Detailed information for compound 314286

Basic information

Technical information
  • TDR Targets ID: 314286
  • Name: 3-[(E)-2-(4-aminophenyl)-2-cyanoethenyl]-4,6- dichloro-1H-indole-2-carboxylic acid
  • MW: 372.205 | Formula: C18H11Cl2N3O2
  • H donors: 3 H acceptors: 3 LogP: 4.26 Rotable bonds: 3
    Rule of 5 violations (Lipinski): 1
  • SMILES: N#C/C(=C/c1c([nH]c2c1c(Cl)cc(c2)Cl)C(=O)O)/c1ccc(cc1)N
  • InChi: 1S/C18H11Cl2N3O2/c19-11-6-14(20)16-13(17(18(24)25)23-15(16)7-11)5-10(8-21)9-1-3-12(22)4-2-9/h1-7,23H,22H2,(H,24,25)/b10-5-
  • InChiKey: ISPWDIPEJBTYKY-YHYXMXQVSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 3-[(E)-2-(4-aminophenyl)-2-cyano-vinyl]-4,6-dichloro-1H-indole-2-carboxylic acid
  • 3-[(E)-2-(4-aminophenyl)-2-cyanovinyl]-4,6-dichloro-1H-indole-2-carboxylic acid
  • 3-[(E)-2-(4-aminophenyl)-2-cyano-ethenyl]-4,6-dichloro-1H-indole-2-carboxylic acid

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Rattus norvegicus Glutamate NMDA receptor Starlite/ChEMBL References

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
Loa Loa (eye worm) transcription factor SMAD2 0.0088 0.0229 0.0835
Plasmodium vivax JmjC domain containing protein 0.0014 0.0015 0.0052
Schistosoma mansoni subfamily A1A unassigned peptidase (A01 family) 0.0302 0.0853 0.0842
Plasmodium falciparum plasmepsin I 0.0953 0.2748 0.9395
Trypanosoma brucei trypanothione reductase 0.0017 0.0023 1
Treponema pallidum ATP-dependent Clp protease proteolytic subunit 0.0077 0.0197 0.5012
Toxoplasma gondii eukaryotic aspartyl protease superfamily protein 0.0302 0.0853 0.2917
Mycobacterium tuberculosis Probable fructose-bisphosphate aldolase Fba 0.0605 0.1733 1
Echinococcus granulosus thioredoxin glutathione reductase 0.0017 0.0023 0.0039
Schistosoma mansoni cathepsin D (A01 family) 0.3445 1 1
Echinococcus granulosus tumor protein p63 0.0238 0.0665 0.2384
Echinococcus multilocularis nmda type glutamate receptor 0.0032 0.0066 0.0196
Schistosoma mansoni memapsin-2 (A01 family) 0.0302 0.0853 0.0842
Mycobacterium leprae Probable fructose bisphosphate aldolase Fba 0.0605 0.1733 1
Mycobacterium ulcerans fructose-bisphosphate aldolase 0.0605 0.1733 1
Plasmodium vivax aspartyl proteinase, putative 0.0302 0.0853 0.2917
Loa Loa (eye worm) MH2 domain-containing protein 0.0088 0.0229 0.0835
Plasmodium falciparum plasmepsin IX 0.1014 0.2925 1
Mycobacterium tuberculosis Probable dehydrogenase 0.0039 0.0088 0.0376
Schistosoma mansoni Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein) 0.0042 0.0095 0.0083
Schistosoma mansoni cellular tumor antigen P53 0.0035 0.0075 0.0062
Brugia malayi jmjC domain containing protein 0.0014 0.0015 0.0131
Toxoplasma gondii thioredoxin reductase 0.0017 0.0023 0.008
Brugia malayi MH2 domain containing protein 0.0088 0.0229 0.1991
Schistosoma mansoni Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein) 0.0042 0.0095 0.0083
Brugia malayi hypothetical protein 0.0302 0.0853 0.7402
Giardia lamblia Fructose-bisphosphate aldolase 0.0131 0.0354 0.5
Entamoeba histolytica fructose-1,6-bisphosphate aldolase, putative 0.0131 0.0354 0.5
Schistosoma mansoni Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein) 0.0042 0.0095 0.0083
Loa Loa (eye worm) thioredoxin reductase 0.0017 0.0023 0.0085
Loa Loa (eye worm) hypothetical protein 0.0077 0.0197 0.0718
