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Compound Detail

CHEMBL4088272

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CCCN1CCC=C(c2cc(-c3ccc(C)cc3)no2)C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4088272
Phase Preclinical
Structure Type MOL
InChI Key FOQRKFCLRMMKAT-UHFFFAOYSA-N
12
Targets
14
Activities
2
Assay Types
1
PK Parameters
17
Publications
0
Known Names

Molecular Properties

282.4
MW (Da)
4.15
ALogP
3
HBA
0
HBD
29.3
PSA (Ų)
0.84
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C18H22N2O
MW 282.39
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness -1.09

Activity Summary

Ki 13 meas. best 10.1
IC50 1 meas. best 4.94

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 10.1 9.4 0.1 2
Sigma non-opioid intracellular receptor 1
CHEMBL4153
 Ki 8.37 8.37 4.3 1
Sigma intracellular receptor 2
CHEMBL4105907
 Ki 6.1 5.98 794.3 2
Alpha-2A adrenergic receptor
CHEMBL1867
 Ki 5.08 5.08 8317.6 1
Alpha-2C adrenergic receptor
CHEMBL1916
 Ki 5.0 5.0 10000.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 Ki 5.0 5.0 10000.0 1
SARS-CoV-2
CHEMBL4303835
 IC50 4.94 4.94 11455.1 1
Alpha-2B adrenergic receptor
CHEMBL1942
 Ki 4.69 4.69 20417.4 1
Muscarinic acetylcholine receptor M2
CHEMBL211
 Ki 4.62 4.62 23988.3 1
Muscarinic acetylcholine receptor M3
CHEMBL245
 Ki 4.62 4.62 23988.3 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
 Ki 4.61 4.61 24547.1 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
 Ki 4.55 4.55 28183.8 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 241.8 - Chlorocebus sabaeus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sigma non-opioid intracellular receptor 1 Ki = 0.08 nM 10.1 Binding affinity to human sigma 1 receptor 36202063
Sigma non-opioid intracellular receptor 1 Ki = 1.995 nM 8.7 Displacement of [3H]-pentazocin from the Sigma1 receptor 32353859
Sigma non-opioid intracellular receptor 1 Ki = 4.3 nM 8.37 Displacement of [3H]-(+)-pentazocine from sigma1 receptor in guinea pig brain me... 29220177
Sigma intracellular receptor 2 Ki = 794.33 nM 6.1 Displacement of [3H]-DTG from the Sigma2 receptor 32353859
Sigma intracellular receptor 2 Ki = 1377.0 nM 5.86 Binding affinity to human sigma 2 receptor 36202063
Alpha-2A adrenergic receptor Ki = 8317.64 nM 5.08 Activity of compound against Alpha-2A (ADRA2A) adrenergic receptor by displaceme... 32353859
Voltage-gated inwardly rectifying potassium channel KCNH2 Ki = 10000.0 nM 5.0 hERG binding assays: Displacement of [3H]-Dofetilide (5 nM final) from hERG memb... 32353859
Alpha-2C adrenergic receptor Ki = 10000.0 nM 5.0 Activity of compound against Alpha 2C (ADRA2C) adrenergic receptor by displaceme... 32353859
SARS-CoV-2 IC50 = 11455.13 nM 4.94 IC50 for antiviral activity against SARS-CoV-2 in the Vero E6 cell line at 48 h ... 32353859
Alpha-2B adrenergic receptor Ki = 20417.38 nM 4.69 Activity of compound against Alpha 2B (ADRA2B) adrenergic receptor by displaceme... 32353859
Muscarinic acetylcholine receptor M2 Ki = 23988.33 nM 4.62 Activity of compound against Muscarinic acetylcholine receptor M2 (CHRM2) by dis... 32353859
Muscarinic acetylcholine receptor M3 Ki = 23988.33 nM 4.62 Activity of compound against Muscarinic acetylcholine receptor M3 (CHRM3) by dis... 32353859
Muscarinic acetylcholine receptor M4 Ki = 24547.09 nM 4.61 Activity of compound against Muscarinic acetylcholine receptor M4 (CHRM4) by di... 32353859
Muscarinic acetylcholine receptor M5 Ki = 28183.83 nM 4.55 Activity of compound against Muscarinic acetylcholine receptor M5 (CHRM5) by dis... 32353859

Literature References

PubMed DOI Target Context # Activities
32353859 10.1038/s41586-020-2286-9 SARS-CoV-2 3
32353859 10.1038/s41586-020-2286-9 ADMET 2
32353859 10.1038/s41586-020-2286-9 Vero C1008 2
36202063 10.1016/j.bmc.2022.117032 Sigma intracellular receptor 2 1
29220177 10.1021/acs.jmedchem.7b01584 Sigma non-opioid intracellular receptor 1 1
36202063 10.1016/j.bmc.2022.117032 Sigma non-opioid intracellular receptor 1 1
32353859 10.1038/s41586-020-2286-9 Muscarinic acetylcholine receptor M5 1
32353859 10.1038/s41586-020-2286-9 Muscarinic acetylcholine receptor M4 1
32353859 10.1038/s41586-020-2286-9 Muscarinic acetylcholine receptor M3 1
32353859 10.1038/s41586-020-2286-9 Muscarinic acetylcholine receptor M2 1
32353859 10.1038/s41586-020-2286-9 Muscarinic acetylcholine receptor M1 1
32353859 10.1038/s41586-020-2286-9 Alpha-2C adrenergic receptor 1
32353859 10.1038/s41586-020-2286-9 Alpha-2B adrenergic receptor 1
32353859 10.1038/s41586-020-2286-9 Alpha-2A adrenergic receptor 1
32353859 10.1038/s41586-020-2286-9 Sigma intracellular receptor 2 1
32353859 10.1038/s41586-020-2286-9 Sigma non-opioid intracellular receptor 1 1
32353859 10.1038/s41586-020-2286-9 Voltage-gated inwardly rectifying potassium channel KCNH2 1

Data from ChEMBL 36 via Core Engine