Detailed information for compound 1666967

Basic information

Technical information
  • TDR Targets ID: 1666967
  • Name: 2-[2-(3-oxo-1,2-benzoselenazol-2-yl)ethyl]-1, 2-benzoselenazol-3-one
  • MW: 422.199 | Formula: C16H12N2O2Se2
  • H donors: 0 H acceptors: 2 LogP: 2.21 Rotable bonds: 3
    Rule of 5 violations (Lipinski): 1
  • SMILES: O=c1n(CCn2[se]c3c(c2=O)cccc3)[se]c2c1cccc2
  • InChi: 1S/C16H12N2O2Se2/c19-15-11-5-1-3-7-13(11)21-17(15)9-10-18-16(20)12-6-2-4-8-14(12)22-18/h1-8H,9-10H2
  • InChiKey: SFFSGPCYJCMDJM-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 2-[2-(3-keto-1,2-benzoselenazol-2-yl)ethyl]-1,2-benzoselenazol-3-one

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Escherichia coli thioredoxin reductase, FAD/NAD(P)-binding Starlite/ChEMBL No references
Homo sapiens thioredoxin reductase 3 Starlite/ChEMBL References
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Starlite/ChEMBL References
Homo sapiens thioredoxin reductase 2 References
Homo sapiens thioredoxin reductase 1 References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Candida albicans similar to S. cerevisiae GLR1 (YPL091W) glutathione oxidoreductase 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
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
Plasmodium berghei glutathione reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Trichomonas vaginalis dihydrolipoamide dehydrogenase, putative Get druggable targets OG5_127532 All targets in OG5_127532
Mycobacterium tuberculosis NADPH-dependent mycothiol reductase Mtr Get druggable targets OG5_126785 All targets in OG5_126785
Trichomonas vaginalis disulfide oxidoreductase, putative Get druggable targets OG5_127532 All targets in OG5_127532
Mycobacterium ulcerans thioredoxin reductase TrxB2 Get druggable targets OG5_127532 All targets in OG5_127532
Candida albicans single gene similar to S. cerevisiae TRR1 (YDR353W) and TRR2 (YHR106W) cytoplasmic and mitochondrial thioredoxin reductases Get druggable targets OG5_127532 All targets in OG5_127532
Trichomonas vaginalis disulfide oxidoreductase, putative Get druggable targets OG5_127532 All targets in OG5_127532
Candida albicans single gene similar to S. cerevisiae TRR1 (YDR353W) and TRR2 (YHR106W) cytoplasmic and mitochondrial thioredoxin reductases Get druggable targets OG5_127532 All targets in OG5_127532
Trypanosoma congolense trypanothione reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Cryptosporidium parvum thioredoxin reductase 1 Get druggable targets OG5_126785 All targets in OG5_126785
Wolbachia endosymbiont of Brugia malayi thioredoxin reductase Get druggable targets OG5_127532 All targets in OG5_127532
Plasmodium vivax glutathione reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Brugia malayi glutathione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Giardia lamblia Thioredoxin reductase Get druggable targets OG5_127532 All targets in OG5_127532
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
Chlamydia trachomatis thioredoxin reductase Get druggable targets OG5_127532 All targets in OG5_127532
Trypanosoma brucei trypanothione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Plasmodium falciparum glutathione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Plasmodium knowlesi thioredoxin reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Leishmania infantum trypanothione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Neospora caninum MGC84926 protein, related 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
Mycobacterium tuberculosis Probable thioredoxin reductase TrxB2 (TRXR) (TR) Get druggable targets OG5_127532 All targets in OG5_127532
Echinococcus multilocularis thioredoxin glutathione 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
Trichomonas vaginalis disulfide oxidoreductase, putative Get druggable targets OG5_127532 All targets in OG5_127532
Leishmania major trypanothione reductase Get druggable targets OG5_126785 All targets in OG5_126785
