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Compound Detail

CHEMBL293950

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CO[C@H]1CC=C2CCN3CCC4=C(CC(=O)OC4)[C@]23C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL293950
Phase Preclinical
Structure Type MOL
InChI Key ALSKYCOJJPXPFS-BBRMVZONSA-N
10
Targets
18
Activities
2
Assay Types
0
PK Parameters
16
Publications
0
Known Names

Molecular Properties

275.4
MW (Da)
1.81
ALogP
4
HBA
0
HBD
38.8
PSA (Ų)
0.54
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C16H21NO3
MW 275.35
Aromatic Rings 0
Heavy Atoms 20
NP-Likeness 2.83

Activity Summary

IC50 12 meas. best 8.44
Ki 6 meas. best 7.01

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Neuronal acetylcholine receptor subunit alpha-4
CHEMBL307
 IC50 8.44 8.44 3.7 1
Nicotinic acetylcholine receptor alpha4/beta2/alpha5
CHEMBL3038461
 IC50 7.96 7.96 11.0 1
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907589
 IC50 7.7 6.7167 20.0 3
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907596
 IC50 7.52 7.52 30.0 1
Striatum
CHEMBL613663
 IC50 7.52 7.52 30.0 1
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907589
 Ki 7.01 7.01 98.0 1
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907596
 Ki 6.85 6.47 140.0 2
Nicotinic acetylcholine receptor alpha-4/beta-2
CHEMBL3301382
 IC50 5.92 5.92 1200.0 1
Unchecked
CHEMBL612545
 IC50 5.66 5.66 2200.0 1
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL2492
 Ki 4.98 4.98 10500.0 1
Neuronal acetylcholine receptor; alpha3/beta4
CHEMBL1907593
 IC50 4.64 4.2133 23000.0 3
Neuronal acetylcholine receptor; alpha3/beta4
CHEMBL1907593
 Ki 4.0 4.0 100000.0 1
Neuronal acetylcholine receptor; alpha4/beta4
CHEMBL1907595
 Ki 4.0 4.0 100000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Neuronal acetylcholine receptor subunit alpha-4 IC50 = 3.66 nM 8.44 Blockade of Nicotinic acetylcholine receptor alpha4-beta2 15050620
Nicotinic acetylcholine receptor alpha4/beta2/alpha5 IC50 = 11.0 nM 7.96 Antagonist activity at (alpha4beta2)2alpha5 nAChR (unknown origin) expressed in ... 23561269
Neuronal acetylcholine receptor; alpha4/beta2 IC50 = 20.0 nM 7.7 Antagonist activity at (alpha4beta2)2alpha4 nAChR (unknown origin) expressed in ... 23561269
Striatum IC50 = 30.0 nM 7.52 Inhibition of nicotine-induced [3H]dopamine release in rat striatum 24901260
Neuronal acetylcholine receptor; alpha4/beta2 IC50 = 30.0 nM 7.52 Antagonist activity at rat alpha4beta2 nAChR 24901260
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 98.0 nM 7.01 Displacement of [3H]cytisine from alpha4/beta2 nAChR (unknown origin) 24187998
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 140.0 nM 6.85 Inhibition of rat membrane alpha4beta2 nAChR by [3H]cytisine binding assay 25050162
Neuronal acetylcholine receptor; alpha4/beta2 IC50 = 410.0 nM 6.39 Antagonist activity at (alpha4beta2)2beta2 nAChR (unknown origin) expressed in X... 23561269
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 820.0 nM 6.09 Displacement of [3H]epibatidine from rat alpha4beta2 nAChR transfected in HEK293... 25050162
Neuronal acetylcholine receptor; alpha4/beta2 IC50 = 880.0 nM 6.06 Antagonist activity at human alpha4beta2 nAChR expressed in HEK293 cells assesse... 38151460
Nicotinic acetylcholine receptor alpha-4/beta-2 IC50 = 1200.0 nM 5.92 Antagonist activity at mouse alpha4beta2 nAChR transfected in HEK293 cells by FL... 25050162
Unchecked IC50 = 2200.0 nM 5.66 Antagonist activity at nAChR in Sprague-Dawley rat striatal slices assessed as i... 26164842
Neuronal acetylcholine receptor subunit alpha-7 Ki = 10500.0 nM 4.98 Displacement of [3H]cytisine from alpha7 nAChR (unknown origin) 24187998
Neuronal acetylcholine receptor; alpha3/beta4 IC50 = 23000.0 nM 4.64 Antagonist activity at rat alpha3beta4 nAChR 24901260
Neuronal acetylcholine receptor; alpha3/beta4 IC50 = 100000.0 nM 4.0 Antagonist activity at rat alpha3beta4 nAChR transfected in HEK293 cells by FLIP... 25050162
Neuronal acetylcholine receptor; alpha3/beta4 IC50 = 100000.0 nM 4.0 Activity at rat alpha3beta4 nicotinic receptor expressed in KXalpha-3-beta-4R2 c... 17067175
Neuronal acetylcholine receptor; alpha4/beta4 Ki = 100000.0 nM 4.0 Displacement of [3H]epibatidine from rat alpha4beta4 nAChR transfected in HEK293... 25050162
Neuronal acetylcholine receptor; alpha3/beta4 Ki = 100000.0 nM 4.0 Displacement of [3H]epibatidine from rat alpha3beta4 nAChR transfected in HEK293... 25050162

Literature References

PubMed DOI Target Context # Activities
23561269 10.1016/j.bmc.2013.03.024 Neuronal acetylcholine receptor; alpha4/beta2 2
25050162 10.1021/ml500094c Neuronal acetylcholine receptor; alpha4/beta2 2
25050162 10.1021/ml500094c Neuronal acetylcholine receptor; alpha3/beta4 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
15050620 10.1016/j.bmcl.2004.01.004 Neuronal acetylcholine receptor subunit alpha-4 1
17067175 10.1021/np060291a Neuronal acetylcholine receptor; alpha3/beta4 1
23561269 10.1016/j.bmc.2013.03.024 Nicotinic acetylcholine receptor alpha4/beta2/alpha5 1
24187998 10.1021/jm4013592 Neuronal acetylcholine receptor subunit alpha-7 1
24187998 10.1021/jm4013592 Neuronal acetylcholine receptor; alpha4/beta2 1
24901260 10.1021/jm401937a Striatum 1
24901260 10.1021/jm401937a Neuronal acetylcholine receptor; alpha3/beta4 1
24901260 10.1021/jm401937a Neuronal acetylcholine receptor; alpha4/beta2 1
25050162 10.1021/ml500094c Neuronal acetylcholine receptor; alpha4/beta4 1
25050162 10.1021/ml500094c Nicotinic acetylcholine receptor alpha-4/beta-2 1
26164842 10.1016/j.ejmech.2015.06.039 Unchecked 1
38151460 10.1021/acs.jmedchem.3c01758 Neuronal acetylcholine receptor; alpha4/beta2 1

Data from ChEMBL 36 via Core Engine