Compound Detail

CHEMBL1518572

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CCOC(=O)c1ncc2[nH]c3ccc(OCc4ccccc4)cc3c2c1COC

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL1518572
Phase	Preclinical
Structure Type	MOL
InChI Key	ALBKMJDFBZVHAK-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

390.4

MW (Da)

4.62

ALogP

HBA

HBD

73.4

PSA (Å²)

0.47

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C23H22N2O4
MW	390.44
Aromatic Rings	4
Heavy Atoms	29
NP-Likeness	-0.31

Activity Summary

Ki 12 meas. best 8.4

IC50 8 meas. best 9.3

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
GABA-A receptor; anion channel CHEMBL2093872	IC50	9.3	9.3	0.5	1
GABA-A receptor; anion channel CHEMBL1907607	IC50	9.0	8.86	1.0	5
Unchecked CHEMBL612545	IC50	9.0	9.0	1.0	1
Gamma-aminobutyric acid receptor subunit alpha-1 CHEMBL1962	Ki	8.4	8.4	4.0	1
Gamma-aminobutyric acid receptor subunit alpha-2 CHEMBL4956	Ki	8.4	8.4	4.0	1
GABA-A receptor; alpha-1/beta-3/gamma-2 CHEMBL2094121	Ki	8.39	8.39	4.1	2
GABA-A receptor; alpha-2/beta-3/gamma-2 CHEMBL2094130	Ki	8.38	8.38	4.2	2
GABA-A receptor; alpha-5/beta-3/gamma-2 CHEMBL2094122	Ki	8.35	8.35	4.5	2
Gamma-aminobutyric acid receptor subunit alpha-5 CHEMBL5112	Ki	8.3	8.3	5.0	1
GABA-A receptor; alpha-3/beta-3/gamma-2 CHEMBL2094120	Ki	8.22	8.22	6.0	2
Gamma-aminobutyric acid receptor subunit alpha-3 CHEMBL3026	Ki	8.22	8.22	6.0	1
SARS-CoV-2 CHEMBL4303835	IC50	5.87	5.87	1340.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
GABA-A receptor; anion channel	IC50	=	0.5	nM	9.3	Displacement of [3H]flunitrazepam from GABAA (unknown origin ) receptor by radio...	33528252
GABA-A receptor; anion channel	IC50	=	1.0	nM	9.0	Effect on [3H]flunitrazepam binding to Benzodiazepine receptor	1674542
GABA-A receptor; anion channel	IC50	=	1.0	nM	9.0	Displacement of [3H]flunitrazepam from GABA-A Benzodiazepine receptor of rat bra...	9651158
GABA-A receptor; anion channel	IC50	=	1.0	nM	9.0	Inhibition of [3H]-Ro- 15-1788 binding to GABA-A benzodiazepine receptor in rat ...	7699711
GABA-A receptor; anion channel	IC50	=	1.0	nM	9.0	In vitro inhibition of [3H]flunitrazepam binding to GABA-A Benzodiazepine recept...	1968513
Unchecked	IC50	=	1.0	nM	9.0	Binding affinity to GABA-A receptor benzodiazepine site (unknown origin)	-
Gamma-aminobutyric acid receptor subunit alpha-1	Ki	=	4.0	nM	8.4	Binding affinity to human recombinant GABAA alpha1 receptor assessed as inhibiti...	33528252
Gamma-aminobutyric acid receptor subunit alpha-2	Ki	=	4.0	nM	8.4	Binding affinity to human recombinant GABAA alpha2 receptor assessed as inhibiti...	33528252
GABA-A receptor; alpha-1/beta-3/gamma-2	Ki	=	4.1	nM	8.39	Binding affinity for human recombinant gamma-aminobutyric-acid (GABA) A receptor...	10633039
GABA-A receptor; alpha-1/beta-3/gamma-2	Ki	=	4.1	nM	8.39	Binding affinity measured using LtK- cell membranes expressing GABA alpha-1-beta...	9651158
