Compound Detail

CHEMBL432038

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N[C@](CC1c2ccccc2Oc2ccccc21)(C(=O)O)[C@H]1C[C@@H]1C(=O)O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL432038
Phase	Preclinical
Structure Type	MOL
InChI Key	VLZBRVJVCCNPRJ-KPHUOKFYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

353.4

MW (Da)

2.82

ALogP

HBA

HBD

109.8

PSA (Å²)

0.76

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C20H19NO5
MW	353.37
Aromatic Rings	2
Heavy Atoms	26
NP-Likeness	0.32

Activity Summary

IC50 28 meas. best 8.55

Ki 12 meas. best 8.89

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Metabotropic glutamate receptor 3 CHEMBL2888	Ki	8.89	8.37	1.3	2
Metabotropic glutamate receptor 3 CHEMBL2888	IC50	8.55	8.1275	2.8	4
Unchecked CHEMBL612545	IC50	8.54	8.54	2.9	1
Metabotropic glutamate receptor 2 CHEMBL5137	IC50	8.54	7.7067	2.9	6
Metabotropic glutamate receptor 3 CHEMBL3067	Ki	8.52	8.52	3.0	1
Metabotropic glutamate receptor 2 CHEMBL2851	Ki	8.5	8.5	3.1	1
Metabotropic glutamate receptor 2 CHEMBL5137	Ki	8.37	8.025	4.3	2
Rattus norvegicus CHEMBL376	IC50	8.0	8.0	10.0	1
Metabotropic glutamate receptor 3 CHEMBL3067	IC50	7.85	7.8167	14.2	3
Metabotropic glutamate receptor 2 CHEMBL2851	IC50	7.63	7.165	23.2	2
Metabotropic glutamate receptor 7 CHEMBL3879	Ki	6.96	6.96	110.0	1
Metabotropic glutamate receptor 8 CHEMBL3228	Ki	6.77	6.77	170.0	1
Metabotropic glutamate receptor 8 CHEMBL3228	IC50	6.77	6.77	170.0	1
Metabotropic glutamate receptor 7 CHEMBL3879	IC50	6.72	6.72	190.0	1
Metabotropic glutamate receptor 7 CHEMBL3777	IC50	6.0	5.9	990.0	2
Metabotropic glutamate receptor 7 CHEMBL3777	Ki	6.0	6.0	990.0	1
Metabotropic glutamate receptor 6 CHEMBL3842	IC50	5.94	5.94	1140.0	1
Metabotropic glutamate receptor 4 CHEMBL2787	IC50	5.58	5.58	2650.0	1
Metabotropic glutamate receptor 1 CHEMBL3772	Ki	5.17	5.17	6800.0	1
Metabotropic glutamate receptor 1 CHEMBL3772	IC50	5.11	5.11	7800.0	1
Metabotropic glutamate receptor 5 CHEMBL3227	Ki	5.09	5.09	8200.0	1
Metabotropic glutamate receptor 5 CHEMBL3227	IC50	5.09	5.09	8200.0	1
Metabotropic glutamate receptor 1 CHEMBL4477	IC50	5.05	5.05	8990.0	1
Metabotropic glutamate receptor 5 CHEMBL2564	IC50	4.94	4.94	11400.0	1
Metabotropic glutamate receptor 4 CHEMBL2736	Ki	4.66	4.66	22000.0	1
Metabotropic glutamate receptor 4 CHEMBL2736	IC50	4.66	4.66	22000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	8374.0	ng.hr.mL-1	Rattus norvegicus
AUC	12727.0	ng.hr.mL-1	Rattus norvegicus
AUC	217.4	ng.hr.mL-1	Rattus norvegicus
AUC	1378.0	ng.hr.mL-1	Rattus norvegicus
AUC	8399.0	ng.hr.mL-1	Rattus norvegicus
AUC	12752.0	ng.hr.mL-1	Rattus norvegicus
AUC	283.9	ng.hr.mL-1	Rattus norvegicus
AUC	1663.0	ng.hr.mL-1	Rattus norvegicus
AUC	701.4	ng.hr.mL-1	Rattus norvegicus
AUC	773.5	ng.hr.mL-1	Rattus norvegicus
AUC	26.4	ng.hr.mL-1	Rattus norvegicus
AUC	120.4	ng.hr.mL-1	Rattus norvegicus
AUC	1837.0	ng.hr.mL-1	Rattus norvegicus
AUC	1794.0	ng.hr.mL-1	Rattus norvegicus
AUC	-	ng.hr.mL-1	Rattus norvegicus
AUC	-	ng.hr.mL-1	Rattus norvegicus
AUC	284.0	ng.hr.mL-1	Rattus norvegicus
CL	19.83	mL.min-1.kg-1	Rattus norvegicus
CL	13.0	mL.min-1.kg-1	Rattus norvegicus
Cmax	40382.6	nM	Rattus norvegicus
Cmax	34015.34	nM	Rattus norvegicus
Cmax	181.4	nM	Rattus norvegicus
Cmax	1345.05	nM	Rattus norvegicus
Cmax	243.3	ng g-1	Rattus norvegicus
Cmax	245.5	ng g-1	Rattus norvegicus
Cmax	7.4	ng g-1	Rattus norvegicus
Cmax	30.0	ng g-1	Rattus norvegicus
Cmax	181.4	nM	Rattus norvegicus
F	-	%	Rattus norvegicus
F	152.0	%	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Metabotropic glutamate receptor 3	Ki	=	1.3	nM	8.89	Displacement of [3H]-LY459477 from recombinant human mGlu3 receptor expressed in...	28002967
Metabotropic glutamate receptor 3	IC50	=	2.8	nM	8.55	Antagonist activity at human recombinant mGlu3 stably expressed in golden hamste...	28002967
Unchecked	IC50	=	2.9	nM	8.54	Binding affinity for Group II Metabotropic glutamate receptor was measured using...	9464367
Metabotropic glutamate receptor 2	IC50	=	2.9	nM	8.54	Displacement of [3H]-MGS0008 from mGluR2 expressed in CHO cells	18348906
Metabotropic glutamate receptor 3	Ki	=	3.04	nM	8.52	Binding affinity towards metabotropic glutamate receptor 3 of rat expressed in C...	15317467
Metabotropic glutamate receptor 2	Ki	=	3.13	nM	8.5	Binding affinity towards metabotropic glutamate receptor 2 of rat expressed in C...	15317467
Metabotropic glutamate receptor 2	Ki	=	4.3	nM	8.37	Displacement of [3H]-LY459477 from recombinant human mGlu2 receptor expressed in...	28002967
Metabotropic glutamate receptor 2	IC50	=	7.8	nM	8.11	Antagonist activity at human recombinant mGlu2 receptor stably expressed in gold...	28002967
Metabotropic glutamate receptor 3	IC50	=	7.7	nM	8.11	Antagonist activity at human recombinant mGlu3 receptor stably expressed in gold...	28002967
Rattus norvegicus	IC50	=	10.0	nM	8.0	Antagonistic activity was evaluated by using ACPD sensitive [3H]-glutamate bindi...	9873635
Metabotropic glutamate receptor 3	IC50	=	10.0	nM	8.0	Effect on 1S,3R-ACPD-induced inhibition of forskolin stimulated cyclic-AMP in RG...	9464367
Metabotropic glutamate receptor 3	Ki	=	14.0	nM	7.85	Agonist potency against cloned Metabotropic glutamate receptor 3 (mGluR-3).	10893301
Metabotropic glutamate receptor 3	IC50	=	14.0	nM	7.85	Antagonist activity at human mGLUR3 expressed in RGT cells assessed as inhibitio...	22318160
Metabotropic glutamate receptor 3	IC50	=	14.2	nM	7.85	Concentration required to inhibit metabotropic glutamate receptor 3 activity of ...	15317467
Metabotropic glutamate receptor 3	IC50	=	16.0	nM	7.8	Antagonistic activity against metabotropic glutamate receptor 3 (mGluR3) was eva...	9873635
Metabotropic glutamate receptor 3	IC50	=	16.0	nM	7.8	Compound was evaluated for the inhibition of binding of [3H]glutamate against ra...	11720869
Metabotropic glutamate receptor 2	IC50	=	21.0	nM	7.68	Antagonist activity at human mGLUR2 expressed in RGT cells assessed as inhibitio...	22318160
Metabotropic glutamate receptor 2	Ki	=	21.0	nM	7.68	Antagonist potency against cloned Metabotropic glutamate receptor 2	10893301
Metabotropic glutamate receptor 2	IC50	=	23.0	nM	7.64	Effect on 1S,3R-ACPD-induced inhibition of forskolin stimulated cyclic-AMP in RG...	9464367
Metabotropic glutamate receptor 2	IC50	=	23.2	nM	7.63	Concentration required to inhibit metabotropic glutamate receptor 2 activity of ...	15317467

