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Compound Detail

CHEMBL178942

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c1ccc(-c2nnc3c4c(c(OCc5ccccn5)nn23)C2CCC4CC2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL178942
Phase Preclinical
Structure Type MOL
InChI Key HRJQUDZTLASEPW-UHFFFAOYSA-N
8
Targets
18
Activities
1
Assay Types
1
PK Parameters
19
Publications
0
Known Names

Molecular Properties

383.4
MW (Da)
4.52
ALogP
6
HBA
0
HBD
65.2
PSA (Ų)
0.52
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H21N5O
MW 383.45
Aromatic Rings 4
Heavy Atoms 29
NP-Likeness -1.40

Activity Summary

Ki 18 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
GABA-A receptor; alpha-5/beta-3/gamma-2
CHEMBL2094122
 Ki 9.0 8.9467 1.0 3
GABA-A receptor; alpha-3/beta-3/gamma-2
CHEMBL2094120
 Ki 8.0 7.9325 10.0 4
Gamma-aminobutyric acid receptor subunit alpha-3
CHEMBL3026
 Ki 7.92 7.92 12.0 1
GABA-A receptor; alpha-2/beta-3/gamma-2
CHEMBL2094130
 Ki 7.66 7.6067 21.7 3
Gamma-aminobutyric acid receptor subunit alpha-2
CHEMBL4956
 Ki 7.58 7.58 26.0 1
Unchecked
CHEMBL612545
 Ki 7.58 7.58 26.0 1
GABA-A receptor; alpha-1/beta-3/gamma-2
CHEMBL2094121
 Ki 7.25 7.175 56.0 4
Gamma-aminobutyric acid receptor subunit alpha-1
CHEMBL1962
 Ki 7.15 7.15 71.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 33.0 % Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
GABA-A receptor; alpha-5/beta-3/gamma-2 Ki = 1.0 nM 9.0 Displacement of [3H]Ro-151788 from human recombinant GABAA alpha5 in combination... 16392789
GABA-A receptor; alpha-5/beta-3/gamma-2 Ki = 1.2 nM 8.92 Inhibition of [3H]Ro-151788 binding to recombinant human gamma-aminobutyric-acid... 15743180
GABA-A receptor; alpha-5/beta-3/gamma-2 Ki = 1.2 nM 8.92 Binding affinity to recombinant human GABA-A alpha5beta3gamma2 receptor expresse... 30928713
GABA-A receptor; alpha-3/beta-3/gamma-2 Ki = 10.0 nM 8.0 Displacement of [3H]Ro-151788 from human recombinant GABAA alpha3 in combination... 16392789
GABA-A receptor; alpha-3/beta-3/gamma-2 Ki = 12.0 nM 7.92 Displacement of [3H]Ro 15-1788 from human recombinant GABAA alpha-3-beta-3-gamma... 16279764
GABA-A receptor; alpha-3/beta-3/gamma-2 Ki = 12.0 nM 7.92 Binding affinity to recombinant human GABA-A alpha3beta3gamma2 receptor expresse... 30928713
Gamma-aminobutyric acid receptor subunit alpha-3 Ki = 12.0 nM 7.92 Binding affinity to GABA-A alpha3 (unknown origin) 31738537
GABA-A receptor; alpha-3/beta-3/gamma-2 Ki = 13.0 nM 7.89 Inhibition of [3H]Ro-151788 binding to recombinant human gamma-aminobutyric-acid... 15743180
GABA-A receptor; alpha-2/beta-3/gamma-2 Ki = 21.7 nM 7.66 Displacement of [3H]-Ro15-1788 from human recombinant GABAA alpha2 in combinatio... 16392789
GABA-A receptor; alpha-2/beta-3/gamma-2 Ki = 26.0 nM 7.58 Inhibition of [3H]Ro-151788 binding to recombinant human gamma-aminobutyric acid... 15743180
Gamma-aminobutyric acid receptor subunit alpha-2 Ki = 26.0 nM 7.58 Binding affinity to GABA-A alpha2 (unknown origin) 31738537
Unchecked Ki = 26.0 nM 7.58 Binding affinity to recombinant human GABA-A alpha2beta3gamma2 receptor expresse... 30928713
GABA-A receptor; alpha-2/beta-3/gamma-2 Ki = 26.0 nM 7.58 Displacement of [3H]Ro 15-1788 from human recombinant GABAA alpha-2-beta-3-gamma... 16279764
GABA-A receptor; alpha-1/beta-3/gamma-2 Ki = 56.0 nM 7.25 Displacement of [3H]-Ro15-1788 from human recombinant GABAA alpha1 in combinatio... 16392789
GABA-A receptor; alpha-1/beta-3/gamma-2 Ki = 71.0 nM 7.15 Inhibition of [3H]Ro-151788 binding to recombinant human gamma-aminobutyric-acid... 15743180
GABA-A receptor; alpha-1/beta-3/gamma-2 Ki = 71.0 nM 7.15 Displacement of [3H]Ro 15-1788 from human recombinant GABAA alpha-1-beta-3-gamma... 16279764
GABA-A receptor; alpha-1/beta-3/gamma-2 Ki = 71.0 nM 7.15 Binding affinity to recombinant human GABA-A alpha1beta3gamma2 receptor expresse... 30928713
Gamma-aminobutyric acid receptor subunit alpha-1 Ki = 71.0 nM 7.15 Binding affinity to GABA-A alpha1 (unknown origin) 31738537

Literature References

PubMed DOI Target Context # Activities
15743180 10.1021/jm040883v GABA-A receptor; alpha-2/beta-3/gamma-2 2
16279764 10.1021/jm058034a GABA-A receptor; alpha-3/beta-3/gamma-2 2
16279764 10.1021/jm058034a GABA-A receptor; alpha-2/beta-3/gamma-2 2
16279764 10.1021/jm058034a GABA-A receptor; alpha-1/beta-3/gamma-2 2
16392789 10.1021/jm051065l GABA-A receptor; alpha-5/beta-3/gamma-2 2
16392789 10.1021/jm051065l GABA-A receptor; alpha-3/beta-3/gamma-2 2
16392789 10.1021/jm051065l GABA-A receptor; alpha-1/beta-3/gamma-2 2
15743180 10.1021/jm040883v GABA-A receptor; alpha-5/beta-3/gamma-2 2
15743180 10.1021/jm040883v GABA-A receptor; alpha-3/beta-3/gamma-2 2
15743180 10.1021/jm040883v GABA-A receptor; alpha-1/beta-3/gamma-2 2
16392789 10.1021/jm051065l GABA-A receptor; alpha-2/beta-3/gamma-2 1
30928713 10.1016/j.ejmech.2019.03.043 ADMET 1
30928713 10.1016/j.ejmech.2019.03.043 GABA-A receptor; alpha-5/beta-3/gamma-2 1
30928713 10.1016/j.ejmech.2019.03.043 GABA-A receptor; alpha-3/beta-3/gamma-2 1
30928713 10.1016/j.ejmech.2019.03.043 Unchecked 1
30928713 10.1016/j.ejmech.2019.03.043 GABA-A receptor; alpha-1/beta-3/gamma-2 1
31738537 10.1021/acs.jmedchem.9b01312 Gamma-aminobutyric acid receptor subunit alpha-1 1
31738537 10.1021/acs.jmedchem.9b01312 Gamma-aminobutyric acid receptor subunit alpha-2 1
31738537 10.1021/acs.jmedchem.9b01312 Gamma-aminobutyric acid receptor subunit alpha-3 1

Data from ChEMBL 36 via Core Engine