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Compound Detail

CHEMBL464099

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COc1cc2c(cc1O)C[C@H]1c3c(cc(OC)c(OC)c3-2)CCN1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL464099
Phase Preclinical
Structure Type MOL
InChI Key ZFLRVRLYWHNAEC-AWEZNQCLSA-N
7
Targets
11
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

341.4
MW (Da)
3.17
ALogP
5
HBA
1
HBD
51.2
PSA (Ų)
0.93
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C20H23NO4
MW 341.41
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness 1.55

Activity Summary

Ki 7 meas. best 7.7
IC50 3 meas. best 5.08
EC50 1 meas. best 6.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 7
CHEMBL3155
 Ki 7.7 7.7 20.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 7.07 6.785 85.0 2
5-hydroxytryptamine receptor 1A
CHEMBL214
 EC50 6.8 6.8 160.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
 Ki 6.51 6.51 306.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
 Ki 6.49 6.49 323.0 1
D(1A) dopamine receptor
CHEMBL2056
 Ki 6.43 6.43 373.0 1
5-hydroxytryptamine receptor 5A
CHEMBL3426
 Ki 6.25 6.25 566.0 1
Neutrophil
CHEMBL5314326
 IC50 5.08 5.08 8360.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 7 Ki = 20.0 nM 7.7 Displacement of [3H]LSD from human recombinant 5-HT7 receptor expressed in HEK c... 25695425
5-hydroxytryptamine receptor 1A Ki = 85.0 nM 7.07 Displacement of [3H]8-OH-DPAT from human recombinant 5HT1A receptor expressed in... 16562853
5-hydroxytryptamine receptor 1A EC50 = 160.0 nM 6.8 Displacement of [3H]8-OH-DPAT from human recombinant 5HT1A receptor expressed in... 16562853
5-hydroxytryptamine receptor 6 Ki = 306.0 nM 6.51 Displacement of [3H]LSD from human recombinant 5-HT6 receptor expressed in HEK c... 25695425
5-hydroxytryptamine receptor 1A Ki = 314.0 nM 6.5 Displacement of [3H]Way100635 from human recombinant 5-HT1A receptor expressed i... 25695425
5-hydroxytryptamine receptor 2B Ki = 323.0 nM 6.49 Displacement of [3H]LSD from human recombinant 5-HT2B receptor expressed in HEK ... 25695425
D(1A) dopamine receptor Ki = 373.0 nM 6.43 Displacement of [3H]SCH23390 from human recombinant dopamine D1 receptor express... 25695425
5-hydroxytryptamine receptor 5A Ki = 566.0 nM 6.25 Displacement of [3H]LSD from human recombinant 5-HT5A receptor expressed in Flp-... 25695425
Neutrophil IC50 = 8360.0 nM 5.08 Antiinflammatory activity in human neutrophils assessed as inhibition of fMLF/cy... 32359855

Literature References

PubMed DOI Target Context # Activities
9584402 10.1021/np970382v Poliovirus 2 7
25695425 10.1021/np500893h Unchecked 3
9584402 10.1021/np970382v Vero 2
27492195 10.1016/j.bmc.2016.07.043 Acetylcholinesterase 2
27492195 10.1016/j.bmc.2016.07.043 Cholinesterase 2
32359855 10.1016/j.bmcl.2020.127224 Neutrophil 2
16562853 10.1021/np058114h 5-hydroxytryptamine receptor 1A 2
8786363 10.1021/np960195h Plasmodium falciparum 2
25695425 10.1021/np500893h Alpha-1A adrenergic receptor 1
25695425 10.1021/np500893h 5-hydroxytryptamine receptor 3A 1
25695425 10.1021/np500893h 5-hydroxytryptamine receptor 2A 1
37172474 10.1016/j.ejmech.2023.115414 Prolyl endopeptidase 1
25695425 10.1021/np500893h D(1A) dopamine receptor 1
25695425 10.1021/np500893h 5-hydroxytryptamine receptor 7 1
25695425 10.1021/np500893h 5-hydroxytryptamine receptor 6 1
25695425 10.1021/np500893h 5-hydroxytryptamine receptor 5A 1
25695425 10.1021/np500893h 5-hydroxytryptamine receptor 2B 1
25695425 10.1021/np500893h Alpha-1D adrenergic receptor 1
25695425 10.1021/np500893h Alpha-2B adrenergic receptor 1
25695425 10.1021/np500893h D(2) dopamine receptor 1

Data from ChEMBL 36 via Core Engine