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Compound Detail

CHEMBL4848517

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

Basic Information

ChEMBL ID CHEMBL4848517
Phase Preclinical
Structure Type MOL
InChI Key JGZKIGWXPPFMRG-CYSPOEIOSA-N
10
Targets
17
Activities
3
Assay Types
8
PK Parameters
18
Publications
0
Known Names

Molecular Properties

396.5
MW (Da)
3.60
ALogP
5
HBA
1
HBD
63.8
PSA (Ų)
0.36
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 C23H28N2O4
MW 396.49
Aromatic Rings 2
Heavy Atoms 29
NP-Likeness 1.63

Activity Summary

Ki 13 meas. best 7.7
EC50 2 meas. best 5.45
IC50 2 meas. best 5.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 7.7 7.39 20.0 2
5-hydroxytryptamine receptor 1A
CHEMBL214
Ki 7.5 7.32 32.0 2
Mu-type opioid receptor
CHEMBL233
Ki 6.39 6.39 410.0 2
Mu-type opioid receptor
CHEMBL2858
Ki 6.18 6.18 665.7 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 6.09 6.09 815.0 1
5-hydroxytryptamine receptor 7
CHEMBL3155
Ki 6.06 6.06 870.0 1
Kappa-type opioid receptor
CHEMBL4329
Ki 6.05 6.05 883.3 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 5.75 5.75 1770.0 1
Mu-type opioid receptor
CHEMBL233
IC50 5.66 5.66 2200.0 1
Kappa-type opioid receptor
CHEMBL237
Ki 5.59 5.59 2560.0 1
Delta-type opioid receptor
CHEMBL3222
Ki 5.47 5.47 3395.0 1
Kappa-type opioid receptor
CHEMBL4329
EC50 5.45 5.45 3586.3 1
Mu-type opioid receptor
CHEMBL2858
EC50 5.03 5.03 9384.0 1
Kappa-type opioid receptor
CHEMBL237
IC50 5.0 5.0 10000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 235.2 ng.hr.mL-1 Rattus norvegicus
CL 88.33 mL.min-1.kg-1 Rattus norvegicus
Cmax 13.37 nM Rattus norvegicus
Cmax 5.044 nM Rattus norvegicus
Ke 0.08 L/hr Rattus norvegicus
Tmax 0.1667 hr Rattus norvegicus
Tmax 0.08333 hr Rattus norvegicus
Vd 71.9 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 = 20.0 nM 7.7 Displacement of [3H]LSD from human recombinant 5-HT2B receptor expressed in CHO ... 34467758
5-hydroxytryptamine receptor 1A Ki = 32.0 nM 7.5 Displacement of [3H]8-OH-DAPT from human recombinant 5-HT1A receptor expressed i... 34467758
5-hydroxytryptamine receptor 1A Ki = 71.8 nM 7.14 Displacement of [3H]8-OH-DAPT from human recombinant 5-HT1A receptor expressed i... 34467758
5-hydroxytryptamine receptor 2B Ki = 83.1 nM 7.08 Displacement of [3H]LSD from human recombinant 5-HT2B receptor expressed in HEK ... 34467758
Mu-type opioid receptor Ki = 410.0 nM 6.39 Displacement of [3H]DAMGO from human recombinant mu opioid receptor expressed in... 33635670
Mu-type opioid receptor Ki = 410.0 nM 6.39 Binding affinity to MOP (unknown origin) 34995453
Mu-type opioid receptor Ki = 665.7 nM 6.18 Displacement of [125]IBNtxA from mouse MOR stably expressed in CHO cell membrane... 34783240
5-hydroxytryptamine receptor 2A Ki = 815.0 nM 6.09 Displacement of [3H]LSD from human recombinant 5-HT2A receptor expressed in HEK ... 34467758
5-hydroxytryptamine receptor 7 Ki = 870.0 nM 6.06 Displacement of [3H]5-CT from human recombinant 5-HT7A receptor expressed in HEK... 34467758
Kappa-type opioid receptor Ki = 883.33 nM 6.05 Displacement of [125]IBNtxA from mouse KOR stably expressed in CHO cell membrane... 34783240
5-hydroxytryptamine receptor 2C Ki = 1770.0 nM 5.75 Displacement of [3H]LSD from human recombinant 5-HT2C receptor expressed in HEK ... 34467758
Mu-type opioid receptor IC50 = 2200.0 nM 5.66 Inhibition of MOP (unknown origin) 34995453
Kappa-type opioid receptor Ki = 2560.0 nM 5.59 Binding affinity to KOP (unknown origin) 34995453
Delta-type opioid receptor Ki = 3395.0 nM 5.47 Displacement of [125]IBNtxA from mouse DOR stably expressed in CHO cell membrane... 34783240
Kappa-type opioid receptor EC50 = 3586.3 nM 5.45 Agonist activity at mouse KOR expressed in CHO cell membranes assessed as stimul... 34783240
Mu-type opioid receptor EC50 = 9384.0 nM 5.03 Agonist activity at mouse MOR expressed in CHO cell membranes assessed as stimul... 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 2A 3
34783240 10.1021/acs.jmedchem.1c01111 Kappa-type opioid receptor 3
34783240 10.1021/acs.jmedchem.1c01111 Mu-type opioid receptor 3
34467758 10.1021/acs.jmedchem.1c00726 5-hydroxytryptamine receptor 2C 3
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
34467758 10.1021/acs.jmedchem.1c00726 5-hydroxytryptamine receptor 1B 2
34783240 10.1021/acs.jmedchem.1c01111 Delta-type opioid receptor 2
34783240 10.1021/acs.jmedchem.1c01111 Mus musculus 1
33635670 10.1021/acs.jnatprod.0c01055 Mu-type opioid receptor 1
34467758 10.1021/acs.jmedchem.1c00726 5-hydroxytryptamine receptor 7 1

Data from ChEMBL 36 via Core Engine