Detailed information for compound 176101

Basic information

Technical information
  • TDR Targets ID: 176101
  • Name: 3-(2-chlorophenothiazin-10-yl)propyl-[(7-meth oxy-2-oxochromen-4-yl)methyl]-dimethylazanium
  • MW: 508.052 | Formula: C28H28ClN2O3S+
  • H donors: 0 H acceptors: 1 LogP: 5.79 Rotable bonds: 7
    Rule of 5 violations (Lipinski): 2
  • SMILES: COc1ccc2c(c1)oc(=O)cc2C[N+](CCCN1c2ccccc2Sc2c1cc(Cl)cc2)(C)C
  • InChi: 1S/C28H28ClN2O3S/c1-31(2,18-19-15-28(32)34-25-17-21(33-3)10-11-22(19)25)14-6-13-30-23-7-4-5-8-26(23)35-27-12-9-20(29)16-24(27)30/h4-5,7-12,15-17H,6,13-14,18H2,1-3H3/q+1
  • InChiKey: KWKDENFXTSYISJ-UHFFFAOYSA-N  

Network

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Synonyms

  • 3-(2-chlorophenothiazin-10-yl)propyl-[(7-methoxy-2-oxo-chromen-4-yl)methyl]-dimethyl-ammonium
  • 3-(2-chloro-10-phenothiazinyl)propyl-[(7-methoxy-2-oxo-1-benzopyran-4-yl)methyl]-dimethylammonium
  • 3-(2-chlorophenothiazin-10-yl)propyl-[(7-methoxy-2-oxo-chromen-4-yl)methyl]-dimethyl-azanium
  • 3-(2-chlorophenothiazin-10-yl)propyl-[(2-keto-7-methoxy-chromen-4-yl)methyl]-dimethyl-ammonium
  • 3-(2-chloro-10-phenothiazinyl)propyl-[(7-methoxy-2-oxo-4-chromenyl)methyl]-dimethylammonium

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Trypanosoma cruzi trypanothione reductase, putative Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Toxoplasma gondii 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
Leishmania donovani trypanothione 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
Brugia malayi glutathione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Leishmania infantum trypanothione 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 falciparum thioredoxin 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
Plasmodium yoelii 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
Echinococcus multilocularis thioredoxin 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 brucei trypanothione 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 berghei glutathione reductase, putative 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
Mycobacterium tuberculosis NADPH-dependent mycothiol reductase Mtr 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 similar to S. cerevisiae GLR1 (YPL091W) glutathione oxidoreductase 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 vivax glutathione 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
Schistosoma japonicum ko:K00384 thioredoxin reductase (NADPH) [EC1.8.1.9], putative Get druggable targets OG5_126785 All targets in OG5_126785
Cryptosporidium hominis thioredoxin 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
Leishmania braziliensis trypanothione 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
Neospora caninum MGC84926 protein, related 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
Cryptosporidium parvum thioredoxin reductase 1 Get druggable targets OG5_126785 All targets in OG5_126785
Plasmodium yoelii glutathione 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 cruzi trypanothione reductase, putative 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

By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Plasmodium falciparum dihydrolipoyl dehydrogenase, apicoplast trypanothione reductase, putative 492 aa 548 aa 21.5 %

