Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL20730

VESAMICOL
Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
O[C@@H]1CCCC[C@H]1N1CCC(c2ccccc2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL20730
Name VESAMICOL
Phase Preclinical
Structure Type MOL
InChI Key YSSBJODGIYRAMI-IAGOWNOFSA-N
8
Targets
32
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

259.4
MW (Da)
3.17
ALogP
2
HBA
1
HBD
23.5
PSA (Ų)
0.88
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C17H25NO
MW 259.39
Aromatic Rings 1
Heavy Atoms 19
NP-Likeness 0.13

Activity Summary

Ki 30 meas. best 9.0
IC50 2 meas. best 7.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Vesicular acetylcholine transporter
CHEMBL3313
 Ki 9.0 8.9 1.0 3
Vesicular acetylcholine transporter
CHEMBL4767
 Ki 8.7 8.35 2.0 6
Unchecked
CHEMBL612545
 Ki 8.12 7.0529 7.6 7
Vesicular acetylcholine transporter
CHEMBL4767
 IC50 7.7 7.7 20.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL3602
 Ki 7.69 7.58 20.4 2
Sigma non-opioid intracellular receptor 1
CHEMBL4153
 Ki 7.59 7.314 25.8 5
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 7.58 7.58 26.0 2
Vesicular acetylcholine transporter
CHEMBL3313
 IC50 7.47 7.47 34.0 1
Sigma 2 receptor
CHEMBL613288
 Ki 7.47 7.47 34.0 1
Vesicular acetylcholine transporter
CHEMBL2125
 Ki 7.34 7.2467 46.1 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Vesicular acetylcholine transporter Ki = 1.0 nM 9.0 In vitro binding affinity to vesamicol receptor using [3H]vesamicol. 8057300
Vesicular acetylcholine transporter Ki = 1.0 nM 9.0 Binding affinity to VAChT Torpedo californica electric organ synaptic vesicles 26071858
Vesicular acetylcholine transporter Ki = 2.0 nM 8.7 Binding to vesicular acetylcholine transporter of torpedo synaptic vesicles 9397171
Vesicular acetylcholine transporter Ki = 2.0 nM 8.7 Displacement of [3H]vesamicol from Vesicular Acetylcholine Transporter (VAChT) 10425095
Vesicular acetylcholine transporter Ki = 2.0 nM 8.7 Displacement of [3H]vesamicol from human vesicular acetylcholine transporter exp... 19203271
Vesicular acetylcholine transporter Ki = 2.0 nM 8.7 Displacement of [3H]vesamicol from VAChT in Torpedo californica cholinergic syna... 20218624
Vesicular acetylcholine transporter Ki = 4.4 nM 8.36 Displacement of (-)-[3H]vesamicol from human VAChT expressed in rat PC12 A123.7 ... 21732626
Unchecked Ki = 7.6 nM 8.12 Displacement of [3H]vesamicol from VAChT receptor in torpedo electrical organ sy... 18324757
Vesicular acetylcholine transporter Ki = 15.2 nM 7.82 Displacement of [3H]-vesamicol from human VAChT after 24 hrs by by liquid scinti... 26138195
Vesicular acetylcholine transporter Ki = 15.2 nM 7.82 Displacement of [3H]vesamicol from human VAChT expressed in rat PC12 cells after... 22739089
Vesicular acetylcholine transporter IC50 = 20.0 nM 7.7 Inhibition of active transport of [3H]acetylcholine using purified Torpedo calif... 2724295
Sigma non-opioid intracellular receptor 1 Ki = 20.4 nM 7.69 Displacement of (-)-[3H]pentazocine from sigma1 receptor in Sprague-Dawley rat c... 26071858
Sigma non-opioid intracellular receptor 1 Ki = 25.8 nM 7.59 Displacement of [3H](+)-pentazocine from sigma1 receptor in guinea pig brain mem... 19203271
Sigma non-opioid intracellular receptor 1 Ki = 25.8 nM 7.59 Displacement of [3H](+)-pentazocine from sigma 1 receptor in guinea pig brain me... 20218624
Sigma non-opioid intracellular receptor 1 Ki = 26.0 nM 7.58 Sigma-1 binding assay was done in guinea pig membranes by labeling the binding s... 9397171
Sigma non-opioid intracellular receptor 1 Ki = 26.0 nM 7.58 Binding affinity against Sigma opioid receptor type 1 in guinea pig brain membra... 10425095
Vesicular acetylcholine transporter IC50 = 34.0 nM 7.47 Inhibition of [3H]- vesamicol binding to synaptic vesicles preparation from the ... 8478910
Sigma non-opioid intracellular receptor 1 Ki = 34.0 nM 7.47 Binding affinity against Sigma opioid receptor type 2 in rat liver membranes usi... 10425095
Sigma 2 receptor Ki = 34.0 nM 7.47 Sigma 2 binding assay was done rat liver membrane, by labeling the binding site ... 9397171
Unchecked Ki = 34.5 nM 7.46 Displacement of [3H]DTG from sigma2 receptor in rat liver membrane 19203271

Literature References

PubMed DOI Target Context # Activities
19203271 10.1021/jm8012344 Unchecked 3
22739089 10.1016/j.bmc.2012.05.045 Unchecked 3
26071858 10.1016/j.ejmech.2015.05.033 Vesicular acetylcholine transporter 3
21732626 10.1021/jm200203f Unchecked 3
20218624 10.1021/jm9017916 Unchecked 3
26071858 10.1016/j.ejmech.2015.05.033 Unchecked 3
26138195 10.1016/j.bmc.2015.05.058 Unchecked 3
18324757 10.1021/jm700961r Unchecked 2
10425095 10.1021/jm980560x Sigma non-opioid intracellular receptor 1 2
2724295 10.1021/jm00126a013 Vesicular acetylcholine transporter 1
2724295 10.1021/jm00126a013 Mus musculus 1
38318365 10.1016/j.isci.2024.108907 Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 1
19203271 10.1021/jm8012344 Sigma non-opioid intracellular receptor 1 1
19203271 10.1021/jm8012344 Vesicular acetylcholine transporter 1
20218624 10.1021/jm9017916 Vesicular acetylcholine transporter 1
10425095 10.1021/jm980560x Vesicular acetylcholine transporter 1
21732626 10.1021/jm200203f Sigma non-opioid intracellular receptor 1 1
8478910 10.1021/jm00060a005 Vesicular acetylcholine transporter 1
21732626 10.1021/jm200203f Vesicular acetylcholine transporter 1
9397171 10.1021/jm970326r Sigma 2 receptor 1

Data from ChEMBL 36 via Core Engine