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Compound Detail

CHEMBL8165

5-METHOXYTRYPTAMINE
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COc1ccc2[nH]cc(CCN)c2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL8165
Name 5-METHOXYTRYPTAMINE
Phase Preclinical
Structure Type MOL
InChI Key JTEJPPKMYBDEMY-UHFFFAOYSA-N
18
Targets
39
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

190.2
MW (Da)
1.68
ALogP
2
HBA
2
HBD
51.0
PSA (Ų)
0.77
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 C11H14N2O
MW 190.25
Aromatic Rings 2
Heavy Atoms 14
NP-Likeness 0.01

Activity Summary

Ki 34 meas. best 9.03
EC50 3 meas. best 9.3
IC50 2 meas. best 4.94

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2A
CHEMBL224
 EC50 9.3 9.3 0.5 1
5-hydroxytryptamine receptor 7
CHEMBL3223
 Ki 9.03 9.03 0.9 1
Serotonin 1 (5-HT1) receptor
CHEMBL2095159
 Ki 8.7 8.7 2.0 1
5-hydroxytryptamine receptor 7
CHEMBL3155
 Ki 8.7 8.5 2.0 2
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 8.49 8.49 3.2 1
5-hydroxytryptamine receptor 1A
CHEMBL273
 Ki 8.49 8.26 3.2 5
5-hydroxytryptamine receptor 1B
CHEMBL1898
 Ki 8.46 8.46 3.5 1
5-hydroxytryptamine receptor 1B
CHEMBL3459
 Ki 8.4 7.3475 4.0 4
5-hydroxytryptamine receptor 1D
CHEMBL1983
 Ki 8.39 8.33 4.1 2
Serotonin 2 (5-HT2) receptor
CHEMBL2093870
 Ki 8.32 6.85 4.8 8
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 8.32 7.42 4.8 2
5-hydroxytryptamine receptor 4
CHEMBL1875
 Ki 7.57 7.09 26.9 2
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 7.35 7.35 45.0 1
Unchecked
CHEMBL612545
 Ki 7.34 6.82 45.8 2
5-hydroxytryptamine receptor 6
CHEMBL3371
 Ki 7.06 7.06 88.0 1
5-hydroxytryptamine receptor 2C
CHEMBL324
 Ki 6.3 6.3 500.0 1
Sodium-dependent serotonin transporter
CHEMBL313
 EC50 5.66 5.66 2169.0 1
Sodium-dependent dopamine transporter
CHEMBL338
 EC50 4.96 4.96 11031.0 1
Transient receptor potential cation channel subfamily M member 8
CHEMBL1075319
 IC50 4.94 4.925 11600.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2A EC50 = 0.503 nM 9.3 Agonist activity at 5HT2A receptor (unknown origin) by cell based calcium mobili... 25193229
5-hydroxytryptamine receptor 7 Ki = 0.9333 nM 9.03 Binding affinity at rat 5-hydroxytryptamine 7 receptor. 14640545
5-hydroxytryptamine receptor 7 Ki = 2.0 nM 8.7 Binding affinity of compound towards rodent 5-hydroxytryptamine 7 receptor 12825922
Serotonin 1 (5-HT1) receptor Ki = 2.0 nM 8.7 Evaluated for binding affinity towards rat cortical membranes at 5-hydroxytrypta... 3543362
5-hydroxytryptamine receptor 1A Ki = 3.2 nM 8.49 Binding affinity towards 5-hydroxytryptamine 1A receptor 2965244
5-hydroxytryptamine receptor 1A Ki = 3.2 nM 8.49 In vitro affinity at human cloned 5-hydroxytryptamine 1A receptor by [3H]8-OH-DP... 8568822
5-hydroxytryptamine receptor 1A Ki = 3.2 nM 8.49 Binding affinity of compound towards 5-hydroxytryptamine 1A receptor in rat stri... 2754715
5-hydroxytryptamine receptor 1B Ki = 3.5 nM 8.46 Displacement of [3H]-5-HT from human 5-hydroxytryptamine 1D receptor beta 8568822
5-hydroxytryptamine receptor 1B Ki = 4.0 nM 8.4 Evaluated for binding affinity towards 5-hydroxytryptamine 1B receptor 2965244
5-hydroxytryptamine receptor 1D Ki = 4.1 nM 8.39 Binding affinity towards 5-hydroxytryptamine 1D receptor was determined in calf ... 8568822
5-hydroxytryptamine receptor 2A Ki = 4.8 nM 8.32 Affinity against 5-hydroxytryptamine 2A receptor (D) labeled with [125I]DOI. 8027974
Serotonin 2 (5-HT2) receptor Ki = 4.8 nM 8.32 Binding affinity towards 5-hydroxytryptamine 2 receptor using [3H]- 1-(4-bromo-2... 2965244
5-hydroxytryptamine receptor 7 Ki = 5.012 nM 8.3 Displacement of [3H]5-HT from recombinant human 5-HT7 receptor expressed in Afri... 31581003
5-hydroxytryptamine receptor 1A Ki = 5.0 nM 8.3 Binding affinity against 5-hydroxytryptamine 1A receptor using [3H]-8-OH-DPAT as... 2213830
5-hydroxytryptamine receptor 1D Ki = 5.4 nM 8.27 Selectivity towards 5-hydroxytryptamine 1D receptor beta to that of 5-hydroxytry... 8568822
5-hydroxytryptamine receptor 1B Ki = 6.457 nM 8.19 Displacement of [3H]5-HT from 5-HT1B receptor of rat frontal cortex homogenate 3385733
5-hydroxytryptamine receptor 1A Ki = 9.0 nM 8.05 Evaluated for the binding affinity to hippocampus striatal membranes at 5-hydrox... 3543362
5-hydroxytryptamine receptor 1A Ki = 10.72 nM 7.97 Binding affinity of a compound to rat brain 5-hydroxytryptamine 1A (serotonin) r... 8568799
Serotonin 2 (5-HT2) receptor Ki = 14.0 nM 7.85 Binding affinity to rat cortical membranes at 5-hydroxytryptamine 2 receptor bin... 3543362
Serotonin 2 (5-HT2) receptor Ki = 14.0 nM 7.85 Binding affinity to rat cortical membranes at 5-hydroxytryptamine 2 receptor bin... 3543362

