Detailed information for compound 21642

Basic information

Technical information
  • TDR Targets ID: 21642
  • Name: 2-[4-[(E)-2-naphthalen-1-ylethenyl]pyridin-1- ium-1-yl]ethanol bromide
  • MW: 356.256 | Formula: C19H18BrNO
  • H donors: 1 H acceptors: 1 LogP: 4.72 Rotable bonds: 4
    Rule of 5 violations (Lipinski): 1
  • SMILES: OCC[n+]1ccc(cc1)/C=C/c1cccc2c1cccc2.[Br-]
  • InChi: 1S/C19H18NO.BrH/c21-15-14-20-12-10-16(11-13-20)8-9-18-6-3-5-17-4-1-2-7-19(17)18;/h1-13,21H,14-15H2;1H/q+1;/p-1/b9-8+;
  • InChiKey: ZPGZAGRMHJDYMQ-HRNDJLQDSA-M  


Substructure search Similarity search

Network

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Synonyms

  • 2-[4-[(E)-2-(1-naphthyl)vinyl]pyridin-1-ium-1-yl]ethanol bromide
  • 2-[4-[(E)-2-(1-naphthalenyl)vinyl]-1-pyridin-1-iumyl]ethanol bromide
  • N-(2-hydroxyethyl)-4-(beta-(1-naphthylvinyl)pyridinium bromide)

