54	2860.0	1
Unchecked CHEMBL612545	IC50	4.96	4.96	11000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	6.8	mL.min-1.kg-1	Mus musculus
CL	5.0	mL.min-1.kg-1	Rattus norvegicus
CL	13.0	mL.min-1.kg-1	Canis lupus familiaris
Cmax	2000.0	nM	Mus musculus
Cmax	4800.0	nM	Rattus norvegicus
Cmax	1100.0	nM	Canis lupus familiaris
F	8.4	%	Mus musculus
F	25.0	%	Rattus norvegicus
F	78.0	%	Canis lupus familiaris
Fu	0.2	-	Homo sapiens
T1/2	2.1	hr	Mus musculus
T1/2	1.7	hr	Rattus norvegicus
T1/2	2.4	hr	Canis lupus familiaris
Tmax	1.0	hr	Mus musculus
Tmax	0.5	hr	Rattus norvegicus
Tmax	0.5	hr	Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
AMPK alpha2/beta1/gamma1	EC50	=	8.0	nM	8.1	Agonist activity at human recombinant phosphorylated AMPK complex 7 alpha2/beta1...	29035567
AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1	EC50	=	8.0	nM	8.1	Agonist activity at human recombinant phosphorylated AMPK complex 1 alpha1/beta1...	29035567
Unchecked	EC50	=	8.0	nM	8.1	Activation of rat hepatocytes AMPK alpha1/beta1/gamma1 expressed in baculovirus ...	31930920
AMPK alpha1/beta1/gamma3	EC50	=	19.0	nM	7.72	Agonist activity at human recombinant phosphorylated AMPK complex 3 alpha1/beta1...	29035567
AMPK alpha1/beta1/gamma2	EC50	=	21.0	nM	7.68	Agonist activity at human recombinant phosphorylated AMPK complex 2 alpha1/beta1...	29035567
5'-AMP-activated protein kinase catalytic subunit alpha-2/beta-1/gamma-2	EC50	=	22.0	nM	7.66	Agonist activity at human recombinant phosphorylated AMPK complex 8 alpha2/beta1...	29035567
AMP-activated protein kinase alpha-2/beta-2/gamma-2	EC50	=	23.0	nM	7.64	Agonist activity at human recombinant phosphorylated AMPK complex 11 alpha2/beta...	29035567
AMP-activated protein kinase alpha-2/beta-1/gamma-3	EC50	=	26.0	nM	7.58	Agonist activity at human recombinant phosphorylated AMPK complex 9 alpha2/beta1...	29035567
AMPK alpha2/beta2/gamma3	EC50	=	35.0	nM	7.46	Agonist activity at human recombinant phosphorylated AMPK complex 12 alpha2/beta...	29035567
AMPK alpha2/beta2/gamma1	EC50	=	39.0	nM	7.41	Agonist activity at human recombinant phosphorylated AMPK complex 10 alpha2/beta...	29035567
AMPK alpha1/beta2/gamma1	EC50	=	40.0	nM	7.4	Agonist activity at human recombinant phosphorylated AMPK complex 4 alpha1/beta2...	29035567
Prkaa1/Prkab2/Prkag1	EC50	=	40.0	nM	7.4	Activation of rat hepatocytes AMPK alpha1/beta2/gamma1 expressed in baculovirus ...	31930920
AMP-activated protein kinase alpha-1/beta-2/gamma-2	EC50	=	118.0	nM	6.93	Agonist activity at human recombinant phosphorylated AMPK complex 5 alpha1/beta2...	29035567
Transcription factor Dp-2	IC50	=	1800.0	nM	5.75	Binding affinity to DP2 receptor (unknown origin)	29035567
AMP-activated protein kinase alpha-1/beta-2/gamma-3	EC50	=	2860.0	nM	5.54	Agonist activity at human recombinant phosphorylated AMPK complex 6 alpha1/beta2...	29035567
Unchecked	IC50	=	11000.0	nM	4.96	Activation of AMPK in mouse 3T3L1 cells assessed as inhibition of de novo lipoge...	29348809

Literature References

PubMed	DOI	Target Context	# Activities
29035567	10.1021/acs.jmedchem.7b01344	Mus musculus	25
29035567	10.1021/acs.jmedchem.7b01344	Canis familiaris	7
29035567	10.1021/acs.jmedchem.7b01344	Rattus norvegicus	7
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
29348809	10.1021/acsmedchemlett.7b00417	ADMET	3
29035567	10.1021/acs.jmedchem.7b01344	AMPK alpha2/beta1/gamma1	3
29035567	10.1021/acs.jmedchem.7b01344	AMP-activated protein kinase alpha-2/beta-2/gamma-2	2
29035567	10.1021/acs.jmedchem.7b01344	Transcription factor Dp-2	2
29348809	10.1021/acsmedchemlett.7b00417	AMPK alpha2/beta2/gamma1	2
29035567	10.1021/acs.jmedchem.7b01344	Cytochrome P450 3A4	2
29035567	10.1021/acs.jmedchem.7b01344	AMPK alpha2/beta2/gamma3	2
29035567	10.1021/acs.jmedchem.7b01344	AMPK alpha2/beta2/gamma1	2
29035567	10.1021/acs.jmedchem.7b01344	AMP-activated protein kinase alpha-2/beta-1/gamma-3	2
29035567	10.1021/acs.jmedchem.7b01344	5'-AMP-activated protein kinase catalytic subunit alpha-2/beta-1/gamma-2	2
29035567	10.1021/acs.jmedchem.7b01344	AMP-activated protein kinase alpha-1/beta-2/gamma-3	2
29035567	10.1021/acs.jmedchem.7b01344	AMP-activated protein kinase alpha-1/beta-2/gamma-2	2
29035567	10.1021/acs.jmedchem.7b01344	AMPK alpha1/beta2/gamma1	2
29035567	10.1021/acs.jmedchem.7b01344	AMPK alpha1/beta1/gamma3	2
29035567	10.1021/acs.jmedchem.7b01344	AMPK alpha1/beta1/gamma2	2
29035567	10.1021/acs.jmedchem.7b01344	AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1	2

Data from ChEMBL 36 via Core Engine