Chlamydia trachomatis ATP-dependent Clp protease proteolytic subunit 0.0077 0.0197 1
Echinococcus granulosus guanine nucleotide binding protein Gs subunit 0.0042 0.0095 0.0301
Mycobacterium tuberculosis Probable oxidoreductase 0.0044 0.01 0.045
Echinococcus granulosus Transcription factor JmjC domain containing protein 0.0054 0.013 0.0429
Brugia malayi Pepsin A precursor 0.0302 0.0853 0.7402
Mycobacterium tuberculosis Probable ATP-dependent CLP protease proteolytic subunit 1 ClpP1 (endopeptidase CLP) 0.005 0.012 0.0566
Toxoplasma gondii ATP-dependent Clp endopeptidase, proteolytic subunit ClpP domain-containing protein 0.0077 0.0197 0.0675
Mycobacterium leprae PROBABLE ATP-DEPENDENT CLP PROTEASE PROTEOLYTIC SUBUNIT 1 CLPP1 (ENDOPEPTIDASE CLP) 0.005 0.012 0.0414
Schistosoma mansoni phosphatidylserine receptor 0.0014 0.0015 0.0002
Onchocerca volvulus 0.0302 0.0853 1
Loa Loa (eye worm) hypothetical protein 0.0302 0.0853 0.3105
Toxoplasma gondii ATP-dependent Clp endopeptidase, proteolytic subunit ClpP domain-containing protein 0.0077 0.0197 0.0675
Toxoplasma gondii histone lysine demethylase JMJD6a 0.0014 0.0015 0.0052
Schistosoma mansoni ubiquitously transcribed sex (X/Y) chromosome tetratricopeptide repeat protein-related 0.0014 0.0015 0.0002
Echinococcus multilocularis aldehyde dehydrogenase, mitochondrial 0.006 0.0147 0.0492
Toxoplasma gondii aldehyde dehydrogenase 0.006 0.0147 0.0504
Onchocerca volvulus 0.0302 0.0853 1
Plasmodium vivax aspartyl protease, putative 0.1014 0.2925 1
Schistosoma mansoni subfamily A1A unassigned peptidase (A01 family) 0.0302 0.0853 0.0842
Schistosoma mansoni 3-hydroxyacyl-CoA dehydrogenase 0.006 0.0148 0.0135
Treponema pallidum fructose-bisphosphate aldolase 0.0131 0.0354 1
Loa Loa (eye worm) jmjC domain-containing protein 0.0014 0.0015 0.0055
Brugia malayi Eukaryotic aspartyl protease family protein 0.0302 0.0853 0.7402
Echinococcus granulosus jumonji domain containing 1A 0.0014 0.0015 0.0008
Brugia malayi 3-hydroxyacyl-CoA dehydrogenase type II 0.006 0.0148 0.1284
Echinococcus multilocularis tumor protein p63 0.0238 0.0665 0.2384
Brugia malayi Thioredoxin reductase 0.0017 0.0023 0.0203
Schistosoma mansoni subfamily A1A unassigned peptidase (A01 family) 0.0302 0.0853 0.0842
Plasmodium falciparum plasmepsin X 0.1014 0.2925 1
Loa Loa (eye worm) NNMT/PNMT/TEMT family protein 0.0405 0.1153 0.4195
Mycobacterium ulcerans aldehyde dehydrogenase 0.006 0.0147 0.0633
Brugia malayi hypothetical protein 0.0302 0.0853 0.7402
Schistosoma mansoni jumonji domain containing protein 0.0014 0.0015 0.0002
Toxoplasma gondii aspartyl protease ASP3 0.1014 0.2925 1
Entamoeba histolytica fructose-1,6-bisphosphate aldolase, putative 0.0131 0.0354 0.5
Toxoplasma gondii aspartyl protease ASP1 0.0953 0.2748 0.9395
Plasmodium vivax aspartyl protease, putative 0.1014 0.2925 1
Plasmodium vivax glutathione reductase, putative 0.0017 0.0023 0.008
Mycobacterium tuberculosis Probable ATP-dependent CLP protease proteolytic subunit 2 ClpP2 (endopeptidase CLP 2) 0.005 0.012 0.0566
Brugia malayi jmjC domain containing protein 0.0054 0.013 0.1128
Echinococcus multilocularis cathepsin d (lysosomal aspartyl protease) 0.0953 0.2748 1
Mycobacterium leprae DIHYDROLIPOAMIDE DEHYDROGENASE LPD (LIPOAMIDE REDUCTASE (NADH)) (LIPOYL DEHYDROGENASE) (DIHYDROLIPOYL DEHYDROGENASE) (DIAPHORASE 0.0044 0.01 0.0296
