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Compound Detail

CHEMBL378471

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O=C(N[C@H]1CN2CCC1CC2)c1ccc2occc2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL378471
Phase Preclinical
Structure Type MOL
InChI Key CXDMUUBLDHSHNL-AWEZNQCLSA-N
6
Targets
9
Activities
3
Assay Types
6
PK Parameters
13
Publications
0
Known Names

Molecular Properties

270.3
MW (Da)
2.26
ALogP
3
HBA
1
HBD
45.5
PSA (Ų)
0.91
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C16H18N2O2
MW 270.33
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness -0.11

Activity Summary

Ki 5 meas. best 8.8
EC50 2 meas. best 7.37
IC50 2 meas. best 6.24

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL2492
 Ki 8.8 8.8 1.6 1
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL4980
 Ki 8.8 8.8 1.6 1
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL2492
 EC50 7.37 7.37 43.0 1
Unchecked
CHEMBL612545
 EC50 7.33 7.33 47.0 1
5-hydroxytryptamine receptor 3A
CHEMBL1899
 IC50 6.24 6.24 580.0 1
Serotonin 3 (5-HT3) receptor
CHEMBL2094132
 Ki 6.24 6.21 580.0 2
5-hydroxytryptamine receptor 3A
CHEMBL1899
 Ki 6.18 6.18 663.0 1
Cytochrome P450 2D6
CHEMBL289
 IC50 5.44 5.44 3600.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 39.0 mL.min-1.kg-1 Rattus norvegicus
CL 5.3 mL.min-1.kg-1 Homo sapiens
CL 20.1 mL.min-1.kg-1 Rattus norvegicus
F 88.0 % Rattus norvegicus
T1/2 2.0 hr Rattus norvegicus
T1/2 2.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Neuronal acetylcholine receptor subunit alpha-7 Ki = 1.6 nM 8.8 Displacement of [3H]MLA from alpha-7 nAChR in Sprague-Dawley rat brain homogenat... 16821801
Neuronal acetylcholine receptor subunit alpha-7 Ki = 1.6 nM 8.8 Binding affinity to alpha7 nAChR 21919481
Neuronal acetylcholine receptor subunit alpha-7 EC50 = 43.0 nM 7.37 Agonist activity at alpha7 nAChR 21919481
Unchecked EC50 = 47.0 nM 7.33 Activity at alpha7-5HT3 chimera expressed in SHEP1 cells by FLIPR assay 16821801
5-hydroxytryptamine receptor 3A IC50 = 580.0 nM 6.24 Inhibition of 5HT3 receptor 21919481
Serotonin 3 (5-HT3) receptor Ki = 580.0 nM 6.24 Activity at 5HT3 receptor expressed in SHEP1 cells by FLIPR assay 16821801
Serotonin 3 (5-HT3) receptor Ki = 663.0 nM 6.18 Binding affinity to 5HT3 receptor 16821801
5-hydroxytryptamine receptor 3A Ki = 663.0 nM 6.18 Binding affinity to 5HT3 receptor 21919481
Cytochrome P450 2D6 IC50 = 3600.0 nM 5.44 Inhibition of CYP2D6 16821801

Literature References

PubMed DOI Target Context # Activities
16821801 10.1021/jm0602413 Liver microsomes 5
16821801 10.1021/jm0602413 Rattus norvegicus 4
16821801 10.1021/jm0602413 Voltage-gated inwardly rectifying potassium channel KCNH2 2
16821801 10.1021/jm0602413 Serotonin 3 (5-HT3) receptor 2
21919481 10.1021/jm2007672 Neuronal acetylcholine receptor subunit alpha-7 2
21919481 10.1021/jm2007672 5-hydroxytryptamine receptor 3A 2
16821801 10.1021/jm0602413 Cytochrome P450 2D6 1
16821801 10.1021/jm0602413 Neuronal acetylcholine receptor; alpha4/beta2 1
16821801 10.1021/jm0602413 Acetylcholine receptor; alpha1/beta1/delta/gamma 1
16821801 10.1021/jm0602413 Neuronal acetylcholine receptor; alpha3/beta4 1
16821801 10.1021/jm0602413 Neuronal acetylcholine receptor subunit alpha-7 1
16821801 10.1021/jm0602413 Unchecked 1
21919481 10.1021/jm2007672 Voltage-gated inwardly rectifying potassium channel KCNH2 1

Data from ChEMBL 36 via Core Engine