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens choline O-acetyltransferase Starlite/ChEMBL References
Rattus norvegicus Choline acetylase Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Echinococcus granulosus choline O acetyltransferase Get druggable targets OG5_133080 All targets in OG5_133080
Brugia malayi Choline O-acetyltransferase Get druggable targets OG5_133080 All targets in OG5_133080
Schistosoma mansoni choline o-acyltransferase Get druggable targets OG5_133080 All targets in OG5_133080
Schistosoma japonicum ko:K00623 choline O-acetyltransferase [EC2.3.1.6], putative Get druggable targets OG5_133080 All targets in OG5_133080
Echinococcus multilocularis choline O acetyltransferase Get druggable targets OG5_133080 All targets in OG5_133080
Loa Loa (eye worm) choline O-acetyltransferase Get druggable targets OG5_133080 All targets in OG5_133080
Schistosoma japonicum Choline O-acetyltransferase, putative Get druggable targets OG5_133080 All targets in OG5_133080
Brugia malayi Choline O-acetyltransferase Get druggable targets OG5_133080 All targets in OG5_133080
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_133080 All targets in OG5_133080
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Leishmania infantum carnitine palmitoyltransferase-like protein Choline acetylase   640 aa 642 aa 24.1 %
Trypanosoma cruzi hypothetical protein, conserved Choline acetylase   640 aa 575 aa 23.5 %
Trypanosoma brucei carnitine O-acetyltransferase, putative choline O-acetyltransferase 630 aa 632 aa 31.6 %
Echinococcus multilocularis carnitine O palmitoyltransferase 1, liver Choline acetylase   640 aa 519 aa 27.9 %
Leishmania infantum choline/Carnitine o-acyltransferase-like protein Choline acetylase   640 aa 682 aa 26.0 %
Leishmania braziliensis carnitine palmitoyltransferase-like protein Choline acetylase   640 aa 656 aa 25.0 %
Echinococcus granulosus carnitine O palmitoyltransferase 2 Choline acetylase   640 aa 617 aa 22.0 %
Trypanosoma brucei gambiense carnitine O-acetyltransferase, putative Choline acetylase   640 aa 630 aa 31.6 %
Echinococcus granulosus carnitine O palmitoyltransferase 1 liver Choline acetylase   640 aa 518 aa 27.2 %
Trypanosoma brucei gambiense carnitine O-palmitoyltransferase, putative Choline acetylase   640 aa 673 aa 21.1 %
Trypanosoma cruzi choline/carnitine O-acetyltransferase, putative Choline acetylase   640 aa 640 aa 29.4 %
Trypanosoma cruzi hypothetical protein, conserved Choline acetylase   640 aa 575 aa 23.5 %
Leishmania mexicana choline/Carnitine o-acyltransferase-like protein Choline acetylase   640 aa 682 aa 27.0 %
Echinococcus multilocularis carnitine O palmitoyltransferase 2 Choline acetylase   640 aa 620 aa 22.3 %
Leishmania donovani choline/Carnitine o-acyltransferase-like protein Choline acetylase   640 aa 682 aa 26.0 %
Onchocerca volvulus Choline acetylase   640 aa 609 aa 28.6 %
Brugia malayi Choline/Carnitine o-acyltransferase family protein Choline acetylase   640 aa 634 aa 28.1 %
Candida albicans similar to mitochondrial outer carnitine acetyltransferase Choline acetylase   640 aa 542 aa 28.2 %
Trypanosoma brucei carnitine O-palmitoyltransferase II, putative Choline acetylase   640 aa 641 aa 29.3 %
Leishmania major carnitine palmitoyltransferase-like protein Choline acetylase   640 aa 637 aa 24.5 %
Trypanosoma congolense carnitine O-palmitoyltransferase II, putative Choline acetylase   640 aa 635 aa 27.9 %
Trypanosoma cruzi carnitine O-acetyltransferase, putative Choline acetylase   640 aa 644 aa 29.7 %
Trypanosoma brucei carnitine O-acetyltransferase, putative Choline acetylase   640 aa 630 aa 31.6 %
Onchocerca volvulus Choline acetylase   640 aa 615 aa 31.1 %
Onchocerca volvulus Vesicular acetylcholine transporter homolog Choline acetylase   640 aa 623 aa 38.0 %
Brugia malayi Choline/Carnitine o-acyltransferase family protein Choline acetylase   640 aa 619 aa 29.7 %
Candida albicans similar to S. cerevisiae YAT2 putative carnitine O-acetyltransferase Choline acetylase   640 aa 567 aa 22.8 %
Trypanosoma brucei carnitine O-palmitoyltransferase, putative Choline acetylase   640 aa 673 aa 21.1 %
Leishmania braziliensis choline/Carnitine o-acyltransferase-like protein Choline acetylase   640 aa 685 aa 25.7 %
