Detailed information for compound 205771

Basic information

Technical information
  • TDR Targets ID: 205771
  • Name: 4-(4-chlorophenoxy)-N-ethylthieno[2,3-c]pyrid ine-2-carboxamide
  • MW: 332.805 | Formula: C16H13ClN2O2S
  • H donors: 1 H acceptors: 2 LogP: 4 Rotable bonds: 5
    Rule of 5 violations (Lipinski): 1
  • SMILES: CCNC(=O)c1sc2c(c1)c(cnc2)Oc1ccc(cc1)Cl
  • InChi: 1S/C16H13ClN2O2S/c1-2-19-16(20)14-7-12-13(8-18-9-15(12)22-14)21-11-5-3-10(17)4-6-11/h3-9H,2H2,1H3,(H,19,20)
  • InChiKey: DFFPNDMXOZUGLU-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 4-(4-chlorophenoxy)-N-ethyl-thieno[2,3-c]pyridine-2-carboxamide
  • 4-(4-chlorophenoxy)-N-ethyl-2-thieno[2,3-c]pyridinecarboxamide
  • 4-(4-chlorophenoxy)-N-ethylthieno[5,4-c]pyridine-2-carboxamide
  • 4-(4-chlorophenoxy)-N-ethyl-thieno[5,4-c]pyridine-2-carboxamide
  • 4-(4-chlorophenoxy)-N-ethyl-2-thieno[5,4-c]pyridinecarboxamide

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens cyclin C Starlite/ChEMBL References
Homo sapiens vascular cell adhesion molecule 1 Starlite/ChEMBL References
Homo sapiens cyclin-dependent kinase 8 References
Trypanosoma cruzi trypanothione reductase, putative Curated by TDR Targets References
Homo sapiens intercellular adhesion molecule 1 Starlite/ChEMBL References
Homo sapiens selectin E Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Brugia malayi Cyclin C Get druggable targets OG5_129826 All targets in OG5_129826
Cryptosporidium parvum thioredoxin reductase 1 Get druggable targets OG5_126785 All targets in OG5_126785
Leishmania donovani trypanothione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Cryptosporidium hominis thioredoxin reductase Get druggable targets OG5_126785 All targets in OG5_126785
Mycobacterium tuberculosis NADPH-dependent mycothiol reductase Mtr Get druggable targets OG5_126785 All targets in OG5_126785
Loa Loa (eye worm) cyclin C Get druggable targets OG5_129826 All targets in OG5_129826
Brugia malayi glutathione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Loa Loa (eye worm) thioredoxin reductase Get druggable targets OG5_126785 All targets in OG5_126785
Plasmodium berghei thioredoxin reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Plasmodium yoelii glutathione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Brugia malayi Protein kinase domain containing protein Get druggable targets OG5_129229 All targets in OG5_129229
Trypanosoma brucei gambiense trypanothione reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Schistosoma japonicum ko:K02208 cyclin-dependent kinase 8/11, putative Get druggable targets OG5_129229 All targets in OG5_129229
Candida albicans similar to S. cerevisiae GLR1 (YPL091W) glutathione oxidoreductase Get druggable targets OG5_126785 All targets in OG5_126785
Trypanosoma congolense trypanothione reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Echinococcus multilocularis cyclin dependent kinase 19 Get druggable targets OG5_129229 All targets in OG5_129229
Toxoplasma gondii thioredoxin reductase Get druggable targets OG5_126785 All targets in OG5_126785
Plasmodium knowlesi glutathione reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Theileria parva thioredoxin reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Schistosoma mansoni g1/s-specific cyclin C Get druggable targets OG5_129826 All targets in OG5_129826
Leishmania infantum trypanothione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Schistosoma mansoni serine/threonine protein kinase Get druggable targets OG5_129229 All targets in OG5_129229
Loa Loa (eye worm) gastrulation defective protein 1 Get druggable targets OG5_129229 All targets in OG5_129229
Entamoeba histolytica cyclin C, putative Get druggable targets OG5_129826 All targets in OG5_129826