Obtained from network model

Ranking Plot


Putative Targets List


Species Potential target Raw Global Species
Brugia malayi Cathepsin L-like cysteine proteinase 0.0079 0.5748 0.5748
Loa Loa (eye worm) ctsf protein 0.0119 1 1
Plasmodium vivax unspecified product 0.0061 0.3764 0.3764
Onchocerca volvulus Cathepsin L homolog 0.0119 1 1
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0119 1 1
Schistosoma mansoni cathepsin F (C01 family) 0.0119 1 1
Brugia malayi Cathepsin L-like precursor 0.0079 0.5748 0.5748
Trypanosoma cruzi cysteine proteinase, putative 0.0061 0.3764 0.3764
Trypanosoma cruzi cysteine peptidase, putative 0.0039 0.1391 0.1391
Echinococcus multilocularis cysteine protease 0.0119 1 1
Loa Loa (eye worm) hypothetical protein 0.0079 0.5748 0.5061
Onchocerca volvulus Cathepsin F homolog 0.0119 1 1
Trypanosoma cruzi cysteine peptidase (N-terminal), putative 0.0061 0.3764 0.3764
Echinococcus multilocularis cathepsin L cysteine protease 0.0119 1 1
Trypanosoma cruzi cruzipain precursor, putative 0.0039 0.1391 0.1391
Brugia malayi Cathepsin L-like precursor 0.0119 1 1
Echinococcus granulosus cathepsin L 0.0061 0.3764 0.3764
Plasmodium vivax unspecified product 0.0039 0.1391 0.1391
Trichomonas vaginalis Clan CA, family C1, cathepsin L or K-like cysteine peptidase 0.0119 1 1
Wolbachia endosymbiont of Brugia malayi dihydrolipoamide dehydrogenase E3 component 0.0026 0 0.5
Brugia malayi Thioredoxin reductase 0.0076 0.5394 0.5394
Onchocerca volvulus 0.0119 1 1
Trypanosoma cruzi cysteine proteinase, putative 0.0061 0.3764 0.3764
Giardia lamblia NADH oxidase lateral transfer candidate 0.0026 0 0.5
Trypanosoma cruzi cysteine peptidase, putative 0.0119 1 1
Onchocerca volvulus Cathepsin L homolog 0.0119 1 1
Echinococcus granulosus cathepsin L cysteine protease 0.0061 0.3764 0.3764
Trichomonas vaginalis Clan CA, family C1, papain-like cysteine peptidase 0.0119 1 1
Plasmodium falciparum cysteine proteinase falcipain 2a 0.0119 1 1
Loa Loa (eye worm) hypothetical protein 0.0119 1 1
Plasmodium falciparum thioredoxin reductase 0.0076 0.5394 0.5394
Brugia malayi cathepsin L-like precursor 0.0079 0.5748 0.5748
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0119 1 1
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0119 1 1
Trypanosoma cruzi cruzipain precursor, putative 0.0119 1 1
Trypanosoma cruzi cysteine peptidase, clan CA, family C1, cathepsin L-like, putative 0.0079 0.5748 0.5748
Leishmania major cathepsin L-like protease 0.0119 1 1
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0119 1 1
Loa Loa (eye worm) Papain cysteine protease/cathepsin propeptide inhibitor-containing protein 0.0119 1 1
Mycobacterium tuberculosis NADPH-dependent mycothiol reductase Mtr 0.0076 0.5394 1
Brugia malayi Papain family cysteine protease containing protein 0.0061 0.3764 0.3764
Leishmania major cathepsin L-like protease 0.0119 1 1
Echinococcus granulosus thioredoxin glutathione reductase 0.0076 0.5394 0.5394
Brugia malayi glutathione reductase 0.0076 0.5394 0.5394
Mycobacterium ulcerans flavoprotein disulfide reductase 0.0026 0 0.5
Trichomonas vaginalis Clan CA, family C1, papain-like cysteine peptidase 0.0119 1 1
Plasmodium vivax vivapain-3 0.0061 0.3764 0.3764
Chlamydia trachomatis dihydrolipoyl dehydrogenase 0.0026 0 0.5
Plasmodium vivax thioredoxin reductase, putative 0.0076 0.5394 0.5394
Toxoplasma gondii thioredoxin reductase 0.0076 0.5394 0.5394
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0119 1 1
Trypanosoma brucei trypanothione reductase 0.0076 0.5394 0.5394
Echinococcus granulosus cathepsin l1 0.0079 0.5748 0.5748
Echinococcus multilocularis cathepsin L cysteine protease 0.0119 1 1
Schistosoma mansoni SmCL2-like peptidase (C01 family) 0.0061 0.3764 0.3764
