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Compound Detail

CHEMBL68684

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Cc1cc(-c2nnc3c4ccccc4c(OCc4ccccn4)nn23)no1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL68684
Phase Preclinical
Structure Type MOL
InChI Key YTGZSWOWFGVAFH-UHFFFAOYSA-N
8
Targets
17
Activities
2
Assay Types
1
PK Parameters
18
Publications
0
Known Names

Molecular Properties

358.4
MW (Da)
3.21
ALogP
8
HBA
0
HBD
91.2
PSA (Ų)
0.49
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 C19H14N6O2
MW 358.36
Aromatic Rings 5
Heavy Atoms 27
NP-Likeness -2.06

Activity Summary

Ki 16 meas. best 9.4
EC50 1 meas. best 8.6

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Gamma-aminobutyric acid receptor subunit alpha-1
CHEMBL1962
 Ki 9.4 9.4 0.4 1
Gamma-aminobutyric acid receptor subunit alpha-5
CHEMBL5112
 Ki 9.3 9.3 0.5 1
GABA-A receptor; alpha-5/beta-3/gamma-2
CHEMBL2094122
 Ki 9.21 9.0433 0.6 3
GABA-A receptor; alpha-1/beta-3/gamma-2
CHEMBL2094121
 Ki 9.03 8.9 0.9 3
GABA-A receptor; alpha-3/beta-3/gamma-2
CHEMBL2094120
 Ki 9.02 8.8967 1.0 3
GABA-A receptor; alpha-2/beta-3/gamma-2
CHEMBL2094130
 Ki 8.82 8.7367 1.5 3
GABA-A receptor; alpha-5/beta-3/gamma-2
CHEMBL2094122
 EC50 8.6 8.6 2.5 1
GABA A receptor alpha-4/beta-3/gamma-2
CHEMBL2111366
 Ki 6.61 6.61 244.0 1
GABA-A receptor; alpha-6/beta-3/gamma-2
CHEMBL2095190
 Ki 5.36 5.36 4410.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 41.0 % Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Gamma-aminobutyric acid receptor subunit alpha-1 Ki = 0.4 nM 9.4 Negative allosteric modulation of alpha1 GABAA (unknown origin) 36549396
Gamma-aminobutyric acid receptor subunit alpha-5 Ki = 0.5 nM 9.3 Negative allosteric modulation of alpha5 GABAA (unknown origin) 36549396
GABA-A receptor; alpha-5/beta-3/gamma-2 Ki = 0.62 nM 9.21 Displacement of [3H]-Ro- 15-1788 from human GABA-A alpha-5-beta-3-gamma-2 recept... 15084116
GABA-A receptor; alpha-5/beta-3/gamma-2 Ki = 0.8 nM 9.1 Binding affinity towards human alpha-5-beta-3-gamma-2 GABA-A receptor using [3H]... 15214791
GABA-A receptor; alpha-1/beta-3/gamma-2 Ki = 0.93 nM 9.03 Displacement of [3H]-Ro- 15-1788 from human GABA-A alpha-1-beta-3-gamma-2 recept... 15084116
GABA-A receptor; alpha-3/beta-3/gamma-2 Ki = 0.96 nM 9.02 Displacement of [3H]-Ro- 15-1788 from human GABA-A alpha-3-beta-3-gamma-2 recept... 15084116
GABA-A receptor; alpha-3/beta-3/gamma-2 Ki = 1.4 nM 8.85 Binding affinity towards human gamma-aminobutyric-acid A receptor alpha-3-beta-3... 15214791
GABA-A receptor; alpha-1/beta-3/gamma-2 Ki = 1.4 nM 8.85 Binding affinity towards human alpha-1-beta-3-gamma-2 GABA-A receptor using [3H]... 15214791
GABA-A receptor; alpha-2/beta-3/gamma-2 Ki = 1.5 nM 8.82 Displacement of [3H]-Ro- 15-1788 from human GABA-A alpha-2-beta-3-gamma-2 recept... 15084116
GABA-A receptor; alpha-3/beta-3/gamma-2 Ki = 1.5 nM 8.82 Displacement of [3H]flumazenil from GABAA alpha-3-beta-3-gamma-2 receptor 19740657
GABA-A receptor; alpha-2/beta-3/gamma-2 Ki = 1.5 nM 8.82 Displacement of [3H]flumazenil from GABAA alpha-2-beta-3-gamma-2 receptor 19740657
GABA-A receptor; alpha-1/beta-3/gamma-2 Ki = 1.5 nM 8.82 Displacement of [3H]flumazenil from GABAA alpha-1-beta-3-gamma-2 receptor 19740657
GABA-A receptor; alpha-5/beta-3/gamma-2 Ki = 1.5 nM 8.82 Displacement of [3H]flumazenil from GABAA alpha-5-beta-3-gamma-2 receptor 19740657
GABA-A receptor; alpha-5/beta-3/gamma-2 EC50 = 2.5 nM 8.6 Effective concentration against human Alpha-5-beta-3-gamma-2 GABA-A receptor was... 15214791
GABA-A receptor; alpha-2/beta-3/gamma-2 Ki = 2.7 nM 8.57 Binding affinity towards human gamma-aminobutyric-acid A receptor alpha-2-beta-3... 15214791
GABA A receptor alpha-4/beta-3/gamma-2 Ki = 244.0 nM 6.61 Inhibition of [3H]-Ro-15-1788 binding to human alpha-4-beta-3-gamma-2 GABA-A rec... 15214791
GABA-A receptor; alpha-6/beta-3/gamma-2 Ki = 4410.0 nM 5.36 Inhibition of [3H]Ro-151788 binding to human alpha-6-beta-3-gamma-2 GABA-A recep... 15214791

