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Compound Detail

CHEMBL4546925

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CC[C@@H]1CN2CCc3c([nH]c4cccc(OC)c34)[C@H]2C[C@@H]1/C(=C\OC)C(=O)OC

Basic Information

ChEMBL ID CHEMBL4546925
Phase Preclinical
Structure Type MOL
InChI Key LELBFTMXCIIKKX-MYLQJJOTSA-N
5
Targets
15
Activities
3
Assay Types
11
PK Parameters
20
Publications
0
Known Names

Molecular Properties

398.5
MW (Da)
3.83
ALogP
5
HBA
1
HBD
63.8
PSA (Ų)
0.47
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C23H30N2O4
MW 398.50
Aromatic Rings 2
Heavy Atoms 29
NP-Likeness 1.54

Activity Summary

Ki 8 meas. best 7.26
IC50 4 meas. best 5.38
EC50 3 meas. best 7.41

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mu-type opioid receptor
CHEMBL233
EC50 7.41 7.41 39.2 1
Mu-type opioid receptor
CHEMBL233
Ki 7.26 6.9233 54.5 3
Mu-type opioid receptor
CHEMBL2858
EC50 7.14 7.14 72.7 1
Mu-type opioid receptor
CHEMBL2858
Ki 7.11 7.11 78.6 1
Kappa-type opioid receptor
CHEMBL237
Ki 6.94 6.71 116.0 2
Kappa-type opioid receptor
CHEMBL4329
Ki 6.19 6.19 649.0 1
Delta-type opioid receptor
CHEMBL3222
Ki 5.94 5.94 1154.3 1
Kappa-type opioid receptor
CHEMBL4329
EC50 5.87 5.87 1355.0 1
Mu-type opioid receptor
CHEMBL233
IC50 5.38 5.38 4200.0 1
Kappa-type opioid receptor
CHEMBL237
IC50 5.0 5.0 10000.0 1
Mu-type opioid receptor
CHEMBL2858
IC50 4.96 4.96 10851.0 1
Delta-type opioid receptor
CHEMBL3222
IC50 4.9 4.9 12562.7 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 107.4 ng.hr.mL-1 Rattus norvegicus
AUC 222.7 ng.hr.mL-1 Rattus norvegicus
CL 0.5 mL.min-1.kg-1 Homo sapiens
CL 14.9 mL.min-1.kg-1 Homo sapiens
Cmax 52.95 nM Rattus norvegicus
Cmax 59.72 nM Rattus norvegicus
Fu 0.276 - Homo sapiens
Fu 0.01 - Homo sapiens
T1/2 0.6967 hr Homo sapiens
Tmax 1.8 hr Rattus norvegicus
Tmax 3.2 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mu-type opioid receptor EC50 = 39.2 nM 7.41 Agonist activity at human recombinant mu opioid receptor expressed in CHO cells ... 31834797
Mu-type opioid receptor Ki = 54.5 nM 7.26 Displacement of [3H]DAMGO from human recombinant mu opioid receptor expressed in... 31834797
Mu-type opioid receptor Ki = 54.5 nM 7.26 Displacement of [3H]DAMGO from human recombinant mu opioid receptor expressed in... 33635670
Mu-type opioid receptor EC50 = 72.7 nM 7.14 Partial agonist activity at mouse MOR expressed in CHO cell membranes assessed a... 34783240
Mu-type opioid receptor Ki = 78.6 nM 7.11 Displacement of [125]IBNtxA from mouse MOR stably expressed in CHO cell membrane... 34783240
Kappa-type opioid receptor Ki = 116.0 nM 6.94 Displacement of [3H]U69,593 from human recombinant kappa opioid receptor express... 31834797
Kappa-type opioid receptor Ki = 329.0 nM 6.48 Binding affinity to KOP (unknown origin) 34995453
Mu-type opioid receptor Ki = 560.0 nM 6.25 Binding affinity to MOP (unknown origin) 34995453
Kappa-type opioid receptor Ki = 649.0 nM 6.19 Displacement of [125]IBNtxA from mouse KOR stably expressed in CHO cell membrane... 34783240
Delta-type opioid receptor Ki = 1154.3 nM 5.94 Displacement of [125]IBNtxA from mouse DOR stably expressed in CHO cell membrane... 34783240
Kappa-type opioid receptor EC50 = 1355.0 nM 5.87 Agonist activity at mouse KOR expressed in CHO cell membranes assessed as stimul... 34783240
Mu-type opioid receptor IC50 = 4200.0 nM 5.38 Inhibition of MOP (unknown origin) 34995453
Kappa-type opioid receptor IC50 = 10000.0 nM 5.0 Inhibition of KOP (unknown origin) 34995453
Mu-type opioid receptor IC50 = 10851.0 nM 4.96 Antagonist activity at mouse MOR expressed in CHO cell membranes assessed as inh... 34783240
Delta-type opioid receptor IC50 = 12562.7 nM 4.9 Antagonist activity at mouse DOR expressed in CHO cell membranes assessed as inh... 34783240

Literature References

PubMed DOI Target Context # Activities
33620222 10.1021/acs.jnatprod.0c01163 ADMET 21
31834797 10.1021/acs.jmedchem.9b01465 ADMET 8
31834797 10.1021/acs.jmedchem.9b01465 Kappa-type opioid receptor 5
31834797 10.1021/acs.jmedchem.9b01465 Mu-type opioid receptor 4
34783240 10.1021/acs.jmedchem.1c01111 Mu-type opioid receptor 4
31834797 10.1021/acs.jmedchem.9b01465 Delta-type opioid receptor 3
34783240 10.1021/acs.jmedchem.1c01111 Kappa-type opioid receptor 3
31834797 10.1021/acs.jmedchem.9b01465 Rattus norvegicus 3
34995453 10.1021/acs.jmedchem.0c01915 Mu-type opioid receptor 2
34467758 10.1021/acs.jmedchem.1c00726 5-hydroxytryptamine receptor 2A 2
34467758 10.1021/acs.jmedchem.1c00726 5-hydroxytryptamine receptor 2C 2
34467758 10.1021/acs.jmedchem.1c00726 5-hydroxytryptamine receptor 3A 2
34467758 10.1021/acs.jmedchem.1c00726 5-hydroxytryptamine receptor 1A 2
34467758 10.1021/acs.jmedchem.1c00726 5-hydroxytryptamine receptor 1B 2
31834797 10.1021/acs.jmedchem.9b01465 Nociceptin receptor 2
31834797 10.1021/acs.jmedchem.9b01465 Alpha-1A adrenergic receptor 2
31834797 10.1021/acs.jmedchem.9b01465 Alpha-1B adrenergic receptor 2
31834797 10.1021/acs.jmedchem.9b01465 Alpha-1D adrenergic receptor 2
31834797 10.1021/acs.jmedchem.9b01465 Alpha-2A adrenergic receptor 2
31834797 10.1021/acs.jmedchem.9b01465 Alpha-2B adrenergic receptor 2

Data from ChEMBL 36 via Core Engine