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Compound Detail

CHEMBL134713

GTS-21
🧪 Phase II
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🧪 Phase II
COc1ccc(/C=C2\CCCN=C2c2cccnc2)c(OC)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL134713
Name GTS-21
Phase Phase II
Structure Type MOL
InChI Key RPYWXZCFYPVCNQ-RVDMUPIBSA-N

Known Names

3-(2,4-dimethoxybenzylidene)anabaseine Dimethoxybenzylidene anabaseine Dmxb-a Gts-21
9
Targets
19
Activities
3
Assay Types
3
PK Parameters
20
Publications
4
Known Names
7
Indications
1
Mechanisms

Molecular Properties

308.4
MW (Da)
3.77
ALogP
4
HBA
0
HBD
43.7
PSA (Ų)
0.86
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product

Extended Properties

Molecular Formula C19H20N2O2
MW 308.38
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness -0.50

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Neuronal acetylcholine receptor protein alpha-7 subunit agonist AGONIST Neuronal acetylcholine receptor subunit alpha-7 ✓ ✓

Indications

Alzheimer Disease Psychotic Disorders Schizophrenia Tobacco Use Disorder Autistic Disorder Mental Disorders Obesity

Activity Summary

Ki 12 meas. best 7.29
Kd 4 meas. best 7.72
EC50 3 meas. best 5.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Acetylcholine-binding protein
CHEMBL6084
 Kd 7.72 7.72 19.0 1
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907589
 Ki 7.29 7.29 51.0 1
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907596
 Ki 7.29 6.99 51.0 3
Unchecked
CHEMBL612545
 Kd 7.23 6.855 59.0 2
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL4980
 Ki 6.89 6.48 130.0 3
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL2492
 Kd 6.8 6.8 158.0 1
Unchecked
CHEMBL612545
 Ki 5.89 5.89 1300.0 1
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL2492
 EC50 5.7 5.46 1995.3 2
Neuronal acetylcholine receptor; alpha3/beta4
CHEMBL1907594
 Ki 5.6 5.6 2500.0 2
Acetylcholine receptor; alpha1/beta1/delta/gamma
CHEMBL1907588
 Ki 5.41 5.41 3900.0 2
Rattus norvegicus
CHEMBL376
 EC50 5.0 5.0 10000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 453.0 ng.hr.mL-1 Rattus norvegicus
Cmax 447.5 nM Rattus norvegicus
T1/2 0.47 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Acetylcholine-binding protein Kd = 19.0 nM 7.72 Displacement of [3H]-epibatidine from Lymnaea stagnalis N-terminal FLAG-tagged A... 21986237
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 51.0 nM 7.29 Displacement of [3H]-epibatidine from alpha4beta2 nAChR in rat cortical membrane... 21986237
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 51.0 nM 7.29 Displacement of [3H]epibatidine from human alpha4beta2 nAchR expressed in SH-EP1... 22177081
Unchecked Kd = 59.0 nM 7.23 Displacement of [3H]-epibatidine from Bulinus truncatus N-terminal FLAG-tagged A... 21986237
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 84.0 nM 7.08 Inhibition of [3H]cytisine binding to nicotinic acetylcholine receptor alpha4-be... 15801858
Neuronal acetylcholine receptor subunit alpha-7 Ki = 130.0 nM 6.89 Displacement of [125I]-alpha-bungarotoxin from alpha7 nAChR in rat brain membran... 20236734
Neuronal acetylcholine receptor subunit alpha-7 Kd = 158.0 nM 6.8 Displacement of [125I]alpha-bungarotoxin from alpha7 nAChR 18826295
Neuronal acetylcholine receptor subunit alpha-7 Ki = 220.0 nM 6.66 Inhibition of [125I]alpha-bungarotoxin binding to rat nicotinic acetylcholine re... 15801858
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 250.0 nM 6.6 Displacement of [3H]cytisine from alpha4beta2 nAChR in rat brain membrane after ... 20236734
Unchecked Kd = 330.0 nM 6.48 Displacement of [3H]-epibatidine from Aplysia californica N-terminal FLAG-tagged... 21986237
Unchecked Ki = 1300.0 nM 5.89 Displacement of [3H]methyllycaconitine from rat alpha7 nAchR in rat hippocampal ... 22177081
Neuronal acetylcholine receptor subunit alpha-7 Ki = 1300.0 nM 5.89 Displacement of [3H]-methyllycaconitine from alpha7 nAChR in rat hippocampal mem... 21986237
Neuronal acetylcholine receptor subunit alpha-7 EC50 = 1995.26 nM 5.7 Agonist activity at human recombinant alpha7 nAChR expressed in rat GH3 cells by... 19208472
Neuronal acetylcholine receptor; alpha3/beta4 Ki = 2500.0 nM 5.6 Displacement of [3H]-epibatidine from alpha3beta4 nAChR in human SH-SY5Y cellula... 21986237
Neuronal acetylcholine receptor; alpha3/beta4 Ki = 2500.0 nM 5.6 Displacement of [3H]epibatidine from human alpha3beta4 nAchR expressed in SH-SY5... 22177081
Acetylcholine receptor; alpha1/beta1/delta/gamma Ki = 3900.0 nM 5.41 Displacement of [3H]-epibatidine from alpha1betagammadelta nAChR in human TE671 ... 21986237
Acetylcholine receptor; alpha1/beta1/delta/gamma Ki = 3900.0 nM 5.41 Displacement of [3H]epibatidine from human alpha1/beta/gamma/delta nAchR express... 22177081
Neuronal acetylcholine receptor subunit alpha-7 EC50 = 6000.0 nM 5.22 Partial agonist activity at human alpha7 nAChR expressed in Xenopus laevis oocyt... 30317024
Rattus norvegicus EC50 = 10000.0 nM 5.0 Compound was evaluated for functional potencies and efficacies at rat nAChR subt... 9435889

Literature References

PubMed DOI Target Context # Activities
35576655 10.1016/j.bmc.2022.116811 RAW264.7 8
15801858 10.1021/jm049188d ADMET 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
16033252 10.1021/jm040219e Neuronal acetylcholine receptor; alpha4/beta2 2
21986237 10.1016/j.ejmech.2011.09.033 Unchecked 2
16033252 10.1021/jm040219e Neuronal acetylcholine receptor subunit alpha-7 2
9435889 10.1021/jm970377o Neuronal acetylcholine receptor; alpha4/beta2 2
19208472 10.1016/j.bmcl.2009.01.073 Neuronal acetylcholine receptor subunit alpha-7 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 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
15801858 10.1021/jm049188d Unchecked 1
21986237 10.1016/j.ejmech.2011.09.033 Neuronal acetylcholine receptor subunit alpha-7 1
21986237 10.1016/j.ejmech.2011.09.033 Acetylcholine-binding protein 1
15801858 10.1021/jm049188d Neuronal acetylcholine receptor subunit alpha-7 1
16033252 10.1021/jm040219e Neuronal acetylcholine receptor; alpha4/beta4 1
16033252 10.1021/jm040219e Neuronal acetylcholine receptor; alpha3/beta4 1
9435889 10.1021/jm970377o Rattus norvegicus 1

Data from ChEMBL 36 via Core Engine