Detailed information for compound 427925

Basic information

Technical information
  • TDR Targets ID: 427925
  • Name: (Z)-3-(4-chloroanilino)-2-(2-chlorobenzoyl)-N -pentan-3-ylprop-2-enamide
  • MW: 405.318 | Formula: C21H22Cl2N2O2
  • H donors: 2 H acceptors: 2 LogP: 6.54 Rotable bonds: 9
    Rule of 5 violations (Lipinski): 1
  • SMILES: CCC(NC(=O)/C(=C\Nc1ccc(cc1)Cl)/C(=O)c1ccccc1Cl)CC
  • InChi: 1S/C21H22Cl2N2O2/c1-3-15(4-2)25-21(27)18(13-24-16-11-9-14(22)10-12-16)20(26)17-7-5-6-8-19(17)23/h5-13,15,24H,3-4H2,1-2H3,(H,25,27)/b18-13-
  • InChiKey: TYETXZTUVIKLFD-AQTBWJFISA-N  

Network

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Synonyms

  • (Z)-3-(4-chloroanilino)-2-(2-chlorobenzoyl)-N-(1-ethylpropyl)prop-2-enamide
  • (Z)-3-(4-chloroanilino)-2-[(2-chlorophenyl)-oxomethyl]-N-(1-ethylpropyl)-2-propenamide
  • (Z)-3-[(4-chlorophenyl)amino]-2-(2-chlorophenyl)carbonyl-N-pentan-3-yl-prop-2-enamide
  • (Z)-3-(4-chloroanilino)-2-(2-chlorobenzoyl)-N-(1-ethylpropyl)acrylamide
  • (Z)-2-(2-chlorobenzoyl)-3-[(4-chlorophenyl)amino]-N-pentan-3-ylprop-2-enamide
  • (Z)-2-(2-chlorobenzoyl)-3-[(4-chlorophenyl)amino]-N-(1-ethylpropyl)prop-2-enamide
  • (Z)-3-[(4-chlorophenyl)amino]-2-[(2-chlorophenyl)-oxomethyl]-N-(1-ethylpropyl)prop-2-enamide
  • (Z)-2-(2-chlorobenzoyl)-3-[(4-chlorophenyl)amino]-N-(1-ethylpropyl)acrylamide

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Rattus norvegicus GABA-A receptor; alpha-1/beta-2/gamma-2 Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_129441 All targets in OG5_129441
Brugia malayi gamma-aminobutyric-acid receptor beta subunit precursor Get druggable targets OG5_129441 All targets in OG5_129441
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_129441 All targets in OG5_129441

By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Onchocerca volvulus Gamma-aminobutyric acid receptor subunit beta homolog GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 449 aa 31.8 %
Onchocerca volvulus GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 473 aa 27.5 %
Onchocerca volvulus Putative cys-loop ligand gated ion channel subunit GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 420 aa 33.1 %
Schistosoma japonicum ko:K05194 glycine receptor, alpha 2, putative GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 432 aa 29.9 %
Echinococcus granulosus glycine receptor subunit alpha 1 GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 449 aa 29.8 %
Loa Loa (eye worm) hypothetical protein GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 460 aa 26.5 %
Schistosoma japonicum ko:K05195 glycine receptor, alpha 3, putative GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 489 aa 29.2 %
Brugia malayi Cation transporter family protein GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 448 aa 27.7 %
Onchocerca volvulus Large subunit GTPase 1 homolog GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 455 aa 25.7 %
Onchocerca volvulus GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 438 aa 26.0 %
Onchocerca volvulus GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 412 aa 33.7 %
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 451 aa 30.2 %
Loa Loa (eye worm) excitatory GABA receptor EXP-1A GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 435 aa 29.0 %
Loa Loa (eye worm) hypothetical protein GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 444 aa 25.4 %
Echinococcus multilocularis Cys loop ligand gated ion channel subunit GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 397 aa 29.2 %
Onchocerca volvulus Eukaryotic initiation factor 4A-III homolog GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 441 aa 23.8 %
Onchocerca volvulus GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 461 aa 27.8 %
Loa Loa (eye worm) hypothetical protein GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 445 aa 33.5 %
Loa Loa (eye worm) hypothetical protein GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 451 aa 28.4 %
Onchocerca volvulus GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 461 aa 24.5 %
Onchocerca volvulus GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 438 aa 27.9 %
Onchocerca volvulus GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 421 aa 26.8 %
Schistosoma mansoni Cys-loop ligand gated ion channel subunit GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 490 aa 29.6 %
Echinococcus multilocularis glycine receptor subunit beta GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 422 aa 28.2 %
Schistosoma mansoni nAChR subunit (ShAR1-alpha-like) GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 391 aa 21.7 %
Echinococcus granulosus glycine receptor subunit beta GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 424 aa 28.5 %
Onchocerca volvulus GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 434 aa 28.3 %
Echinococcus multilocularis glycine receptor subunit alpha 1 GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 449 aa 29.8 %
Onchocerca volvulus GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 447 aa 28.0 %
Loa Loa (eye worm) hypothetical protein GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 401 aa 26.2 %

