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Compound Detail

CHEMBL1162395

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COc1cc(O)ccc1/C=C1\CCCN=C1c1cccnc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1162395
Phase Preclinical
Structure Type MOL
InChI Key KXAAIPFSUGPVMQ-GXDHUFHOSA-N
7
Targets
15
Activities
3
Assay Types
0
PK Parameters
15
Publications
0
Known Names

Molecular Properties

294.4
MW (Da)
3.46
ALogP
4
HBA
1
HBD
54.7
PSA (Ų)
0.94
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C18H18N2O2
MW 294.35
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness -0.08

Activity Summary

Ki 8 meas. best 7.72
Kd 4 meas. best 9.4
EC50 3 meas. best 5.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Acetylcholine-binding protein
CHEMBL6084
 Kd 9.4 9.4 0.4 1
Unchecked
CHEMBL612545
 Kd 8.52 8.09 3.0 2
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907589
 Ki 7.72 7.72 19.0 1
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907596
 Ki 7.72 7.44 19.0 2
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL2492
 Kd 7.64 7.64 23.0 1
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL4980
 Ki 6.62 6.5 240.0 2
Unchecked
CHEMBL612545
 Ki 6.38 6.38 420.0 1
Neuronal acetylcholine receptor; alpha3/beta4
CHEMBL1907594
 Ki 6.01 6.01 970.0 2
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL4980
 EC50 5.8 5.8 1600.0 1
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL2492
 EC50 5.52 5.52 3000.0 1
Unchecked
CHEMBL612545
 EC50 5.28 5.28 5200.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Acetylcholine-binding protein Kd = 0.4 nM 9.4 Displacement of [3H]-epibatidine from Lymnaea stagnalis N-terminal FLAG-tagged A... 21986237
Unchecked Kd = 3.0 nM 8.52 Displacement of [3H]-epibatidine from Aplysia californica N-terminal FLAG-tagged... 21986237
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 19.0 nM 7.72 Displacement of [3H]-epibatidine from alpha4beta2 nAChR in rat cortical membrane... 21986237
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 19.0 nM 7.72 Displacement of [3H]epibatidine from human alpha4beta2 nAchR expressed in SH-EP1... 22177081
Unchecked Kd = 22.0 nM 7.66 Displacement of [3H]-epibatidine from Bulinus truncatus N-terminal FLAG-tagged A... 21986237
Neuronal acetylcholine receptor subunit alpha-7 Kd = 23.0 nM 7.64 Displacement of [125I]alpha-bungarotoxin from alpha7 nAChR 18826295
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 70.0 nM 7.16 Displacement of [3H]cytisine from alpha4beta2 nAChR in rat brain membrane after ... 20236734
Neuronal acetylcholine receptor subunit alpha-7 Ki = 240.0 nM 6.62 Displacement of [125I]-alpha-bungarotoxin from alpha7 nAChR in rat brain membran... 20236734
Neuronal acetylcholine receptor subunit alpha-7 Ki = 420.0 nM 6.38 Displacement of [3H]-methyllycaconitine from alpha7 nAChR in rat hippocampal mem... 21986237
Unchecked Ki = 420.0 nM 6.38 Displacement of [3H]methyllycaconitine from rat alpha7 nAchR in rat hippocampal ... 22177081
Neuronal acetylcholine receptor; alpha3/beta4 Ki = 970.0 nM 6.01 Displacement of [3H]-epibatidine from alpha3beta4 nAChR in human SH-SY5Y cellula... 21986237
Neuronal acetylcholine receptor; alpha3/beta4 Ki = 970.0 nM 6.01 Displacement of [3H]epibatidine from human alpha3beta4 nAchR expressed in SH-SY5... 22177081
Neuronal acetylcholine receptor subunit alpha-7 EC50 = 1600.0 nM 5.8 Agonist activity at rat recombinant alpha7 nAChR expressed in GH4C1 cells by pat... 21986237
Neuronal acetylcholine receptor subunit alpha-7 EC50 = 3000.0 nM 5.52 Agonist activity at human cloned wild-type alpha7 nAChR expressed in Xenopus lae... 18826295
Unchecked EC50 = 5200.0 nM 5.28 Agonist activity at human cloned alpha7 nAChR Gln117Phe mutant expressed in Xeno... 18826295

Literature References

PubMed DOI Target Context # Activities
21986237 10.1016/j.ejmech.2011.09.033 Neuronal acetylcholine receptor subunit alpha-7 4
18826295 10.1021/jm800607u Neuronal acetylcholine receptor subunit alpha-7 2
20236734 10.1016/j.ejmech.2010.02.027 Neuronal acetylcholine receptor subunit alpha-7 2
20236734 10.1016/j.ejmech.2010.02.027 Neuronal acetylcholine receptor; alpha4/beta2 2
21986237 10.1016/j.ejmech.2011.09.033 Unchecked 2
21986237 10.1016/j.ejmech.2011.09.033 Neuronal acetylcholine receptor; alpha4/beta2 2
22177081 10.1016/j.bmcl.2011.11.090 Unchecked 2
22177081 10.1016/j.bmcl.2011.11.090 Neuronal acetylcholine receptor; alpha4/beta2 2
22177081 10.1016/j.bmcl.2011.11.090 Neuronal acetylcholine receptor; alpha3/beta4 2
18826295 10.1021/jm800607u Unchecked 1
21986237 10.1016/j.ejmech.2011.09.033 Acetylcholine-binding protein 1
21986237 10.1016/j.ejmech.2011.09.033 Neuronal acetylcholine receptor; alpha3/beta4 1
21986237 10.1016/j.ejmech.2011.09.033 Acetylcholine receptor; alpha1/beta1/delta/gamma 1
22177081 10.1016/j.bmcl.2011.11.090 Acetylcholine receptor; alpha1/beta1/delta/gamma 1
- 10.6019/CHEMBL3301361 No relevant target 1

Data from ChEMBL 36 via Core Engine