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
Theileria parva thioredoxin reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Plasmodium falciparum 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
Trichomonas vaginalis disulfide oxidoreductase, putative Get druggable targets OG5_127532 All targets in OG5_127532
Entamoeba histolytica thioredoxin reductase, putative Get druggable targets OG5_127532 All targets in OG5_127532
Plasmodium vivax thioredoxin reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Leishmania donovani trypanothione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Mycobacterium leprae THIOREDOXIN TRXC (TRX) (MPT46) Get druggable targets OG5_127532 All targets in OG5_127532
Trypanosoma brucei gambiense trypanothione reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Toxoplasma gondii thioredoxin reductase Get druggable targets OG5_126785 All targets in OG5_126785
Treponema pallidum thioredoxin reductase (trxB) Get druggable targets OG5_127532 All targets in OG5_127532
Leishmania mexicana 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
Brugia malayi Thioredoxin reductase Get druggable targets OG5_126785 All targets in OG5_126785
Plasmodium yoelii glutathione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Babesia bovis thiodoxin reductase, putative 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
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Trypanosoma brucei dihydrolipoamide dehydrogenase Thioredoxin reductase 1, cytoplasmic   499 aa 492 aa 23.4 %
Leishmania mexicana acetoin dehydrogenase e3 component-like protein Thioredoxin reductase 1, cytoplasmic   499 aa 499 aa 24.4 %
Plasmodium vivax dihydrolipoyl dehydrogenase, mitochondrial, putative Thioredoxin reductase 1, cytoplasmic   499 aa 460 aa 25.4 %
Trypanosoma congolense dihydrolipoamide dehydrogenase, putative Thioredoxin reductase 1, cytoplasmic   499 aa 492 aa 23.2 %
Plasmodium yoelii dihydrolipoamide dehydrogenase Thioredoxin reductase 1, cytoplasmic   499 aa 540 aa 23.3 %
Neospora caninum glutathione reductase, putative Thioredoxin reductase 1, cytoplasmic   499 aa 492 aa 32.7 %
Trypanosoma congolense dihydrolipoamide dehydrogenase, point mutation Thioredoxin reductase 1, cytoplasmic   499 aa 489 aa 22.5 %
Leishmania donovani dihydrolipoamide dehydrogenase, putative Thioredoxin reductase 1, cytoplasmic   499 aa 466 aa 20.6 %
Leishmania donovani acetoin dehydrogenase e3 component-like protein Thioredoxin reductase 1, cytoplasmic   499 aa 497 aa 24.1 %
Leishmania braziliensis 2-oxoglutarate dehydrogenase, e3 component, lipoamidedehydrogenase-like protein Thioredoxin reductase 1, cytoplasmic   499 aa 450 aa 25.6 %
Trypanosoma cruzi dihydrolipoamide dehydrogenase, putative Thioredoxin reductase 1, cytoplasmic   499 aa 489 aa 22.7 %
Trypanosoma cruzi dihydrolipoamide dehydrogenase, putative Thioredoxin reductase 1, cytoplasmic   499 aa 489 aa 22.9 %
Toxoplasma gondii NADPH-glutathione reductase thioredoxin reductase 3 607 aa 541 aa 27.2 %
Trypanosoma congolense dihydrolipoamide dehydrogenase, point mutation Thioredoxin reductase 1, cytoplasmic   499 aa 489 aa 22.3 %
Plasmodium berghei dihydrolipoyl dehydrogenase, apicoplast, putative Thioredoxin reductase 1, cytoplasmic   499 aa 539 aa 22.3 %
Onchocerca volvulus Thioredoxin reductase 1, cytoplasmic   499 aa 499 aa 57.3 %
Neospora caninum hypothetical protein Thioredoxin reductase 1, cytoplasmic   499 aa 448 aa 27.0 %
Leishmania infantum dihydrolipoamide dehydrogenase, putative Thioredoxin reductase 1, cytoplasmic   499 aa 466 aa 20.6 %
Trypanosoma brucei gambiense dihydrolipoamide dehydrogenase, point mutation,acetoin dehydrogenase e3 component, putative Thioredoxin reductase 1, cytoplasmic   499 aa 490 aa 23.3 %
Leishmania braziliensis dihydrolipoamide dehydrogenase Thioredoxin reductase 1, cytoplasmic   499 aa 488 aa 21.9 %
Trypanosoma congolense dihydrolipoamide dehydrogenase, putative Thioredoxin reductase 1, cytoplasmic   499 aa 492 aa 23.2 %
