Detailed information for compound 368173

Basic information

Technical information
  • TDR Targets ID: 368173
  • Name: [3-(dimethylcarbamoyloxy)phenyl]-trimethylaza nium; methyl sulfate
  • MW: 334.389 | Formula: C13H22N2O6S
  • H donors: 0 H acceptors: 4 LogP: 0.68 Rotable bonds: 5
    Rule of 5 violations (Lipinski): 1
  • SMILES: O=C(N(C)C)Oc1cccc(c1)[N+](C)(C)C.COS(=O)(=O)[O-]
  • InChi: 1S/C12H19N2O2.CH4O4S/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5;1-5-6(2,3)4/h6-9H,1-5H3;1H3,(H,2,3,4)/q+1;/p-1
  • InChiKey: OSZNNLWOYWAHSS-UHFFFAOYSA-M  


Substructure search Similarity search

Network

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Synonyms

  • [3-(dimethylcarbamoyloxy)phenyl]-trimethyl-ammonium; methyl sulfate
  • [3-[dimethylamino(oxo)methoxy]phenyl]-trimethylammonium; methyl sulfate
  • [3-(dimethylcarbamoyloxy)phenyl]-trimethyl-azanium; methyl sulfate
  • Neostigmine
  • methyl sulfate
  • [3-(dimethylamino-oxomethoxy)phenyl]-trimethylammonium; methyl sulfate
  • 51-60-5
  • 59954-03-9
  • MLS000028383
  • Prostigmin methyl sulfate
  • Prostigmine methyl sulfate
  • [3-(Dimethylcarbamoyl)oxyphenyl]trimethylammonium methyl sulfate
  • WLN: 1N1&VOR CK1&1&1 &Q &OSW1
  • SMR000058592
  • 3-(N,N-Dimethylcarbamoyloxy)-N,N,N,-trimethylanilinium methyl sulfate
  • N2126_SIGMA
  • (3-(Dimethylcarbamoxy)phenyl)trimethylammonium methyl sulfate
  • (3-(Dimethylcarbamoyl)oxyphenyl)trimethylammonium methyl sulfate
  • (3-Hydroxyphenyl)trimethylammonium methyl sulfate dimethylcarbamic ester
  • (m-Hydroxyphenyl)trimethylammonium methyl sulfate dimethylcarbamate
  • 3-(Dimethylcarbamoxy)phenyl trimethylammonium methyl sulfate
  • AR-32
  • Ammonium, (3-(dimethylcarbamoyloxy)phenyl)trimethyl-, methylsulfate
  • Ammonium, (m-hydroxyphenyl)trimethyl-, methyl sulfate, dimethylcarbamate
  • Ammonium, (m-hydroxyphenyl)trimethyl-, methyl sulfate, dimethylcarbamate (8CI)
  • Benzenaminium, 3-(((dimethylamino)carbonyl)oxy)-N,N,N-trimethyl-, methyl sulfate
  • CCRIS 3274
  • Carbamic acid, N,N-dimethyl-, 3-(trimethylammonio)phenyl ester, methylsulfate
  • Carbamic acid, N,N-dimethyl-, 3-dimethylaminophenyl ester, methosulfate
  • Carbamic acid, dimethyl-, ester with (m-hydroxyphenyl)trimethylammonium methyl sulfate
  • Dimethylcarbamic ester of 3-oxyphenyltrimethylammonium methylsulfate
  • EINECS 200-109-5
  • Eustigmin methyl sulfate
  • Eustigmin methylsulfate
  • GD 65
  • Hodostin
  • Kirkstigmine methyl sulfate
  • Leostigmine methyl sulfate
  • NEOSTIGMINE METHYLSULFATE
  • NSC 93753
  • Neoeserine methyl sulfate
  • Neostigmeth
  • Neostigmine Methylsulfate [USAN:JAN]
  • Neostigmine methosulfate
  • Neostigmine methyl sulfate
  • Neostigmine methylsulphate
  • Neostigmine metilsulfate
  • Neostigmine monomethyl sulfate
  • Neostigmine monomethylsulfate
  • Normastigmin
  • Philostigmin methyl sulfate
  • Polstigmine
  • Proserine
  • Proserine methyl sulfate
  • Prostigmin
  • SB-23
  • Stigmanol methyl sulfate
  • Stigmosan methyl sulfate
  • Synstigmine
  • Synthostigmine methyl sulfate
  • Syntostigmin
  • Syntostigmin (VAN)
  • Syntostigmin (injection)
  • Syntostigmin methyl sulfate
  • Syntostigmine methyl sulfate
  • TL-1394
  • Vagostigmine methyl sulfate
  • Juvastigmin
  • Ammonium, [3-(dimethylcarbamoyloxy)phenyl]trimethyl-, methyl sulfate
  • Dimethylcarbamic ester of 3-oxyphenyltrimethylammonium methylsulfato
  • Benzenaminium, 3-[[(dimethylamino)carbonyl]oxy]-N,N,N-trimethyl-, methyl sulfate
  • NSC93753
  • Carbamic acid, N,N-dimethyl-, 3-(trimethylammonio)phenyl ester, methyl sulfate
  • D00998
  • Neostigmine methylsulfate (JP15/USP)
  • Kirkstigmine
  • Prostigmin (TN)
  • [3-(Dimethylcarbamoxy)phenyl]trimethylammonium methyl sulfate
  • Proserin