Trypanosoma cruzi carnitine O-palmitoyltransferase II, putative Choline acetylase   640 aa 635 aa 29.1 %
Brugia malayi Choline/Carnitine o-acyltransferase family protein Choline acetylase   640 aa 545 aa 27.5 %
Candida albicans similar to S. cerevisiae YAT2 putative carnitine O-acetyltransferase Choline acetylase   640 aa 567 aa 22.8 %
Candida albicans similar to mitochondrial outer carnitine acetyltransferase Choline acetylase   640 aa 542 aa 28.2 %
Leishmania mexicana carnitine palmitoyltransferase-like protein Choline acetylase   640 aa 655 aa 25.5 %
Trypanosoma congolense carnitine O-palmitoyltransferase, putative Choline acetylase   640 aa 695 aa 25.6 %
Trypanosoma brucei gambiense carnitine O-palmitoyltransferase II, putative Choline acetylase   640 aa 643 aa 29.4 %
Loa Loa (eye worm) carnitine O-palmitoyltransferase I isoform Choline acetylase   640 aa 610 aa 26.1 %
Leishmania major choline/Carnitine o-acyltransferase-like protein Choline acetylase   640 aa 683 aa 28.1 %
Leishmania donovani carnitine palmitoyltransferase-like protein Choline acetylase   640 aa 642 aa 24.0 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Echinococcus granulosus nicotinic acetylcholine receptor beta 1 subunit 0.0222 0.3707 0.3707
Loa Loa (eye worm) hypothetical protein 0.0396 1 1
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein 0.0222 0.3707 0.3707
Schistosoma mansoni nAChR subunit 0.0222 0.3707 0.3707
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein 0.0222 0.3707 0.3707
Schistosoma mansoni nAChR subunit (ShAR1-beta-like) 0.0222 0.3707 0.3707
Loa Loa (eye worm) hypothetical protein 0.0222 0.3707 0.3707
Brugia malayi acetylcholine receptor protein, alpha-like chain, putative 0.0222 0.3707 0.3707
Loa Loa (eye worm) hypothetical protein 0.0222 0.3707 0.3707
Brugia malayi Cation transporter family protein 0.0222 0.3707 0.3707
Echinococcus multilocularis acetylcholine receptor subunit beta 1 0.0222 0.3707 0.3707
Loa Loa (eye worm) nicotinic acetylcholine receptor non-alpha subunit 0.0222 0.3707 0.3707
Loa Loa (eye worm) glutamate-gated chloride channel alpha3A subunit 0.0222 0.3707 0.3707
Echinococcus multilocularis nicotinic acetylcholine receptor beta 1 subunit 0.0222 0.3707 0.3707
Loa Loa (eye worm) hypothetical protein 0.0222 0.3707 0.3707
Brugia malayi Cation transporter family protein 0.0222 0.3707 0.3707
Onchocerca volvulus 0.0222 0.3707 1
Loa Loa (eye worm) LGC-31 protein 0.0222 0.3707 0.3707
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein 0.0222 0.3707 0.3707
Echinococcus granulosus nicotinic acetylcholine receptor subunit alpha 8 0.0222 0.3707 0.3707
Schistosoma mansoni nAChR subunit 0.0222 0.3707 0.3707
Loa Loa (eye worm) hypothetical protein 0.0222 0.3707 0.3707
Loa Loa (eye worm) nicotinic acetylcholine receptor alpha subunit 0.0222 0.3707 0.3707
Loa Loa (eye worm) ligand-Gated ion Channel family member 0.0222 0.3707 0.3707
Loa Loa (eye worm) excitatory GABA receptor EXP-1A 0.0222 0.3707 0.3707
Brugia malayi Neurotransmitter-gated ion-channel transmembrane region family protein 0.0222 0.3707 0.3707
Onchocerca volvulus 0.0222 0.3707 1
Echinococcus multilocularis choline O acetyltransferase 0.0396 1 1
Echinococcus multilocularis nAChR subunit 0.0222 0.3707 0.3707
Echinococcus granulosus glycine receptor subunit alpha 1 0.0222 0.3707 0.3707
Schistosoma mansoni nAChR subunit 0.0222 0.3707 0.3707
Brugia malayi nicotinic acetylcholine receptor beta-1 chain precursor 0.0222 0.3707 0.3707
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein 0.0222 0.3707 0.3707
Loa Loa (eye worm) hypothetical protein 0.0222 0.3707 0.3707
Brugia malayi acetylcholine receptor alpha subunit precursor, putative 0.0222 0.3707 0.3707
Loa Loa (eye worm) hypothetical protein 0.0222 0.3707 0.3707
Schistosoma mansoni nAChR subunit 0.0222 0.3707 0.3707
Loa Loa (eye worm) hypothetical protein 0.0222 0.3707 0.3707
Schistosoma mansoni Cys-loop ligand gated ion channel subunit 0.0222 0.3707 0.3707
Brugia malayi Neurotransmitter-gated ion-channel transmembrane region family protein 0.0222 0.3707 0.3707
Echinococcus multilocularis glycine receptor subunit beta 0.0222 0.3707 0.3707
Schistosoma mansoni nAChR subunit (ShAR1-beta2-like) 0.0222 0.3707 0.3707
Onchocerca volvulus 0.0222 0.3707 1
