Detailed information for compound 1190126

Basic information

Technical information
  • TDR Targets ID: 1190126
  • Name: N-(4-bromophenyl)-2-[[3-(2-methoxyethyl)-4-ox o-5H-pyrimido[5,4-b]indol-2-yl]sulfanyl]aceta mide
  • MW: 487.37 | Formula: C21H19BrN4O3S
  • H donors: 2 H acceptors: 2 LogP: 3.73 Rotable bonds: 8
    Rule of 5 violations (Lipinski): 1
  • SMILES: COCCn1c(SCC(=O)Nc2ccc(cc2)Br)nc2c(c1=O)[nH]c1c2cccc1
  • InChi: 1S/C21H19BrN4O3S/c1-29-11-10-26-20(28)19-18(15-4-2-3-5-16(15)24-19)25-21(26)30-12-17(27)23-14-8-6-13(22)7-9-14/h2-9,24H,10-12H2,1H3,(H,23,27)
  • InChiKey: VPWHZQXQZZDVME-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • N-(4-bromophenyl)-2-[[3-(2-methoxyethyl)-4-oxo-5H-pyrimido[5,4-b]indol-2-yl]thio]acetamide
  • N-(4-bromophenyl)-2-[[4-keto-3-(2-methoxyethyl)-5H-pyrimido[5,4-b]indol-2-yl]thio]acetamide
  • N-(4-bromophenyl)-2-[[3-(2-methoxyethyl)-4-oxo-5H-pyrimido[5,4-b]indol-2-yl]sulfanyl]ethanamide
  • G856-1364
  • NCGC00135591-01

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Starlite/ChEMBL No references

