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Compound Detail

CHEMBL3759092

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C[C@H]1[C@H]2Cc3ccc(O)cc3[C@]1(C)CCN2CCC(=O)Nc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3759092
Phase Preclinical
Structure Type MOL
InChI Key VGNUFLUEYYNYCK-POCHDABASA-N
11
Targets
16
Activities
4
Assay Types
2
PK Parameters
18
Publications
0
Known Names

Molecular Properties

364.5
MW (Da)
3.95
ALogP
3
HBA
2
HBD
52.6
PSA (Ų)
0.86
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 C23H28N2O2
MW 364.49
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness 0.32

Activity Summary

Ki 11 meas. best 9.08
EC50 2 meas. best 6.1
IC50 2 meas. best 8.72
Kd 1 meas. best 7.2

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mu-type opioid receptor
CHEMBL233
 Ki 9.08 9.08 0.8 2
Mu-type opioid receptor
CHEMBL270
 Ki 9.08 8.195 0.8 2
mu/kappa opioid receptor
CHEMBL3038518
 IC50 8.72 8.72 1.9 1
Delta-type opioid receptor
CHEMBL236
 Ki 7.54 7.54 29.0 2
Delta-type opioid receptor
CHEMBL269
 Ki 7.54 7.51 29.1 2
Delta-type opioid receptor
CHEMBL3222
 Kd 7.2 7.2 63.1 1
Kappa-type opioid receptor
CHEMBL3614
 Ki 6.96 6.96 110.0 1
Kappa-type opioid receptor
CHEMBL3952
 Ki 6.96 6.96 110.0 1
Mu-type opioid receptor
CHEMBL4354
 EC50 6.1 6.1 794.3 1
Unchecked
CHEMBL612545
 IC50 5.91 5.91 1240.0 1
Kappa-type opioid receptor
CHEMBL237
 Ki 5.12 5.12 7500.0 1

Pharmacokinetic Data

Parameter Value Units Species
Ke 10.8 nM Cavia porcellus
Ke 2.3 nM Cavia porcellus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mu-type opioid receptor Ki = 0.83 nM 9.08 Binding affinity at mu opioid receptor (unknown origin) 26656913
Mu-type opioid receptor Ki = 0.83 nM 9.08 Displacement of [3H]-DAMGO from MOR in rat brain membranes by liquid scintillati... 28734666
Mu-type opioid receptor Ki = 0.83 nM 9.08 Displacement of [3H]DAMGO from MOR in HEK293 cells 27624520
mu/kappa opioid receptor IC50 = 1.9 nM 8.72 Agonist activity at MOR/KOR in Dunkin-Hartley guinea pig ileum assessed as inhib... 28734666
Delta-type opioid receptor Ki = 29.0 nM 7.54 Binding affinity at delta opioid receptor (unknown origin) 26656913
Delta-type opioid receptor Ki = 29.1 nM 7.54 Displacement of [3H]-DPDPE from DOR in rat brain membranes by liquid scintillati... 28734666
Delta-type opioid receptor Ki = 29.01 nM 7.54 Displacement of [3H]DPDPE from human DOR expressed in CHO cells 27624520
Delta-type opioid receptor Ki = 33.0 nM 7.48 Displacement of [3H]-DPN from rat DOR expressed in EE-HEK293 cell membranes by l... 27234885
Mu-type opioid receptor Ki = 49.0 nM 7.31 Displacement of [3H]-DPN from rat MOR expressed in EE-HEK293 cell membranes by l... 27234885
Delta-type opioid receptor Kd = 63.1 nM 7.2 Antagonist activity at DOR in CD1 mouse vas deferens assessed as reduction in DP... 27234885
Kappa-type opioid receptor Ki = 110.0 nM 6.96 Displacement of [3H]-(+)-U69,593 from KOR in guinea pig brain membranes by liqui... 28734666
Kappa-type opioid receptor Ki = 110.0 nM 6.96 Displacement of [3H]U69593 from rat KOR expressed in CHO cells 27624520
Mu-type opioid receptor EC50 = 794.33 nM 6.1 Agonist activity at MOR in Dunkin-Hartley guinea pig ileum assessed as inhibitio... 27234885
Unchecked IC50 = 1240.0 nM 5.91 Agonist activity at DOR in CD-1 mouse vasa deferentia assessed as inhibition of ... 28734666
Kappa-type opioid receptor Ki = 7500.0 nM 5.12 Displacement of [3H]-DPN from human KOR expressed in EE-HEK293 cell membranes by... 27234885

Literature References

PubMed DOI Target Context # Activities
27234885 10.1016/j.bmc.2016.05.005 Delta-type opioid receptor 4
28734666 10.1016/j.bmc.2017.07.021 Unchecked 3
32435370 10.1021/acsmedchemlett.9b00549 Mu-type opioid receptor 2
27624520 10.1016/j.bmc.2016.08.057 Unchecked 2
27234885 10.1016/j.bmc.2016.05.005 Mu-type opioid receptor 2
27234885 10.1016/j.bmc.2016.05.005 Unchecked 2
28734666 10.1016/j.bmc.2017.07.021 Kappa-type opioid receptor 2
28734666 10.1016/j.bmc.2017.07.021 Mu-type opioid receptor 2
32435370 10.1021/acsmedchemlett.9b00549 ADMET 1
26656913 10.1016/j.ejmech.2015.11.028 Mu-type opioid receptor 1
27624520 10.1016/j.bmc.2016.08.057 Delta-type opioid receptor 1
27624520 10.1016/j.bmc.2016.08.057 Kappa-type opioid receptor 1
27624520 10.1016/j.bmc.2016.08.057 Mu-type opioid receptor 1
28734666 10.1016/j.bmc.2017.07.021 Delta-type opioid receptor 1
28734666 10.1016/j.bmc.2017.07.021 mu/kappa opioid receptor 1
27234885 10.1016/j.bmc.2016.05.005 Kappa-type opioid receptor 1
26656913 10.1016/j.ejmech.2015.11.028 Rattus norvegicus 1
26656913 10.1016/j.ejmech.2015.11.028 Delta-type opioid receptor 1

Data from ChEMBL 36 via Core Engine