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Compound Detail

CHEMBL8389

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COc1cc(OC)c(OC)cc1CC(C)N
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL8389
Phase Preclinical
Structure Type MOL
InChI Key TVSIMAWGATVNGK-UHFFFAOYSA-N
7
Targets
14
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

225.3
MW (Da)
1.60
ALogP
4
HBA
1
HBD
53.7
PSA (Ų)
0.83
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C12H19NO3
MW 225.29
Aromatic Rings 1
Heavy Atoms 16
NP-Likeness 0.24

Activity Summary

Ki 10 meas. best 7.24
Kd 4 meas. best 6.81

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 7.24 6.58 57.9 2
5-hydroxytryptamine receptor 2A
CHEMBL322
 Ki 7.09 6.31 81.0 3
Serotonin (5-HT) receptor
CHEMBL2094123
 Kd 6.81 6.81 154.9 3
5-hydroxytryptamine receptor 2B
CHEMBL323
 Kd 6.81 6.81 154.9 1
Serotonin 2 (5-HT2) receptor
CHEMBL2093870
 Ki 5.9 5.86 1250.0 3
5-hydroxytryptamine receptor 2C
CHEMBL324
 Ki 5.57 5.57 2666.0 1
Serotonin 1 (5-HT1) receptor
CHEMBL2095159
 Ki 4.33 4.33 46400.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2A Ki = 57.9 nM 7.24 Displacement of [125I]DOI from recombinant human 5HT2A expressed in Syrian hamst... 28244748
5-hydroxytryptamine receptor 2A Ki = 81.0 nM 7.09 Displacement of [3H]DOB from 5HT2A in Sprague-Dawley rat cortex membranes measur... 28244748
Serotonin (5-HT) receptor Kd = 154.88 nM 6.81 Affinity against 5-hydroxytryptamine receptors in rat fundus model 7365744
Serotonin (5-HT) receptor Kd = 154.88 nM 6.81 Binding affinity at rat 5-hydroxytryptamine receptor. 7143352
5-hydroxytryptamine receptor 2B Kd = 154.88 nM 6.81 Affinity against 5-hydroxytryptamine 2B receptor in the isolated rat stomach fun... 7310818
Serotonin (5-HT) receptor Kd = 154.88 nM 6.81 Competitive antagonist activity at 5-HT serotonin receptor in Sprague-Dawley rat... 278843
5-hydroxytryptamine receptor 2A Ki = 1200.0 nM 5.92 Binding affinity towards 5-hydroxytryptamine 2A receptor sites by using [3H]keta... 12852967
5-hydroxytryptamine receptor 2A Ki = 1200.0 nM 5.92 Displacement of [3H]ketanserin from 5HT2A receptor expressed in NIH3T3 cells 18847250
5-hydroxytryptamine receptor 2A Ki = 1200.0 nM 5.92 Displacement of [3H]ketanserin from 5HT2A in Sprague-Dawley rat cortex membranes... 28244748
Serotonin 2 (5-HT2) receptor Ki = 1250.0 nM 5.9 Binding affinity against 5-hydroxytryptamine 2 receptor of rat frontal cortex us... 2308135
Serotonin 2 (5-HT2) receptor Ki = 1250.0 nM 5.9 Binding affinity towards 5-hydroxytryptamine 2 receptor from frontal cortical re... 1542100
Serotonin 2 (5-HT2) receptor Ki = 1650.0 nM 5.78 Binding affinity to rat cortical membranes at 5-hydroxytryptamine 2 (5-HT2) rece... 3543362
5-hydroxytryptamine receptor 2C Ki = 2666.0 nM 5.57 Binding affinity towards 5-hydroxytryptamine 1C receptor from frontal cortical r... 1542100
Serotonin 1 (5-HT1) receptor Ki = 46400.0 nM 4.33 Evaluated for binding affinity towards rat cortical membranes at 5-hydroxytrypta... 3543362

Literature References

PubMed DOI Target Context # Activities
7143352 10.1021/jm00352a013 Rattus norvegicus 11
28244748 10.1021/acs.jmedchem.7b00085 5-hydroxytryptamine receptor 2A 3
1542100 10.1021/jm00082a014 Serotonin 2 (5-HT2) receptor 2
2299636 10.1021/jm00164a036 Homo sapiens 2
7310818 10.1021/jm00144a009 No relevant target 2
2299636 10.1021/jm00164a036 Rattus norvegicus 1
592329 10.1021/jm00222a019 Homo sapiens 1
18847250 10.1021/jm800771x 5-hydroxytryptamine receptor 2A 1
9748359 10.1021/jm980144c Homo sapiens 1
7310818 10.1021/jm00144a009 Unchecked 1
7310818 10.1021/jm00144a009 5-hydroxytryptamine receptor 2B 1
7310818 10.1021/jm00144a009 Oryctolagus cuniculus 1
7310818 10.1021/jm00144a009 Homo sapiens 1
12852967 10.1016/s0960-894x(03)00504-3 5-hydroxytryptamine receptor 2A 1
3543362 10.1021/jm00384a001 Serotonin 1 (5-HT1) receptor 1
1542100 10.1021/jm00082a014 5-hydroxytryptamine receptor 2C 1
2308135 10.1021/jm00165a023 Serotonin 2 (5-HT2) receptor 1
7143352 10.1021/jm00352a013 Homo sapiens 1
7143352 10.1021/jm00352a013 Serotonin (5-HT) receptor 1
7365744 10.1021/jm00177a017 Serotonin (5-HT) receptor 1

Data from ChEMBL 36 via Core Engine