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens butyrylcholinesterase Starlite/ChEMBL References
Homo sapiens nuclear factor, erythroid 2-like 2 Starlite/ChEMBL No references
Homo sapiens acetylcholinesterase (Yt blood group) Starlite/ChEMBL References
Homo sapiens SMAD family member 2 Starlite/ChEMBL No references
Rattus norvegicus Acetylcholinesterase Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Loa Loa (eye worm) acetylcholinesterase 1 Get druggable targets OG5_126875 All targets in OG5_126875
Echinococcus granulosus acetylcholinesterase Get druggable targets OG5_126875 All targets in OG5_126875
Echinococcus multilocularis acetylcholinesterase Get druggable targets OG5_126875 All targets in OG5_126875
Echinococcus multilocularis acetylcholinesterase Get druggable targets OG5_126875 All targets in OG5_126875
Loa Loa (eye worm) transcription factor SMAD2 Get druggable targets OG5_131716 All targets in OG5_131716
Schistosoma japonicum Acetylcholinesterase 1 precursor, putative Get druggable targets OG5_126875 All targets in OG5_126875
Loa Loa (eye worm) MH2 domain-containing protein Get druggable targets OG5_131716 All targets in OG5_131716
Loa Loa (eye worm) carboxylesterase Get druggable targets OG5_126875 All targets in OG5_126875
Schistosoma mansoni family S9 non-peptidase homologue (S09 family) Get druggable targets OG5_126875 All targets in OG5_126875
Echinococcus multilocularis carboxylesterase 5A Get druggable targets OG5_126875 All targets in OG5_126875
Schistosoma japonicum ko:K01049 acetylcholinesterase [EC3.1.1.7], putative Get druggable targets OG5_126875 All targets in OG5_126875
Echinococcus granulosus acetylcholinesterase Get druggable targets OG5_126875 All targets in OG5_126875
Brugia malayi MH2 domain containing protein Get druggable targets OG5_131716 All targets in OG5_131716
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_126875 All targets in OG5_126875
Echinococcus granulosus carboxylesterase 5A Get druggable targets OG5_126875 All targets in OG5_126875
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_126875 All targets in OG5_126875
Brugia malayi Carboxylesterase family protein Get druggable targets OG5_126875 All targets in OG5_126875
Brugia malayi Carboxylesterase family protein Get druggable targets OG5_126875 All targets in OG5_126875
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Brugia malayi Carboxylesterase family protein Acetylcholinesterase   614 aa 507 aa 26.4 %
Onchocerca volvulus Putative nuclear protein Acetylcholinesterase   614 aa 577 aa 40.7 %
Drosophila melanogaster CG10175 gene product from transcript CG10175-RE Acetylcholinesterase   614 aa 547 aa 32.5 %
Echinococcus multilocularis BC026374 protein (S09 family) Acetylcholinesterase   614 aa 642 aa 34.0 %
Onchocerca volvulus Acetylcholinesterase   614 aa 581 aa 27.0 %
Schistosoma mansoni family S9 non-peptidase homologue (S09 family) Acetylcholinesterase   614 aa 602 aa 24.3 %
Onchocerca volvulus Molybdopterin synthase catalytic subunit homolog Acetylcholinesterase   614 aa 564 aa 29.8 %