Plasmodium knowlesi dihydrolipoyl dehydrogenase, mitochondrial, putative Thioredoxin reductase 1, cytoplasmic   499 aa 462 aa 25.8 %
Leishmania major 2-oxoglutarate dehydrogenase, e3 component, lipoamidedehydrogenase-like protein Thioredoxin reductase 1, cytoplasmic   499 aa 454 aa 25.3 %
Plasmodium vivax dihydrolipoyl dehydrogenase, apicoplast, putative Thioredoxin reductase 1, cytoplasmic   499 aa 518 aa 24.9 %
Plasmodium vivax dihydrolipoyl dehydrogenase, apicoplast, putative thioredoxin reductase 1 649 aa 538 aa 23.8 %
Plasmodium berghei dihydrolipoyl dehydrogenase, mitochondrial, putative Thioredoxin reductase 1, cytoplasmic   499 aa 465 aa 26.9 %
Trypanosoma cruzi dihydrolipoamide dehydrogenase, putative Thioredoxin reductase 1, cytoplasmic   499 aa 483 aa 23.0 %
Plasmodium falciparum thioredoxin reductase Thioredoxin reductase 1, cytoplasmic   499 aa 511 aa 45.2 %
Plasmodium falciparum dihydrolipoyl dehydrogenase, mitochondrial Thioredoxin reductase 1, cytoplasmic   499 aa 465 aa 27.3 %
Toxoplasma gondii NADPH-glutathione reductase Thioredoxin reductase 1, cytoplasmic   499 aa 529 aa 31.8 %
Trypanosoma congolense dihydrolipoamide dehydrogenase, point mutation, putative Thioredoxin reductase 1, cytoplasmic   499 aa 489 aa 22.7 %
Leishmania mexicana 2-oxoglutarate dehydrogenase, e3 component, lipoamidedehydrogenase-like protein Thioredoxin reductase 1, cytoplasmic   499 aa 452 aa 25.7 %
Trypanosoma cruzi dihydrolipoamide dehydrogenase, putative Thioredoxin reductase 1, cytoplasmic   499 aa 483 aa 23.0 %
Trypanosoma brucei gambiense dihydrolipoamide dehydrogenase, putative,acetoin dehydrogenase e3 component, putative Thioredoxin reductase 1, cytoplasmic   499 aa 491 aa 23.2 %
Plasmodium falciparum glutathione reductase Thioredoxin reductase 1, cytoplasmic   499 aa 500 aa 32.2 %
Trypanosoma brucei dihydrolipoamide dehydrogenase, point mutation Thioredoxin reductase 1, cytoplasmic   499 aa 490 aa 23.5 %
Plasmodium yoelii dihydrolipoamide dehydrogenase Thioredoxin reductase 1, cytoplasmic   499 aa 465 aa 27.5 %
Plasmodium falciparum dihydrolipoyl dehydrogenase, apicoplast Thioredoxin reductase 1, cytoplasmic   499 aa 506 aa 23.7 %
Leishmania infantum acetoin dehydrogenase e3 component-like protein Thioredoxin reductase 1, cytoplasmic   499 aa 497 aa 24.1 %
Leishmania braziliensis acetoin dehydrogenase e3 component-like protein Thioredoxin reductase 1, cytoplasmic   499 aa 499 aa 22.8 %
Plasmodium knowlesi dihydrolipoyl dehydrogenase, apicoplast, putative Thioredoxin reductase 1, cytoplasmic   499 aa 519 aa 23.7 %
Leishmania major acetoin dehydrogenase e3 component-like protein Thioredoxin reductase 1, cytoplasmic   499 aa 497 aa 24.1 %
Toxoplasma gondii pyruvate dehydrogenase complex subunit PDH-E3II Thioredoxin reductase 1, cytoplasmic   499 aa 448 aa 27.2 %
Trypanosoma brucei gambiense dihydrolipoamide dehydrogenase, putative Thioredoxin reductase 1, cytoplasmic   499 aa 491 aa 23.6 %
Neospora caninum Dihydrolipoyl dehydrogenase (EC 1.8.1.4), related Thioredoxin reductase 1, cytoplasmic   499 aa 464 aa 24.8 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Loa Loa (eye worm) glutathione reductase 0.0267 0.4539 0.5
Trichomonas vaginalis disulfide oxidoreductase, putative 0.0199 0.1623 0.5
Brugia malayi glutathione reductase 0.0267 0.4539 0.5
Treponema pallidum thioredoxin reductase (trxB) 0.0199 0.1623 0.5
Mycobacterium tuberculosis NAD(P)H quinone reductase LpdA 0.0205 0.1882 0.4146
Trichomonas vaginalis disulfide oxidoreductase, putative 0.0199 0.1623 0.5
Trichomonas vaginalis disulfide oxidoreductase, putative 0.0199 0.1623 0.5
Leishmania major trypanothione reductase 0.0267 0.4539 0.5
Mycobacterium tuberculosis Probable thioredoxin reductase TrxB2 (TRXR) (TR) 0.0199 0.1623 0.3575
Brugia malayi Thioredoxin reductase 0.0267 0.4539 0.5
Chlamydia trachomatis thioredoxin reductase 0.0199 0.1623 0.5
