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Compound Detail

CHEMBL17468

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CCc1c(C(=O)OC)[nH]cc2nc3cc(OC)c(OC)cc3c1-2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL17468
Phase Preclinical
Structure Type MOL
InChI Key MZTRNWROWIGTRB-UHFFFAOYSA-N
8
Targets
45
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

314.3
MW (Da)
3.03
ALogP
5
HBA
1
HBD
73.4
PSA (Ų)
0.75
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 C17H18N2O4
MW 314.34
Aromatic Rings 1
Heavy Atoms 23
NP-Likeness -0.22

Activity Summary

Ki 35 meas. best 9.0
IC50 6 meas. best 5.1
EC50 4 meas. best 8.52

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 8.7825 1.0 8
GABA-A receptor; alpha-5/beta-3/gamma-2
CHEMBL2094122
 EC50 8.52 8.52 3.0 1
GABA-A receptor; alpha-3/beta-3/gamma-2
CHEMBL2094120
 Ki 8.4 8.21 4.0 8
GABA-A receptor; alpha-1/beta-3/gamma-2
CHEMBL2094121
 Ki 8.24 8.065 5.7 8
GABA-A receptor; anion channel
CHEMBL1907607
 Ki 8.12 8.12 7.6 1
GABA-A receptor; alpha-2/beta-3/gamma-2
CHEMBL2094130
 Ki 8.08 7.97 8.3 8
GABA-A receptor; alpha-1/beta-2/gamma-2
CHEMBL2095172
 EC50 8.05 8.05 9.0 1
GABA-A receptor; alpha-3/beta-3/gamma-2
CHEMBL2094120
 EC50 8.0 8.0 10.0 1
GABA-A receptor; alpha-2/beta-3/gamma-2
CHEMBL2094130
 EC50 7.85 7.85 14.0 1
GABA-A receptor; alpha-6/beta-3/gamma-2
CHEMBL2095190
 Ki 6.87 6.87 134.0 2
Plasmodium falciparum
CHEMBL364
 IC50 5.1 4.9667 7943.3 6

