Detailed information for compound 606076

Basic information

Technical information
  • TDR Targets ID: 606076
  • Name: ethyl 6-bromo-5-hydroxy-1-methyl-2-[(pyridin- 4-ylamino)methyl]indole-3-carboxylate
  • MW: 404.258 | Formula: C18H18BrN3O3
  • H donors: 2 H acceptors: 3 LogP: 3 Rotable bonds: 6
    Rule of 5 violations (Lipinski): 1
  • SMILES: CCOC(=O)c1c2cc(O)c(cc2n(c1CNc1ccncc1)C)Br
  • InChi: 1S/C18H18BrN3O3/c1-3-25-18(24)17-12-8-16(23)13(19)9-14(12)22(2)15(17)10-21-11-4-6-20-7-5-11/h4-9,23H,3,10H2,1-2H3,(H,20,21)
  • InChiKey: KWEKHEFJSXTKGY-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • ethyl 6-bromo-5-hydroxy-1-methyl-2-[(4-pyridylamino)methyl]indole-3-carboxylate
  • 6-bromo-5-hydroxy-1-methyl-2-[(4-pyridylamino)methyl]-3-indolecarboxylic acid ethyl ester
  • 6-bromo-5-hydroxy-1-methyl-2-[(4-pyridylamino)methyl]indole-3-carboxylic acid ethyl ester
  • BAS 01530349
  • Oprea1_729772
  • Oprea1_092664

