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Compound Detail

CHEMBL327745

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CN1CC[C@]2(c3cccc(O)c3)Cc3nc4ccccc4cc3C[C@H]2C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL327745
Phase Preclinical
Structure Type MOL
InChI Key LEPBHAAYNPPRRA-WMZHIEFXSA-N
10
Targets
24
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

344.5
MW (Da)
3.93
ALogP
3
HBA
1
HBD
36.4
PSA (Ų)
0.73
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H24N2O
MW 344.46
Aromatic Rings 3
Heavy Atoms 26
NP-Likeness 0.36

Activity Summary

Ki 15 meas. best 9.64
EC50 9 meas. best 9.15

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Delta-type opioid receptor
CHEMBL3222
 Ki 9.64 9.24 0.2 2
Delta-type opioid receptor
CHEMBL236
 EC50 9.15 8.2925 0.7 4
Delta-type opioid receptor
CHEMBL269
 Ki 8.84 8.84 1.4 2
Mu-type opioid receptor
CHEMBL2858
 Ki 7.22 6.885 59.6 2
Delta-type opioid receptor
CHEMBL236
 Ki 6.67 6.67 215.8 1
Mu-type opioid receptor
CHEMBL270
 Ki 6.55 6.55 284.1 2
Mas-related G-protein coupled receptor member X2
CHEMBL5849
 EC50 6.54 6.4833 288.4 3
Kappa-type opioid receptor
CHEMBL4329
 Ki 6.51 6.51 312.0 1
Kappa-type opioid receptor
CHEMBL3952
 Ki 6.13 6.13 732.5 3
Mu-type opioid receptor
CHEMBL233
 Ki 5.81 5.81 1557.0 1
Mu-type opioid receptor
CHEMBL233
 EC50 5.68 5.68 2109.0 1
Kappa-type opioid receptor
CHEMBL237
 Ki 5.56 5.56 2762.0 1
Kappa-type opioid receptor
CHEMBL237
 EC50 4.95 4.95 11140.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Delta-type opioid receptor Ki = 0.23 nM 9.64 inhibition of [3H]DADLE binding to delta-opioid receptor of mouse brain homogena... -
Delta-type opioid receptor EC50 = 0.7 nM 9.15 Agonist activity at human recombinant delta opioid receptor expressed in human H... 22197670
Delta-type opioid receptor EC50 = 0.7 nM 9.15 Agonist activity at human recombinant delta opioid receptor expressed in HEK293 ... 19362480
Delta-type opioid receptor EC50 = 1.4 nM 8.85 Agonist activity at human recombinant delta opioid receptor expressed in CHO cel... 19362480
Delta-type opioid receptor Ki = 1.44 nM 8.84 Displacement of [3H]DADLE from delta opioid receptor in rat cerebrum membranes 22197670
Delta-type opioid receptor Ki = 1.44 nM 8.84 Displacement of [3H]DPDPE from delta opioid receptor in mouse whole brain membra... 20850307
Delta-type opioid receptor Ki = 1.44 nM 8.84 Displacement of [3H]DADLE from delta opioid receptor in rat cerebellum membrane 19362480
Mu-type opioid receptor Ki = 59.6 nM 7.22 Inhibition of [3H]DAMGO from mouse brain homogenate Mu opioid receptor -
Delta-type opioid receptor Ki = 215.8 nM 6.67 Displacement of [3H]-Naltrindole from DOR (unknown origin) 28288109
Mu-type opioid receptor Ki = 284.14 nM 6.55 Displacement of [3H]DAMGO from mu opioid receptor in rat cerebellum membrane 19362480
Mu-type opioid receptor Ki = 284.14 nM 6.55 Displacement of [3H]DAMGO from mu opioid receptor in mouse whole brain membranes 20850307
Mu-type opioid receptor Ki = 284.1 nM 6.55 Displacement of [3H]DAMGO from mu opioid receptor in rat cerebrum membranes 22197670
Mas-related G-protein coupled receptor member X2 EC50 = 290.0 nM 6.54 Agonist activity at N-terminal Flag-tagged human MRGPRX2 receptor expressed in t... 28288109
Mas-related G-protein coupled receptor member X2 EC50 = 288.4 nM 6.54 Agonist activity at N-terminal Flag-tagged human MRGPRX2 receptor expressed in t... 28288109
Kappa-type opioid receptor Ki = 312.0 nM 6.51 Binding affinity against Kappa opioid receptor using [3H]U-69593 radioligand in ... -
Mas-related G-protein coupled receptor member X2 EC50 = 426.58 nM 6.37 Agonist activity at MRGPRX2 (unknown origin) expressed in HTLA cells assessed as... 28288109
Kappa-type opioid receptor Ki = 732.45 nM 6.13 Displacement of [3H]U-69593 from kappa opioid receptor in guinea pig cerebellum 19362480
Kappa-type opioid receptor Ki = 732.45 nM 6.13 Displacement of [3H]U-69,593 from kappa opioid receptor in guinea pig cerebellum... 20850307
Kappa-type opioid receptor Ki = 732.5 nM 6.13 Displacement of [3H]U-69,593 from kappa opioid receptor in guinea pig cerebrum m... 22197670
Delta-type opioid receptor EC50 = 961.2 nM 6.02 Displacement of [3H]-Naltrindole from DOR (unknown origin) 28288109

Literature References

PubMed DOI Target Context # Activities
25901762 10.1021/acs.jmedchem.5b00007 Delta-type opioid receptor 6
28288109 10.1038/nchembio.2334 Mas-related G-protein coupled receptor member X2 5
19362480 10.1016/j.bmcl.2009.03.099 Delta-type opioid receptor 3
28288109 10.1038/nchembio.2334 Delta-type opioid receptor 2
22197670 10.1016/j.bmc.2011.11.047 Unchecked 2
28288109 10.1038/nchembio.2334 Mu-type opioid receptor 2
22197670 10.1016/j.bmc.2011.11.047 Delta-type opioid receptor 2
19362480 10.1016/j.bmcl.2009.03.099 Unchecked 2
28288109 10.1038/nchembio.2334 Kappa-type opioid receptor 2
20850307 10.1016/j.bmcl.2010.08.083 Unchecked 2
20850307 10.1016/j.bmcl.2010.08.083 Delta-type opioid receptor 1
22197670 10.1016/j.bmc.2011.11.047 Mu-type opioid receptor 1
20850307 10.1016/j.bmcl.2010.08.083 Mus musculus 1
20850307 10.1016/j.bmcl.2010.08.083 Kappa-type opioid receptor 1
- 10.1016/S0960-894X(97)10119-6 Delta-type opioid receptor 1
19362480 10.1016/j.bmcl.2009.03.099 Mus musculus 1
19362480 10.1016/j.bmcl.2009.03.099 Kappa-type opioid receptor 1
19362480 10.1016/j.bmcl.2009.03.099 Mu-type opioid receptor 1
18637671 10.1021/jm701440h Rattus norvegicus 1
- 10.1016/S0960-894X(97)10119-6 Kappa-type opioid receptor 1

Data from ChEMBL 36 via Core Engine