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Compound Detail

CHEMBL522143

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O=C(N[C@@H]1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5)c1ccncc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL522143
Phase Preclinical
Structure Type MOL
InChI Key XQWZTPWKACKUMJ-HJUABUFYSA-N
5
Targets
14
Activities
3
Assay Types
0
PK Parameters
17
Publications
0
Known Names

Molecular Properties

447.5
MW (Da)
2.15
ALogP
6
HBA
3
HBD
94.9
PSA (Ų)
0.66
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 C26H29N3O4
MW 447.54
Aromatic Rings 2
Heavy Atoms 33
NP-Likeness 0.77

Activity Summary

Ki 6 meas. best 9.43
IC50 5 meas. best 8.79
EC50 3 meas. best 8.94

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mu-type opioid receptor
CHEMBL233
 Ki 9.43 9.195 0.4 2
Unchecked
CHEMBL612545
 Ki 9.11 9.11 0.8 1
Mu-type opioid receptor
CHEMBL233
 EC50 8.94 8.94 1.1 1
Unchecked
CHEMBL612545
 IC50 8.79 8.79 1.6 2
Mu-type opioid receptor
CHEMBL233
 IC50 8.64 8.33 2.3 3
Mu-type opioid receptor
CHEMBL270
 Ki 8.32 8.32 4.8 1
Delta-type opioid receptor
CHEMBL236
 EC50 7.82 7.82 15.2 1
Kappa-type opioid receptor
CHEMBL237
 EC50 7.54 7.54 28.8 1
Kappa-type opioid receptor
CHEMBL237
 Ki 7.22 7.22 60.7 1
Delta-type opioid receptor
CHEMBL236
 Ki 6.56 6.56 277.5 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mu-type opioid receptor Ki = 0.37 nM 9.43 Displacement of [3H]naloxone from monocloned mu opioid receptor expressed in CHO... 19199782
Unchecked Ki = 0.77 nM 9.11 Binding affinity to MOR Y210A mutant (unknown origin) expressed in CHO cells aft... 24055076
Mu-type opioid receptor Ki = 1.09 nM 8.96 Binding affinity to wild type MOR (unknown origin) expressed in CHO cells after ... 24055076
Mu-type opioid receptor EC50 = 1.14 nM 8.94 Activity at monocloned mu opioid receptor expressed in CHO cells by [35S]GTPgamm... 19199782
Unchecked IC50 = 1.61 nM 8.79 Binding affinity to mu opioid Y210A mutant receptor expressed in CHO cells 19199782
Unchecked IC50 = 1.61 nM 8.79 Binding affinity to MOR Y210A mutant (unknown origin) expressed in CHO cells aft... 24055076
Mu-type opioid receptor IC50 = 2.29 nM 8.64 Binding affinity to wild type mu opioid receptor expressed in CHO cells 19199782
Mu-type opioid receptor IC50 = 2.29 nM 8.64 Binding affinity to wild type MOR (unknown origin) expressed in CHO cells after ... 24055076
Mu-type opioid receptor Ki = 4.8 nM 8.32 Antagonist activity at mu-opioid receptor in rat thalamus membrane assessed as i... 38544305
Delta-type opioid receptor EC50 = 15.2 nM 7.82 Agonist activity at delta opioid receptor expressed in CHO cells assessed as sti... 23116124
Mu-type opioid receptor IC50 = 19.5 nM 7.71 Antagonist activity at MOR (unknown origin) assessed as inhibition of DAMGO-indu... 24055076
Kappa-type opioid receptor EC50 = 28.8 nM 7.54 Agonist activity at kappa opioid receptor expressed in CHO cells assessed as sti... 23116124
Kappa-type opioid receptor Ki = 60.72 nM 7.22 Displacement of [3H]norBNI from monocloned kappa opioid receptor expressed in CH... 19199782
Delta-type opioid receptor Ki = 277.51 nM 6.56 Displacement of [3H]NTI from monocloned delta opioid receptor expressed in CHO c... 19199782

Literature References

PubMed DOI Target Context # Activities
22683223 10.1016/j.bmcl.2012.05.075 Mus musculus 19
19199782 10.1021/jm801272c Mu-type opioid receptor 5
24055076 10.1016/j.bmc.2013.08.042 Mu-type opioid receptor 5
19199782 10.1021/jm801272c Unchecked 4
22506484 10.1021/jm201136z Caco-2 3
38544305 10.1021/acs.jmedchem.4c00139 ADMET 2
35255685 10.1021/acs.jmedchem.2c00087 ADMET 2
35255683 10.1021/acs.jmedchem.1c02185 Mus musculus 2
24055076 10.1016/j.bmc.2013.08.042 Unchecked 2
23116124 10.1021/jm301247n Kappa-type opioid receptor 2
23116124 10.1021/jm301247n Delta-type opioid receptor 2
22683223 10.1016/j.bmcl.2012.05.075 Mu-type opioid receptor 1
19199782 10.1021/jm801272c Delta-type opioid receptor 1
19199782 10.1021/jm801272c Kappa-type opioid receptor 1
38544305 10.1021/acs.jmedchem.4c00139 Mu-type opioid receptor 1
38544305 10.1021/acs.jmedchem.4c00139 ATP-dependent translocase ABCB1 1
19199782 10.1021/jm801272c Mus musculus 1

Data from ChEMBL 36 via Core Engine