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Compound Detail

CHEMBL58362

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CC[C@@H]1CN2CC[C@]3(Nc4cccc(OC)c4C3=O)[C@@H]2C[C@@H]1/C(=C\OC)C(=O)OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL58362
Phase Preclinical
Structure Type MOL
InChI Key BAEJBRCYKACTAA-WGUOAFTMSA-N
8
Targets
25
Activities
3
Assay Types
0
PK Parameters
18
Publications
0
Known Names

Molecular Properties

414.5
MW (Da)
2.87
ALogP
7
HBA
1
HBD
77.1
PSA (Ų)
0.45
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H30N2O5
MW 414.50
Aromatic Rings 1
Heavy Atoms 30
NP-Likeness 1.64

Activity Summary

IC50 9 meas. best 9.55
Ki 9 meas. best 11.0
EC50 7 meas. best 8.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mu-type opioid receptor
CHEMBL233
 Ki 11.0 11.0 0.0 1
Mu-type opioid receptor
CHEMBL4354
 Ki 10.06 10.06 0.1 1
Mu-type opioid receptor
CHEMBL233
 IC50 9.55 8.4 0.3 3
Mu-type opioid receptor
CHEMBL2858
 Ki 9.12 9.12 0.8 1
Delta-type opioid receptor
CHEMBL236
 IC50 8.9 8.835 1.3 2
Delta-type opioid receptor
CHEMBL236
 EC50 8.77 8.77 1.7 2
Kappa-type opioid receptor
CHEMBL237
 EC50 8.77 8.77 1.7 2
Mu-type opioid receptor
CHEMBL2858
 EC50 8.77 8.77 1.7 1
Mu-type opioid receptor
CHEMBL233
 EC50 8.77 8.77 1.7 2
Delta-type opioid receptor
CHEMBL236
 Ki 8.52 8.52 3.0 2
Delta-type opioid receptor
CHEMBL3222
 Ki 8.52 8.52 3.0 1
Kappa-type opioid receptor
CHEMBL4329
 Ki 7.62 7.62 24.0 1
Kappa-type opioid receptor
CHEMBL4329
 IC50 7.51 7.51 31.0 1
Delta-type opioid receptor
CHEMBL3222
 IC50 7.21 7.21 61.0 1
Kappa-type opioid receptor
CHEMBL237
 Ki 7.1 7.1 79.0 1
Kappa-type opioid receptor
CHEMBL3952
 Ki 7.1 7.1 79.4 1
Kappa-type opioid receptor
CHEMBL237
 IC50 6.88 6.88 131.8 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mu-type opioid receptor Ki = 0.01 nM 11.0 Binding affinity to mu opioid receptor (unknown origin) 23517479
Mu-type opioid receptor Ki = 0.0871 nM 10.06 Binding affinity using guinea pig brain membrane preparations, towards Opioid re... 11960505
Mu-type opioid receptor IC50 = 0.2818 nM 9.55 Inhibition of mu opioid receptor (unknown origin) in presence of DPDPE by [35S]-... 31550662
Mu-type opioid receptor Ki = 0.75 nM 9.12 Displacement of [125I]-IBNtxA from mouse mu opioid receptor-1 expressed in CHO c... 27556704
Delta-type opioid receptor IC50 = 1.259 nM 8.9 Inhibition of delta opioid receptor (unknown origin) in presence of DPDPE by [35... 31550662
Kappa-type opioid receptor EC50 = 1.7 nM 8.77 Inhibition of kappa opioid receptor (unknown origin) in presence of DAMGO by [35... 31550662
Delta-type opioid receptor EC50 = 1.7 nM 8.77 Inhibition of delta opioid receptor (unknown origin) in presence of DPDPE by [35... 31550662
Mu-type opioid receptor EC50 = 1.7 nM 8.77 Inhibition of mu opioid receptor (unknown origin) in presence of DPDPE by [35S]-... 31550662
Delta-type opioid receptor EC50 = 1.7 nM 8.77 Inhibition of delta opioid receptor (unknown origin) in presence of DAMGO by [35... 31550662
Mu-type opioid receptor EC50 = 1.7 nM 8.77 Inhibition of mu opioid receptor (unknown origin) in presence of DAMGO by [35S]-... 31550662
Mu-type opioid receptor EC50 = 1.7 nM 8.77 Agonist activity at mouse mu opioid receptor-1 expressed in CHO cell membranes a... 27556704
Delta-type opioid receptor IC50 = 1.698 nM 8.77 Inhibition of delta opioid receptor (unknown origin) in presence of DAMGO by [35... 31550662
Kappa-type opioid receptor EC50 = 1.7 nM 8.77 Inhibition of kappa opioid receptor (unknown origin) in presence of DPDPE by [35... 31550662
Delta-type opioid receptor Ki = 3.02 nM 8.52 Binding affinity using guinea pig brain membrane preparations, towards Opioid re... 11960505
Delta-type opioid receptor Ki = 3.0 nM 8.52 Binding affinity to delta opioid receptor (unknown origin) 23517479
Delta-type opioid receptor Ki = 3.0 nM 8.52 Displacement of [125I]-IBNtxA from mouse delta opioid receptor-1 expressed in CH... 27556704
Mu-type opioid receptor IC50 = 6.607 nM 8.18 Inhibition of mu opioid receptor (unknown origin) in presence of DAMGO by [35S]-... 31550662
Kappa-type opioid receptor Ki = 24.0 nM 7.62 Displacement of [125I]-IBNtxA from mouse kappa opioid receptor-1 expressed in CH... 27556704
Kappa-type opioid receptor IC50 = 31.0 nM 7.51 Antagonist activity at mouse kappa opioid receptor-1 expressed in CHO cell membr... 27556704
Mu-type opioid receptor IC50 = 34.0 nM 7.47 Inhibition of DAMGO-induced beta-arrestin-2 recruitment at mu opioid receptor-1 ... 27556704

Literature References

PubMed DOI Target Context # Activities
27556704 10.1021/acs.jmedchem.6b00748 Mus musculus 26
27556704 10.1021/acs.jmedchem.6b00748 ADMET 10
27556704 10.1021/acs.jmedchem.6b00748 Mu-type opioid receptor 6
31550662 10.1016/j.ejmech.2019.111701 Kappa-type opioid receptor 6
31550662 10.1016/j.ejmech.2019.111701 Delta-type opioid receptor 6
31550662 10.1016/j.ejmech.2019.111701 Mu-type opioid receptor 5
11960505 10.1021/jm010576e Cavia porcellus 4
27556704 10.1021/acs.jmedchem.6b00748 Kappa-type opioid receptor 2
27556704 10.1021/acs.jmedchem.6b00748 Delta-type opioid receptor 2
11960505 10.1021/jm010576e Kappa-type opioid receptor 2
11960505 10.1021/jm010576e Delta-type opioid receptor 2
11960505 10.1021/jm010576e Mu-type opioid receptor 2
23517479 10.1021/jm400143z Mu-type opioid receptor 1
23517479 10.1021/jm400143z Kappa-type opioid receptor 1
23517479 10.1021/jm400143z Delta-type opioid receptor 1
27556704 10.1021/acs.jmedchem.6b00748 Alpha-2C adrenergic receptor 1
27556704 10.1021/acs.jmedchem.6b00748 Alpha-2A adrenergic receptor 1
27556704 10.1021/acs.jmedchem.6b00748 5-hydroxytryptamine receptor 7 1

Data from ChEMBL 36 via Core Engine