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Compound Detail

CHEMBL2403781

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COc1ccc(C(/C=C/CN2CCC[C@H](C(=O)O)C2)(c2ccc(OC)cc2)c2ccc(OC)cc2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2403781
Phase Preclinical
Structure Type MOL
InChI Key RNLUGOUUDNQOGZ-AVDOZPHPSA-N
5
Targets
20
Activities
2
Assay Types
0
PK Parameters
14
Publications
0
Known Names

Molecular Properties

501.6
MW (Da)
5.40
ALogP
5
HBA
1
HBD
68.2
PSA (Ų)
0.30
QED
2
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C31H35NO5
MW 501.62
Aromatic Rings 3
Heavy Atoms 37
NP-Likeness -0.30

Activity Summary

IC50 18 meas. best 5.87
Ki 2 meas. best 4.33

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
GABA transporter 4
CHEMBL3699
 IC50 5.87 5.6986 1349.0 7
Sodium- and chloride-dependent GABA transporter 3
CHEMBL5208
 IC50 5.8 5.8 1590.0 1
GABA transporter 3
CHEMBL5205
 IC50 5.47 4.6825 3388.4 4
GABA transporter 2
CHEMBL4228
 IC50 4.42 4.42 38018.9 1
Sodium- and chloride-dependent GABA transporter 1
CHEMBL5445
 IC50 4.4 4.386 39810.0 5
Sodium- and chloride-dependent GABA transporter 1
CHEMBL5445
 Ki 4.33 4.33 46773.5 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
GABA transporter 4 IC50 = 1348.96 nM 5.87 Inhibition of mouse GAT4 expressed in HEK293 cells assessed as decrease in [3H]G... 29886082
GABA transporter 4 IC50 = 1348.96 nM 5.87 Inhibition of mouse GAT4 expressed in HEK293 cells assessed as reduction in [3H]... 30718063
GABA transporter 4 IC50 = 1350.0 nM 5.87 Inhibition of mouse GAT4 expressed in HEK293 cell line assessed as reduction in ... 33838585
GABA transporter 4 IC50 = 1348.96 nM 5.87 Inhibition of GABA uptake at murine GAT-3 expressed in HEK293 cells 23770450
Sodium- and chloride-dependent GABA transporter 3 IC50 = 1590.0 nM 5.8 Inhibition of human GAT3 expressed in COS-7 cells assessed as reduction in [2H6]... 33838585
GABA transporter 3 IC50 = 3388.44 nM 5.47 Inhibition of GABA uptake at murine GAT-2 expressed in HEK293 cells 23770450
GABA transporter 4 IC50 = 3388.44 nM 5.47 Inhibition of mouse GAT3 expressed in HEK293 cells assessed as decrease in [3H]G... 29886082
GABA transporter 4 IC50 = 3388.44 nM 5.47 Inhibition of mouse GAT3 expressed in HEK293 cells assessed as reduction in [3H]... 30718063
GABA transporter 4 IC50 = 3390.0 nM 5.47 Inhibition of mouse GAT3 expressed in HEK293 cell line assessed as reduction in ... 33838585
GABA transporter 3 IC50 = 38018.94 nM 4.42 Inhibition of mouse GAT2 expressed in HEK293 cells assessed as decrease in [3H]G... 29886082
GABA transporter 3 IC50 = 38020.0 nM 4.42 Inhibition of mouse GAT2 expressed in HEK293 cell line assessed as reduction in ... 33838585
GABA transporter 3 IC50 = 38018.94 nM 4.42 Inhibition of mouse GAT2 expressed in HEK293 cells assessed as reduction in [3H]... 30718063
GABA transporter 2 IC50 = 38018.94 nM 4.42 Inhibition of GABA uptake at murine BGT-1 expressed in HEK293 cells 23770450
Sodium- and chloride-dependent GABA transporter 1 IC50 = 39810.72 nM 4.4 Inhibition of GABA uptake at murine GAT-1 expressed in HEK293 cells 23770450
Sodium- and chloride-dependent GABA transporter 1 IC50 = 39810.72 nM 4.4 Inhibition of mouse GAT1 expressed in HEK293 cells assessed as decrease in [3H]G... 29886082
Sodium- and chloride-dependent GABA transporter 1 IC50 = 39810.72 nM 4.4 Inhibition of mouse GAT1 expressed in HEK293 cells assessed as reduction in [3H]... 30718063
Sodium- and chloride-dependent GABA transporter 1 IC50 = 39810.0 nM 4.4 Inhibition of mouse GAT1 expressed in HEK293 cell line assessed as reduction in ... 33838585
Sodium- and chloride-dependent GABA transporter 1 IC50 = 46770.0 nM 4.33 Inhibition of NO711 binding to mouse GAT1 expressed in HEK cell membranes incuba... 33838585
Sodium- and chloride-dependent GABA transporter 1 Ki = 46773.51 nM 4.33 Inhibition of [2H10]NO 711 binding to mouse GAT1 expressed in HEK293 cell membra... 29886082
Sodium- and chloride-dependent GABA transporter 1 Ki = 46773.51 nM 4.33 Displacement of NO711 from mouse GAT1 expressed in stable HEK293 cell membranes ... 30718063

Literature References

PubMed DOI Target Context # Activities
29886082 10.1016/j.bmc.2018.05.049 Sodium- and chloride-dependent GABA transporter 1 2
29886082 10.1016/j.bmc.2018.05.049 GABA transporter 4 2
30718063 10.1016/j.bmc.2019.01.024 Sodium- and chloride-dependent GABA transporter 1 2
30718063 10.1016/j.bmc.2019.01.024 GABA transporter 4 2
33838585 10.1016/j.ejmech.2021.113397 Sodium- and chloride-dependent GABA transporter 1 2
33838585 10.1016/j.ejmech.2021.113397 GABA transporter 4 2
23770450 10.1016/j.ejmech.2013.04.063 GABA transporter 4 1
23770450 10.1016/j.ejmech.2013.04.063 GABA transporter 3 1
23770450 10.1016/j.ejmech.2013.04.063 GABA transporter 2 1
23770450 10.1016/j.ejmech.2013.04.063 Sodium- and chloride-dependent GABA transporter 1 1
29886082 10.1016/j.bmc.2018.05.049 GABA transporter 3 1
30718063 10.1016/j.bmc.2019.01.024 GABA transporter 3 1
33838585 10.1016/j.ejmech.2021.113397 GABA transporter 3 1
33838585 10.1016/j.ejmech.2021.113397 Sodium- and chloride-dependent GABA transporter 3 1

Data from ChEMBL 36 via Core Engine