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Compound Detail

CHEMBL4069231

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O=C(Cc1ccc(Cl)c(Cl)c1)N1CCN[C@H]2CCC[C@H](N3CCCC3)[C@H]21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4069231
Phase Preclinical
Structure Type MOL
InChI Key LWDJYEJRZVMWMH-BJLQDIEVSA-N
5
Targets
9
Activities
2
Assay Types
0
PK Parameters
13
Publications
0
Known Names

Molecular Properties

396.4
MW (Da)
3.35
ALogP
3
HBA
1
HBD
35.6
PSA (Ų)
0.85
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 C20H27Cl2N3O
MW 396.36
Aromatic Rings 1
Heavy Atoms 26
NP-Likeness -0.48

Activity Summary

Ki 6 meas. best 9.46
EC50 3 meas. best 8.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Kappa-type opioid receptor
CHEMBL3952
 Ki 9.46 9.365 0.3 2
Kappa-type opioid receptor
CHEMBL237
 EC50 8.92 8.59 1.2 3
Kappa-type opioid receptor
CHEMBL237
 Ki 8.32 8.32 4.8 1
Delta-type opioid receptor
CHEMBL269
 Ki 6.69 6.69 205.0 1
Mu-type opioid receptor
CHEMBL4354
 Ki 6.66 6.66 217.0 1
Unchecked
CHEMBL612545
 Ki 6.04 6.04 915.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Kappa-type opioid receptor Ki = 0.35 nM 9.46 Displacement of [3H]U-69,593 from kappa-type opioid receptor in guinea pig brain... 28218838
Kappa-type opioid receptor Ki = 0.54 nM 9.27 Displacement of [3H]U-69,593 from KOR in guinea pig brain membranes after 120 mi... 30543421
Kappa-type opioid receptor EC50 = 1.2 nM 8.92 Agonist activity at human KOR expressed in HEK293T cells assessed as inhibition ... 30543421
Kappa-type opioid receptor EC50 = 3.7 nM 8.43 Agonist activity at recombinant human kappa-type opioid receptor expressed in HE... 28218838
Kappa-type opioid receptor EC50 = 3.8 nM 8.42 Agonist activity at Tango-KOR (unknown origin) expressed in HTLA cells harboring... 30543421
Kappa-type opioid receptor Ki = 4.8 nM 8.32 Displacement of [3H]diprenorphine from human KOR expressed in HEK293T cell membr... 30543421
Delta-type opioid receptor Ki = 205.0 nM 6.69 Displacement of [3H]DPDPE from DOR in Sprague-Dawley rat brain membranes after 1... 30543421
Mu-type opioid receptor Ki = 217.0 nM 6.66 Displacement of [3H]DAMGO from mu-type opioid receptor in guinea pig brain membr... 28218838
Unchecked Ki = 915.0 nM 6.04 Displacement of [3H]DPDPE from delta-type opioid receptor in guinea pig brain me... 28218838

Literature References

PubMed DOI Target Context # Activities
30543421 10.1021/acs.jmedchem.8b01609 Mus musculus 9
30543421 10.1021/acs.jmedchem.8b01609 Kappa-type opioid receptor 6
30543421 10.1021/acs.jmedchem.8b01609 Unchecked 5
30543421 10.1021/acs.jmedchem.8b01609 T-cell 5
28218838 10.1021/acs.jmedchem.6b01868 Kappa-type opioid receptor 3
28218838 10.1021/acs.jmedchem.6b01868 Unchecked 3
30543421 10.1021/acs.jmedchem.8b01609 Delta-type opioid receptor 2
28218838 10.1021/acs.jmedchem.6b01868 Mu-type opioid receptor 1
28218838 10.1021/acs.jmedchem.6b01868 Sigma non-opioid intracellular receptor 1 1
30543421 10.1021/acs.jmedchem.8b01609 Mu-type opioid receptor 1
30543421 10.1021/acs.jmedchem.8b01609 Sigma non-opioid intracellular receptor 1 1
30543421 10.1021/acs.jmedchem.8b01609 Sigma intracellular receptor 2 1
30543421 10.1021/acs.jmedchem.8b01609 Dendritic cell 1

Data from ChEMBL 36 via Core Engine