Targets

Known targets for this compound

No curated genes were found associated with this compound

Predicted pathogen targets for this compound

By orthology
No druggable targets predicted by orthology data
By sequence similarity to non orthologous known druggable targets
No druggable targets predicted by sequence similarity
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Leishmania major cysteine peptidase A (CPA) 0.0017 0.0157 0.0249
Echinococcus multilocularis thioredoxin glutathione reductase 0.0046 0.0954 0.0908
Plasmodium falciparum cysteine proteinase falcipain 2a 0.0017 0.0157 0.041
Loa Loa (eye worm) transcription factor SMAD2 0.0122 0.3068 0.3068
Trichomonas vaginalis Clan CA, family C1, papain-like cysteine peptidase 0.0017 0.0157 1
Schistosoma mansoni tar DNA-binding protein 0.0129 0.3267 0.3267
Loa Loa (eye worm) TAR-binding protein 0.0129 0.3267 0.3267
Onchocerca volvulus 0.0028 0.0447 0.545
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0065 0.1492 1
Echinococcus granulosus lamin dm0 0.0028 0.0447 0.0447
Echinococcus granulosus thioredoxin glutathione reductase 0.0046 0.0954 0.0954
Trichomonas vaginalis Clan CA, family C1, papain-like cysteine peptidase 0.0017 0.0157 1
Brugia malayi Papain family cysteine protease containing protein 0.0017 0.0157 0.0157
Loa Loa (eye worm) hypothetical protein 0.0013 0.0037 0.0037
Leishmania major cathepsin L-like protease 0.0017 0.0157 0.0249
Echinococcus multilocularis cysteine protease 0.0017 0.0157 0.0106
Brugia malayi Intermediate filament tail domain containing protein 0.0028 0.0447 0.0447
Mycobacterium tuberculosis NADPH-dependent mycothiol reductase Mtr 0.0046 0.0954 0.2985
Echinococcus granulosus high affinity choline transporter 1 0.0371 1 1
Onchocerca volvulus 0.0017 0.0157 0.1914
Echinococcus multilocularis cathepsin L cysteine protease 0.0017 0.0157 0.0106
Echinococcus multilocularis musashi 0.0028 0.0447 0.0398
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0017 0.0157 1
Loa Loa (eye worm) hypothetical protein 0.0371 1 1
Leishmania major cathepsin L-like protease 0.0017 0.0157 0.0249
Onchocerca volvulus Cathepsin F homolog 0.0017 0.0157 0.1914
Mycobacterium tuberculosis Dihydrolipoamide dehydrogenase LpdC (lipoamide reductase (NADH)) (lipoyl dehydrogenase) (dihydrolipoyl dehydrogenase) (diaphoras 0.0116 0.2908 1
Schistosoma mansoni cathepsin F (C01 family) 0.0017 0.0157 0.0157
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0017 0.0157 1
Trichomonas vaginalis mercuric reductase, putative 0.0016 0.0123 0.7831
Loa Loa (eye worm) hypothetical protein 0.0027 0.0433 0.0433
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0017 0.0157 1
Echinococcus multilocularis lamin dm0 0.0028 0.0447 0.0398
Brugia malayi Pyridine nucleotide-disulphide oxidoreductase, dimerisation domain containing protein 0.0012 0.0006 0.0006
Schistosoma mansoni high-affinity choline transporter 0.0371 1 1
Leishmania major trypanothione reductase 0.0046 0.0954 0.6075
Chlamydia trachomatis dihydrolipoyl dehydrogenase 0.0016 0.0123 0.5
Mycobacterium tuberculosis NAD(P)H quinone reductase LpdA 0.0116 0.2908 1
Echinococcus granulosus intermediate filament protein 0.0028 0.0447 0.0447
Leishmania major cathepsin L-like protease 0.0017 0.0157 0.0249
Brugia malayi RNA binding protein 0.0129 0.3267 0.3267
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0017 0.0157 1
Treponema pallidum NADH oxidase 0.0016 0.0123 0.5
Brugia malayi Cathepsin L-like precursor 0.0017 0.0157 0.0157
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0065 0.1492 1
Mycobacterium tuberculosis Putative ferredoxin reductase 0.0104 0.2584 0.8837
Mycobacterium tuberculosis Probable dehydrogenase 0.0104 0.2584 0.8837
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0017 0.0157 1
Plasmodium falciparum thioredoxin reductase 0.0046 0.0954 1
Plasmodium falciparum cysteine proteinase falcipain 3 0.0017 0.0157 0.041
Echinococcus multilocularis tar DNA binding protein 0.0129 0.3267 0.3232
Giardia lamblia NADH oxidase lateral transfer candidate 0.0016 0.0123 0.5
Echinococcus multilocularis sodium:glucose cotransporter 2 0.0041 0.082 0.0773
Schistosoma mansoni tar DNA-binding protein 0.0129 0.3267 0.3267
Trypanosoma cruzi cysteine peptidase, putative 0.0065 0.1492 1
Echinococcus multilocularis sodium coupled monocarboxylate transporter 1 0.0041 0.082 0.0773
Onchocerca volvulus 0.0017 0.0157 0.1914
Schistosoma mansoni lamin 0.0028 0.0447 0.0447
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0065 0.1492 1
Echinococcus multilocularis solute carrier family 5 0.0041 0.082 0.0773
Trichomonas vaginalis Clan CA, family C1, papain-like cysteine peptidase 0.0017 0.0157 1
