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Compound Detail

CHEMBL473104

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O=C(O)C1=CCCN(CCON=C(c2ccccc2)c2ccccc2)C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL473104
Phase Preclinical
Structure Type MOL
InChI Key NGNALWDRPKNJGR-UHFFFAOYSA-N
3
Targets
15
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

350.4
MW (Da)
3.17
ALogP
4
HBA
1
HBD
62.1
PSA (Ų)
0.47
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H22N2O3
MW 350.42
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness -0.01

Activity Summary

IC50 13 meas. best 7.4
Kd 1 meas. best 7.58
Ki 1 meas. best 6.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium- and chloride-dependent GABA transporter 1
CHEMBL5445
 Kd 7.58 7.58 26.5 1
Sodium- and chloride-dependent GABA transporter 1
CHEMBL4054
 IC50 7.4 7.4 40.0 1
Sodium- and chloride-dependent GABA transporter 1
CHEMBL5445
 IC50 7.4 7.042 39.8 5
Unchecked
CHEMBL612545
 IC50 6.7 6.7 200.0 1
Unchecked
CHEMBL612545
 Ki 6.7 6.7 200.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium- and chloride-dependent GABA transporter 1 Kd = 26.5 nM 7.58 Inhibition of NO711 binding to mouse GAT1 expressed in HEK293 cell membranes ass... 31097402
Sodium- and chloride-dependent GABA transporter 1 IC50 = 39.81 nM 7.4 Inhibition of [3H]GABA uptake at mouse GAT1 expressed in HEK293 cells after 25 m... 23336362
Sodium- and chloride-dependent GABA transporter 1 IC50 = 40.0 nM 7.4 Inhibition of [3H]GABA uptake at mouse GAT1 expressed in HEK293 cells after 25 m... 23336362
Sodium- and chloride-dependent GABA transporter 1 IC50 = 40.0 nM 7.4 Inhibition of GAT-1 in rat brain homogenate assessed as decrease in [3H]GABA upt... 30777661
Sodium- and chloride-dependent GABA transporter 1 IC50 = 147.91 nM 6.83 Inhibition of [3H]GABA uptake at mouse GAT1 expressed in HEK cells 18395300
Sodium- and chloride-dependent GABA transporter 1 IC50 = 147.91 nM 6.83 Inhibition of mouse GAT1 expressed in HEK293 cell line assessed as inhibition of... 31901745
Sodium- and chloride-dependent GABA transporter 1 IC50 = 180.0 nM 6.75 Inhibition of mouse GAT1 mediated [3]GABA uptake expressed in HEK293 cells after... 26706177
Unchecked IC50 = 200.0 nM 6.7 Displacement of [3H]GABA from GABA transporter in Wistar rat cerebral cortex aft... 23403082
Unchecked Ki = 200.0 nM 6.7 Displacement of [3H]GABA from GABA transporter in Wistar rat cerebral cortex aft... 23403082

Literature References

PubMed DOI Target Context # Activities
23336362 10.1021/jm301800j Sodium- and chloride-dependent GABA transporter 1 4
23403082 10.1016/j.bmcl.2013.01.025 Unchecked 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
31901745 10.1016/j.ejmech.2019.111920 GABA transporter 4 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
31901745 10.1016/j.ejmech.2019.111920 Sodium- and chloride-dependent GABA transporter 1 1
31901745 10.1016/j.ejmech.2019.111920 GABA transporter 3 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
30777661 10.1016/j.bmc.2019.02.015 Sodium- and chloride-dependent GABA transporter 1 1
30376325 10.1021/acs.jmedchem.8b01602 Sodium- and chloride-dependent GABA transporter 1 1
31097402 10.1016/j.bmc.2019.05.001 Sodium- and chloride-dependent GABA transporter 1 1
18395300 10.1016/j.ejmech.2008.01.005 Sodium- and chloride-dependent GABA transporter 1 1
26706177 10.1016/j.bmcl.2015.11.100 GABA transporter 4 1
26706177 10.1016/j.bmcl.2015.11.100 GABA transporter 3 1
26706177 10.1016/j.bmcl.2015.11.100 GABA transporter 2 1
26706177 10.1016/j.bmcl.2015.11.100 Sodium- and chloride-dependent GABA transporter 1 1
18395300 10.1016/j.ejmech.2008.01.005 GABA transporter 4 1
18395300 10.1016/j.ejmech.2008.01.005 GABA transporter 3 1
18395300 10.1016/j.ejmech.2008.01.005 GABA transporter 2 1

Data from ChEMBL 36 via Core Engine