Literature References

PubMed DOI Target Context # Activities
3543362 10.1021/jm00384a001 Serotonin 2 (5-HT2) receptor 4
19223092 10.1016/j.ejmech.2009.01.015 5-hydroxytryptamine receptor 4 3
8568822 10.1021/jm950498t 5-hydroxytryptamine receptor 1D 3
22425563 10.1016/j.bmcl.2012.02.057 Acetylcholinesterase 3
8027974 10.1021/jm00039a004 5-hydroxytryptamine receptor 2A 2
14640545 10.1021/jm030826m 5-hydroxytryptamine receptor 7 2
8496700 10.1021/np50094a001 Unchecked 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
24699367 10.1016/j.ejmech.2014.03.055 Plasmodium falciparum 2
8027974 10.1021/jm00039a004 5-hydroxytryptamine receptor 2C 2
27765507 10.1016/j.bmcl.2016.10.004 Escherichia coli 2
3543362 10.1021/jm00384a001 5-hydroxytryptamine receptor 1B 2
20965726 10.1016/j.bmcl.2010.09.099 Transient receptor potential cation channel subfamily M member 8 2
25193229 10.1016/j.bmcl.2014.07.062 5-hydroxytryptamine receptor 2A 2
2965244 10.1021/jm00399a031 Serotonin 2 (5-HT2) receptor 2
3543362 10.1021/jm00384a001 5-hydroxytryptamine receptor 2C 1
8027974 10.1021/jm00039a004 Unchecked 1
10715164 10.1021/jm990550b 5-hydroxytryptamine receptor 6 1
8568822 10.1021/jm950498t 5-hydroxytryptamine receptor 1A 1
36067397 10.1021/acs.jmedchem.2c01075 POU domain, class 2, transcription factor 1 1

Data from ChEMBL 36 via Core Engine