Loa Loa (eye worm) cytoplasmic intermediate filament protein 0.0015 0.0092 0.0092
Onchocerca volvulus Cathepsin L homolog 0.0017 0.0157 0.1914
Brugia malayi Sodium:solute symporter family protein 0.0041 0.082 0.082
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0017 0.0157 1
Onchocerca volvulus 0.0041 0.082 1
Echinococcus multilocularis cathepsin L cysteine protease 0.0017 0.0157 0.0106
Brugia malayi MH2 domain containing protein 0.0122 0.3068 0.3068
Mycobacterium ulcerans dihydrolipoamide dehydrogenase, LpdB 0.0016 0.0123 0.5
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0017 0.0157 1
Echinococcus granulosus sodium:glucose cotransporter 2 0.0041 0.082 0.082
Brugia malayi Thioredoxin reductase 0.0046 0.0954 0.0954
Schistosoma mansoni cathepsin F (C01 family) 0.0017 0.0157 0.0157
Brugia malayi Cathepsin L-like precursor 0.0017 0.0157 0.0157
Brugia malayi alpha keto acid dehydrogenase complex, E3 component, lipoamide dehydrogenase 0.0012 0.0006 0.0006
Trichomonas vaginalis Clan CA, family C1, cathepsin L or K-like cysteine peptidase 0.0017 0.0157 1
Trypanosoma cruzi cysteine peptidase, putative 0.0065 0.1492 1
Echinococcus multilocularis lamin 0.0028 0.0447 0.0398
Echinococcus multilocularis dihydrolipoamide dehydrogenase 0.0016 0.0123 0.0072
Entamoeba histolytica cysteine protease, putative 0.0017 0.0157 1
Trichomonas vaginalis glutathione reductase, putative 0.0016 0.0123 0.7831
Loa Loa (eye worm) thioredoxin reductase 0.0046 0.0954 0.0954
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0065 0.1492 1
Schistosoma mansoni inositol transporter 0.0041 0.082 0.082
Trichomonas vaginalis Clan CA, family C1, cathepsin L or K-like cysteine peptidase 0.0017 0.0157 1
Echinococcus granulosus cathepsin l1 0.0017 0.0157 0.0157
Plasmodium vivax glutathione reductase, putative 0.0046 0.0954 1
Schistosoma mansoni lamin 0.0028 0.0447 0.0447
Loa Loa (eye worm) RNA recognition domain-containing protein domain-containing protein 0.0129 0.3267 0.3267
Onchocerca volvulus 0.0017 0.0157 0.1914
Leishmania major cathepsin L-like protease 0.0065 0.1492 1
Echinococcus multilocularis cathepsin l cysteine peptidase 0.0017 0.0157 0.0106
Brugia malayi dihydrolipoyl dehydrogenase, mitochondrial precursor, putative 0.0016 0.0123 0.0123
Brugia malayi RNA recognition motif domain containing protein 0.0129 0.3267 0.3267
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0017 0.0157 1
Echinococcus multilocularis cathepsin l cysteine peptidase 0.0017 0.0157 0.0106
Schistosoma mansoni dihydrolipoamide dehydrogenase 0.0016 0.0123 0.0123
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0065 0.1492 1
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0017 0.0157 1
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0065 0.1492 1
Loa Loa (eye worm) ctsf protein 0.0017 0.0157 0.0157
Schistosoma mansoni intermediate filament proteins 0.0028 0.0447 0.0447
Loa Loa (eye worm) hypothetical protein 0.0028 0.0447 0.0447
Echinococcus granulosus cathepsin L cysteine proteinase 0.0017 0.0157 0.0157
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0065 0.1492 1
Loa Loa (eye worm) hypothetical protein 0.0017 0.0157 0.0157
Plasmodium vivax vivapain-2 0.0017 0.0157 0.041
Trichomonas vaginalis Clan CA, family C1, papain-like cysteine peptidase 0.0017 0.0157 1
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0017 0.0157 1
Onchocerca volvulus 0.0028 0.0447 0.545
Loa Loa (eye worm) RNA binding protein 0.0129 0.3267 0.3267
Brugia malayi Cathepsin L-like precursor 0.0017 0.0157 0.0157
Mycobacterium tuberculosis Probable reductase 0.0104 0.2584 0.8837
Onchocerca volvulus 0.0017 0.0157 0.1914
Brugia malayi glutathione reductase 0.0046 0.0954 0.0954
Mycobacterium tuberculosis Probable NADH dehydrogenase Ndh 0.0104 0.2584 0.8837
Mycobacterium tuberculosis Probable nitrite reductase [NAD(P)H] large subunit [FAD flavoprotein] NirB 0.0104 0.2584 0.8837
Onchocerca volvulus 0.0017 0.0157 0.1914
Echinococcus granulosus sodium:myo inositol cotransporter 0.0041 0.082 0.082
Trichomonas vaginalis Clan CA, family C1, papain-like cysteine peptidase 0.0017 0.0157 1
Echinococcus granulosus tar DNA binding protein 0.0129 0.3267 0.3267
Loa Loa (eye worm) intermediate filament protein 0.0028 0.0447 0.0447
Brugia malayi Cathepsin L-like precursor 0.0017 0.0157 0.0157
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0065 0.1492 1
Toxoplasma gondii thioredoxin reductase 0.0046 0.0954 1
Loa Loa (eye worm) hypothetical protein 0.0013 0.0051 0.0051
Onchocerca volvulus 0.0017 0.0157 0.1914
Schistosoma mansoni tar DNA-binding protein 0.0129 0.3267 0.3267
Leishmania major cathepsin L-like protease 0.0017 0.0157 0.0249
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0017 0.0157 1