Plasmodium falciparum thioredoxin reductase Get druggable targets OG5_126785 All targets in OG5_126785
Leishmania major trypanothione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Trypanosoma brucei trypanothione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Loa Loa (eye worm) CMGC/CDK/CDK8 protein kinase Get druggable targets OG5_129229 All targets in OG5_129229
Plasmodium yoelii thioredoxin reductase Get druggable targets OG5_126785 All targets in OG5_126785
Candida albicans similar to S. cerevisiae GLR1 (YPL091W) glutathione oxidoreductase Get druggable targets OG5_126785 All targets in OG5_126785
Brugia malayi Thioredoxin reductase Get druggable targets OG5_126785 All targets in OG5_126785
Plasmodium vivax glutathione reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Echinococcus multilocularis thioredoxin glutathione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Candida albicans RNA polymerase II holoenzyme cyclin-like subunit Get druggable targets OG5_129826 All targets in OG5_129826
Babesia bovis thiodoxin reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Leishmania mexicana trypanothione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Plasmodium vivax thioredoxin reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Neospora caninum Glutathione reductase, related Get druggable targets OG5_126785 All targets in OG5_126785
Echinococcus granulosus thioredoxin glutathione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Leishmania braziliensis trypanothione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Trypanosoma cruzi trypanothione reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Candida albicans Cyclin-dependent serine/threonin protein kinase Get druggable targets OG5_129229 All targets in OG5_129229
Plasmodium berghei glutathione reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Schistosoma japonicum ko:K00960 DNA-directed RNA polymerase [EC2.7.7.6], putative Get druggable targets OG5_129826 All targets in OG5_129826
Echinococcus granulosus cyclin dependent kinase 19 Get druggable targets OG5_129229 All targets in OG5_129229
Neospora caninum MGC84926 protein, related Get druggable targets OG5_126785 All targets in OG5_126785
Schistosoma japonicum ko:K00384 thioredoxin reductase (NADPH) [EC1.8.1.9], putative Get druggable targets OG5_126785 All targets in OG5_126785
Loa Loa (eye worm) glutathione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Candida albicans Cyclin-dependent serine/threonin protein kinase Get druggable targets OG5_129229 All targets in OG5_129229
Plasmodium knowlesi thioredoxin reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Plasmodium falciparum glutathione reductase Get druggable targets OG5_126785 All targets in OG5_126785
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Echinococcus granulosus c4b binding protein beta chain selectin E 610 aa 551 aa 22.1 %
Plasmodium falciparum dihydrolipoyl dehydrogenase, apicoplast trypanothione reductase, putative 492 aa 548 aa 21.5 %
Plasmodium falciparum cyclin cyclin C 198 aa 188 aa 24.5 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Onchocerca volvulus 0.0014 0.0126 0.5
Loa Loa (eye worm) glutathione reductase 0.0076 0.2755 0.2755
Echinococcus multilocularis neuroglian 0.0014 0.0122 0.0195
Toxoplasma gondii thioredoxin reductase 0.0076 0.2755 1
Brugia malayi hypothetical protein 0.0014 0.0126 0.0126
Mycobacterium ulcerans flavoprotein disulfide reductase 0.0026 0.0643 0.5
Brugia malayi alpha keto acid dehydrogenase complex, E3 component, lipoamide dehydrogenase 0.0019 0.0346 0.0346
Echinococcus granulosus cyclin 0.0123 0.4724 0.7581
Onchocerca volvulus 0.0014 0.0126 0.5
Plasmodium falciparum glutathione reductase 0.0026 0.0643 0.1966
