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Compound Detail

CHEMBL269236

TRYPTOLINE
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c1ccc2c3c([nH]c2c1)CNCC3
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL269236
Name TRYPTOLINE
Phase Preclinical
Structure Type MOL
InChI Key CFTOTSJVQRFXOF-UHFFFAOYSA-N
8
Targets
14
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

172.2
MW (Da)
1.81
ALogP
1
HBA
2
HBD
27.8
PSA (Ų)
0.62
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C11H12N2
MW 172.23
Aromatic Rings 2
Heavy Atoms 13

Activity Summary

Ki 12 meas. best 8.03
EC50 1 meas. best 4.13
IC50 1 meas. best 4.01

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 8.03 8.03 9.4 3
Nischarin
CHEMBL3923
 Ki 6.75 6.75 180.0 1
Adrenergic receptor alpha-2
CHEMBL2093864
 Ki 6.15 5.9167 710.0 3
5-hydroxytryptamine receptor 5A
CHEMBL3597
 Ki 5.61 5.61 2470.0 1
5-hydroxytryptamine receptor 2A
CHEMBL322
 Ki 5.52 5.4533 3000.0 3
5-hydroxytryptamine receptor 5A
CHEMBL3426
 Ki 5.5 5.5 3200.0 1
Nuclear receptor subfamily 2 group E member 1
CHEMBL1961788
 EC50 4.13 4.13 74000.0 1
Acetylcholinesterase
CHEMBL4078
 IC50 4.01 4.01 97080.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 9.4 nM 8.03 Binding affinity at rat imidazoline receptor I-2 15013009
Unchecked Ki = 9.4 nM 8.03 Displacement of [3H]2-BFI from imidazoline receptor I-2 15013010
Unchecked Ki = 9.4 nM 8.03 Binding affinity for rat imidazoline I2 receptor from crude P2 membranes 14698196
Nischarin Ki = 180.0 nM 6.75 Binding affinity for rat imidazoline receptor I-1 from crude P2 membranes 14698196
Adrenergic receptor alpha-2 Ki = 710.0 nM 6.15 Binding affinity for rat alpha-2 adrenergic receptor from crude P2 membranes 14698196
Adrenergic receptor alpha-2 Ki = 1600.0 nM 5.8 Binding affinity at alpha-2 adrenergic receptors of rat. 15013009
Adrenergic receptor alpha-2 Ki = 1600.0 nM 5.8 Displacement of [3H]RX-821002 from alpha-2 adrenergic receptor 15013010
5-hydroxytryptamine receptor 5A Ki = 2470.0 nM 5.61 Binding affinity towards mouse 5-hydroxytryptamine 5A receptor 12825922
5-hydroxytryptamine receptor 2A Ki = 3000.0 nM 5.52 Binding affinity for rat 5-hydroxytryptamine 2A receptor using [3H]DOB 14643338
5-hydroxytryptamine receptor 5A Ki = 3200.0 nM 5.5 Binding affinity towards 5-hydroxytryptamine 5A receptor using lysergic acid die... 12930153
5-hydroxytryptamine receptor 2A Ki = 3800.0 nM 5.42 Binding affinity for 5-hydroxytryptamine 2A receptor 15013010
5-hydroxytryptamine receptor 2A Ki = 3800.0 nM 5.42 Binding affinity towards cloned rat 5-hydroxytryptamine 2A receptor by [3H]ketan... 14643338
Nuclear receptor subfamily 2 group E member 1 EC50 = 74000.0 nM 4.13 Agonist activity at in human TLX LBD expressed in human HEK293T cells coexpressi... 34115934
Acetylcholinesterase IC50 = 97080.0 nM 4.01 Inhibition of electric eel AChE using acetylcholine iodide as substrate measured... 22425563

Literature References

PubMed DOI Target Context # Activities
34115934 10.1021/acs.jmedchem.1c00733 Nuclear receptor subfamily 2 group E member 1 7
22425563 10.1016/j.bmcl.2012.02.057 Acetylcholinesterase 4
14643338 10.1016/j.bmcl.2003.09.027 5-hydroxytryptamine receptor 2A 2
14643338 10.1016/j.bmcl.2003.09.027 5-hydroxytryptamine receptor 2C 1
20943389 10.1016/j.bmcl.2010.09.043 No relevant target 1
20943389 10.1016/j.bmcl.2010.09.043 Hepatocyte 1
20943389 10.1016/j.bmcl.2010.09.043 ADMET 1
20943389 10.1016/j.bmcl.2010.09.043 Cytochrome P450 2D6 1
8709108 10.1021/jm960062t 5-hydroxytryptamine receptor 2B 1
14698196 10.1016/j.bmcl.2003.09.092 Adrenergic receptor alpha-2 1
14698196 10.1016/j.bmcl.2003.09.092 Nischarin 1
14698196 10.1016/j.bmcl.2003.09.092 Unchecked 1
12825922 10.1021/jm030030n 5-hydroxytryptamine receptor 5A 1
15013010 10.1016/j.bmcl.2003.12.033 5-hydroxytryptamine receptor 2A 1
15013010 10.1016/j.bmcl.2003.12.033 Adrenergic receptor alpha-2 1
15013010 10.1016/j.bmcl.2003.12.033 Monoamine oxidase 1
15013010 10.1016/j.bmcl.2003.12.033 Unchecked 1
12930153 10.1021/jm030080s 5-hydroxytryptamine receptor 5A 1
15013009 10.1016/j.bmcl.2003.11.078 Adrenergic receptor alpha-2 1
15013009 10.1016/j.bmcl.2003.11.078 Unchecked 1

Data from ChEMBL 36 via Core Engine