Mycobacterium tuberculosis Probable membrane NADH dehydrogenase NdhA 0.0039 0.0088 0.0376
Echinococcus multilocularis Jumonji, AT rich interactive domain 1B 0.0014 0.0015 0.0008
Plasmodium vivax aspartyl proteinase, putative 0.0953 0.2748 0.9395
Trypanosoma brucei JmjC domain, hydroxylase, putative 0.0014 0.0015 0.6444
Loa Loa (eye worm) hypothetical protein 0.0405 0.1153 0.4195
Plasmodium falciparum plasmepsin III 0.0302 0.0853 0.2917
Loa Loa (eye worm) glutathione reductase 0.0017 0.0023 0.0085
Echinococcus multilocularis phd:f box containing protein 0.0014 0.0015 0.0008
Trypanosoma cruzi JmjC domain, hydroxylase, putative 0.0014 0.0015 0.6444
Mycobacterium ulcerans short-chain type dehydrogenase/reductase 0.006 0.0148 0.0637
Loa Loa (eye worm) jmjC domain-containing protein 0.0014 0.0015 0.0055
Echinococcus granulosus Jumonji AT rich interactive domain 1B 0.0014 0.0015 0.0008
Mycobacterium tuberculosis NAD(P)H quinone reductase LpdA 0.0044 0.01 0.045
Loa Loa (eye worm) GTP-binding regulatory protein Gs alpha-S chain 0.0042 0.0095 0.0346
Plasmodium vivax thioredoxin reductase, putative 0.0017 0.0023 0.008
Leishmania major aldehyde dehydrogenase, mitochondrial precursor 0.006 0.0147 0.9954
Plasmodium falciparum plasmepsin II 0.0953 0.2748 0.9395
Brugia malayi aspartic protease BmAsp-2, identical 0.0302 0.0853 0.7402
Mycobacterium ulcerans ATP-dependent Clp protease proteolytic subunit 0.0077 0.0197 0.0928
Mycobacterium tuberculosis Probable nitrite reductase [NAD(P)H] large subunit [FAD flavoprotein] NirB 0.0039 0.0088 0.0376
Plasmodium vivax plasmepsin V, putative 0.0302 0.0853 0.2917
Schistosoma mansoni subfamily A1A unassigned peptidase (A01 family) 0.0953 0.2748 0.2739
Mycobacterium leprae PROBABLE NADH DEHYDROGENASE NDH 0.0039 0.0088 0.0221
Plasmodium falciparum plasmepsin IV 0.0953 0.2748 0.9395
Echinococcus multilocularis lysine specific demethylase 6a 0.0014 0.0015 0.0008
Toxoplasma gondii histone lysine demethylase JMJC1/KDM5D/JARID1D 0.0014 0.0015 0.0052
Echinococcus multilocularis peptidase Clp (S14 family) 0.005 0.012 0.0393
Mycobacterium tuberculosis Dihydrolipoamide dehydrogenase LpdC (lipoamide reductase (NADH)) (lipoyl dehydrogenase) (dihydrolipoyl dehydrogenase) (diaphoras 0.0044 0.01 0.045
Echinococcus multilocularis thioredoxin glutathione reductase 0.0017 0.0023 0.0039
Loa Loa (eye worm) aspartic protease BmAsp-2 0.0953 0.2748 1
Mycobacterium tuberculosis Probable reductase 0.0039 0.0088 0.0376
Schistosoma mansoni jumonji domain containing protein 0.0054 0.013 0.0117
Echinococcus multilocularis guanine nucleotide binding protein G(s) subunit 0.0042 0.0095 0.0301
Echinococcus multilocularis lysine specific demethylase 5A 0.0054 0.013 0.0429
Schistosoma mansoni subfamily A1A unassigned peptidase (A01 family) 0.0302 0.0853 0.0842
Plasmodium vivax ATP-dependent Clp protease proteolytic subunit, putative 0.0027 0.005 0.0173
Leishmania major trypanothione reductase 0.0017 0.0023 0.1582
Plasmodium vivax ATP-dependent Clp protease proteolytic subunit, putative 0.0077 0.0197 0.0675
Loa Loa (eye worm) hypothetical protein 0.0405 0.1153 0.4195
Mycobacterium tuberculosis Probable glutamine-binding lipoprotein GlnH (GLNBP) 0.0023 0.004 0.0098
Echinococcus granulosus JmjC domain containing protein 4 0.0014 0.0015 0.0008
