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Compound Detail

CHEMBL61630

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CC[C@@H]1CN2CC[C@@]3(O)C(=Nc4cccc(OC)c43)[C@@H]2C[C@@H]1/C(=C\OC)C(=O)OC

Basic Information

ChEMBL ID CHEMBL61630
Phase Preclinical
Structure Type MOL
InChI Key RYENLSMHLCNXJT-CYXFISRXSA-N
9
Targets
28
Activities
3
Assay Types
11
PK Parameters
20
Publications
0
Known Names

Molecular Properties

414.5
MW (Da)
2.79
ALogP
7
HBA
1
HBD
80.6
PSA (Ų)
0.45
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 C23H30N2O5
MW 414.50
Aromatic Rings 1
Heavy Atoms 30
NP-Likeness 1.92

Activity Summary

Ki 17 meas. best 8.14
EC50 8 meas. best 8.23
IC50 3 meas. best 6.16

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mu-type opioid receptor
CHEMBL233
EC50 8.23 7.6075 5.9 4
Mu-type opioid receptor
CHEMBL233
Ki 8.14 8.14 7.2 1
Mu-type opioid receptor
CHEMBL4354
Ki 8.14 7.9775 7.2 4
Mu-type opioid receptor
CHEMBL2858
Ki 7.43 7.43 37.0 1
Unchecked
CHEMBL612545
EC50 7.28 7.28 53.0 1
Mu-type opioid receptor
CHEMBL2858
EC50 7.28 7.28 53.0 1
Kappa-type opioid receptor
CHEMBL3952
EC50 7.28 7.28 53.0 1
Mu-type opioid receptor
CHEMBL4354
EC50 7.28 7.28 53.0 1
Unchecked
CHEMBL612545
Ki 7.22 6.9567 60.0 3
Kappa-type opioid receptor
CHEMBL237
Ki 7.13 7.13 74.1 1
Delta-type opioid receptor
CHEMBL3222
Ki 7.05 7.05 90.0 1
Kappa-type opioid receptor
CHEMBL3952
Ki 6.91 6.8433 123.0 3
Kappa-type opioid receptor
CHEMBL4329
Ki 6.88 6.88 131.0 1
Delta-type opioid receptor
CHEMBL236
Ki 6.81 6.72 154.9 2
Delta-type opioid receptor
CHEMBL3222
IC50 6.16 6.16 691.0 1
Mu-type opioid receptor
CHEMBL233
IC50 6.14 6.14 725.0 1
Kappa-type opioid receptor
CHEMBL4329
IC50 5.6 5.6 2524.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 41.0 ng.hr.mL-1 Rattus norvegicus
AUC 17.4 ng.hr.mL-1 Rattus norvegicus
CL 0.4 mL.min-1.kg-1 Homo sapiens
CL 3.7 mL.min-1.kg-1 Homo sapiens
Cmax 9.65 nM Rattus norvegicus
Cmax 10.37 nM Rattus norvegicus
Fu 0.852 - Homo sapiens
Fu 0.1 - Homo sapiens
T1/2 2.835 hr Homo sapiens
Tmax 3.1 hr Rattus norvegicus
Tmax 0.9 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mu-type opioid receptor EC50 = 5.93 nM 8.23 Agonist activity at human MOR expressed in HEK293T cells assessed as inhibition ... 34505767
Mu-type opioid receptor Ki = 7.2 nM 8.14 Inhibition of mu opioid receptor in guinea pig brain membranes 31550662
Mu-type opioid receptor Ki = 7.16 nM 8.14 Displacement of [3H]DAMGO from human recombinant mu opioid receptor expressed in... 31834797
Mu-type opioid receptor EC50 = 7.6 nM 8.12 Agonist activity at human recombinant mu opioid receptor expressed in CHO cells ... 31834797
Mu-type opioid receptor Ki = 9.8 nM 8.01 Displacement of [3H]DAMGO from guinea pig brain mu opoid receptor after 3 hrs by... 23517479
Mu-type opioid receptor Ki = 13.0 nM 7.89 Displacement of [3H]DAMGO from mu opoid receptor in Dunkin-Hartley guinea pig br... 23517479
Mu-type opioid receptor Ki = 13.49 nM 7.87 Binding affinity using guinea pig brain membrane preparations, towards Opioid re... 11960505
Mu-type opioid receptor EC50 = 34.5 nM 7.46 Agonist activity at human recombinant mu opioid receptor expressed in CHO cells ... 31834797
Mu-type opioid receptor Ki = 37.0 nM 7.43 Displacement of [125I]-IBNtxA from mouse mu opioid receptor-1 expressed in CHO c... 27556704
Mu-type opioid receptor EC50 = 53.0 nM 7.28 Agonist activity at mouse mu opioid receptor-1 expressed in CHO cell membranes a... 27556704
Kappa-type opioid receptor EC50 = 53.0 nM 7.28 Agonist activity at kappa opioid receptor in guinea pig brain membranes by [35S]... 31550662
Unchecked EC50 = 53.0 nM 7.28 Agonist activity at delta opioid receptor in guinea pig brain membranes by [35S]... 31550662
Mu-type opioid receptor EC50 = 53.0 nM 7.28 Agonist activity at mu opioid receptor in guinea pig brain membranes by [35S]-GT... 31550662
Unchecked Ki = 60.0 nM 7.22 Inhibition of delta opioid receptor in guinea pig brain membranes 31550662
Kappa-type opioid receptor Ki = 74.1 nM 7.13 Displacement of [3H]U69,593 from human recombinant kappa opioid receptor express... 31834797
Delta-type opioid receptor Ki = 90.0 nM 7.05 Displacement of [125I]-IBNtxA from mouse delta opioid receptor-1 expressed in CH... 27556704
Kappa-type opioid receptor Ki = 123.03 nM 6.91 Binding affinity using guinea pig brain membrane preparations, towards Opioid re... 11960505
Kappa-type opioid receptor Ki = 123.0 nM 6.91 Displacement of [3H]U-69593 from kappa opoid receptor in Dunkin-Hartley guinea p... 23517479
Kappa-type opioid receptor Ki = 131.0 nM 6.88 Displacement of [125I]-IBNtxA from mouse kappa opioid receptor-1 expressed in CH... 27556704
Unchecked Ki = 145.0 nM 6.84 Displacement of [3H]DPDPE from guinea pig brain delta opoid receptor after 4 hrs... 23517479

