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Compound Detail

CHEMBL299250

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CCOc1cc2c3ccccc3nc-2c[nH]1

Basic Information

ChEMBL ID CHEMBL299250
Phase Preclinical
Structure Type MOL
InChI Key MBBOXTKOOFAZLI-UHFFFAOYSA-N
10
Targets
21
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

212.2
MW (Da)
3.07
ALogP
2
HBA
1
HBD
37.9
PSA (Ų)
0.71
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C13H12N2O
MW 212.25
Aromatic Rings 1
Heavy Atoms 16
NP-Likeness -0.61

Activity Summary

Ki 12 meas. best 8.19
IC50 7 meas. best 7.62
Kd 2 meas. best 8.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Gamma-aminobutyric acid receptor subunit alpha-1
CHEMBL1962
Kd 8.92 8.92 1.2 1
GABA-A receptor; alpha-1/beta-3/gamma-2
CHEMBL2094121
Ki 8.19 8.19 6.4 3
GABA-A receptor; anion channel
CHEMBL1907607
IC50 7.62 7.62 24.0 5
GABA-A receptor; anion channel
CHEMBL2093872
IC50 7.62 7.62 24.0 1
Unchecked
CHEMBL612545
IC50 7.62 7.62 24.0 1
GABA-A receptor; alpha-2/beta-3/gamma-2
CHEMBL2094130
Ki 7.6 7.6 25.1 3
GABA-A receptor; alpha-3/beta-3/gamma-2
CHEMBL2094120
Ki 7.55 7.55 28.2 2
GABA-A receptor; alpha-5/beta-3/gamma-2
CHEMBL2094122
Ki 6.08 6.0733 826.0 3
Gamma-aminobutyric acid receptor subunit alpha-5
CHEMBL5112
Kd 6.08 6.08 826.0 1
GABA-A receptor; alpha-6/beta-3/gamma-2
CHEMBL2095190
Ki 6.0 6.0 1000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Gamma-aminobutyric acid receptor subunit alpha-1 Kd = 1.2 nM 8.92 Binding affinity to GABAA alpha-1-beta-2-gamma-2 receptor 18537233
GABA-A receptor; alpha-1/beta-3/gamma-2 Ki = 6.43 nM 8.19 Displacement of [3H]flunitrazepam from human recombinant GABAA alpha-1-beta-3-ga... 20888240
GABA-A receptor; alpha-1/beta-3/gamma-2 Ki = 6.43 nM 8.19 Binding affinity measured using LtK- cell membranes expressing GABA alpha-1-beta... 9651158
GABA-A receptor; alpha-1/beta-3/gamma-2 Ki = 6.43 nM 8.19 Binding affinity for human recombinant gamma-aminobutyric-acid (GABA) A receptor... 10633039
GABA-A receptor; anion channel IC50 = 24.0 nM 7.62 In vitro binding affinity at benzodiazepine receptor of rat cerebral cortical me... 1331452
Unchecked IC50 = 23.99 nM 7.62 Displacement of [3H]diazepam from benzodiazepine receptor in rat brain 18346822
GABA-A receptor; anion channel IC50 = 24.0 nM 7.62 In vitro inhibition of 3[H]Diazepam binding to Benzodiazepine receptor from rat ... 2167977
GABA-A receptor; anion channel IC50 = 23.99 nM 7.62 Inhibition on Benzodiazepine receptor 9435905
GABA-A receptor; anion channel IC50 = 23.99 nM 7.62 Binding affinity towards benzodiazepine receptor inverse agonist site by the dis... 8411009
GABA-A receptor; anion channel IC50 = 24.0 nM 7.62 In vitro inhibition of binding to the benzodiazepine receptor in rat cerebral co... 2842507
GABA-A receptor; anion channel IC50 = 23.99 nM 7.62 Binding affinity for rat benzodiazepine receptor inverse agonist site 8667357
GABA-A receptor; alpha-2/beta-3/gamma-2 Ki = 25.1 nM 7.6 Binding affinity to human recombinant gamma-aminobutyric-acid (GABA) A receptor ... 10633039
GABA-A receptor; alpha-2/beta-3/gamma-2 Ki = 25.1 nM 7.6 Binding affinity for GABA-A alpha-2-beta-3-gamma-2 receptor expressed in L(tk-) ... 9651158
GABA-A receptor; alpha-2/beta-3/gamma-2 Ki = 25.1 nM 7.6 Displacement of [3H]flunitrazepam from human recombinant GABAA alpha-2-beta-3-ga... 20888240
GABA-A receptor; alpha-3/beta-3/gamma-2 Ki = 28.2 nM 7.55 Binding affinity for human recombinant gamma-aminobutyric-acid (GABA) A receptor... 10633039
GABA-A receptor; alpha-3/beta-3/gamma-2 Ki = 28.2 nM 7.55 Displacement of [3H]flunitrazepam from human recombinant GABAA alpha-3-beta-3-ga... 20888240
Gamma-aminobutyric acid receptor subunit alpha-5 Kd = 826.0 nM 6.08 Binding affinity to GABAA alpha-5-beta-2-gamma-2 receptor 18537233
GABA-A receptor; alpha-5/beta-3/gamma-2 Ki = 826.0 nM 6.08 Binding affinity for human recombinant gamma-aminobutyric-acid (GABA) A receptor... 10633039
GABA-A receptor; alpha-5/beta-3/gamma-2 Ki = 826.0 nM 6.08 Displacement of [3H]flunitrazepam from human recombinant GABAA alpha-5-beta-3-ga... 20888240
GABA-A receptor; alpha-5/beta-3/gamma-2 Ki = 868.0 nM 6.06 Binding affinity measured using LtK- cell membranes expressing Gamma-aminobutyri... 9651158

Literature References

PubMed DOI Target Context # Activities
2842507 10.1021/jm00117a029 Mus musculus 6
1331452 10.1021/jm00100a004 Mus musculus 2
9651158 10.1021/jm970460b GABA-A receptor; alpha-1/beta-3/gamma-2 1
20888240 10.1016/j.bmc.2010.08.049 GABA-A receptor; alpha-6/beta-3/gamma-2 1
18346822 10.1016/j.ejmech.2008.01.030 Unchecked 1
18537233 10.1021/jm701433b Gamma-aminobutyric acid receptor subunit alpha-5 1
18537233 10.1021/jm701433b Gamma-aminobutyric acid receptor subunit alpha-1 1
2167977 10.1021/jm00171a007 GABA-A receptor; anion channel 1
9435905 10.1021/jm970488n GABA-A receptor; anion channel 1
8411009 10.1021/jm00072a012 GABA-A receptor; anion channel 1
9651158 10.1021/jm970460b GABA-A receptor; alpha-6/beta-3/gamma-2 1
9651158 10.1021/jm970460b GABA-A receptor; alpha-5/beta-3/gamma-2 1
9651158 10.1021/jm970460b GABA-A receptor; alpha-2/beta-3/gamma-2 1
8667357 10.1021/jm950589q GABA-A receptor; anion channel 1
2842507 10.1021/jm00117a029 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
10633039 10.1021/jm990341r GABA-A receptor; alpha-1/beta-3/gamma-2 1

Data from ChEMBL 36 via Core Engine