Trypanosoma cruzi cruzipain precursor, putative 0.0065 0.1492 1
Loa Loa (eye worm) MH2 domain-containing protein 0.0122 0.3068 0.3068
Loa Loa (eye worm) papain family cysteine protease containing protein 0.0017 0.0157 0.0157
Echinococcus granulosus cathepsin l cysteine peptidase 0.0017 0.0157 0.0157
Echinococcus granulosus lamin 0.0028 0.0447 0.0447
Trichomonas vaginalis Clan CA, family C1, papain-like cysteine peptidase 0.0017 0.0157 1
Toxoplasma gondii transporter, solute:sodium symporter (SSS) family protein 0.0041 0.082 0.8386
Wolbachia endosymbiont of Brugia malayi dihydrolipoamide dehydrogenase E3 component 0.0016 0.0123 0.5
Trypanosoma brucei trypanothione reductase 0.0046 0.0954 0.6075
Trypanosoma cruzi cysteine peptidase, clan CA, family C1, cathepsin L-like, putative 0.0059 0.1335 0.8853
Schistosoma mansoni sodium/solute symporter 0.0041 0.082 0.082
Trichomonas vaginalis Clan CA, family C1, papain-like cysteine peptidase 0.0017 0.0157 1
Leishmania major cathepsin L-like protease 0.0065 0.1492 1
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0017 0.0157 1
Toxoplasma gondii cathepsin CPL 0.0017 0.0157 0.041
Trichomonas vaginalis Clan CA, family C1, papain-like cysteine peptidase 0.0017 0.0157 1
Loa Loa (eye worm) hypothetical protein 0.0013 0.0037 0.0037
Schistosoma mansoni tar DNA-binding protein 0.0129 0.3267 0.3267
Brugia malayi Cathepsin L-like precursor 0.0017 0.0157 0.0157
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0065 0.1492 1
Trypanosoma cruzi cysteine peptidase, putative 0.0017 0.0157 0.0249
Plasmodium falciparum glutathione reductase 0.0046 0.0954 1
Trypanosoma cruzi trypanothione reductase, putative 0.0046 0.0954 0.6075
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0065 0.1492 1
Echinococcus granulosus dihydrolipoamide dehydrogenase 0.0016 0.0123 0.0123
Schistosoma mansoni inositol transporter 0.0041 0.082 0.082
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0017 0.0157 1
Trypanosoma cruzi cysteine peptidase, putative 0.0065 0.1492 1
Echinococcus granulosus solute carrier family 5 0.0041 0.082 0.082
Onchocerca volvulus 0.0017 0.0157 0.1914
Mycobacterium leprae DIHYDROLIPOAMIDE DEHYDROGENASE LPD (LIPOAMIDE REDUCTASE (NADH)) (LIPOYL DEHYDROGENASE) (DIHYDROLIPOYL DEHYDROGENASE) (DIAPHORASE 0.0116 0.2908 1
Echinococcus multilocularis high affinity choline transporter 1 0.0371 1 1
Trichomonas vaginalis Clan CA, family C1, papain-like cysteine peptidase 0.0017 0.0157 1
Echinococcus granulosus sodium:glucose cotransporter 0.0041 0.082 0.082
Echinococcus granulosus sodium coupled monocarboxylate transporter 1 0.0041 0.082 0.082
Brugia malayi TAR-binding protein 0.0129 0.3267 0.3267
Mycobacterium ulcerans flavoprotein disulfide reductase 0.0016 0.0123 0.5
Brugia malayi cytoplasmic intermediate filament protein 0.0015 0.0092 0.0092
Entamoeba histolytica cysteine proteinase, putative 0.0017 0.0157 1
Echinococcus granulosus cytoplasmic intermediate filament protein 0.0013 0.0051 0.0051
Plasmodium falciparum cysteine proteinase falcipain 2b 0.0017 0.0157 0.041
Schistosoma mansoni tar DNA-binding protein 0.0129 0.3267 0.3267
Trypanosoma cruzi major cysteine proteinase, putative 0.0051 0.1104 0.717
Echinococcus multilocularis cysteine protease 0.0017 0.0157 0.0106
Leishmania major cathepsin L-like protease 0.0017 0.0157 0.0249
Brugia malayi Cathepsin L-like precursor 0.0017 0.0157 0.0157
Loa Loa (eye worm) Papain cysteine protease/cathepsin propeptide inhibitor-containing protein 0.0017 0.0157 0.0157
Mycobacterium tuberculosis Probable oxidoreductase 0.0116 0.2908 1
Mycobacterium ulcerans dihydrolipoamide dehydrogenase 0.0016 0.0123 0.5
Loa Loa (eye worm) cysteine protease 0.0017 0.0157 0.0157
Plasmodium vivax thioredoxin reductase, putative 0.0046 0.0954 1
Wolbachia endosymbiont of Brugia malayi dihydrolipoamide dehydrogenase E3 component 0.0016 0.0123 0.5
Loa Loa (eye worm) glutathione reductase 0.0046 0.0954 0.0954
Loa Loa (eye worm) fibroinase 0.0017 0.0157 0.0157
Leishmania major cathepsin L-like protease 0.0065 0.1492 1
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0065 0.1492 1
Brugia malayi intermediate filament protein 0.0028 0.0447 0.0447
Plasmodium vivax vivapain-2 0.0017 0.0157 0.041
Loa Loa (eye worm) intermediate filament tail domain-containing protein 0.0028 0.0447 0.0447
Echinococcus multilocularis sodium:myo inositol cotransporter 0.0041 0.082 0.0773
Entamoeba histolytica cysteine proteinase, putative 0.0017 0.0157 1
Loa Loa (eye worm) hypothetical protein 0.0041 0.082 0.082
Mycobacterium tuberculosis Probable membrane NADH dehydrogenase NdhA 0.0104 0.2584 0.8837
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0017 0.0157 1
Onchocerca volvulus Cathepsin L homolog 0.0017 0.0157 0.1914