Literature References

PubMed DOI Target Context # Activities
15214791 10.1021/jm0407613 GABA-A receptor; alpha-5/beta-3/gamma-2 4
15214791 10.1021/jm0407613 GABA-A receptor; alpha-1/beta-3/gamma-2 3
15214791 10.1021/jm0407613 GABA-A receptor; alpha-2/beta-3/gamma-2 3
15214791 10.1021/jm0407613 GABA-A receptor; alpha-3/beta-3/gamma-2 3
15084116 10.1021/jm031076j GABA-A receptor; alpha-2/beta-3/gamma-2 2
15084116 10.1021/jm031076j GABA-A receptor; alpha-3/beta-3/gamma-2 2
15084116 10.1021/jm031076j GABA-A receptor; alpha-5/beta-3/gamma-2 2
15084116 10.1021/jm031076j GABA-A receptor; alpha-1/beta-3/gamma-2 2
36549396 10.1016/j.bmcl.2022.129107 Gamma-aminobutyric acid receptor subunit alpha-5 2
15214791 10.1021/jm0407613 Rattus norvegicus 2
19740657 10.1016/j.bmcl.2009.08.027 GABA-A receptor; alpha-2/beta-3/gamma-2 2
19740657 10.1016/j.bmcl.2009.08.027 GABA-A receptor; alpha-3/beta-3/gamma-2 2
19740657 10.1016/j.bmcl.2009.08.027 GABA-A receptor; alpha-1/beta-3/gamma-2 2
19740657 10.1016/j.bmcl.2009.08.027 GABA-A receptor; alpha-5/beta-3/gamma-2 2
36549396 10.1016/j.bmcl.2022.129107 Gamma-aminobutyric acid receptor subunit alpha-1 1
19740657 10.1016/j.bmcl.2009.08.027 Rattus norvegicus 1
15214791 10.1021/jm0407613 GABA-A receptor; alpha-6/beta-3/gamma-2 1
15214791 10.1021/jm0407613 GABA A receptor alpha-4/beta-3/gamma-2 1

Data from ChEMBL 36 via Core Engine