Plasmodium falciparum plasmepsin VII 0.0302 0.0853 0.2917
Echinococcus multilocularis 3 hydroxyacyl coenzyme A dehydrogenase type 2 0.006 0.0148 0.0494
Mycobacterium ulcerans short-chain type dehydrogenase/reductase 0.006 0.0148 0.0637
Loa Loa (eye worm) 3-hydroxyacyl-CoA dehydrogenase type II 0.0053 0.0127 0.0461
Brugia malayi GTP-binding regulatory protein Gs alpha-S chain, putative 0.0042 0.0095 0.0826
Plasmodium falciparum plasmepsin VI 0.0953 0.2748 0.9395
Loa Loa (eye worm) jmjC domain-containing protein 0.0014 0.0015 0.0055
Echinococcus multilocularis JmjC domain containing protein 4 0.0014 0.0015 0.0008
Schistosoma mansoni subfamily A1A unassigned peptidase (A01 family) 0.0302 0.0853 0.0842
Echinococcus granulosus 3 hydroxyacyl coenzyme A dehydrogenase type 2 0.006 0.0148 0.0494
Echinococcus multilocularis jumonji domain containing 1A 0.0014 0.0015 0.0008
Brugia malayi jmjC domain containing protein 0.0054 0.013 0.1128
Plasmodium vivax aspartyl protease, putative 0.0302 0.0853 0.2917
Echinococcus multilocularis guanine nucleotide binding protein G(s) subunit 0.0042 0.0095 0.0301
Leishmania major 3-oxoacyl-(acyl-carrier protein) reductase, putative 0.006 0.0148 1
Toxoplasma gondii aspartyl proteinase (eimepsin), putative 0.0953 0.2748 0.9395
Echinococcus granulosus aldehyde dehydrogenase mitochondrial 0.006 0.0147 0.0492
Brugia malayi NNMT/PNMT/TEMT family protein 0.0405 0.1153 1
Mycobacterium tuberculosis Probable aldehyde dehydrogenase 0.006 0.0147 0.0724
Mycobacterium ulcerans aldehyde dehydrogenase 0.006 0.0147 0.0633
Plasmodium vivax plasmepsin IV, putative 0.0953 0.2748 0.9395
Brugia malayi jmjC domain containing protein 0.0014 0.0015 0.0131
Mycobacterium leprae PROBABLE ATP-DEPENDENT CLP PROTEASE PROTEOLYTIC SUBUNIT 2 CLPP2 (ENDOPEPTIDASE CLP 2) 0.0077 0.0197 0.0873
Plasmodium vivax multidrug resistance-associated protein 1, putative 0.0188 0.0522 0.1784
Loa Loa (eye worm) hypothetical protein 0.0014 0.0015 0.0055
Echinococcus multilocularis Transcription factor, JmjC domain containing protein 0.0054 0.013 0.0429
Plasmodium falciparum ATP-dependent Clp protease proteolytic subunit 0.0027 0.005 0.0173
Plasmodium falciparum JmjC domain-containing protein, putative 0.0014 0.0015 0.0052
Echinococcus multilocularis ATP dependent Clp protease proteolytic subunit 0.0077 0.0197 0.0675
Loa Loa (eye worm) aspartyl protease 6 0.0302 0.0853 0.3105
Brugia malayi jmjC domain containing protein 0.0014 0.0015 0.0131
Loa Loa (eye worm) hypothetical protein 0.0014 0.0015 0.0055
Plasmodium falciparum glutathione reductase 0.0017 0.0023 0.008
Mycobacterium tuberculosis Probable short-chain type dehydrogenase/reductase 0.006 0.0148 0.0728
Loa Loa (eye worm) aspartic protease BmAsp-1 0.0302 0.0853 0.3105
Schistosoma mansoni protein phosphatase 2C 0.0014 0.0015 0.0002
Brugia malayi glutathione reductase 0.0017 0.0023 0.0203
Mycobacterium tuberculosis Putative ferredoxin reductase 0.0039 0.0088 0.0376
Echinococcus granulosus guanine nucleotide binding protein Gs subunit 0.0042 0.0095 0.0301
Schistosoma mansoni peptidase Clp (S14 family) 0.0077 0.0197 0.0185
Wolbachia endosymbiont of Brugia malayi ATP-dependent Clp protease proteolytic subunit 0.0077 0.0197 0.5
Loa Loa (eye worm) jmjC domain-containing protein 0.0054 0.013 0.0473
