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Compound Detail

CHEMBL146756

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O=C(/C=C/C(=O)Oc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)N(CC1CCC1)CC3)Oc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)N(CC1CCC1)CC3
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL146756
Phase Preclinical
Structure Type MOL
InChI Key AJIAOWVCYKDFGH-KBJNHENKSA-N
3
Targets
16
Activities
3
Assay Types
0
PK Parameters
17
Publications
0
Known Names

Molecular Properties

703.0
MW (Da)
8.47
ALogP
6
HBA
0
HBD
59.1
PSA (Ų)
0.16
QED
2
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C46H58N2O4
MW 702.98
Aromatic Rings 2
Heavy Atoms 52
NP-Likeness 0.36

Activity Summary

Ki 11 meas. best 10.11
EC50 3 meas. best 8.64
IC50 2 meas. best 6.21

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Kappa-type opioid receptor
CHEMBL237
 Ki 10.11 10.105 0.1 4
Mu-type opioid receptor
CHEMBL233
 Ki 9.7 9.7 0.2 4
Kappa-type opioid receptor
CHEMBL237
 EC50 8.64 8.505 2.3 2
Mu-type opioid receptor
CHEMBL233
 EC50 8.54 8.54 2.9 1
Delta-type opioid receptor
CHEMBL236
 Ki 8.03 8.03 9.4 3
Mu-type opioid receptor
CHEMBL233
 IC50 6.21 6.21 610.0 1
Kappa-type opioid receptor
CHEMBL237
 IC50 5.62 5.62 2400.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Kappa-type opioid receptor Ki = 0.078 nM 10.11 Inhibitory activity against Opioid receptor kappa 1 in chinese Hamster Ovary (CH... 14613319
Kappa-type opioid receptor Ki = 0.078 nM 10.11 Displacement of [3H]U69593 from human kappa opioid receptor expressed in CHO cel... 26656913
Kappa-type opioid receptor Ki = 0.08 nM 10.1 Displacement of [3H]U69593 from human kappa opioid receptor expressed in CHO cel... 16392810
Kappa-type opioid receptor Ki = 0.08 nM 10.1 Displacement of [3H]U69563 from human kappa-opioid receptor expressed in CHO cel... 21482470
Mu-type opioid receptor Ki = 0.2 nM 9.7 Inhibitory activity against Opioid receptor mu 1 in chinese Hamster Ovary (CHO) ... 14613319
Mu-type opioid receptor Ki = 0.2 nM 9.7 Displacement of [3H]DAMGO from human mu opioid receptor expressed in CHO cells 16392810
Mu-type opioid receptor Ki = 0.2 nM 9.7 Displacement of [3H]DAMGO from human mu-opioid receptor expressed in CHO cells a... 21482470
Mu-type opioid receptor Ki = 0.2 nM 9.7 Displacement of [3H]DAMGO from human mu opioid receptor expressed in CHO cell me... 26656913
Kappa-type opioid receptor EC50 = 2.3 nM 8.64 Inhibitory activity in stimulating [35S]-GTP-gamma S binding mediated by the Opi... 14613319
Mu-type opioid receptor EC50 = 2.9 nM 8.54 Inhibitory activity in stimulating [35S]-GTP-gamma S binding mediated by the Opi... 14613319
Kappa-type opioid receptor EC50 = 4.3 nM 8.37 Agonist activity at human kappa opioid receptor expressed in CHO cell membrane b... 26656913
Delta-type opioid receptor Ki = 9.4 nM 8.03 Inhibitory activity against Opioid receptor delta 1 in chinese Hamster Ovary (CH... 14613319
Delta-type opioid receptor Ki = 9.4 nM 8.03 Displacement of [3H]naltrindole from human delta opioid receptor expressed in CH... 16392810
Delta-type opioid receptor Ki = 9.4 nM 8.03 Displacement of [3H]naltrindole from human delta-opioid receptor expressed in CH... 21482470
Mu-type opioid receptor IC50 = 610.0 nM 6.21 Inhibitory activity was determined in stimulating [35S]-GTP-gamma S binding medi... 14613319
Kappa-type opioid receptor IC50 = 2400.0 nM 5.62 Inhibitory activity in stimulating [35S]-GTP-gamma S binding mediated by the Opi... 14613319

Literature References

PubMed DOI Target Context # Activities
14613319 10.1021/jm030139v Kappa-type opioid receptor 5
14613319 10.1021/jm030139v Mu-type opioid receptor 5
26656913 10.1016/j.ejmech.2015.11.028 Kappa-type opioid receptor 3
26656913 10.1016/j.ejmech.2015.11.028 Mu-type opioid receptor 2
21482470 10.1016/j.bmc.2011.03.052 Unchecked 2
16392810 10.1021/jm050577x Opioid receptors; mu & kappa 1
26656913 10.1016/j.ejmech.2015.11.028 Mus musculus 1
21482470 10.1016/j.bmc.2011.03.052 Mu-type opioid receptor 1
21482470 10.1016/j.bmc.2011.03.052 Kappa-type opioid receptor 1
21482470 10.1016/j.bmc.2011.03.052 Delta-type opioid receptor 1
16392810 10.1021/jm050577x Opioid receptors; delta & kappa 1
16392810 10.1021/jm050577x Kappa-type opioid receptor 1
16392810 10.1021/jm050577x Delta-type opioid receptor 1
16392810 10.1021/jm050577x Mu-type opioid receptor 1
14613319 10.1021/jm030139v Opioid receptors; delta & kappa 1
14613319 10.1021/jm030139v Opioid receptors; mu & kappa 1
14613319 10.1021/jm030139v Delta-type opioid receptor 1

Data from ChEMBL 36 via Core Engine