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Babesia bovis thiodoxin 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
Brugia malayi 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
Plasmodium falciparum 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
Trypanosoma congolense trypanothione reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Leishmania major trypanothione 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
Theileria parva 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
Trypanosoma brucei 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
Neospora caninum MGC84926 protein, related 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
Plasmodium berghei glutathione reductase, putative 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
Plasmodium vivax glutathione reductase, putative 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
Toxoplasma gondii thioredoxin reductase 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
Echinococcus granulosus thioredoxin glutathione reductase 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
Brugia malayi glutathione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Leishmania mexicana trypanothione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Trypanosoma brucei gambiense trypanothione reductase, putative 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
Leishmania braziliensis 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
Plasmodium knowlesi glutathione 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
Leishmania donovani 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
Plasmodium yoelii thioredoxin reductase 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
Plasmodium berghei thioredoxin reductase, 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
Leishmania major acetoin dehydrogenase e3 component-like protein Thioredoxin reductase 1, cytoplasmic   499 aa 497 aa 24.1 %
Plasmodium falciparum dihydrolipoyl dehydrogenase, mitochondrial Thioredoxin reductase 1, cytoplasmic   499 aa 465 aa 27.3 %
Plasmodium knowlesi dihydrolipoyl dehydrogenase, apicoplast, putative Thioredoxin reductase 1, cytoplasmic   499 aa 519 aa 23.7 %
Plasmodium berghei dihydrolipoyl dehydrogenase, apicoplast, putative Thioredoxin reductase 1, cytoplasmic   499 aa 539 aa 22.3 %
Trypanosoma congolense dihydrolipoamide dehydrogenase, point mutation, putative Thioredoxin reductase 1, cytoplasmic   499 aa 489 aa 22.7 %
Plasmodium falciparum dihydrolipoyl dehydrogenase, apicoplast Thioredoxin reductase 1, cytoplasmic   499 aa 506 aa 23.7 %
Trypanosoma brucei gambiense dihydrolipoamide dehydrogenase, putative,acetoin dehydrogenase e3 component, putative Thioredoxin reductase 1, cytoplasmic   499 aa 491 aa 23.2 %
Plasmodium knowlesi dihydrolipoyl dehydrogenase, mitochondrial, putative Thioredoxin reductase 1, cytoplasmic   499 aa 462 aa 25.8 %
Trypanosoma brucei dihydrolipoamide dehydrogenase Thioredoxin reductase 1, cytoplasmic   499 aa 492 aa 23.4 %
Trypanosoma brucei gambiense dihydrolipoamide dehydrogenase, putative Thioredoxin reductase 1, cytoplasmic   499 aa 491 aa 23.6 %
Trypanosoma cruzi dihydrolipoamide dehydrogenase, putative Thioredoxin reductase 1, cytoplasmic   499 aa 483 aa 23.0 %
Neospora caninum hypothetical protein Thioredoxin reductase 1, cytoplasmic   499 aa 448 aa 27.0 %
Leishmania mexicana 2-oxoglutarate dehydrogenase, e3 component, lipoamidedehydrogenase-like protein Thioredoxin reductase 1, cytoplasmic   499 aa 452 aa 25.7 %
Plasmodium falciparum thioredoxin reductase Thioredoxin reductase 1, cytoplasmic   499 aa 511 aa 45.2 %
Plasmodium vivax dihydrolipoyl dehydrogenase, apicoplast, putative Thioredoxin reductase 1, cytoplasmic   499 aa 518 aa 24.9 %
Trypanosoma congolense dihydrolipoamide dehydrogenase, point mutation Thioredoxin reductase 1, cytoplasmic   499 aa 489 aa 22.5 %
Toxoplasma gondii NADPH-glutathione reductase Thioredoxin reductase 1, cytoplasmic   499 aa 529 aa 31.8 %
Toxoplasma gondii pyruvate dehydrogenase complex subunit PDH-E3II Thioredoxin reductase 1, cytoplasmic   499 aa 448 aa 27.2 %