Echinococcus multilocularis Glutamate receptor, ionotropic kainate 3 0.0032 0.0066 0.0196
Brugia malayi jmjC domain containing protein 0.0014 0.0015 0.0131
Brugia malayi aspartic protease BmAsp-1, identical 0.0302 0.0853 0.7402
Treponema pallidum ATP-dependent Clp protease proteolytic subunit 0.0027 0.005 0.0329
Chlamydia trachomatis ATP-dependent Clp protease proteolytic subunit 0.0077 0.0197 1
Schistosoma mansoni phd/f-box containing protein 0.0014 0.0015 0.0002
Echinococcus granulosus peptidase Clp S14 family 0.005 0.012 0.0393
Loa Loa (eye worm) hypothetical protein 0.0302 0.0853 0.3105
Mycobacterium tuberculosis Probable NADH dehydrogenase Ndh 0.0039 0.0088 0.0376
Trichomonas vaginalis Clan AA, family A1, cathepsin D-like aspartic peptidase 0.0953 0.2748 1
Toxoplasma gondii aspartyl protease 0.0302 0.0853 0.2917
Echinococcus granulosus phd:f box containing protein 0.0014 0.0015 0.0008
Trypanosoma cruzi JmjC domain, hydroxylase, putative 0.0014 0.0015 0.6444
Schistosoma mansoni jumonji/arid domain-containing protein 0.0054 0.013 0.0117
Schistosoma mansoni aldehyde dehydrogenase 0.006 0.0147 0.0135
Echinococcus granulosus cathepsin d lysosomal aspartyl protease 0.0953 0.2748 1
Loa Loa (eye worm) hypothetical protein 0.0953 0.2748 1
Schistosoma mansoni aldehyde dehydrogenase 0.006 0.0147 0.0135
Plasmodium falciparum plasmepsin V 0.0302 0.0853 0.2917
Loa Loa (eye worm) hypothetical protein 0.0014 0.0015 0.0055
Toxoplasma gondii hypothetical protein 0.0027 0.005 0.0173
Loa Loa (eye worm) hypothetical protein 0.0035 0.0075 0.0271
Schistosoma mansoni jumonji/arid domain-containing protein 0.0054 0.013 0.0117
Plasmodium falciparum thioredoxin reductase 0.0017 0.0023 0.008
Schistosoma mansoni subfamily A1A unassigned peptidase (A01 family) 0.0302 0.0853 0.0842
Brugia malayi Probable ClpP-like protease 0.0077 0.0197 0.1712
Plasmodium falciparum ATP-dependent Clp protease proteolytic subunit 0.0077 0.0197 0.0675
Plasmodium falciparum plasmepsin VIII, putative 0.0302 0.0853 0.2917
Schistosoma mansoni subfamily A1A unassigned peptidase (A01 family) 0.0302 0.0853 0.0842
Schistosoma mansoni subfamily A1A unassigned peptidase (A01 family) 0.0302 0.0853 0.0842
Echinococcus granulosus ATP dependent Clp protease proteolytic subunit 0.0077 0.0197 0.0675
Leishmania major hypothetical protein, conserved 0.0014 0.0015 0.1019
Echinococcus granulosus nmda type glutamate receptor 0.0032 0.0066 0.0196
Echinococcus granulosus lysine specific demethylase 6a 0.0014 0.0015 0.0008
Mycobacterium ulcerans aldehyde dehydrogenase 0.006 0.0147 0.0633
Trypanosoma cruzi trypanothione reductase, putative 0.0017 0.0023 1
Mycobacterium ulcerans ATP-dependent Clp protease proteolytic subunit 0.0077 0.0197 0.0928
Echinococcus granulosus lysine specific demethylase 5A 0.0054 0.013 0.0429

Activities

Activity type Activity value Assay description Source Reference
IC50 (functional) = 4.664 uM Antagonist activity of compound against rat N-methyl-D-aspartate glutamate receptor using 11 nM [3H]-glycine ChEMBL. 15715469
IC50 (functional) = 4.664 uM Antagonist activity of compound against rat N-methyl-D-aspartate glutamate receptor using 11 nM [3H]-glycine ChEMBL. 15715469

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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