GABA-A receptor; alpha-2/beta-3/gamma-2	Ki	=	4.2	nM	8.38	Binding affinity to human recombinant gamma-aminobutyric-acid (GABA) A receptor ...	10633039
GABA-A receptor; alpha-2/beta-3/gamma-2	Ki	=	4.2	nM	8.38	Binding affinity measured using LtK- cell membranes expressing GABA alpha-2-beta...	9651158
GABA-A receptor; alpha-5/beta-3/gamma-2	Ki	=	4.5	nM	8.35	Binding affinity for human recombinant gamma-aminobutyric-acid (GABA) A receptor...	10633039
GABA-A receptor; alpha-5/beta-3/gamma-2	Ki	=	4.5	nM	8.35	Binding affinity measured using LtK- cell membranes expressing Gamma-aminobutyri...	9651158
GABA-A receptor; anion channel	IC50	=	5.0	nM	8.3	In vitro inhibitory concentration of compound against benzodiazepine receptor fr...	8145224
Gamma-aminobutyric acid receptor subunit alpha-5	Ki	=	5.0	nM	8.3	Binding affinity to human recombinant GABAA alpha5 receptor assessed as inhibiti...	33528252
GABA-A receptor; alpha-3/beta-3/gamma-2	Ki	=	6.0	nM	8.22	Binding affinity for human recombinant gamma-aminobutyric-acid (GABA) A receptor...	10633039
GABA-A receptor; alpha-3/beta-3/gamma-2	Ki	=	6.0	nM	8.22	Binding affinity measured using LtK- cell membranes expressing GABA alpha-3-beta...	9651158
Gamma-aminobutyric acid receptor subunit alpha-3	Ki	=	6.0	nM	8.22	Binding affinity to human recombinant GABAA alpha3 receptor assessed as inhibiti...	33528252
SARS-CoV-2	IC50	=	1340.0	nM	5.87	Determination of IC50 values for inhibition of SARS-CoV-2 induced cytotoxicity o...	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
-	10.6019/CHEMBL4808148	Histone deacetylase 6	2
-	10.21203/rs.3.rs-23951/v1	SARS-CoV-2	2
9651158	10.1021/jm970460b	GABA-A receptor; alpha-5/beta-3/gamma-2	1
-	10.1007/s00044-008-9111-6	Unchecked	1
1968513	10.1021/jm00165a028	No relevant target	1
33528252	10.1021/acs.jmedchem.0c01887	Gamma-aminobutyric acid receptor subunit alpha-6	1
1968513	10.1021/jm00165a028	GABA-A receptor; anion channel	1
7699711	10.1021/jm00006a014	GABA-A receptor; anion channel	1
8145224	10.1021/jm00032a007	GABA-A receptor; anion channel	1
9651158	10.1021/jm970460b	GABA-A receptor; alpha-6/beta-3/gamma-2	1
1674542	10.1021/jm00109a035	GABA-A receptor; anion channel	1
9651158	10.1021/jm970460b	GABA-A receptor; alpha-3/beta-3/gamma-2	1
9651158	10.1021/jm970460b	GABA-A receptor; alpha-2/beta-3/gamma-2	1
9651158	10.1021/jm970460b	GABA-A receptor; alpha-1/beta-3/gamma-2	1
9651158	10.1021/jm970460b	GABA-A receptor; anion channel	1
10633039	10.1021/jm990341r	GABA-A receptor; alpha-6/beta-3/gamma-2	1
10633039	10.1021/jm990341r	GABA-A receptor; alpha-5/beta-3/gamma-2	1
10633039	10.1021/jm990341r	GABA-A receptor; alpha-3/beta-3/gamma-2	1
10633039	10.1021/jm990341r	GABA-A receptor; alpha-2/beta-3/gamma-2	1

Data from ChEMBL 36 via Core Engine