Loa Loa (eye worm) hypothetical protein 0.0018 0.0277 0.0277
Schistosoma mansoni serine/threonine protein kinase 0.0158 0.6231 0.6231
Leishmania major trypanothione reductase 0.0076 0.2755 1
Brugia malayi hypothetical protein 0.0014 0.0126 0.0126
Echinococcus granulosus neurotracting:lsamp:neurotrimin:obcam 0.0015 0.0155 0.025
Loa Loa (eye worm) hypothetical protein 0.0014 0.0126 0.0126
Loa Loa (eye worm) TK/KIN16 protein kinase 0.0015 0.0155 0.0155
Onchocerca volvulus 0.0014 0.0126 0.5
Trypanosoma cruzi trypanothione reductase, putative 0.0076 0.2755 1
Schistosoma mansoni g1/s-specific cyclin C 0.0247 1 1
Brugia malayi Cyclin, N-terminal domain containing protein 0.0123 0.4724 0.4724
Loa Loa (eye worm) CMGC/CDK/CDK8 protein kinase 0.0158 0.6231 0.6231
Echinococcus granulosus roundabout 2 0.0018 0.0277 0.0445
Trichomonas vaginalis glutathione reductase, putative 0.0026 0.0643 0.5
Echinococcus multilocularis dihydrolipoamide dehydrogenase 0.0026 0.0643 0.1032
Brugia malayi hypothetical protein 0.0014 0.0126 0.0126
Brugia malayi hypothetical protein 0.0014 0.0126 0.0126
Loa Loa (eye worm) hypothetical protein 0.0014 0.0126 0.0126
Brugia malayi hypothetical protein 0.0014 0.0126 0.0126
Brugia malayi dihydrolipoyl dehydrogenase, mitochondrial precursor, putative 0.0026 0.0643 0.0643
Chlamydia trachomatis dihydrolipoyl dehydrogenase 0.0026 0.0643 0.5
Toxoplasma gondii NADPH-glutathione reductase 0.0026 0.0643 0.1966
Echinococcus granulosus thioredoxin glutathione reductase 0.0076 0.2755 0.4421
Toxoplasma gondii pyruvate dehydrogenase complex subunit PDH-E3II 0.0026 0.0643 0.1966
Wolbachia endosymbiont of Brugia malayi dihydrolipoamide dehydrogenase E3 component 0.0026 0.0643 0.5
Loa Loa (eye worm) hypothetical protein 0.0014 0.0126 0.0126
Onchocerca volvulus 0.0014 0.0126 0.5
Trypanosoma brucei trypanothione reductase 0.0076 0.2755 1
Treponema pallidum NADH oxidase 0.0026 0.0643 0.5
Brugia malayi Protein kinase domain containing protein 0.0158 0.6231 0.6231
Loa Loa (eye worm) cyclin C 0.0247 1 1
Loa Loa (eye worm) hypothetical protein 0.0016 0.0194 0.0194
Schistosoma mansoni c4b-binding protein beta chain 0.0014 0.0126 0.0126
Echinococcus multilocularis cyclin dependent kinase 19 0.0158 0.6231 1
Loa Loa (eye worm) hypothetical protein 0.0022 0.0452 0.0452
Brugia malayi GCC2 and GCC3 family protein 0.0022 0.0452 0.0452
Onchocerca volvulus 0.0014 0.0126 0.5
Echinococcus granulosus c4b binding protein beta chain 0.0014 0.0126 0.0202
Loa Loa (eye worm) pregnancy-associated plasma protein-E 0.0014 0.0126 0.0126
Trichomonas vaginalis mercuric reductase, putative 0.0026 0.0643 0.5
Brugia malayi glutathione reductase 0.0076 0.2755 0.2755
Onchocerca volvulus 0.0014 0.0126 0.5
Wolbachia endosymbiont of Brugia malayi dihydrolipoamide dehydrogenase E3 component 0.0026 0.0643 0.5
Onchocerca volvulus 0.0014 0.0126 0.5
Loa Loa (eye worm) cyclin domain-containing protein 0.0123 0.4724 0.4724
Echinococcus multilocularis C type lectin domian containing protein 0.0014 0.0126 0.0202
Echinococcus granulosus twitchin 0.0015 0.0145 0.0233
Loa Loa (eye worm) hypothetical protein 0.0014 0.0126 0.0126
Brugia malayi pregnancy-associated plasma protein-A 0.0014 0.0126 0.0126
Brugia malayi Pyridine nucleotide-disulphide oxidoreductase, dimerisation domain containing protein 0.0019 0.0346 0.0346
Loa Loa (eye worm) thioredoxin reductase 0.0076 0.2755 0.2755
Echinococcus multilocularis oligomeric golgi complex subunit 3 0.0123 0.4724 0.7581
Echinococcus multilocularis c4b binding protein beta chain 0.0014 0.0126 0.0202
Mycobacterium ulcerans dihydrolipoamide dehydrogenase, LpdB 0.0026 0.0643 0.5
Loa Loa (eye worm) hypothetical protein 0.0014 0.0126 0.0126
