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Compound Detail

CHEMBL8642

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COc1ccc(OC)c(CC(C)N)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL8642
Phase Preclinical
Structure Type MOL
InChI Key LATVFYDIBMDBSY-UHFFFAOYSA-N
7
Targets
20
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

195.3
MW (Da)
1.59
ALogP
3
HBA
1
HBD
44.5
PSA (Ų)
0.79
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 C11H17NO2
MW 195.26
Aromatic Rings 1
Heavy Atoms 14
NP-Likeness -0.05

Activity Summary

Ki 16 meas. best 6.68
Kd 4 meas. best 6.83

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Serotonin (5-HT) receptor
CHEMBL2094123
 Kd 6.83 6.83 147.9 3
5-hydroxytryptamine receptor 2B
CHEMBL323
 Kd 6.83 6.83 147.9 1
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 6.68 5.98 211.0 2
5-hydroxytryptamine receptor 2A
CHEMBL322
 Ki 6.57 5.5117 268.0 6
Serotonin 2 (5-HT2) receptor
CHEMBL2093870
 Ki 6.33 5.49 465.0 5
Serotonin 1 (5-HT1) receptor
CHEMBL2095159
 Ki 5.99 5.99 1020.0 2
5-hydroxytryptamine receptor 2C
CHEMBL324
 Ki 5.92 5.92 1217.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Serotonin (5-HT) receptor Kd = 147.91 nM 6.83 Binding affinity at rat 5-hydroxytryptamine receptor. 7143352
5-hydroxytryptamine receptor 2B Kd = 147.91 nM 6.83 Affinity against 5-hydroxytryptamine 2B receptor in the isolated rat stomach fun... 7310818
Serotonin (5-HT) receptor Kd = 147.91 nM 6.83 Competitive antagonist activity at 5-HT serotonin receptor in Sprague-Dawley rat... 278843
Serotonin (5-HT) receptor Kd = 147.91 nM 6.83 Affinity against 5-hydroxytryptamine receptors in rat fundus model 7365744
5-hydroxytryptamine receptor 2A Ki = 211.0 nM 6.68 Displacement of [125I]DOI from recombinant human 5HT2A expressed in Syrian hamst... 28244748
5-hydroxytryptamine receptor 2A Ki = 268.0 nM 6.57 Displacement of [3H]DOB from 5HT2A in Sprague-Dawley rat cortex membranes measur... 28244748
Serotonin 2 (5-HT2) receptor Ki = 465.0 nM 6.33 Compound was evaluated for its ability to displace 0.25 nM [125I](R)-DOI from bi... 1992127
Serotonin 1 (5-HT1) receptor Ki = 1020.0 nM 5.99 Evaluated for binding affinity towards rat cortical membranes at 5-hydroxytrypta... 3543362
Serotonin 1 (5-HT1) receptor Ki = 1020.0 nM 5.99 Binding affinity for 5-hydroxytryptamine 1 receptor of rat prefrontal cortex 3950904
5-hydroxytryptamine receptor 2C Ki = 1217.0 nM 5.92 Binding affinity towards 5-hydroxytryptamine 1C receptor from frontal cortical r... 1542100
5-hydroxytryptamine receptor 2A Ki = 4720.0 nM 5.33 Displacement of [3H]ketanserin from NIH3T3 cells stably expressing rat 5-hydroxy... 10956215
5-hydroxytryptamine receptor 2A Ki = 4720.0 nM 5.33 Displacement of [3H]ketanserin from rat 5HT2A expressed in mouse NIH/3T3 cell me... 28244748
Serotonin 2 (5-HT2) receptor Ki = 5200.0 nM 5.28 Binding affinity to rat cortical membranes at 5-hydroxytryptamine 2 (5-HT2) rece... 3543362
Serotonin 2 (5-HT2) receptor Ki = 5200.0 nM 5.28 Binding affinity against 5-hydroxytryptamine 2 receptor of rat frontal cortex us... 2308135
Serotonin 2 (5-HT2) receptor Ki = 5200.0 nM 5.28 Binding affinity towards 5-hydroxytryptamine 2 receptor from frontal cortical re... 1542100
Serotonin 2 (5-HT2) receptor Ki = 5200.0 nM 5.28 Displacement of [3H]ketanserin from rat prefrontal cortex 5-hydroxytryptamine 2 ... 3950904
5-hydroxytryptamine receptor 2A Ki = 5200.0 nM 5.28 Binding affinity towards 5-hydroxytryptamine 2A receptor sites by using [3H]keta... 12852967
5-hydroxytryptamine receptor 2A Ki = 5200.0 nM 5.28 Displacement of [3H]ketanserin from 5HT2A receptor in Sprague-Dawley rat brain b... 18296055
5-hydroxytryptamine receptor 2A Ki = 5200.0 nM 5.28 Displacement of [3H]ketanserin from 5HT2A receptor expressed in NIH3T3 cells 18847250
5-hydroxytryptamine receptor 2A Ki = 5200.0 nM 5.28 Displacement of [3H]ketanserin from 5HT2A in Sprague-Dawley rat cortex membranes... 28244748

Literature References

PubMed DOI Target Context # Activities
1992127 10.1021/jm00105a043 Rattus norvegicus 5
28244748 10.1021/acs.jmedchem.7b00085 5-hydroxytryptamine receptor 2A 4
7310818 10.1021/jm00144a009 No relevant target 2
2299636 10.1021/jm00164a036 Homo sapiens 2
1542100 10.1021/jm00082a014 Serotonin 2 (5-HT2) receptor 2
10956215 10.1021/jm9906062 5-hydroxytryptamine receptor 2C 1
3950904 10.1021/jm00152a005 Serotonin 2 (5-HT2) receptor 1
3950904 10.1021/jm00152a005 Serotonin 1 (5-HT1) receptor 1
6779006 10.1021/jm00185a014 Rattus norvegicus 1
2299636 10.1021/jm00164a036 Rattus norvegicus 1
1542100 10.1021/jm00082a014 5-hydroxytryptamine receptor 2C 1
2308135 10.1021/jm00165a023 Serotonin 2 (5-HT2) receptor 1
10956215 10.1021/jm9906062 5-hydroxytryptamine receptor 2A 1
7143352 10.1021/jm00352a013 Homo sapiens 1
7143352 10.1021/jm00352a013 Rattus norvegicus 1
7143352 10.1021/jm00352a013 Serotonin (5-HT) receptor 1
7365744 10.1021/jm00177a017 Serotonin (5-HT) receptor 1
3543362 10.1021/jm00384a001 Serotonin 2 (5-HT2) receptor 1
3543362 10.1021/jm00384a001 Serotonin 1 (5-HT1) receptor 1
1992127 10.1021/jm00105a043 ADMET 1

Data from ChEMBL 36 via Core Engine