Brugia malayi Neurotransmitter-gated ion-channel transmembrane region family protein 0.0222 0.3707 0.3707
Echinococcus granulosus neuronal acetylcholine receptor subunit alpha 4 0.0222 0.3707 0.3707
Echinococcus granulosus acetylcholine receptor subunit beta 1 0.0222 0.3707 0.3707
Loa Loa (eye worm) hypothetical protein 0.0222 0.3707 0.3707
Schistosoma mansoni nAChR subunit (ShAR1-alpha-like) 0.0222 0.3707 0.3707
Brugia malayi Hypothetical glycine receptor like protein T20B12.9 in chromosome III 0.0222 0.3707 0.3707
Brugia malayi acetylcholine receptor, alpha-type subunit unc-38 precursor 0.0222 0.3707 0.3707
Loa Loa (eye worm) hypothetical protein 0.0222 0.3707 0.3707
Loa Loa (eye worm) choline O-acetyltransferase 0.0396 1 1
Echinococcus granulosus choline O acetyltransferase 0.0396 1 1
Schistosoma mansoni Cys-loop ligand gated ion channel subunit 0.0222 0.3707 0.3707
Loa Loa (eye worm) hypothetical protein 0.0222 0.3707 0.3707
Echinococcus multilocularis Cys loop ligand gated ion channel subunit 0.0222 0.3707 0.3707
Echinococcus multilocularis glycine receptor subunit alpha 1 0.0222 0.3707 0.3707
Loa Loa (eye worm) hypothetical protein 0.0222 0.3707 0.3707
Loa Loa (eye worm) hypothetical protein 0.0222 0.3707 0.3707
Entamoeba histolytica hypothetical protein 0.012 0 0.5
Loa Loa (eye worm) hypothetical protein 0.0222 0.3707 0.3707
Schistosoma mansoni nAChR subunit 0.0222 0.3707 0.3707
Onchocerca volvulus 0.0222 0.3707 1
Onchocerca volvulus 0.0222 0.3707 1
Echinococcus granulosus glycine receptor subunit beta 0.0222 0.3707 0.3707
Schistosoma mansoni choline o-acyltransferase 0.0396 1 1
Echinococcus multilocularis glycine receptor subunit alpha 1 0.0222 0.3707 0.3707
Echinococcus granulosus Cys loop ligand gated ion channel subunit 0.0222 0.3707 0.3707
Brugia malayi Choline O-acetyltransferase 0.0396 1 1
Onchocerca volvulus Putative nachr subunit 0.0222 0.3707 1
Loa Loa (eye worm) hypothetical protein 0.0222 0.3707 0.3707
Echinococcus granulosus glycine receptor subunit alpha 1 0.0222 0.3707 0.3707
Brugia malayi Cation transporter family protein 0.0222 0.3707 0.3707
Loa Loa (eye worm) hypothetical protein 0.0222 0.3707 0.3707
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein 0.0222 0.3707 0.3707
Brugia malayi nicotinic acetylcholine receptor alpha subunit, putative 0.0222 0.3707 0.3707
Echinococcus multilocularis nicotinic acetylcholine receptor alpha subunit 0.0222 0.3707 0.3707
Echinococcus granulosus glycine receptor subunit beta 0.0222 0.3707 0.3707
Echinococcus multilocularis neuronal acetylcholine receptor subunit alpha 4 0.0222 0.3707 0.3707
Schistosoma mansoni nAChR subunit 0.0222 0.3707 0.3707
Brugia malayi gamma-aminobutyric-acid receptor beta subunit precursor 0.0222 0.3707 0.3707
Echinococcus granulosus glycine receptor subunit alpha 1 0.0222 0.3707 0.3707
Loa Loa (eye worm) hypothetical protein 0.0222 0.3707 0.3707
Echinococcus multilocularis glycine receptor subunit beta 0.0222 0.3707 0.3707
Loa Loa (eye worm) acetylcholine receptor alpha subunit 0.0222 0.3707 0.3707
Echinococcus granulosus nicotinic acetylcholine receptor subunit type 0.0222 0.3707 0.3707
Schistosoma mansoni nAChR subunit 0.0222 0.3707 0.3707
Loa Loa (eye worm) hypothetical protein 0.0222 0.3707 0.3707
Loa Loa (eye worm) hypothetical protein 0.0222 0.3707 0.3707
Schistosoma mansoni Cys-loop ligand gated ion channel subunit 0.0222 0.3707 0.3707
Onchocerca volvulus 0.0222 0.3707 1
Loa Loa (eye worm) ACC-1 protein 0.0222 0.3707 0.3707
Echinococcus multilocularis nicotinic acetylcholine receptor a11 subunit 0.0222 0.3707 0.3707
Echinococcus granulosus nicotinic acetylcholine receptor alpha subunit 0.0222 0.3707 0.3707
Echinococcus granulosus nicotinic acetylcholine receptor a11 subunit 0.0222 0.3707 0.3707
Loa Loa (eye worm) ACC-1 protein 0.0222 0.3707 0.3707
Loa Loa (eye worm) hypothetical protein 0.0222 0.3707 0.3707
Brugia malayi excitatory GABA receptor EXP-1A 0.0222 0.3707 0.3707
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein 0.0222 0.3707 0.3707
Echinococcus multilocularis glycine receptor subunit alpha 1 0.0222 0.3707 0.3707
Echinococcus multilocularis nicotinic acetylcholine receptor subunit alpha 8 0.0222 0.3707 0.3707
Echinococcus granulosus nAChR subunit 0.0222 0.3707 0.3707