Mycobacterium ulcerans thioredoxin reductase TrxB2 0.0199 0.1623 0.5
Trypanosoma cruzi trypanothione reductase, putative 0.0267 0.4539 0.5
Loa Loa (eye worm) thioredoxin reductase 0.0267 0.4539 0.5
Plasmodium vivax glutathione reductase, putative 0.0267 0.4539 0.5
Plasmodium falciparum thioredoxin reductase 0.0267 0.4539 0.5
Echinococcus granulosus thioredoxin glutathione reductase 0.0268 0.4605 0.5
Mycobacterium leprae DIHYDROLIPOAMIDE DEHYDROGENASE LPD (LIPOAMIDE REDUCTASE (NADH)) (LIPOYL DEHYDROGENASE) (DIHYDROLIPOYL DEHYDROGENASE) (DIAPHORASE 0.0205 0.1882 1
Mycobacterium tuberculosis NADPH-dependent mycothiol reductase Mtr 0.0267 0.4539 1
Wolbachia endosymbiont of Brugia malayi thioredoxin reductase 0.0199 0.1623 0.5
Plasmodium falciparum glutathione reductase 0.0267 0.4539 0.5
Plasmodium vivax thioredoxin reductase, putative 0.0267 0.4539 0.5
Mycobacterium tuberculosis Dihydrolipoamide dehydrogenase LpdC (lipoamide reductase (NADH)) (lipoyl dehydrogenase) (dihydrolipoyl dehydrogenase) (diaphoras 0.0205 0.1882 0.4146
Echinococcus multilocularis thioredoxin glutathione reductase 0.0268 0.4605 0.5
Mycobacterium leprae THIOREDOXIN TRXC (TRX) (MPT46) 0.0199 0.1623 0.8623
Entamoeba histolytica thioredoxin reductase, putative 0.0199 0.1623 0.5
Trichomonas vaginalis dihydrolipoamide dehydrogenase, putative 0.0199 0.1623 0.5
Giardia lamblia Thioredoxin reductase 0.0199 0.1623 0.5
Toxoplasma gondii thioredoxin reductase 0.0267 0.4539 0.5
Mycobacterium tuberculosis Probable oxidoreductase 0.0205 0.1882 0.4146
Trypanosoma brucei trypanothione reductase 0.0267 0.4539 0.5
Trichomonas vaginalis disulfide oxidoreductase, putative 0.0199 0.1623 0.5

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 2000 nM BindingDB_Patents: Inhibition Assay. All the benzisoselenazol-3(2H)-one and bisbenzisoselenazol-3(2H)-one derivatives were tested as potential E. coli TrxR inhibitors by standard DTNB assay. ChEMBL. No reference
IC50 (binding) = 2000 nM BindingDB_Patents: Inhibition Assay. All the benzisoselenazol-3(2H)-one and bisbenzisoselenazol-3(2H)-one derivatives were tested as potential E. coli TrxR inhibitors by standard DTNB assay. ChEMBL. No reference
IC50 (binding) = 0.35 uM Inhibition of TrxR1 in rat liver homogenate preincubated for 5 mins measured by DNTB assay ChEMBL. 22579620
IC50 (binding) = 5 uM Inhibition of TrxR in human U87MG cells after 12 hrs by insulin-reducing method ChEMBL. 22579620
IC50 (binding) = 6 uM Non-competitive inhibition of rat TrxR1 ChEMBL. 22579620
IC50 (functional) = 7.67 uM Growth inhibition of human LoVo cells after 48 hrs by MTT assay ChEMBL. 22579620
IC50 (functional) = 15.86 uM Antiproliferative activity against human HeLa cells after 48 hrs by CCK8 assay ChEMBL. 26786698
IC50 (ADMET) > 50 uM Antiproliferative activity against mouse L929 cells after 48 hrs by CCK8 assay ChEMBL. 26786698
Inhibition (binding) Inhibition of human C-terminal truncated TrxR ChEMBL. 22579620
Inhibition (binding) Inhibition of TrxR1 in rat liver homogenate preincubated for 5 mins measured by DNTB assay ChEMBL. 22579620
Inhibition (binding) Inhibition of TrxR in human U87MG cells after 12 hrs by insulin-reducing method ChEMBL. 22579620
Inhibition (binding) Inhibition of human glutathione reductase at 100 uM after 10 mins by GSSH reduction assay ChEMBL. 22579620
Ki (binding) = 50 nM BindingDB_Patents: Inhibition Assay. All the benzisoselenazol-3(2H)-one and bisbenzisoselenazol-3(2H)-one derivatives were tested as potential E. coli TrxR inhibitors by standard DTNB assay. ChEMBL. No reference
Ki (binding) = 50 nM BindingDB_Patents: Inhibition Assay. All the benzisoselenazol-3(2H)-one and bisbenzisoselenazol-3(2H)-one derivatives were tested as potential E. coli TrxR inhibitors by standard DTNB assay. ChEMBL. No reference

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Homo sapiens ChEMBL23 22579620

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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