Plasmodium vivax dihydrolipoyl dehydrogenase, mitochondrial, putative Thioredoxin reductase 1, cytoplasmic   499 aa 460 aa 25.4 %
Leishmania braziliensis acetoin dehydrogenase e3 component-like protein Thioredoxin reductase 1, cytoplasmic   499 aa 499 aa 22.8 %
Trypanosoma cruzi dihydrolipoamide dehydrogenase, putative Thioredoxin reductase 1, cytoplasmic   499 aa 489 aa 22.9 %
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 %
Leishmania infantum dihydrolipoamide dehydrogenase, putative Thioredoxin reductase 1, cytoplasmic   499 aa 466 aa 20.6 %
Neospora caninum Dihydrolipoyl dehydrogenase (EC 1.8.1.4), related Thioredoxin reductase 1, cytoplasmic   499 aa 464 aa 24.8 %
Onchocerca volvulus Thioredoxin reductase 1, cytoplasmic   499 aa 499 aa 57.3 %
Leishmania braziliensis dihydrolipoamide dehydrogenase Thioredoxin reductase 1, cytoplasmic   499 aa 488 aa 21.9 %
Plasmodium yoelii dihydrolipoamide dehydrogenase Thioredoxin reductase 1, cytoplasmic   499 aa 465 aa 27.5 %
Neospora caninum glutathione reductase, putative Thioredoxin reductase 1, cytoplasmic   499 aa 492 aa 32.7 %
Leishmania donovani dihydrolipoamide dehydrogenase, putative Thioredoxin reductase 1, cytoplasmic   499 aa 466 aa 20.6 %
Trypanosoma brucei dihydrolipoamide dehydrogenase, point mutation Thioredoxin reductase 1, cytoplasmic   499 aa 490 aa 23.5 %
Trypanosoma congolense dihydrolipoamide dehydrogenase, putative Thioredoxin reductase 1, cytoplasmic   499 aa 492 aa 23.2 %
Leishmania mexicana acetoin dehydrogenase e3 component-like protein Thioredoxin reductase 1, cytoplasmic   499 aa 499 aa 24.4 %
Trypanosoma cruzi dihydrolipoamide dehydrogenase, putative Thioredoxin reductase 1, cytoplasmic   499 aa 483 aa 23.0 %
Plasmodium berghei dihydrolipoyl dehydrogenase, mitochondrial, putative Thioredoxin reductase 1, cytoplasmic   499 aa 465 aa 26.9 %
Leishmania major 2-oxoglutarate dehydrogenase, e3 component, lipoamidedehydrogenase-like protein Thioredoxin reductase 1, cytoplasmic   499 aa 454 aa 25.3 %
Trypanosoma cruzi dihydrolipoamide dehydrogenase, putative Thioredoxin reductase 1, cytoplasmic   499 aa 489 aa 22.7 %
Plasmodium falciparum glutathione reductase Thioredoxin reductase 1, cytoplasmic   499 aa 500 aa 32.2 %
Trypanosoma congolense dihydrolipoamide dehydrogenase, point mutation Thioredoxin reductase 1, cytoplasmic   499 aa 489 aa 22.3 %
Trypanosoma brucei gambiense dihydrolipoamide dehydrogenase, point mutation,acetoin dehydrogenase e3 component, putative Thioredoxin reductase 1, cytoplasmic   499 aa 490 aa 23.3 %
Leishmania braziliensis 2-oxoglutarate dehydrogenase, e3 component, lipoamidedehydrogenase-like protein Thioredoxin reductase 1, cytoplasmic   499 aa 450 aa 25.6 %
Leishmania infantum acetoin dehydrogenase e3 component-like protein Thioredoxin reductase 1, cytoplasmic   499 aa 497 aa 24.1 %
Leishmania donovani acetoin dehydrogenase e3 component-like protein Thioredoxin reductase 1, cytoplasmic   499 aa 497 aa 24.1 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Mycobacterium ulcerans dihydrolipoamide dehydrogenase 0.002 0.0337 0.5
Mycobacterium tuberculosis NAD(P)H quinone reductase LpdA 0.0145 0.7779 1
Plasmodium vivax thioredoxin reductase, putative 0.0057 0.2558 1
Wolbachia endosymbiont of Brugia malayi dihydrolipoamide dehydrogenase E3 component 0.002 0.0337 0.5
Loa Loa (eye worm) hypothetical protein 0.0026 0.0701 0.2739
Mycobacterium tuberculosis Probable dehydrogenase 0.013 0.6913 0.8837
Echinococcus granulosus intermediate filament protein 0.0026 0.0729 0.1768
Chlamydia trachomatis dihydrolipoyl dehydrogenase 0.002 0.0337 0.5
Loa Loa (eye worm) thioredoxin reductase 0.0057 0.2558 1
Trypanosoma brucei trypanothione reductase 0.0057 0.2558 1
Toxoplasma gondii thioredoxin reductase 0.0057 0.2558 1
Echinococcus multilocularis guanine nucleotide binding protein G(s) subunit 0.0045 0.1823 0.669
Mycobacterium tuberculosis Putative ferredoxin reductase 0.013 0.6913 0.8837
Trypanosoma cruzi trypanothione reductase, putative 0.0057 0.2558 1
Echinococcus multilocularis thioredoxin glutathione reductase 0.0057 0.2558 1
Brugia malayi GTP-binding regulatory protein Gs alpha-S chain, putative 0.0045 0.1823 0.7125
Echinococcus granulosus lamin 0.0026 0.0729 0.1768
