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Compound Detail

CHEMBL69700

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COc1cc(C[C@@H](C)N)c(OC)cc1Br
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL69700
Phase Preclinical
Structure Type MOL
InChI Key FXMWUTGUCAKGQL-SSDOTTSWSA-N
9
Targets
20
Activities
2
Assay Types
0
PK Parameters
19
Publications
0
Known Names

Molecular Properties

274.2
MW (Da)
2.36
ALogP
3
HBA
1
HBD
44.5
PSA (Ų)
0.92
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 C11H16BrNO2
MW 274.16
Aromatic Rings 1
Heavy Atoms 15
NP-Likeness 0.09

Activity Summary

Ki 17 meas. best 9.7
EC50 3 meas. best 7.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2A
CHEMBL322
 Ki 9.7 9.02 0.2 3
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 9.54 9.54 0.3 1
Serotonin 2 (5-HT2) receptor
CHEMBL2093870
 Ki 9.41 8.215 0.4 6
Serotonin receptor 2a and 2c (5HT2A and 5HT2C)
CHEMBL2111383
 Ki 9.4 8.5733 0.4 3
5-hydroxytryptamine receptor 2A
CHEMBL322
 EC50 7.7 7.7 20.0 1
5-hydroxytryptamine receptor 2C
CHEMBL324
 Ki 7.3 7.3 50.0 1
Serotonin 1 (5-HT1) receptor
CHEMBL2095159
 Ki 5.38 5.38 4200.0 2
5-hydroxytryptamine receptor 1A
CHEMBL273
 Ki 5.21 5.21 6100.0 1
Trace amine-associated receptor 1
CHEMBL1926495
 EC50 4.86 4.86 13900.0 1
Trace amine-associated receptor 1
CHEMBL5857
 EC50 4.5 4.5 31940.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2A Ki = 0.2 nM 9.7 Binding affinity for 5-HT2A serotonin receptor 15537358
5-hydroxytryptamine receptor 2A Ki = 0.2 nM 9.7 Displacement of [125I](+/-)DOI from rat 5HT2A after 1 hr by beta scintillation c... 28244748
5-hydroxytryptamine receptor 2A Ki = 0.29 nM 9.54 Displacement of [3H]ketanserin from 5HT2A receptor expressed in NIH3T3 cells 18847250
Serotonin 2 (5-HT2) receptor Ki = 0.39 nM 9.41 Affinity towards [3H]- DOB -labeled 5-hydroxytryptamine 2 receptor sites in rat ... 3572981
Serotonin receptor 2a and 2c (5HT2A and 5HT2C) Ki = 0.4 nM 9.4 Binding affinity at [3H]DOB labeled sites of 5-hydroxytryptamine 2 receptor dete... 3336031
Serotonin 2 (5-HT2) receptor Ki = 0.4 nM 9.4 Binding affinity to rat cortical membranes at 5-hydroxytryptamine 2 receptor bin... 3543362
Serotonin receptor 2a and 2c (5HT2A and 5HT2C) Ki = 1.9 nM 8.72 Binding affinity at 5-hydroxytryptamine 2 receptor determined using [125I]- DOI ... 3336031
5-hydroxytryptamine receptor 2A EC50 = 20.0 nM 7.7 Serotonin 5-HT2A receptor-mediated intracellular calcium [Ca2+] mobilization in ... 15537358
5-hydroxytryptamine receptor 2A Ki = 22.0 nM 7.66 Affinity at [3H]ketanserin-labeled 5-hydroxytryptamine 2A receptor in rat brain ... 9622555
Serotonin 2 (5-HT2) receptor Ki = 24.0 nM 7.62 Binding affinity to rat cortical membranes at 5-hydroxytryptamine 2 (5-HT2) rece... 3543362
Serotonin 2 (5-HT2) receptor Ki = 24.0 nM 7.62 Binding affinity to 5-hydroxytryptamine 2 receptor in rat frontal cortical membr... 3543362
Serotonin 2 (5-HT2) receptor Ki = 24.0 nM 7.62 Binding affinity towards 5-hydroxytryptamine 2 receptor from frontal cortical re... 1542100
Serotonin 2 (5-HT2) receptor Ki = 24.0 nM 7.62 Affinity towards [3H]- ketanserin-labeled 5-hydroxytryptamine 2 receptor sites i... 3572981
Serotonin receptor 2a and 2c (5HT2A and 5HT2C) Ki = 25.0 nM 7.6 Binding affinity at [3H]KET labeled sites of 5-hydroxytryptamine 2 receptor dete... 3336031
5-hydroxytryptamine receptor 2C Ki = 50.0 nM 7.3 Binding affinity towards 5-hydroxytryptamine 1C receptor from frontal cortical r... 1542100
Serotonin 1 (5-HT1) receptor Ki = 4200.0 nM 5.38 Evaluated for binding affinity towards rat cortical membranes at 5-hydroxytrypta... 3543362
Serotonin 1 (5-HT1) receptor Ki = 4200.0 nM 5.38 Evaluated for binding affinity towards rat cortical membranes at 5-hydroxytrypta... 3543362
5-hydroxytryptamine receptor 1A Ki = 6100.0 nM 5.21 Affinity at [3H]8-OH-DPAT-labeled 5-hydroxytryptamine 1A receptor in rat brain h... 9622555
Trace amine-associated receptor 1 EC50 = 13900.0 nM 4.86 Activation of rhesus monkey TAAR1 expressed in RD-HGA16 cells co-expressing Gq p... 22037049
Trace amine-associated receptor 1 EC50 = 31940.0 nM 4.5 Activation of C-terminal HA epitope tagged human TAAR1 expressed in RD-HGA16 cel... 22037049

Literature References

PubMed DOI Target Context # Activities
3572981 10.1021/jm00388a032 Rattus norvegicus 16
7143352 10.1021/jm00352a013 Rattus norvegicus 7
3543362 10.1021/jm00384a001 Serotonin 2 (5-HT2) receptor 4
3336031 10.1021/jm00396a003 Serotonin receptor 2a and 2c (5HT2A and 5HT2C) 4
15537358 10.1021/jm040082s 5-hydroxytryptamine receptor 2A 3
3543362 10.1021/jm00384a001 Serotonin 1 (5-HT1) receptor 2
22037049 10.1016/j.bmc.2011.10.007 Trace amine-associated receptor 1 2
1542100 10.1021/jm00082a014 Serotonin 2 (5-HT2) receptor 2
3572981 10.1021/jm00388a032 Serotonin 2 (5-HT2) receptor 2
28244748 10.1021/acs.jmedchem.7b00085 5-hydroxytryptamine receptor 2A 1
18847250 10.1021/jm800771x 5-hydroxytryptamine receptor 2A 1
9622555 10.1021/jm980076u 5-hydroxytryptamine receptor 1A 1
9622555 10.1021/jm980076u 5-hydroxytryptamine receptor 2A 1
9622555 10.1021/jm980076u Rattus norvegicus 1
1542100 10.1021/jm00082a014 5-hydroxytryptamine receptor 2C 1
3543362 10.1021/jm00384a001 5-hydroxytryptamine receptor 2C 1
3543362 10.1021/jm00384a001 5-hydroxytryptamine receptor 1B 1
3543362 10.1021/jm00384a001 5-hydroxytryptamine receptor 1A 1
7143352 10.1021/jm00352a013 Homo sapiens 1

Data from ChEMBL 36 via Core Engine