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Compound Detail

CHEMBL2165444

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Cc1cc(OC[C@@H]2CCN2)on1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2165444
Phase Preclinical
Structure Type MOL
InChI Key DUGVMSMOUJQMMC-ZETCQYMHSA-N
9
Targets
14
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

168.2
MW (Da)
0.72
ALogP
4
HBA
1
HBD
47.3
PSA (Ų)
0.72
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 C8H12N2O2
MW 168.20
Aromatic Rings 1
Heavy Atoms 12
NP-Likeness -0.32

Activity Summary

Ki 11 meas. best 8.37
EC50 2 meas. best 5.93
IC50 1 meas. best 6.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Neuronal acetylcholine receptor; alpha4/beta4
CHEMBL1907595
 Ki 8.37 7.72 4.3 2
Neuronal acetylcholine receptor; alpha3/beta4
CHEMBL1907594
 Ki 8.34 8.34 4.6 1
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907596
 Ki 8.34 8.34 4.6 1
Neuronal acetylcholine receptor; alpha3/beta2
CHEMBL1907587
 Ki 8.06 8.06 8.7 1
Unchecked
CHEMBL612545
 Ki 7.92 6.545 12.0 2
Neuronal acetylcholine receptor; alpha3/beta4
CHEMBL1907594
 IC50 6.77 6.77 169.0 1
Neuronal acetylcholine receptor; alpha2/beta4
CHEMBL1907590
 Ki 6.51 6.51 311.0 1
Neuronal acetylcholine receptor; alpha3/beta4
CHEMBL1907593
 Ki 6.16 6.16 692.0 1
Neuronal acetylcholine receptors; alpha-3/beta-4, alpha-5, beta-2
CHEMBL2221346
 Ki 6.16 6.16 692.0 1
Neuronal acetylcholine receptor; alpha3/beta4
CHEMBL1907594
 EC50 5.93 5.93 1180.0 1
Neuronal acetylcholine receptors; alpha-3/beta-4, alpha-5, beta-2
CHEMBL2221346
 EC50 5.92 5.92 1200.0 1
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL4980
 Ki 5.54 5.54 2890.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Neuronal acetylcholine receptor; alpha4/beta4 Ki = 4.3 nM 8.37 Displacement of [3H]epibatidine from rat alpha2beta2 nACHR 22148173
Neuronal acetylcholine receptor; alpha3/beta4 Ki = 4.6 nM 8.34 Inhibition of human alpha4beta2 nACHR expressed in SH-EP1 cells by 86Rb+ efflux ... 22148173
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 4.6 nM 8.34 Displacement of [3H]epibatidine from rat alpha4beta2 nACHR 22148173
Neuronal acetylcholine receptor; alpha3/beta2 Ki = 8.7 nM 8.06 Displacement of [3H]epibatidine from rat alpha3beta2 nACHR 22148173
Unchecked Ki = 12.0 nM 7.92 Displacement of [3H]epibatidine from rat forebrain alpha4beta2* nACHR 22148173
Neuronal acetylcholine receptor; alpha4/beta4 Ki = 86.0 nM 7.07 Displacement of [3H]epibatidine from rat alpha4beta4 nACHR 22148173
Neuronal acetylcholine receptor; alpha3/beta4 IC50 = 169.0 nM 6.77 Inhibition of human alpha4beta2 nACHR expressed in SH-EP1 cells by 86Rb+ efflux ... 22148173
Neuronal acetylcholine receptor; alpha2/beta4 Ki = 311.0 nM 6.51 Displacement of [3H]epibatidine from rat alpha2beta4 nACHR 22148173
Neuronal acetylcholine receptors; alpha-3/beta-4, alpha-5, beta-2 Ki = 692.0 nM 6.16 Inhibition of alpha3beta4alpha5beta2 nACHR in human SH-SY5Y cells by 86Rb+ efflu... 22148173
Neuronal acetylcholine receptor; alpha3/beta4 Ki = 692.0 nM 6.16 Displacement of [3H]epibatidine from rat alpha3beta4 nACHR 22148173
Neuronal acetylcholine receptor; alpha3/beta4 EC50 = 1180.0 nM 5.93 Agonist activity at human alpha4beta2 nACHR expressed in SH-EP1 cells by 86Rb+ e... 22148173
Neuronal acetylcholine receptors; alpha-3/beta-4, alpha-5, beta-2 EC50 = 1200.0 nM 5.92 Agonist activity at alpha3beta4alpha5beta2 nACHR in human SH-SY5Y cells by 86Rb+... 22148173
Neuronal acetylcholine receptor subunit alpha-7 Ki = 2890.0 nM 5.54 Binding affinity to rat alpha7 nACHR at 10 uM 22148173
Unchecked Ki = 6790.0 nM 5.17 Binding affinity to rat forebrain alpha7* nACHR at 10 uM 22148173

Literature References

PubMed DOI Target Context # Activities
22148173 10.1021/jm201301h Unchecked 12
22148173 10.1021/jm201301h Neuronal acetylcholine receptor; alpha3/beta4 6
22148173 10.1021/jm201301h Liver microsomes 6
22148173 10.1021/jm201301h Neuronal acetylcholine receptors; alpha-3/beta-4, alpha-5, beta-2 5
22148173 10.1021/jm201301h Cytochrome P450 3A4 4
22148173 10.1021/jm201301h Mus musculus 3
22148173 10.1021/jm201301h Plasma 2
22148173 10.1021/jm201301h Neuronal acetylcholine receptor; alpha4/beta4 2
22148173 10.1021/jm201301h Cytochrome P450 1A2 2
22148173 10.1021/jm201301h Cytochrome P450 2B6 2
22148173 10.1021/jm201301h Cytochrome P450 2C9 2
22148173 10.1021/jm201301h Cytochrome P450 2C19 2
22148173 10.1021/jm201301h Cytochrome P450 2D6 2
22148173 10.1021/jm201301h Neuronal acetylcholine receptor subunit alpha-7 1
22148173 10.1021/jm201301h Acetylcholine receptor; alpha1/beta1/delta/gamma 1
22148173 10.1021/jm201301h Voltage-gated inwardly rectifying potassium channel KCNH2 1
22148173 10.1021/jm201301h Neuronal acetylcholine receptor; alpha4/beta2 1
22148173 10.1021/jm201301h Neuronal acetylcholine receptor; alpha3/beta2 1
22148173 10.1021/jm201301h Neuronal acetylcholine receptor; alpha2/beta4 1
23641311 10.1021/ml3002715 Unchecked 1

Data from ChEMBL 36 via Core Engine