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0119 1 1
Onchocerca volvulus 0.0119 1 1
Entamoeba histolytica cysteine proteinase, putative 0.0119 1 1
Leishmania major cathepsin L-like protease 0.0119 1 1
Trichomonas vaginalis Clan CA, family C1, papain-like cysteine peptidase 0.0119 1 1
Trichomonas vaginalis Clan CA, family C1, papain-like cysteine peptidase 0.0119 1 1
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0119 1 1
Brugia malayi Cathepsin L-like precursor 0.0119 1 1
Entamoeba histolytica cysteine protease, putative 0.0119 1 1
Plasmodium falciparum cysteine proteinase falcipain 3 0.0119 1 1
Trichomonas vaginalis Clan CA, family C1, papain-like cysteine peptidase 0.0119 1 1
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0119 1 1
Schistosoma mansoni SmCL2-like peptidase (C01 family) 0.0061 0.3764 0.3764
Brugia malayi cathepsin L-like cysteine proteinase, identical 0.0039 0.1391 0.1391
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0119 1 1
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0061 0.3764 0.3764
Treponema pallidum NADH oxidase 0.0026 0 0.5
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0119 1 1
Trypanosoma cruzi cysteine peptidase, putative 0.0119 1 1
Wolbachia endosymbiont of Brugia malayi dihydrolipoamide dehydrogenase E3 component 0.0026 0 0.5
Trichomonas vaginalis Clan CA, family C1, papain-like cysteine peptidase 0.0119 1 1
Trypanosoma cruzi cysteine peptidase, putative 0.0119 1 1
Leishmania major cysteine peptidase A (CPA) 0.0119 1 1
Loa Loa (eye worm) thioredoxin reductase 0.0076 0.5394 0.465
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0119 1 1
Loa Loa (eye worm) hypothetical protein 0.0079 0.5748 0.5061
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0061 0.3764 0.3764
Echinococcus granulosus cathepsin l cysteine peptidase 0.0119 1 1
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0119 1 1
Schistosoma mansoni cathepsin F (C01 family) 0.0119 1 1
Trypanosoma cruzi cysteine peptidase, putative 0.0061 0.3764 0.3764
Schistosoma mansoni cathepsin F (C01 family) 0.0079 0.5748 0.5748
Trypanosoma cruzi trypanothione reductase, putative 0.0076 0.5394 0.5394
Plasmodium vivax glutathione reductase, putative 0.0076 0.5394 0.5394
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0119 1 1
Trichomonas vaginalis Clan CA, family C1, papain-like cysteine peptidase 0.0119 1 1
Brugia malayi Cathepsin L-like precursor 0.0119 1 1
Onchocerca volvulus 0.0119 1 1
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0119 1 1
Leishmania major cathepsin L-like protease 0.0119 1 1
Echinococcus multilocularis cathepsin L 0.0061 0.3764 0.3764
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0119 1 1
Schistosoma mansoni SmCL2-like peptidase (C01 family) 0.0061 0.3764 0.3764
Echinococcus granulosus cathepsin L cysteine proteinase 0.0119 1 1
Echinococcus granulosus cathepsin l1 0.0119 1 1
Trichomonas vaginalis Clan CA, family C1, papain-like cysteine peptidase 0.0119 1 1
Plasmodium falciparum cysteine proteinase falcipain 1 0.0061 0.3764 0.3764
Plasmodium vivax vivapain-2 0.0119 1 1
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0119 1 1
Echinococcus multilocularis cathepsin l cysteine peptidase 0.0119 1 1
Leishmania major cathepsin L-like protease 0.0119 1 1
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0079 0.5748 0.5748
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0061 0.3764 0.3764
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0119 1 1
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0119 1 1
Echinococcus multilocularis thioredoxin glutathione reductase 0.0076 0.5394 0.5394
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0119 1 1
Leishmania major cathepsin L-like protease 0.0119 1 1