Activities

Activity type Activity value Assay description Source Reference
Activity (functional) NOVARTIS: Antimalarial liver stage activity measured as a greater than 50% reduction in Plasmodium yoelii schizont area in HepG2-A16-CD81 cells at 10uM compound concentration, determined by immuno-fluorescence. ChEMBL. 22096101
CC50 (functional) > 10 uM Huh7 cytotoxicity for Pf inhibitors Novartis-GNF Malaria Box. No reference
CC50 > 10 uM NOVARTIS: Cytotoxicity against human hepatocellular carcinoma cell line (Huh7) ChEMBL. 18579783
EC50 (functional) = 0.315 uM PF proliferation inhibition 3D7 Novartis-GNF Malaria Box. No reference
EC50 (functional) = 0.315 uM NOVARTIS: Inhibition of Plasmodium falciparum 3D7 (drug-susceptible) proliferation in erythrocyte-based infection assay ChEMBL. 18579783
EC50 (functional) = 0.333 uM W2 Pf proliferation inhibition Novartis-GNF Malaria Box. No reference
EC50 (functional) = 0.333 uM NOVARTIS: Inhibition of Plasmodium falciparum W2 (drug-resistant) proliferation in erythrocyte-based infection assay ChEMBL. 18579783
IFI promiscuity index = 0 IFI promiscuity index Novartis-GNF Malaria Box. No reference

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Plasmodium falciparum ChEMBL23 18579783

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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