Activities

Activity type Activity value Assay description Source Reference
I50 (binding) = 170000000 M Inhibition of choline acetyltransferase (ChAT) activity ChEMBL. 3336013
I50 (binding) = 6800000000 M Inhibition of acetylcholinesterase (AChE) activity ChEMBL. 3336013
I50 (binding) = 3 uM Inhibition of choline acetyltransferase (CAT) enzyme ChEMBL. 3351860
I50 (binding) = 170 uM Inhibitory activity against acetylcholinetransferase (AChE) enzyme ChEMBL. 3351860
IC50 (binding) = 0.0000017 M Inhibition of choline acetyltransferase (ChAT) activity ChEMBL. 3336013
IC50 (binding) = 0.000068 M Inhibition of acetylcholinesterase (AChE) activity ChEMBL. 3336013
IC50 (binding) = 3 uM Inhibition of choline acetyltransferase (CAT) enzyme ChEMBL. 3351860
IC50 (binding) = 170 uM Inhibitory activity against acetylcholinetransferase (AChE) enzyme ChEMBL. 3351860
Ratio (functional) = 1 Effect on rate of aging of soman-inhibited acetylcholinetransferase (AChE) of rat erythocyte lysate at 0.1mM, ratio of control/treated ChEMBL. 3351860
Ratio (binding) = 40 Degree of specificity expressed as the ratio of I50 of AChE to I50 of ChAT ChEMBL. 3336013
Ratio (binding) = 56.7 Selectivity ratio of I50 of AChE to I50 of CAT ChEMBL. 3351860

Phenotypes

Whole-cell/tissue/organism interactions

We have no records of whole-cell/tissue assays done with this compound What does this mean?

Many chemical entities in TDR Targets come from high-throughput screenings with whole cells or tissue samples, and not all assayed compounds have been tested against a single a single target protein, probably because they get ruled out during screening process. Even if these compounds may have not been of interest in the original screening, they may come as interesting leads for other screening assays. Furthermore, we may be able to propose drug-target associations using chemical similarities and network patterns.

Annotated phenotypes:

We have no manually annotated phenotypes for this drug. What does this mean? / Care to help?
In TDR Targets, information about phenotypes that are caused by drugs, or by genetic manipulation of cells (e.g. gene knockouts or knockdowns) is manually curated from the literature. These descriptions help to describe the potential of the target for drug development. If no information is available for this gene or if the information is incomplete, this may mean that i) the papers containing this information either appeared after the curation effort for this organism was carried out or they were inadvertently missed by curators; or that ii) the curation effort for this organism has not yet started.
 
In any case, if you have information about papers containing relevant validation data for this target, please log in using your TDR Targets username and password and send them to us using the corresponding form in this page (only visible to registered users) or contact us.

External resources for this compound

Bibliographic References

2 literature references were collected for this gene.

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