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 Binding affinity measured using LtK- cell membranes expressing Gamma-aminobutyri... 9651158
GABA-A receptor; alpha-5/beta-3/gamma-2 Ki = 1.0 nM 9.0 Inhibition of [3H]Ro-151788 binding to human GABA A receptor (alpha-5-beta-3-gam... 11960500
GABA-A receptor; alpha-5/beta-3/gamma-2 Ki = 1.04 nM 8.98 Binding affinity for human recombinant gamma-aminobutyric-acid (GABA) A receptor... 10633039
GABA-A receptor; alpha-5/beta-3/gamma-2 Ki = 2.2 nM 8.66 Displacement of [3H]-Ro- 15-1788 from human gamma-aminobutyric-acid GABA-A recep... 15537339
GABA-A receptor; alpha-5/beta-3/gamma-2 Ki = 2.2 nM 8.66 Inhibition of [3H]-Ro- 15-1788 binding to human GABA-A receptor alpha-5-beta-3-g... 15125950
GABA-A receptor; alpha-5/beta-3/gamma-2 Ki = 2.2 nM 8.66 Binding affinity to human GABA A alpha-5-beta-3-gamma-2 receptor, using a [3H]-R... 12747794
GABA-A receptor; alpha-5/beta-3/gamma-2 Ki = 2.2 nM 8.66 Displacement of [3H]- Ro 15-1788 binding from human GABA-A receptor alpha-5-beta... 11881985
GABA-A receptor; alpha-5/beta-3/gamma-2 Ki = 2.3 nM 8.64 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 EC50 = 3.0 nM 8.52 Binding affinity to human alpha5beta3gamma2 GABA receptor expressed in Xenopus l... 20980155
GABA-A receptor; alpha-3/beta-3/gamma-2 Ki = 4.0 nM 8.4 Binding affinity by displacement of [3H]Ro-151788 from recombinant human gamma-a... 11960500
GABA-A receptor; alpha-3/beta-3/gamma-2 Ki = 4.0 nM 8.4 Binding affinity for human recombinant gamma-aminobutyric-acid (GABA) A receptor... 10633039
GABA-A receptor; alpha-3/beta-3/gamma-2 Ki = 4.0 nM 8.4 Binding affinity measured using LtK- cell membranes expressing GABA alpha-3-beta... 9651158
GABA-A receptor; alpha-1/beta-3/gamma-2 Ki = 5.7 nM 8.24 Binding affinity measured using LtK- cell membranes expressing GABA alpha-1-beta... 9651158
GABA-A receptor; alpha-1/beta-3/gamma-2 Ki = 5.7 nM 8.24 Inhibition of [3H]Ro-151788 binding to human GABA A receptor (alpha-1-beta-3-gam... 11960500
GABA-A receptor; alpha-1/beta-3/gamma-2 Ki = 5.7 nM 8.24 Binding affinity for human recombinant gamma-aminobutyric-acid (GABA) A receptor... 10633039
GABA-A receptor; anion channel Ki = 7.6 nM 8.12 In vitro affinity against Benzodiazepine receptor binding to rat cortical membra... 10543878
GABA-A receptor; alpha-3/beta-3/gamma-2 Ki = 7.5 nM 8.12 Binding affinity to human gamma-amino butyric-acid A receptor alpha-3-beta-3-gam... 12747794
GABA-A receptor; alpha-3/beta-3/gamma-2 Ki = 7.5 nM 8.12 Inhibition of [3H]-Ro- 15-1788 binding to recombinant human gamma-aminobutyric-a... 15125950
GABA-A receptor; alpha-3/beta-3/gamma-2 Ki = 7.5 nM 8.12 Displacement of [3H]-Ro- 15-1788 from human gamma-aminobutyric-acid GABA-A recep... 15537339
GABA-A receptor; alpha-3/beta-3/gamma-2 Ki = 7.5 nM 8.12 Displacement of [3H]- Ro 15-1788 binding from human GABA-A receptor alpha-3-beta... 11881985

Literature References

PubMed DOI Target Context # Activities
19734910 10.1038/nchembio.215 Plasmodium falciparum 6
12747794 10.1021/jm020582q GABA-A receptor; alpha-5/beta-3/gamma-2 3
15125950 10.1016/j.bmcl.2004.03.054 GABA-A receptor; alpha-5/beta-3/gamma-2 3
11881985 10.1021/jm010471b GABA-A receptor; alpha-5/beta-3/gamma-2 3
11881985 10.1021/jm010471b GABA-A receptor; alpha-2/beta-3/gamma-2 2
20980155 10.1016/j.bmc.2010.09.058 GABA-A receptor; alpha-5/beta-3/gamma-2 2
10543878 10.1021/jm991010h GABA-A receptor; anion channel 2
15537339 10.1021/jm040863t GABA-A receptor; alpha-1/beta-3/gamma-2 2
12747794 10.1021/jm020582q GABA-A receptor; alpha-2/beta-3/gamma-2 2
12747794 10.1021/jm020582q GABA-A receptor; alpha-3/beta-3/gamma-2 2
15537339 10.1021/jm040863t GABA-A receptor; alpha-2/beta-3/gamma-2 2
15537339 10.1021/jm040863t GABA-A receptor; alpha-3/beta-3/gamma-2 2
11881985 10.1021/jm010471b GABA-A receptor; alpha-3/beta-3/gamma-2 2
11960500 10.1021/jm0110789 GABA-A receptor; alpha-1/beta-3/gamma-2 2
11881985 10.1021/jm010471b GABA-A receptor; alpha-1/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-3/beta-3/gamma-2 2
15084116 10.1021/jm031076j GABA-A receptor; alpha-2/beta-3/gamma-2 2
15084116 10.1021/jm031076j GABA-A receptor; alpha-1/beta-3/gamma-2 2
11960500 10.1021/jm0110789 GABA-A receptor; alpha-3/beta-3/gamma-2 2

Data from ChEMBL 36 via Core Engine