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Compound Detail

CHEMBL204696

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CC(C)(O)c1cnn2c(-c3ccc(F)c(-c4c(F)cccc4C#N)c3)cnc2n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL204696
Phase Preclinical
Structure Type MOL
InChI Key PCZLQMGFNUNVOM-UHFFFAOYSA-N
9
Targets
12
Activities
1
Assay Types
9
PK Parameters
20
Publications
0
Known Names

Molecular Properties

391.4
MW (Da)
3.84
ALogP
6
HBA
1
HBD
87.1
PSA (Ų)
0.57
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H15F2N5O
MW 391.38
Aromatic Rings 4
Heavy Atoms 29
NP-Likeness -1.40

Activity Summary

Ki 12 meas. best 9.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
GABA-A receptor; alpha-1/beta-3/gamma-2
CHEMBL2094121
 Ki 9.22 9.18 0.6 2
Gamma-aminobutyric acid receptor subunit alpha-1
CHEMBL1962
 Ki 9.14 9.14 0.7 1
GABA-A receptor; alpha-5/beta-3/gamma-2
CHEMBL2094122
 Ki 9.05 9.005 0.9 2
Gamma-aminobutyric acid receptor subunit alpha-5
CHEMBL5112
 Ki 8.96 8.96 1.1 1
GABA-A receptor; alpha-3/beta-3/gamma-2
CHEMBL2094120
 Ki 8.82 8.76 1.5 2
GABA-A receptor; alpha-2/beta-3/gamma-2
CHEMBL2094130
 Ki 8.74 8.74 1.8 1
Gamma-aminobutyric acid receptor subunit alpha-3
CHEMBL3026
 Ki 8.74 8.74 1.8 1
Gamma-aminobutyric acid receptor subunit alpha-2
CHEMBL4956
 Ki 8.7 8.7 2.0 1
Unchecked
CHEMBL612545
 Ki 8.67 8.67 2.1 1

Pharmacokinetic Data

Parameter Value Units Species
CL 2.4 mL.min-1.kg-1 Rattus norvegicus
CL 4.6 mL.min-1.kg-1 Canis lupus familiaris
CL 5.8 mL.min-1.kg-1 Macaca mulatta
F 22.0 % Canis lupus familiaris
F 29.0 % Macaca mulatta
F 77.0 % Rattus norvegicus
T1/2 4.9 hr Macaca mulatta
T1/2 11.0 hr Rattus norvegicus
T1/2 6.5 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
GABA-A receptor; alpha-1/beta-3/gamma-2 Ki = 0.6 nM 9.22 Displacement of [3H]Ro-151788 from human recombinant GABA-Aalpha1 receptor plus ... 16384707
GABA-A receptor; alpha-1/beta-3/gamma-2 Ki = 0.73 nM 9.14 Displacement of [3H]Ro 15-1788 from recombinant human GABAA alpha-1 receptor plu... 16480260
Gamma-aminobutyric acid receptor subunit alpha-1 Ki = 0.73 nM 9.14 Binding affinity to GABA-A alpha1 (unknown origin) 31738537
GABA-A receptor; alpha-5/beta-3/gamma-2 Ki = 0.9 nM 9.05 Displacement of [3H]Ro-151788 from human recombinant GABA-Aalpha5 receptor plus ... 16384707
GABA-A receptor; alpha-5/beta-3/gamma-2 Ki = 1.1 nM 8.96 Displacement of [3H] Ro15-1788 from recombinant human GABAA alpha-5 receptor plu... 16480260
Gamma-aminobutyric acid receptor subunit alpha-5 Ki = 1.1 nM 8.96 Binding affinity to GABA-A alpha5 (unknown origin) 31738537
GABA-A receptor; alpha-3/beta-3/gamma-2 Ki = 1.5 nM 8.82 Displacement of [3H]Ro-151788 from human recombinant GABA-Aalpha3 receptor plus ... 16384707
GABA-A receptor; alpha-2/beta-3/gamma-2 Ki = 1.8 nM 8.74 Displacement of [3H] Ro15-1788 from recombinant human GABAA alpha2 receptor plus... 16480260
Gamma-aminobutyric acid receptor subunit alpha-3 Ki = 1.8 nM 8.74 Binding affinity to GABA-A alpha3 (unknown origin) 31738537
GABA-A receptor; alpha-3/beta-3/gamma-2 Ki = 2.0 nM 8.7 Displacement of [3H]Ro 15-1788 from recombinant human GABAA alpha3 receptor plus... 16480260
Gamma-aminobutyric acid receptor subunit alpha-2 Ki = 2.0 nM 8.7 Binding affinity to GABA-A alpha2 (unknown origin) 31738537
Unchecked Ki = 2.14 nM 8.67 Displacement of [3H]Ro-15-1788 from human GABA alpha2/beta2/gamma2 receptor expr... 30964988

Literature References

PubMed DOI Target Context # Activities
16480260 10.1021/jm051200u Rattus norvegicus 7
16480260 10.1021/jm051200u Canis familiaris 4
16480260 10.1021/jm051200u Rhesus monkey 4
31738537 10.1021/acs.jmedchem.9b01312 Homo sapiens 3
16384707 10.1016/j.bmcl.2005.12.027 GABA-A receptor; alpha-1/beta-3/gamma-2 2
31738537 10.1021/acs.jmedchem.9b01312 Rattus norvegicus 2
31738537 10.1021/acs.jmedchem.9b01312 Gamma-aminobutyric acid receptor subunit alpha-5 2
31738537 10.1021/acs.jmedchem.9b01312 Gamma-aminobutyric acid receptor subunit alpha-3 2
31738537 10.1021/acs.jmedchem.9b01312 Gamma-aminobutyric acid receptor subunit alpha-2 2
31738537 10.1021/acs.jmedchem.9b01312 Gamma-aminobutyric acid receptor subunit alpha-1 2
30964988 10.1021/acs.jmedchem.9b00322 Unchecked 2
16384707 10.1016/j.bmcl.2005.12.027 GABA-A receptor; alpha-5/beta-3/gamma-2 2
16384707 10.1016/j.bmcl.2005.12.027 GABA-A receptor; alpha-3/beta-3/gamma-2 2
16480260 10.1021/jm051200u GABA-A receptor; alpha-1/beta-3/gamma-2 2
16480260 10.1021/jm051200u GABA-A receptor; alpha-5/beta-3/gamma-2 2
16480260 10.1021/jm051200u Squirrel monkey 2
16480260 10.1021/jm051200u GABA-A receptor; alpha-3/beta-3/gamma-2 2
16480260 10.1021/jm051200u GABA-A receptor; alpha-2/beta-3/gamma-2 2
30964988 10.1021/acs.jmedchem.9b00322 GABA-A receptor; alpha-1/beta-3/gamma-2 1
16480260 10.1021/jm051200u GABA-A receptor; anion channel 1

Data from ChEMBL 36 via Core Engine