Literature References

PubMed DOI Target Context # Activities
33620222 10.1021/acs.jnatprod.0c01163 ADMET 16
31834797 10.1021/acs.jmedchem.9b01465 ADMET 9
27556704 10.1021/acs.jmedchem.6b00748 Mu-type opioid receptor 6
34783240 10.1021/acs.jmedchem.1c01111 ADMET 5
31834797 10.1021/acs.jmedchem.9b01465 Mu-type opioid receptor 5
23517479 10.1021/jm400143z Unchecked 5
34505767 10.1021/acs.jmedchem.1c01273 Mu-type opioid receptor 5
31834797 10.1021/acs.jmedchem.9b01465 Delta-type opioid receptor 4
31550662 10.1016/j.ejmech.2019.111701 Kappa-type opioid receptor 4
11960505 10.1021/jm010576e Cavia porcellus 4
31834797 10.1021/acs.jmedchem.9b01465 Kappa-type opioid receptor 4
31550662 10.1016/j.ejmech.2019.111701 Unchecked 4
31550662 10.1016/j.ejmech.2019.111701 Mu-type opioid receptor 4
34783240 10.1021/acs.jmedchem.1c01111 Mus musculus 4
31834797 10.1021/acs.jmedchem.9b01465 Rattus norvegicus 3
31834797 10.1021/acs.jmedchem.9b01465 Alpha-2B adrenergic receptor 2
31834797 10.1021/acs.jmedchem.9b01465 Alpha-2A adrenergic receptor 2
31834797 10.1021/acs.jmedchem.9b01465 Alpha-1D adrenergic receptor 2
34783240 10.1021/acs.jmedchem.1c01111 Mu-type opioid receptor 2
23517479 10.1021/jm400143z Kappa-type opioid receptor 2

Data from ChEMBL 36 via Core Engine