Echinococcus granulosus thioredoxin glutathione reductase 0.0057 0.2558 1
Giardia lamblia NADH oxidase lateral transfer candidate 0.002 0.0337 0.5
Mycobacterium ulcerans dihydrolipoamide dehydrogenase, LpdB 0.002 0.0337 0.5
Brugia malayi dihydrolipoyl dehydrogenase, mitochondrial precursor, putative 0.002 0.0337 0.1316
Loa Loa (eye worm) intermediate filament tail domain-containing protein 0.0026 0.0729 0.2851
Echinococcus multilocularis guanine nucleotide binding protein G(s) subunit 0.0045 0.1823 0.669
Loa Loa (eye worm) glutathione reductase 0.0057 0.2558 1
Schistosoma mansoni Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein) 0.0045 0.1823 0.1538
Echinococcus multilocularis musashi 0.0026 0.0729 0.1768
Schistosoma mansoni lamin 0.0026 0.0729 0.0406
Mycobacterium tuberculosis Probable reductase 0.013 0.6913 0.8837
Brugia malayi glutathione reductase 0.0057 0.2558 1
Plasmodium falciparum glutathione reductase 0.0057 0.2558 1
Echinococcus granulosus guanine nucleotide binding protein Gs subunit 0.0045 0.1823 0.669
Trichomonas vaginalis mercuric reductase, putative 0.002 0.0337 0.5
Trichomonas vaginalis glutathione reductase, putative 0.002 0.0337 0.5
Brugia malayi intermediate filament protein 0.0026 0.0729 0.2851
Mycobacterium tuberculosis Dihydrolipoamide dehydrogenase LpdC (lipoamide reductase (NADH)) (lipoyl dehydrogenase) (dihydrolipoyl dehydrogenase) (diaphoras 0.0145 0.7779 1
Mycobacterium tuberculosis Probable NADH dehydrogenase Ndh 0.013 0.6913 0.8837
Echinococcus multilocularis lamin 0.0026 0.0729 0.1768
Leishmania major trypanothione reductase 0.0057 0.2558 1
Brugia malayi Thioredoxin reductase 0.0057 0.2558 1
Plasmodium vivax glutathione reductase, putative 0.0057 0.2558 1
Schistosoma mansoni Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein) 0.0045 0.1823 0.1538
Mycobacterium tuberculosis Probable oxidoreductase 0.0145 0.7779 1
Schistosoma mansoni lamin 0.0026 0.0729 0.0406
Mycobacterium tuberculosis Probable membrane NADH dehydrogenase NdhA 0.013 0.6913 0.8837
Schistosoma mansoni intermediate filament proteins 0.0026 0.0729 0.0406
Loa Loa (eye worm) GTP-binding regulatory protein Gs alpha-S chain 0.0045 0.1823 0.7125
Onchocerca volvulus 0.0026 0.0729 0.5
Mycobacterium ulcerans flavoprotein disulfide reductase 0.002 0.0337 0.5
Brugia malayi Pyridine nucleotide-disulphide oxidoreductase, dimerisation domain containing protein 0.0015 0.0024 0.0094
Echinococcus granulosus guanine nucleotide binding protein Gs subunit 0.0045 0.1823 0.669
Mycobacterium tuberculosis Probable nitrite reductase [NAD(P)H] large subunit [FAD flavoprotein] NirB 0.013 0.6913 0.8837
Onchocerca volvulus 0.0026 0.0729 0.5
Brugia malayi alpha keto acid dehydrogenase complex, E3 component, lipoamide dehydrogenase 0.0015 0.0024 0.0094
Echinococcus multilocularis lamin dm0 0.0026 0.0729 0.1768
Schistosoma mansoni Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein) 0.0045 0.1823 0.1538
Mycobacterium tuberculosis NADPH-dependent mycothiol reductase Mtr 0.0057 0.2558 0.2985
Mycobacterium leprae DIHYDROLIPOAMIDE DEHYDROGENASE LPD (LIPOAMIDE REDUCTASE (NADH)) (LIPOYL DEHYDROGENASE) (DIHYDROLIPOYL DEHYDROGENASE) (DIAPHORASE 0.0145 0.7779 1
Loa Loa (eye worm) hypothetical protein 0.0026 0.0729 0.2851
Treponema pallidum NADH oxidase 0.002 0.0337 0.5
Wolbachia endosymbiont of Brugia malayi dihydrolipoamide dehydrogenase E3 component 0.002 0.0337 0.5
Plasmodium falciparum thioredoxin reductase 0.0057 0.2558 1
Echinococcus granulosus lamin dm0 0.0026 0.0729 0.1768
Loa Loa (eye worm) intermediate filament protein 0.0026 0.0729 0.2851
Brugia malayi Intermediate filament tail domain containing protein 0.0026 0.0729 0.2851

Activities

Activity type Activity value Assay description Source Reference
Potency (functional) 0.1 uM PUBCHEM_BIOASSAY: qHTS Assay for Inhibitors of Mammalian Selenoprotein Thioredoxin Reductase 1 (TrxR1): qHTS. (Class of assay: confirmatory) [Related pubchem assays (depositor defined):AID488771] ChEMBL. No reference

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

No literature references available for this target.

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