Brugia malayi Immunoglobulin I-set domain containing protein 0.0015 0.0155 0.0155
Schistosoma mansoni dihydrolipoamide dehydrogenase 0.0026 0.0643 0.0643
Plasmodium falciparum dihydrolipoyl dehydrogenase, apicoplast 0.0026 0.0643 0.1966
Mycobacterium ulcerans dihydrolipoamide dehydrogenase 0.0026 0.0643 0.5
Plasmodium falciparum glutathione reductase 0.0076 0.2755 1
Echinococcus granulosus cyclin dependent kinase 19 0.0158 0.6231 1
Mycobacterium tuberculosis NADPH-dependent mycothiol reductase Mtr 0.0076 0.2755 1
Plasmodium vivax glutathione reductase, putative 0.0076 0.2755 1
Echinococcus multilocularis cyclin 0.0123 0.4724 0.7581
Plasmodium vivax dihydrolipoyl dehydrogenase, apicoplast, putative 0.0026 0.0643 0.1966
Loa Loa (eye worm) hypothetical protein 0.0015 0.0155 0.0155
Echinococcus granulosus dihydrolipoamide dehydrogenase 0.0026 0.0643 0.1032
Plasmodium vivax thioredoxin reductase, putative 0.0076 0.2755 1
Plasmodium vivax dihydrolipoyl dehydrogenase, mitochondrial, putative 0.0026 0.0643 0.1966
Brugia malayi hypothetical protein 0.0014 0.0126 0.0126
Entamoeba histolytica cyclin C, putative 0.0124 0.4799 0.5
Giardia lamblia NADH oxidase lateral transfer candidate 0.0026 0.0643 0.5
Loa Loa (eye worm) hypothetical protein 0.0014 0.0126 0.0126
Plasmodium falciparum dihydrolipoyl dehydrogenase, mitochondrial 0.0026 0.0643 0.1966
Onchocerca volvulus 0.0014 0.0126 0.5
Plasmodium falciparum thioredoxin reductase 0.0076 0.2755 1
Echinococcus multilocularis roundabout 2 0.0018 0.0277 0.0445
Echinococcus granulosus C type lectin domian containing protein 0.0014 0.0126 0.0202
Brugia malayi Thioredoxin reductase 0.0076 0.2755 0.2755
Brugia malayi Sushi domain 0.0014 0.0126 0.0126
Brugia malayi hypothetical protein 0.0014 0.0126 0.0126
Onchocerca volvulus 0.0014 0.0126 0.5
Echinococcus multilocularis thioredoxin glutathione reductase 0.0076 0.2755 0.4421
Mycobacterium leprae DIHYDROLIPOAMIDE DEHYDROGENASE LPD (LIPOAMIDE REDUCTASE (NADH)) (LIPOYL DEHYDROGENASE) (DIHYDROLIPOYL DEHYDROGENASE) (DIAPHORASE 0.0026 0.0643 0.5
Schistosoma mansoni nephrin 0.0014 0.0122 0.0122
Loa Loa (eye worm) gastrulation defective protein 1 0.0157 0.6207 0.6207
Plasmodium falciparum thioredoxin reductase 0.0026 0.0643 0.1966
Onchocerca volvulus 0.0014 0.0126 0.5
Echinococcus granulosus neuroglian 0.0014 0.0122 0.0195
Schistosoma mansoni cell adhesion molecule 0.0015 0.0155 0.0155
Loa Loa (eye worm) hypothetical protein 0.0014 0.0126 0.0126
Echinococcus granulosus oligomeric golgi complex subunit 3 0.0123 0.4724 0.7581
Loa Loa (eye worm) hypothetical protein 0.0018 0.0277 0.0277

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 16 nM Inhibition of full length human recombinant His-tagged CDK8/Cyclin C expressed in baculovirus expression system by fluorescence polarization assay ChEMBL. 26985305
IC50 (binding) = 31 nM Inhibition of selectin E in human endothelial cells ChEMBL. 11585452
IC50 (binding) = 31 nM Inhibition of selectin E in human endothelial cells ChEMBL. 11585452
IC50 (binding) = 34 nM Inhibition of intercellular adhesion molecule-1 (ICAM1) in human endothelial cells ChEMBL. 11585452
IC50 (binding) = 34 nM Inhibition of intercellular adhesion molecule-1 (ICAM1) in human endothelial cells ChEMBL. 11585452
IC50 (binding) > 1000 nM Inhibition of VCAM-1 in human endothelial cells ChEMBL. 11585452
IC50 (binding) > 1000 nM Inhibition of VCAM-1 in human endothelial cells ChEMBL. 11585452
IC50 (ADMET) > 20 uM Toxicity of the compound was tested in HUVEC cell lysates. ChEMBL. 11585452
PPB (ADMET) = 98.8 % Plasma protein binding in mouse ChEMBL. 26985305
PPB (ADMET) = 99.3 % Plasma protein binding in human ChEMBL. 26985305

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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