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL5724801	Fibroblast	304
-	10.6019/CHEMBL5724801	U2OS	304
-	10.6019/CHEMBL5058577	Fibroblast	304
-	10.6019/CHEMBL5058577	HEK-293T	304
-	10.6019/CHEMBL5058577	U2OS	304
-	10.6019/CHEMBL5724801	HEK-293T	304
9464367	10.1021/jm970498o	Rattus norvegicus	46
9464367	10.1021/jm970498o	ADMET	42
-	10.6019/CHEMBL5058564	Fibroblast	7
-	10.6019/CHEMBL5058564	HEK-293T	6
18348906	10.1016/j.bmc.2008.02.066	Rattus norvegicus	4
15317467	10.1021/jm0400294	Metabotropic glutamate receptor 2	3
28002967	10.1021/acs.jmedchem.6b01119	Metabotropic glutamate receptor 2	3
-	10.6019/CHEMBL5058564	U2OS	3
28002967	10.1021/acs.jmedchem.6b01119	Metabotropic glutamate receptor 3	3
15317467	10.1021/jm0400294	Metabotropic glutamate receptor 3	3
-	10.6019/CHEMBL5209801	N-formyl peptide receptor 2	2
15317467	10.1021/jm0400294	Metabotropic glutamate receptor 1	2
15317467	10.1021/jm0400294	Metabotropic glutamate receptor 6	2
-	10.6019/CHEMBL5209801	Glucose-dependent insulinotropic receptor	2

Data from ChEMBL 36 via Core Engine