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Compound Detail

CHEMBL4859858

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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 CHEMBL4859858
Phase Preclinical
Structure Type MOL
InChI Key LELBFTMXCIIKKX-CYSPOEIOSA-N
10
Targets
16
Activities
3
Assay Types
8
PK Parameters
18
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 13 meas. best 7.64
IC50 2 meas. best 5.24
EC50 1 meas. best 5.21

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 7.64 7.305 23.0 2
5-hydroxytryptamine receptor 1A
CHEMBL214
Ki 7.42 7.22 38.5 2
Mu-type opioid receptor
CHEMBL2858
Ki 6.24 6.24 578.2 1
Mu-type opioid receptor
CHEMBL233
Ki 6.14 6.14 728.0 2
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 5.88 5.88 1320.0 1
5-hydroxytryptamine receptor 7
CHEMBL3155
Ki 5.8 5.8 1600.0 1
Kappa-type opioid receptor
CHEMBL4329
Ki 5.66 5.66 2198.0 1
Kappa-type opioid receptor
CHEMBL237
Ki 5.5 5.5 3200.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 5.26 5.26 5430.0 1
Mu-type opioid receptor
CHEMBL233
IC50 5.24 5.24 5700.0 1
Mu-type opioid receptor
CHEMBL2858
EC50 5.21 5.21 6225.7 1
Delta-type opioid receptor
CHEMBL3222
Ki 5.1 5.1 7947.0 1
Kappa-type opioid receptor
CHEMBL237
IC50 5.0 5.0 10000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 495.1 ng.hr.mL-1 Rattus norvegicus
CL 53.33 mL.min-1.kg-1 Rattus norvegicus
Cmax 7.277 nM Rattus norvegicus
Cmax 7.277 nM Rattus norvegicus
Ke 0.13 L/hr Rattus norvegicus
Tmax 0.1667 hr Rattus norvegicus
Tmax 0.08333 hr Rattus norvegicus
Vd 30.1 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2B Ki = 23.0 nM 7.64 Displacement of [3H]LSD from human recombinant 5-HT2B receptor expressed in CHO ... 34467758
5-hydroxytryptamine receptor 1A Ki = 38.5 nM 7.42 Displacement of [3H]8-OH-DAPT from human recombinant 5-HT1A receptor expressed i... 34467758
5-hydroxytryptamine receptor 1A Ki = 95.5 nM 7.02 Displacement of [3H]8-OH-DAPT from human recombinant 5-HT1A receptor expressed i... 34467758
5-hydroxytryptamine receptor 2B Ki = 108.0 nM 6.97 Displacement of [3H]LSD from human recombinant 5-HT2B receptor expressed in HEK ... 34467758
Mu-type opioid receptor Ki = 578.23 nM 6.24 Displacement of [125]IBNtxA from mouse MOR stably expressed in CHO cell membrane... 34783240
Mu-type opioid receptor Ki = 728.0 nM 6.14 Displacement of [3H]DAMGO from human recombinant mu opioid receptor expressed in... 33635670
Mu-type opioid receptor Ki = 728.0 nM 6.14 Binding affinity to MOP (unknown origin) 34995453
5-hydroxytryptamine receptor 2A Ki = 1320.0 nM 5.88 Displacement of [3H]LSD from human recombinant 5-HT2A receptor expressed in HEK ... 34467758
5-hydroxytryptamine receptor 7 Ki = 1600.0 nM 5.8 Displacement of [3H]5-CT from human recombinant 5-HT7A receptor expressed in HEK... 34467758
Kappa-type opioid receptor Ki = 2198.0 nM 5.66 Displacement of [125]IBNtxA from mouse KOR stably expressed in CHO cell membrane... 34783240
Kappa-type opioid receptor Ki = 3200.0 nM 5.5 Binding affinity to KOP (unknown origin) 34995453
5-hydroxytryptamine receptor 2C Ki = 5430.0 nM 5.26 Displacement of [3H]LSD from human recombinant 5-HT2C receptor expressed in HEK ... 34467758
Mu-type opioid receptor IC50 = 5700.0 nM 5.24 Inhibition of MOP (unknown origin) 34995453
Mu-type opioid receptor EC50 = 6225.7 nM 5.21 Agonist activity at mouse MOR expressed in CHO cell membranes assessed as stimul... 34783240
Delta-type opioid receptor Ki = 7947.0 nM 5.1 Displacement of [125]IBNtxA from mouse DOR stably expressed in CHO cell membrane... 34783240
Kappa-type opioid receptor IC50 = 10000.0 nM 5.0 Inhibition of KOP (unknown origin) 34995453

Literature References

PubMed DOI Target Context # Activities
33620222 10.1021/acs.jnatprod.0c01163 ADMET 16
34467758 10.1021/acs.jmedchem.1c00726 ADMET 4
34467758 10.1021/acs.jmedchem.1c00726 5-hydroxytryptamine receptor 1A 4
34467758 10.1021/acs.jmedchem.1c00726 Rattus norvegicus 4
34467758 10.1021/acs.jmedchem.1c00726 5-hydroxytryptamine receptor 2B 4
34467758 10.1021/acs.jmedchem.1c00726 5-hydroxytryptamine receptor 2C 3
34467758 10.1021/acs.jmedchem.1c00726 5-hydroxytryptamine receptor 2A 3
34783240 10.1021/acs.jmedchem.1c01111 Mu-type opioid receptor 3
34467758 10.1021/acs.jmedchem.1c00726 5-hydroxytryptamine receptor 1B 2
34467758 10.1021/acs.jmedchem.1c00726 5-hydroxytryptamine receptor 3A 2
34995453 10.1021/acs.jmedchem.0c01915 Mu-type opioid receptor 2
34995453 10.1021/acs.jmedchem.0c01915 Delta-type opioid receptor 2
34995453 10.1021/acs.jmedchem.0c01915 Kappa-type opioid receptor 2
34783240 10.1021/acs.jmedchem.1c01111 Kappa-type opioid receptor 2
34783240 10.1021/acs.jmedchem.1c01111 Mus musculus 1
33635670 10.1021/acs.jnatprod.0c01055 Mu-type opioid receptor 1
34783240 10.1021/acs.jmedchem.1c01111 Delta-type opioid receptor 1
34467758 10.1021/acs.jmedchem.1c00726 5-hydroxytryptamine receptor 7 1

Data from ChEMBL 36 via Core Engine