Compound Detail

CHEMBL186453

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N[C@]1(C(=O)O)[C@H]2[C@@H](C[C@H]1OCc1ccc(Cl)c(Cl)c1)[C@]2(F)C(=O)O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL186453
Phase	Preclinical
Structure Type	MOL
InChI Key	LFAGGDAZZKUVKO-JAGWWQSPSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

378.2

MW (Da)

2.10

ALogP

HBA

HBD

109.8

PSA (Å²)

0.72

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C15H14Cl2FNO5
MW	378.18
Aromatic Rings	1
Heavy Atoms	24
NP-Likeness	0.35

Activity Summary

IC50 8 meas. best 7.7

Ki 5 meas. best 8.66

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Metabotropic glutamate receptor 2 CHEMBL5137	Ki	8.66	8.66	2.2	1
Metabotropic glutamate receptor 2 CHEMBL2851	Ki	8.62	8.62	2.4	1
Metabotropic glutamate receptor 3 CHEMBL2888	Ki	8.35	8.35	4.5	1
Metabotropic glutamate receptor 3 CHEMBL3067	Ki	8.35	8.35	4.5	1
Metabotropic glutamate receptor 2 CHEMBL2851	IC50	7.7	7.7	20.0	1
Metabotropic glutamate receptor 2 CHEMBL5137	IC50	7.7	7.7	20.0	1
Metabotropic glutamate receptor 3 CHEMBL2888	IC50	7.62	7.62	24.0	1
Metabotropic glutamate receptor 3 CHEMBL3067	IC50	7.62	7.62	24.0	1
Metabotropic glutamate receptor 7 CHEMBL3879	Ki	6.18	6.18	664.0	1
Metabotropic glutamate receptor 4 CHEMBL2787	IC50	5.76	5.76	1740.0	1
Metabotropic glutamate receptor 6 CHEMBL3842	IC50	5.69	5.69	2060.0	1
Metabotropic glutamate receptor 5 CHEMBL2564	IC50	4.93	4.93	11700.0	1
Metabotropic glutamate receptor 1 CHEMBL4477	IC50	4.03	4.03	93300.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
Cmax	565.87	nM	Rattus norvegicus
Cmax	2464.43	nM	Rattus norvegicus
Cmax	7826.96	nM	Rattus norvegicus
Cmax	1300.97	nM	Rattus norvegicus
Cmax	34.9	nM	Rattus norvegicus
T1/2	2.15	hr	Rattus norvegicus
T1/2	2.76	hr	Rattus norvegicus
T1/2	2.77	hr	Rattus norvegicus
T1/2	2.3	hr	Rattus norvegicus
T1/2	10.9	hr	Rattus norvegicus
Tmax	2.0	hr	Rattus norvegicus
Tmax	2.7	hr	Rattus norvegicus
Tmax	3.3	hr	Rattus norvegicus
Tmax	6.0	hr	Rattus norvegicus
Tmax	6.0	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Metabotropic glutamate receptor 2	Ki	=	2.2	nM	8.66	Binding affinity to mGLUR2	22318160
Metabotropic glutamate receptor 2	Ki	=	2.38	nM	8.62	Binding affinity towards metabotropic glutamate receptor 2 of rat expressed in C...	15317467
Metabotropic glutamate receptor 3	Ki	=	4.46	nM	8.35	Binding affinity towards metabotropic glutamate receptor 3 of rat expressed in C...	15317467
Metabotropic glutamate receptor 3	Ki	=	4.5	nM	8.35	Binding affinity to mGLUR3	22318160
Metabotropic glutamate receptor 2	IC50	=	20.0	nM	7.7	Concentration required to inhibit metabotropic glutamate receptor 2 activity of ...	15317467
Metabotropic glutamate receptor 2	IC50	=	20.0	nM	7.7	Antagonist activity at mGLUR2 expressed in CHO cells assessed as inhibition of g...	22318160
Metabotropic glutamate receptor 3	IC50	=	24.0	nM	7.62	Concentration required to inhibit metabotropic glutamate receptor 3 activity of ...	15317467
Metabotropic glutamate receptor 3	IC50	=	24.0	nM	7.62	Antagonist activity at mGLUR3 expressed in CHO cells assessed as inhibition of g...	22318160
Metabotropic glutamate receptor 7	Ki	=	664.0	nM	6.18	Binding affinity towards metabotropic glutamate receptor 7 of rat expressed in C...	15317467
Metabotropic glutamate receptor 4	IC50	=	1740.0	nM	5.76	Concentration required to inhibit metabotropic glutamate receptor 4 activity of ...	15317467
Metabotropic glutamate receptor 6	IC50	=	2060.0	nM	5.69	Concentration required to inhibit metabotropic glutamate receptor 6 activity of ...	15317467
Metabotropic glutamate receptor 5	IC50	=	11700.0	nM	4.93	Concentration required to inhibit metabotropic glutamate receptor 5 activity of ...	15317467
Metabotropic glutamate receptor 1	IC50	=	93300.0	nM	4.03	Concentration required to inhibit metabotropic glutamate receptor 1 activity of ...	15317467

Literature References

PubMed	DOI	Target Context	# Activities
15317467	10.1021/jm0400294	ADMET	23
15317467	10.1021/jm0400294	Metabotropic glutamate receptor 2	3
15317467	10.1021/jm0400294	Metabotropic glutamate receptor 3	3
15317467	10.1021/jm0400294	Metabotropic glutamate receptor 6	2
15317467	10.1021/jm0400294	Metabotropic glutamate receptor 1	2
15317467	10.1021/jm0400294	Metabotropic glutamate receptor 5	2
22318160	10.1016/j.bmcl.2012.01.039	Metabotropic glutamate receptor 3	2
22318160	10.1016/j.bmcl.2012.01.039	Metabotropic glutamate receptor 2	2
15317467	10.1021/jm0400294	Metabotropic glutamate receptor 7	1
15317467	10.1021/jm0400294	Metabotropic glutamate receptor 4	1

Data from ChEMBL 36 via Core Engine