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Compound Detail

CHEMBL292821

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COc1cc(CCN)c(OC)cc1Br
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL292821
Phase Preclinical
Structure Type MOL
InChI Key YMHOBZXQZVXHBM-UHFFFAOYSA-N
6
Targets
13
Activities
2
Assay Types
0
PK Parameters
13
Publications
0
Known Names

Molecular Properties

260.1
MW (Da)
1.97
ALogP
3
HBA
1
HBD
44.5
PSA (Ų)
0.90
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C10H14BrNO2
MW 260.13
Aromatic Rings 1
Heavy Atoms 14
NP-Likeness 0.18

Activity Summary

Ki 9 meas. best 9.18
EC50 4 meas. best 8.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 9.18 8.55 0.7 3
5-hydroxytryptamine receptor 2A
CHEMBL322
 Ki 9.06 8.43 0.9 2
5-hydroxytryptamine receptor 2A
CHEMBL224
 EC50 8.8 8.8 1.6 1
5-hydroxytryptamine receptor 2A
CHEMBL322
 EC50 7.57 7.57 27.0 1
Serotonin 2 (5-HT2) receptor
CHEMBL2093870
 Ki 7.47 7.47 34.0 1
5-hydroxytryptamine receptor 2C
CHEMBL324
 Ki 7.44 7.2 36.0 3
5-hydroxytryptamine receptor 2C
CHEMBL225
 EC50 5.39 5.39 4100.0 1
Trace amine-associated receptor 1
CHEMBL5857
 EC50 5.14 5.14 7190.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2A Ki = 0.66 nM 9.18 Displacement of (+/-)-[125I]DOI from human cloned 5HT2A receptor 16970404
5-hydroxytryptamine receptor 2A Ki = 0.88 nM 9.06 Displacement of (+/-)-[125I]DOI from rat cloned 5HT2A receptor 16970404
5-hydroxytryptamine receptor 2A Ki = 1.0 nM 9.0 Affinity against 5-hydroxytryptamine 2A receptor (D) labeled with [125I]DOI. 8027974
5-hydroxytryptamine receptor 2A EC50 = 1.6 nM 8.8 Agonist activity at human 5-HT2AR expressed in HEK293 cells incubated upto 90 se... 38648420
5-hydroxytryptamine receptor 2A Ki = 16.0 nM 7.8 Displacement of [3H]ketanserin from NIH3T3 cells stably expressing rat 5-hydroxy... 10956215
5-hydroxytryptamine receptor 2A EC50 = 27.0 nM 7.57 Activity at rat 5HT2A receptor expressed in NIH3T3 cells assessed as stimulation... 16970404
5-hydroxytryptamine receptor 2A Ki = 34.0 nM 7.47 Affinity against 5-hydroxytryptamine 2A receptor (K) labeled with [3H]ketanserin... 8027974
Serotonin 2 (5-HT2) receptor Ki = 34.0 nM 7.47 Binding affinity towards 5-hydroxytryptamine 2 receptor from frontal cortical re... 1542100
5-hydroxytryptamine receptor 2C Ki = 36.0 nM 7.44 Affinity against 5-hydroxytryptamine 2C receptor in J1 cells transfected with th... 8027974
5-hydroxytryptamine receptor 2C Ki = 36.0 nM 7.44 Binding affinity towards 5-hydroxytryptamine 1C receptor from frontal cortical r... 1542100
5-hydroxytryptamine receptor 2C Ki = 190.0 nM 6.72 Displacement of [3H]mesulergine from A9 cells stably expressing rat 5-hydroxytry... 10956215
5-hydroxytryptamine receptor 2C EC50 = 4100.0 nM 5.39 Agonist activity at human 5-HT2CR expressed in HEK293 cells incubated upto 90 se... 38648420
Trace amine-associated receptor 1 EC50 = 7190.0 nM 5.14 Agonist activity at human trace amine associated receptor 1 expressed in RD-HGA1... 18602830

Literature References

PubMed DOI Target Context # Activities
16970404 10.1021/jm060656o 5-hydroxytryptamine receptor 2A 6
8027974 10.1021/jm00039a004 5-hydroxytryptamine receptor 2A 2
8027974 10.1021/jm00039a004 Unchecked 2
1542100 10.1021/jm00082a014 Serotonin 2 (5-HT2) receptor 2
18602830 10.1016/j.bmc.2008.06.009 Trace amine-associated receptor 1 2
38648420 10.1021/acs.jmedchem.4c00082 5-hydroxytryptamine receptor 2A 2
38648420 10.1021/acs.jmedchem.4c00082 5-hydroxytryptamine receptor 2C 2
8027974 10.1021/jm00039a004 5-hydroxytryptamine receptor 2C 1
10956215 10.1021/jm9906062 5-hydroxytryptamine receptor 2A 1
10956215 10.1021/jm9906062 5-hydroxytryptamine receptor 2C 1
1542100 10.1021/jm00082a014 5-hydroxytryptamine receptor 2C 1
9748359 10.1021/jm980144c Homo sapiens 1
- 10.1007/s00044-012-9977-1 Whole blood 1

Data from ChEMBL 36 via Core Engine