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Compound Detail

CHEMBL58033

(-)-U-50488
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CN(C(=O)Cc1ccc(Cl)c(Cl)c1)[C@H]1CCCC[C@@H]1N1CCCC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL58033
Name (-)-U-50488
Phase Preclinical
Structure Type MOL
InChI Key VQLPLYSROCPWFF-ROUUACIJSA-N
6
Targets
13
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

369.3
MW (Da)
4.40
ALogP
2
HBA
0
HBD
23.6
PSA (Ų)
0.79
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 C19H26Cl2N2O
MW 369.34
Aromatic Rings 1
Heavy Atoms 24
NP-Likeness -0.64

Activity Summary

Ki 9 meas. best 9.47
EC50 4 meas. best 8.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Kappa-type opioid receptor
CHEMBL3952
 Ki 9.47 8.72 0.3 4
Kappa-type opioid receptor
CHEMBL3614
 Ki 9.44 9.44 0.4 1
Kappa-type opioid receptor
CHEMBL237
 EC50 8.7 7.7933 2.0 3
Kappa-type opioid receptor
CHEMBL237
 Ki 8.21 7.34 6.1 2
Kappa-type opioid receptor
CHEMBL4329
 EC50 7.77 7.77 17.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 6.23 6.23 594.0 1
Mu-type opioid receptor
CHEMBL270
 Ki 5.86 5.86 1397.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Kappa-type opioid receptor Ki = 0.34 nM 9.47 Displacement of [3H]-U-69593 from kappa opioid receptor in guinea pig brain memb... 26411794
Kappa-type opioid receptor Ki = 0.36 nM 9.44 Displacement of [3H]U69593 from rat recombinant kappa opioid receptor expressed ... 25513968
Kappa-type opioid receptor Ki = 0.89 nM 9.05 Compound was evaluated for binding affinity towards kappa opioid receptor using ... 2547074
Kappa-type opioid receptor Ki = 1.0 nM 9.0 Affinity at K opioid receptor on membranes prepared from guinea pig cerebellum b... -
Kappa-type opioid receptor EC50 = 2.0 nM 8.7 Agonist activity at human kappa opioid receptor expressed in CHO cell membrane i... 34387468
Kappa-type opioid receptor Ki = 6.1 nM 8.21 Displacement of [3H]U69,593 from human kappa opioid receptor expressed in CHO ce... 34387468
Kappa-type opioid receptor EC50 = 17.0 nM 7.77 Agonist activity at mouse KOR expressed in CHO cell membranes assessed as induct... 28603600
Kappa-type opioid receptor Ki = 44.0 nM 7.36 Compound was evaluated for binding affinity towards kappa opioid receptor using ... 2547074
Kappa-type opioid receptor EC50 = 46.0 nM 7.34 Activity at human kappa opioid receptor expressed in CHO cells by [35S]GTP-gamma... 16392810
Kappa-type opioid receptor EC50 = 46.0 nM 7.34 Agonist activity at human kappa opioid receptor expressed in CHO cells assessed ... 21351746
Kappa-type opioid receptor Ki = 340.0 nM 6.47 Binding affinity to kappa opioid receptor (unknown origin) 26411794
Sigma non-opioid intracellular receptor 1 Ki = 594.0 nM 6.23 Compound was evaluated for binding affinity towards sigma opioid receptor using ... 2547074
Mu-type opioid receptor Ki = 1397.0 nM 5.86 Displacement of [3H]DAMGO from rat mu opioid receptor expressed in CHO cell memb... 34387468

Literature References

PubMed DOI Target Context # Activities
16392810 10.1021/jm050577x Kappa-type opioid receptor 4
26411794 10.1016/j.bmcl.2015.09.040 Kappa-type opioid receptor 4
34387468 10.1021/acs.jmedchem.1c01082 Kappa-type opioid receptor 3
34387468 10.1021/acs.jmedchem.1c01082 Unchecked 3
34387468 10.1021/acs.jmedchem.1c01082 Mus musculus 2
28603600 10.1039/C6MD00450D Kappa-type opioid receptor 2
28603600 10.1039/C6MD00450D Mu-type opioid receptor 2
21351746 10.1021/jm101542c Kappa-type opioid receptor 2
23618710 10.1016/j.bmc.2013.02.060 Kappa-type opioid receptor 2
2547074 10.1021/jm00128a050 Kappa-type opioid receptor 2
25513968 10.1016/j.ejmech.2014.12.016 Kappa-type opioid receptor 1
26411794 10.1016/j.bmcl.2015.09.040 Delta-type opioid receptor 1
26411794 10.1016/j.bmcl.2015.09.040 Mu-type opioid receptor 1
25513968 10.1016/j.ejmech.2014.12.016 Delta-type opioid receptor 1
25513968 10.1016/j.ejmech.2014.12.016 Mu-type opioid receptor 1
21476493 10.1021/jm200144j Rattus norvegicus 1
- 10.1016/S0960-894X(01)80179-7 Kappa-type opioid receptor 1
2547074 10.1021/jm00128a050 Unchecked 1
2547074 10.1021/jm00128a050 Glutamate receptor ionotropic, NMDA 2C 1
2547074 10.1021/jm00128a050 D(2) dopamine receptor 1

Data from ChEMBL 36 via Core Engine