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Compound Detail

CHEMBL299031

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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 CHEMBL299031
Phase Preclinical
Structure Type MOL
InChI Key LELBFTMXCIIKKX-QVRQZEMUSA-N
20
Targets
37
Activities
2
Assay Types
22
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 Small molecule
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 27 meas. best 8.14
EC50 10 meas. best 9.31

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mu-type opioid receptor
CHEMBL233
EC50 9.31 7.076 0.5 5
Mu-type opioid receptor
CHEMBL4354
Ki 8.14 8.0567 7.2 3
Unchecked
CHEMBL612545
Ki 7.22 7.015 60.0 2
Delta-type opioid receptor
CHEMBL236
Ki 7.22 7.22 60.3 1
Kappa-type opioid receptor
CHEMBL3952
Ki 6.91 6.435 123.0 2
Mu-type opioid receptor
CHEMBL233
Ki 6.79 6.7367 161.0 3
Kappa-type opioid receptor
CHEMBL237
Ki 6.7 6.405 198.0 2
Mu-type opioid receptor
CHEMBL2858
EC50 6.69 6.69 203.0 1
Unchecked
CHEMBL612545
EC50 6.64 6.64 230.0 1
Mu-type opioid receptor
CHEMBL4354
EC50 6.64 6.64 230.0 1
Kappa-type opioid receptor
CHEMBL4329
Ki 6.64 6.64 231.0 1
Mu-type opioid receptor
CHEMBL2858
Ki 6.64 6.64 230.0 1
Kappa-type opioid receptor
CHEMBL3952
EC50 6.64 6.64 230.0 1
Delta-type opioid receptor
CHEMBL3222
Ki 6.0 6.0 1011.0 1
Cytochrome P450 2D6
CHEMBL289
Ki 5.96 5.96 1100.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 5.9 5.9 1260.0 1
Alpha-1A adrenergic receptor
CHEMBL229
Ki 5.87 5.87 1340.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 5.63 5.63 2320.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 5.33 5.33 4720.0 1
Alpha-1B adrenergic receptor
CHEMBL232
Ki 5.32 5.32 4770.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 5.3 5.3 5010.0 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 5.26 5.26 5480.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
Ki 5.23 5.23 5880.0 1
Kappa-type opioid receptor
CHEMBL237
EC50 5.07 5.07 8500.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 5.03 5.03 9290.0 1
5-hydroxytryptamine receptor 7
CHEMBL3155
Ki 5.0 5.0 10000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 479.6 ng.hr.mL-1 Rattus norvegicus
AUC 1306.8 ng.hr.mL-1 Rattus norvegicus
AUC 849.8 ng.hr.mL-1 Rattus norvegicus
CL 1.9 mL.min-1.kg-1 Homo sapiens
CL 31.2 mL.min-1.kg-1 Homo sapiens
CL 21.67 mL.min-1.kg-1 Rattus norvegicus
Cmax 280.8 nM Rattus norvegicus
Cmax 160.1 nM Rattus norvegicus
Fu 0.307 - Homo sapiens
Fu 0.02 - Homo sapiens
Ke 0.12 L/hr Rattus norvegicus
T1/2 0.3333 hr Homo sapiens
T1/2 0.125 hr Homo sapiens
T1/2 0.09833 hr Mus musculus
T1/2 0.225 hr Mus musculus
T1/2 0.6233 hr Homo sapiens
T1/2 0.5967 hr Mus musculus
T1/2 0.4067 hr Mus musculus
T1/2 0.42 hr Mus musculus
Tmax 3.1 hr Rattus norvegicus
Tmax 1.3 hr Rattus norvegicus
Vd 8.0 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mu-type opioid receptor EC50 = 0.4898 nM 9.31 Agonist activity at human MOR expressed in HEK293T cells assessed as inhibition ... 34505767
Mu-type opioid receptor Ki = 7.244 nM 8.14 Binding affinity using guinea pig brain membrane preparations, towards Opioid re... 11960505
Mu-type opioid receptor Ki = 7.2 nM 8.14 Displacement of [3H]DAMGO from mu opoid receptor in Dunkin-Hartley guinea pig br... 23517479
Mu-type opioid receptor Ki = 13.0 nM 7.89 Inhibition of mu opioid receptor in guinea pig brain membranes 31550662
Unchecked Ki = 60.0 nM 7.22 Displacement of [3H]DPDPE from delta opoid receptor in Dunkin-Hartley guinea pig... 23517479
Delta-type opioid receptor Ki = 60.26 nM 7.22 Binding affinity using guinea pig brain membrane preparations, towards Opioid re... 11960505
Kappa-type opioid receptor Ki = 123.0 nM 6.91 Inhibition of kappa opioid receptor in guinea pig brain membranes 31550662
Unchecked Ki = 155.0 nM 6.81 Inhibition of delta opioid receptor in guinea pig brain membranes 31550662
Mu-type opioid receptor Ki = 161.0 nM 6.79 Displacement of [3H]DAMGO from human recombinant mu opioid receptor expressed in... 33635670
Mu-type opioid receptor Ki = 161.0 nM 6.79 Displacement of [3H]DAMGO from human recombinant mu opioid receptor expressed in... 31834797
Kappa-type opioid receptor Ki = 198.0 nM 6.7 Displacement of [3H]U69,593 from human recombinant kappa opioid receptor express... 31834797
Mu-type opioid receptor EC50 = 203.0 nM 6.69 Agonist activity at mouse mu opioid receptor-1 expressed in CHO cell membranes a... 27556704
Mu-type opioid receptor EC50 = 230.0 nM 6.64 Agonist activity at mu opioid receptor in guinea pig brain membranes by [35S]-GT... 31550662
Unchecked EC50 = 230.0 nM 6.64 Agonist activity at delta opioid receptor in guinea pig brain membranes by [35S]... 31550662
Kappa-type opioid receptor EC50 = 230.0 nM 6.64 Agonist activity at kappa opioid receptor in guinea pig brain membranes by [35S]... 31550662
Kappa-type opioid receptor Ki = 231.0 nM 6.64 Displacement of [125I]-IBNtxA from mouse kappa opioid receptor-1 expressed in CH... 27556704
Mu-type opioid receptor Ki = 230.0 nM 6.64 Displacement of [125I]-IBNtxA from mouse mu opioid receptor-1 expressed in CHO c... 27556704
Mu-type opioid receptor Ki = 233.0 nM 6.63 Binding affinity to MOP (unknown origin) 34995453
Mu-type opioid receptor EC50 = 241.2 nM 6.62 Agonist activity at human MOR expressed in HEK293T cells assessed as inhibition ... 34505767
Mu-type opioid receptor EC50 = 307.5 nM 6.51 Agonist activity at human recombinant mu opioid receptor expressed in CHO cells ... 31834797