Obtained from network model

Ranking Plot


Putative Targets List


Species Potential target Raw Global Species
Trichomonas vaginalis Clan CD, family C14, metacaspase-like cysteine peptidase 0.0026 0 0.5
Trypanosoma cruzi metacaspase 5, putative 0.0026 0 0.5
Echinococcus granulosus caspase 3 apoptosis cysteine peptidase 0.0098 0.2611 1
Trypanosoma brucei metacaspase 0.0026 0 0.5
Trichomonas vaginalis conserved hypothetical protein 0.0026 0 0.5
Loa Loa (eye worm) hypothetical protein 0.0211 0.6745 1
Schistosoma mansoni 3-dehydroquinate synthase 0.0117 0.3311 1
Echinococcus multilocularis caspase 3 0.0072 0.1658 0.635
Leishmania major metacaspase, putative 0.0026 0 0.5
Trypanosoma cruzi metacaspase, putative 0.0026 0 0.5
Trichomonas vaginalis conserved hypothetical protein 0.0026 0 0.5
Mycobacterium tuberculosis 3-phosphoshikimate 1-carboxyvinyltransferase AroA (5-enolpyruvylshikimate-3-phosphate synthase) (EPSP synthase) (EPSPS) 0.0117 0.3311 0.5
Trypanosoma cruzi metacaspase 5, putative 0.0026 0 0.5
Echinococcus multilocularis caspase 0.0098 0.2611 1
Mycobacterium ulcerans 3-phosphoshikimate 1-carboxyvinyltransferase 0.03 1 1
Loa Loa (eye worm) hypothetical protein 0.0204 0.6491 0.9625
Plasmodium falciparum metacaspase 1 0.0026 0 0.5
Trichomonas vaginalis conserved hypothetical protein 0.0026 0 0.5
Onchocerca volvulus Cell death protein 3 homolog 0.0026 0 0.5
Wolbachia endosymbiont of Brugia malayi UDP-N-acetylglucosamine 1-carboxyvinyltransferase 0.0183 0.5737 0.5
Mycobacterium leprae probable 3-phosphoshikimate 1-carboxyvinyl transferase AroA (5-ENOLPYRUVYLSHIKIMATE-3-PHOSPHATE SYNTHASE) (EPSP SYNTHASE) (EPSPS 0.03 1 1
Trichomonas vaginalis Clan CD, family C14, metacaspase-like cysteine peptidase 0.0026 0 0.5
Schistosoma mansoni caspase-3 (C14 family) 0.0098 0.2611 0.7886
Trichomonas vaginalis conserved hypothetical protein 0.0026 0 0.5
Trypanosoma cruzi metacaspase, putative 0.0026 0 0.5
Trypanosoma brucei metacaspase 5, putative 0.0026 0 0.5
Trypanosoma brucei metacaspase MCA3 0.0026 0 0.5
Trichomonas vaginalis conserved hypothetical protein 0.0026 0 0.5
Trypanosoma cruzi metacaspase, putative 0.0026 0 0.5
Trypanosoma cruzi metacaspase, putative 0.0026 0 0.5
Plasmodium vivax hypothetical protein, conserved 0.0026 0 0.5
Trypanosoma brucei Metacaspase-4 0.0026 0 0.5
Trichomonas vaginalis Clan CD, family C14, metacaspase-like cysteine peptidase 0.0026 0 0.5
Echinococcus granulosus caspase 0.0098 0.2611 1
Trypanosoma brucei metacaspase MCA2 0.0026 0 0.5
Trichomonas vaginalis Clan CD, family C14, metacaspase-like cysteine peptidase 0.0026 0 0.5
Plasmodium falciparum metacaspase-like protein 0.0026 0 0.5
Trichomonas vaginalis Clan CD, family C14, metacaspase-like cysteine peptidase 0.0026 0 0.5
Chlamydia trachomatis UDP-N-acetylglucosamine 1-carboxyvinyltransferase 0.0183 0.5737 0.3627
Echinococcus multilocularis caspase 3, apoptosis cysteine peptidase 0.0098 0.2611 1
Trichomonas vaginalis conserved hypothetical protein 0.0026 0 0.5
Echinococcus granulosus caspase 3 0.0072 0.1658 0.635
Brugia malayi gamma-aminobutyric-acid receptor beta subunit precursor 0.0211 0.6745 1
Mycobacterium tuberculosis 3-dehydroquinate synthase AroB 0.0117 0.3311 0.5
Trichomonas vaginalis Clan CD, family C14, metacaspase-like cysteine peptidase 0.0026 0 0.5
Toxoplasma gondii shikimate dehydrogenase substrate binding domain-containing protein 0.03 1 1
Trichomonas vaginalis Clan CD, family C14, metacaspase-like cysteine peptidase 0.0026 0 0.5
Mycobacterium ulcerans UDP-N-acetylglucosamine 1-carboxyvinyltransferase 0.0183 0.5737 0.3627
Trichomonas vaginalis Clan CD, family C14, metacaspase-like cysteine peptidase 0.0026 0 0.5
Treponema pallidum UDP-N-acetylglucosamine 1-carboxyvinyltransferase 0.0183 0.5737 0.5
Plasmodium vivax metacaspase 1, putative 0.0026 0 0.5
Schistosoma mansoni caspase-7 (C14 family) 0.0098 0.2611 0.7886
Trichomonas vaginalis Clan CD, family C14, metacaspase-like cysteine peptidase 0.0026 0 0.5

Activities

Activity type Activity value Assay description Source Reference
Activity (functional) Anticonvulsant activity against pentylenetetrazole-induced seizures in non-Swiss Albino mouse at 50 mg/kg, ip ChEMBL. 17571865
Activity (functional) 0 Anticonvulsant activity against pentylenetetrazole-induced seizures in non-Swiss Albino mouse at 50 mg/kg, ip ChEMBL. 17571865
IC50 (binding) = 7.1 Inhibition of rat GABA alpha-1-beta-2-gamma-2 receptor ChEMBL. 20684859
IC50 (binding) = 80 nM Displacement of [35S]TBPS from GABAA receptor in Sprague-Dawley rat cortex membrane ChEMBL. 17571865
Imax (binding) = 86 % Displacement of [35S]TBPS from GABAA receptor in Sprague-Dawley rat cortex membrane ChEMBL. 17571865

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

1 literature reference was collected for this gene.

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