Brugia malayi Carboxylesterase family protein Acetylcholinesterase   614 aa 573 aa 30.5 %
Echinococcus multilocularis neuroligin Acetylcholinesterase   614 aa 496 aa 24.0 %
Loa Loa (eye worm) hypothetical protein Acetylcholinesterase   614 aa 570 aa 25.4 %
Loa Loa (eye worm) hypothetical protein Acetylcholinesterase   614 aa 574 aa 24.0 %
Onchocerca volvulus Carnitine O-palmitoyltransferase 2, mitochondrial homolog Acetylcholinesterase   614 aa 531 aa 39.7 %
Echinococcus granulosus BC026374 protein S09 family Acetylcholinesterase   614 aa 642 aa 34.1 %
Brugia malayi MH2 domain containing protein SMAD family member 2 467 aa 405 aa 31.6 %
Onchocerca volvulus Acetylcholinesterase   614 aa 632 aa 25.6 %
Onchocerca volvulus Acetylcholinesterase   614 aa 583 aa 30.7 %
Brugia malayi Carboxylesterase family protein butyrylcholinesterase 602 aa 546 aa 30.2 %
Brugia malayi Carboxylesterase family protein acetylcholinesterase (Yt blood group) 614 aa 510 aa 26.5 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Entamoeba histolytica hypothetical protein 0.0043 0.0096 0.5
Schistosoma mansoni transcription factor LCR-F1 0.0043 0.0096 0.0096
Echinococcus granulosus Basic leucine zipper bZIP transcription 0.0043 0.0096 0.0096
Trichomonas vaginalis carboxylesterase domain containing protein, putative 0.0041 0 0.5
Entamoeba histolytica hypothetical protein 0.0043 0.0096 0.5
Onchocerca volvulus 0.0041 0 0.5
Brugia malayi Carboxylesterase family protein 0.0246 1 1
Brugia malayi MH2 domain containing protein 0.0144 0.5031 0.5031
Loa Loa (eye worm) acetylcholinesterase 1 0.0246 1 1
Echinococcus granulosus acetylcholinesterase 0.0246 1 1
Echinococcus granulosus carboxylesterase 5A 0.0246 1 1
Entamoeba histolytica hypothetical protein 0.0043 0.0096 0.5
Echinococcus multilocularis acetylcholinesterase 0.0246 1 1
Onchocerca volvulus 0.0041 0 0.5
Onchocerca volvulus 0.0041 0 0.5
Schistosoma mansoni hypothetical protein 0.0043 0.0096 0.0096
Echinococcus granulosus acetylcholinesterase 0.0246 1 1
Trichomonas vaginalis spcc417.12 protein, putative 0.0041 0 0.5
Loa Loa (eye worm) hypothetical protein 0.0246 1 1
Loa Loa (eye worm) carboxylesterase 0.0246 1 1
Echinococcus multilocularis Basic leucine zipper (bZIP) transcription 0.0043 0.0096 0.0096
Onchocerca volvulus 0.0041 0 0.5
Loa Loa (eye worm) MH2 domain-containing protein 0.0144 0.5031 0.5031
Mycobacterium tuberculosis POSSIBLE PARA-NITROBENZYL ESTERASE (FRAGMENT) 0.0041 0 0.5
Onchocerca volvulus 0.0041 0 0.5
Schistosoma mansoni family S9 non-peptidase homologue (S09 family) 0.0246 1 1
Mycobacterium tuberculosis POSSIBLE PARA-NITROBENZYL ESTERASE (FRAGMENT) 0.0041 0 0.5
Echinococcus multilocularis acetylcholinesterase 0.0246 1 1
Loa Loa (eye worm) hypothetical protein 0.0246 1 1
Brugia malayi hypothetical protein 0.0043 0.0096 0.0096
Mycobacterium tuberculosis Carboxylesterase LipT 0.0041 0 0.5
Loa Loa (eye worm) transcription factor SMAD2 0.0144 0.5031 0.5031
Entamoeba histolytica hypothetical protein 0.0043 0.0096 0.5
Echinococcus multilocularis carboxylesterase 5A 0.0246 1 1
Mycobacterium ulcerans carboxylesterase, LipT 0.0041 0 0.5