Literature References

PubMed DOI Target Context # Activities
34783240 10.1021/acs.jmedchem.1c01111 ADMET 61
33620222 10.1021/acs.jnatprod.0c01163 ADMET 26
34783240 10.1021/acs.jmedchem.1c01111 Mus musculus 14
31834797 10.1021/acs.jmedchem.9b01465 ADMET 8
31834797 10.1021/acs.jmedchem.9b01465 Mu-type opioid receptor 6
34505767 10.1021/acs.jmedchem.1c01273 Mu-type opioid receptor 5
31834797 10.1021/acs.jmedchem.9b01465 Alpha-1A adrenergic receptor 5
31834797 10.1021/acs.jmedchem.9b01465 Alpha-1D adrenergic receptor 5
34467758 10.1021/acs.jmedchem.1c00726 ADMET 4
23517479 10.1021/jm400143z Unchecked 4
27556704 10.1021/acs.jmedchem.6b00748 Mu-type opioid receptor 4
34783240 10.1021/acs.jmedchem.1c01111 Cytochrome P450 3A 4
11960505 10.1021/jm010576e Cavia porcellus 4
31834797 10.1021/acs.jmedchem.9b01465 Alpha-1B adrenergic receptor 4
31834797 10.1021/acs.jmedchem.9b01465 Kappa-type opioid receptor 3
34467758 10.1021/acs.jmedchem.1c00726 5-hydroxytryptamine receptor 1A 3
31834797 10.1021/acs.jmedchem.9b01465 Alpha-2A adrenergic receptor 3
31834797 10.1021/acs.jmedchem.9b01465 Alpha-2B adrenergic receptor 3
31834797 10.1021/acs.jmedchem.9b01465 Delta-type opioid receptor 3
31550662 10.1016/j.ejmech.2019.111701 Mu-type opioid receptor 3

Data from ChEMBL 36 via Core Engine