Echinococcus granulosus cysteine protease 0.0061 0.3764 0.3764
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0119 1 1
Brugia malayi cathepsin F-like cysteine proteinase 0.0039 0.1391 0.1391
Onchocerca volvulus 0.0119 1 1
Mycobacterium ulcerans dihydrolipoamide dehydrogenase, LpdB 0.0026 0 0.5
Brugia malayi Papain family cysteine protease containing protein 0.0061 0.3764 0.3764
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0119 1 1
Brugia malayi Cathepsin L-like precursor 0.0119 1 1
Schistosoma mansoni cathepsin s 0.0039 0.1391 0.1391
Leishmania major trypanothione reductase 0.0076 0.5394 0.5394
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0079 0.5748 0.5748
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0119 1 1
Loa Loa (eye worm) cysteine protease 0.0119 1 1
Onchocerca volvulus 0.0119 1 1
Trichomonas vaginalis Clan CA, family C1, papain-like cysteine peptidase 0.0119 1 1
Entamoeba histolytica cysteine proteinase, putative 0.0119 1 1
Trypanosoma cruzi cysteine peptidase, putative 0.0119 1 1
Loa Loa (eye worm) papain family cysteine protease containing protein 0.0119 1 1
Entamoeba histolytica cysteine proteinase, putative 0.0079 0.5748 0.3182
Toxoplasma gondii cathepsin CPL 0.0119 1 1
Echinococcus multilocularis cathepsin l cysteine peptidase 0.0119 1 1
Trypanosoma cruzi cysteine protease, putative 0.0061 0.3764 0.3764
Onchocerca volvulus 0.0119 1 1
Brugia malayi Cathepsin L-like precursor 0.0119 1 1
Plasmodium falciparum glutathione reductase 0.0076 0.5394 0.5394
Brugia malayi Papain family cysteine protease containing protein 0.0119 1 1
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0119 1 1
Echinococcus multilocularis cysteine protease 0.0119 1 1
Brugia malayi Cathepsin L-like precursor 0.0039 0.1391 0.1391
Mycobacterium leprae DIHYDROLIPOAMIDE DEHYDROGENASE LPD (LIPOAMIDE REDUCTASE (NADH)) (LIPOYL DEHYDROGENASE) (DIHYDROLIPOYL DEHYDROGENASE) (DIAPHORASE 0.0026 0 0.5
Brugia malayi Cathepsin L-like precursor 0.0079 0.5748 0.5748
Leishmania major cathepsin L-like protease 0.0119 1 1
Leishmania major cathepsin L-like protease 0.0119 1 1
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0061 0.3764 0.3764
Plasmodium falciparum cysteine proteinase falcipain 2b 0.0119 1 1
Onchocerca volvulus 0.0119 1 1
Loa Loa (eye worm) glutathione reductase 0.0076 0.5394 0.465
Loa Loa (eye worm) fibroinase 0.0119 1 1
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0119 1 1
Plasmodium vivax vivapain-2 0.0119 1 1
Mycobacterium ulcerans dihydrolipoamide dehydrogenase 0.0026 0 0.5
Trichomonas vaginalis Clan CA, family C1, cathepsin L or K-like cysteine peptidase 0.0119 1 1
Plasmodium vivax vivapain-1 0.0061 0.3764 0.3764
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0119 1 1
Loa Loa (eye worm) hypothetical protein 0.0079 0.5748 0.5061

Activities

Activity type Activity value Assay description Source Reference
ED50 (functional) = 3.11 ug ml-1 Antiparasitic activity against T. brucei ChEMBL. 10956223
ED50 (functional) = 3.11 ug ml-1 Antiparasitic activity against T. brucei ChEMBL. 10956223
ED50 (functional) = 5.28 uM Antiparasitic activity against T. brucei ChEMBL. 10956223
ED50 (functional) = 5.28 uM Antiparasitic activity against T. brucei ChEMBL. 10956223
IC50 (binding) = 2.95 uM Inhibitory activity against T. cruzi trypanothione reductase ChEMBL. 10956223
IC50 (binding) = 2.95 uM Inhibitory activity against T. cruzi trypanothione reductase ChEMBL. 10956223
Ki (binding) = 0.56 uM Inhibitory activity against T. cruzi trypanothione reductase ChEMBL. 10956223
Ki (binding) = 0.56 uM Inhibitory activity against T. cruzi trypanothione reductase ChEMBL. 10956223

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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