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 18.8 nM Inhibition of human whole RBC AChE pretreated for 30 mins by Ellman technique ChEMBL. 20627738
IC50 (binding) = 37.5 nM Inhibition of rat brain homogenate AchE ChEMBL. 16735118
IC50 (binding) = 37.5 nM Inhibition of rat brain homogenate AchE ChEMBL. 16735118
IC50 (binding) = 42.1 nM Inhibition of human serum AchE ChEMBL. 16735118
IC50 (binding) = 42.1 nM Inhibition of human serum AchE ChEMBL. 16735118
IC50 (binding) = 60 nM Inhibition of human plasma BChE pretreated for 30 mins by Ellman technique ChEMBL. 20627738
IC50 (binding) = 41.1 uM Inhibition of electric eel AchE ChEMBL. 16735118
IC50 (binding) = 41.1 uM Inhibition of electric eel AchE ChEMBL. 16735118
IC50 (binding) = 69.1 uM Inhibition of acetylcholine esterase (unknown origin) using acetylthiocholine as substrate incubated for 15 mins prior to substrate addition measured after 5 mins by spectrophotometry ChEMBL. 23603045
Inhibition (binding) Inhibition of human LAL at 10 uM after 30 mins by fluorescence assay ChEMBL. 20557099
LD50 (ADMET) = 0.51 mg kg-1 Acute toxicity in ip dosed mouse measured after 72 hrs ChEMBL. 27377327
Potency (functional) 0.3162 uM PUBCHEM_BIOASSAY: qHTS for Inhibitors of TGF-b. (Class of assay: confirmatory) [Related pubchem assays (depositor defined):AID588856, AID588860] ChEMBL. No reference
Potency (functional) 2.9362 uM PUBCHEM_BIOASSAY: Primary qHTS for delayed death inhibitors of the malarial parasite plastid, 96 hour incubation. (Class of assay: confirmatory) [Related pubchem assays (depositor defined):AID488745, AID488752, AID488774, AID504848, AID504850] ChEMBL. No reference
Potency (functional) 6.5131 uM PUBCHEM_BIOASSAY: Nrf2 qHTS screen for inhibitors. (Class of assay: confirmatory) [Related pubchem assays (depositor defined):AID493153, AID493163, AID504648] ChEMBL. No reference
Potency (functional) = 56.2341 um PUBCHEM_BIOASSAY: qHTS Inhibitors of AmpC Beta-Lactamase (assay with detergent). (Class of assay: confirmatory) [Related pubchem assays: 1002 (Confirmation Concentration-Response Assay for Inhibitors of AmpC Beta-Lactamase (assay with detergent)), 585 (Promiscuous and Specific Inhibitors of AmpC Beta-Lactamase (assay without detergent) - a screen old NIH MLSMR collection), 584 (Promiscuous and Specific Inhibitors of AmpC Beta-Lactamase (assay with detergent) - a screen of the old NIH MLSMR collection), 1003 (Confirmation Cuvette-Based Assay for Inhibitors of AmpC Beta-Lactamase (assay with detergent))] ChEMBL. No reference

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Plasmodium falciparum ChEMBL23

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

17 literature references were collected for this gene.

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