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Compound Detail

CHEMBL1446457

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COc1ccccc1C1(O)CCN(CCCn2c3ccccc3c3ccccc32)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1446457
Phase Preclinical
Structure Type MOL
InChI Key XZZYCJOGZYEPPW-UHFFFAOYSA-N
9
Targets
21
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

414.6
MW (Da)
5.18
ALogP
4
HBA
1
HBD
37.6
PSA (Ų)
0.47
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H30N2O2
MW 414.55
Aromatic Rings 4
Heavy Atoms 31
NP-Likeness -0.38

Activity Summary

IC50 17 meas. best 5.85
Ki 4 meas. best 5.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
GABA transporter 2
CHEMBL4228
 IC50 5.85 5.85 1400.0 1
GABA transporter 2
CHEMBL4228
 Ki 5.85 5.85 1400.0 1
GABA transporter 3
CHEMBL5205
 IC50 5.85 5.11 1412.5 3
Sodium- and chloride-dependent betaine transporter
CHEMBL3715
 IC50 5.29 5.29 5100.0 2
Sodium- and chloride-dependent GABA transporter 2
CHEMBL4535
 IC50 5.21 5.21 6200.0 1
Sodium- and chloride-dependent GABA transporter 3
CHEMBL5208
 IC50 5.05 5.05 8920.0 1
Sodium- and chloride-dependent GABA transporter 1
CHEMBL5445
 IC50 4.99 4.81 10232.9 3
Sodium- and chloride-dependent GABA transporter 1
CHEMBL1903
 IC50 4.94 4.94 11400.0 1
GABA transporter 4
CHEMBL3699
 IC50 4.93 4.74 11749.0 4
GABA transporter 4
CHEMBL3699
 Ki 4.82 4.82 15000.0 1
Unchecked
CHEMBL612545
 IC50 4.78 4.78 16595.9 1
Sodium- and chloride-dependent GABA transporter 1
CHEMBL5445
 Ki 4.72 4.72 19000.0 1
GABA transporter 3
CHEMBL5205
 Ki 4.39 4.39 41000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
GABA transporter 2 IC50 = 1400.0 nM 5.85 Inhibition of mouse mGAT2 expressed in HEK293 cells assessed as inhibition of [3... 25882526
GABA transporter 3 IC50 = 1412.54 nM 5.85 Inhibition of mouse GAT2-mediated [3H]GABA uptake expressed in BHK cells 21940173
GABA transporter 2 Ki = 1400.0 nM 5.85 Inhibition of mouse BGT1 expressed in hamster BHK cells assessed as reduction in... 28991462
Sodium- and chloride-dependent betaine transporter IC50 = 5100.0 nM 5.29 Inhibition of human BGT1 transfected in CHO cells assessed as [3H]GABA uptake af... 23886812
Sodium- and chloride-dependent betaine transporter IC50 = 5100.0 nM 5.29 Inhibition of human BGT1 transfected in CHO cells assessed as [3H]GABA uptake af... 25147609
Sodium- and chloride-dependent GABA transporter 2 IC50 = 6200.0 nM 5.21 Inhibition of human GAT2 transfected in CHO cells assessed as [3H]GABA uptake af... 25147609
GABA transporter 3 IC50 = 8128.31 nM 5.09 Inhibition of mouse GAT2-mediated [3H]GABA uptake expressed in human HEK cells 21940173
Sodium- and chloride-dependent GABA transporter 3 IC50 = 8920.0 nM 5.05 Inhibition of human GAT3 transfected in CHO cells assessed as [3H]GABA uptake af... 25147609
Sodium- and chloride-dependent GABA transporter 1 IC50 = 10232.93 nM 4.99 Inhibition of mouse GAT1-mediated [3H]GABA uptake expressed in human HEK cells 21940173
Sodium- and chloride-dependent GABA transporter 1 IC50 = 11400.0 nM 4.94 Inhibition of human GAT1 transfected in CHO cells assessed as [3H]GABA uptake af... 25147609
GABA transporter 4 IC50 = 11748.98 nM 4.93 Inhibition of mouse GAT3-mediated [3H]GABA uptake expressed in human HEK cells 21940173
GABA transporter 4 IC50 = 15135.61 nM 4.82 Inhibition of mouse GAT4-mediated [3H]GABA uptake expressed in BHK cells 21940173
GABA transporter 4 Ki = 15000.0 nM 4.82 Inhibition of mouse GAT3 expressed in hamster BHK cells assessed as reduction in... 28991462
GABA transporter 4 IC50 = 15000.0 nM 4.82 Inhibition of mouse mGAT4 expressed in HEK293 cells assessed as inhibition of [3... 25882526
Unchecked IC50 = 16595.87 nM 4.78 Inhibition of mouse GAT4-mediated [3H]GABA uptake expressed in human HEK cells 21940173
Sodium- and chloride-dependent GABA transporter 1 IC50 = 19054.61 nM 4.72 Inhibition of mouse GAT1-mediated [3H]GABA uptake expressed in BHK cells 21940173
Sodium- and chloride-dependent GABA transporter 1 IC50 = 19000.0 nM 4.72 Inhibition of mouse mGAT1 expressed in HEK293 cells assessed as inhibition of [3... 25882526
Sodium- and chloride-dependent GABA transporter 1 Ki = 19000.0 nM 4.72 Inhibition of mouse GAT1 expressed in hamster BHK cells assessed as reduction in... 28991462
GABA transporter 4 IC50 = 40738.03 nM 4.39 Inhibition of mouse GAT3-mediated [3H]GABA uptake expressed in BHK cells 21940173
GABA transporter 3 IC50 = 41000.0 nM 4.39 Inhibition of mouse mGAT3 expressed in HEK293 cells assessed as inhibition of [3... 25882526

Literature References

PubMed DOI Target Context # Activities
21940173 10.1016/j.bmc.2011.08.039 GABA transporter 4 3
21940173 10.1016/j.bmc.2011.08.039 GABA transporter 3 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
21940173 10.1016/j.bmc.2011.08.039 Sodium- and chloride-dependent GABA transporter 1 2
25882526 10.1016/j.bmc.2015.03.060 GABA transporter 3 1
21940173 10.1016/j.bmc.2011.08.039 Unchecked 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
28991462 10.1021/acs.jmedchem.7b00924 GABA transporter 2 1
28991462 10.1021/acs.jmedchem.7b00924 GABA transporter 4 1
28991462 10.1021/acs.jmedchem.7b00924 GABA transporter 3 1
28991462 10.1021/acs.jmedchem.7b00924 Sodium- and chloride-dependent GABA transporter 1 1
25882526 10.1016/j.bmc.2015.03.060 GABA transporter 4 1
23886812 10.1016/j.bmc.2013.06.063 Sodium- and chloride-dependent betaine transporter 1
25882526 10.1016/j.bmc.2015.03.060 Sodium- and chloride-dependent GABA transporter 1 1
25882526 10.1016/j.bmc.2015.03.060 GABA transporter 2 1
25147609 10.1021/ml500134k Unchecked 1
25147609 10.1021/ml500134k Sodium- and chloride-dependent betaine transporter 1
25147609 10.1021/ml500134k Sodium- and chloride-dependent GABA transporter 1 1
25147609 10.1021/ml500134k Sodium- and chloride-dependent GABA transporter 2 1

Data from ChEMBL 36 via Core Engine