Detailed information for compound 227114

Basic information

Technical information
  • TDR Targets ID: 227114
  • Name: 4-amino-1-[(3,4-dichlorophenyl)methyl]indole- 2-carboxylic acid
  • MW: 335.185 | Formula: C16H12Cl2N2O2
  • H donors: 2 H acceptors: 2 LogP: 4.03 Rotable bonds: 3
    Rule of 5 violations (Lipinski): 1
  • SMILES: OC(=O)c1cc2c(n1Cc1ccc(c(c1)Cl)Cl)cccc2N
  • InChi: 1S/C16H12Cl2N2O2/c17-11-5-4-9(6-12(11)18)8-20-14-3-1-2-13(19)10(14)7-15(20)16(21)22/h1-7H,8,19H2,(H,21,22)
  • InChiKey: XDWPMAKSOJITSN-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 4-amino-1-[(3,4-dichlorophenyl)methyl]-2-indolecarboxylic acid
  • 4-azanyl-1-[(3,4-dichlorophenyl)methyl]indole-2-carboxylic acid
  • 4-amino-1-(3,4-dichlorobenzyl)indole-2-carboxylic acid

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens chemokine (C-C motif) receptor 2 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
Brugia malayi bHLH-PAS transcription factor 0.0041 0.1159 0.1245
Onchocerca volvulus 0.0041 0.1159 1
Toxoplasma gondii DNA topoisomerase I, putative 0.0078 0.3246 0.9597
Plasmodium falciparum glutathione reductase 0.008 0.3365 1
Echinococcus granulosus DNA topoisomerase 1 0.0078 0.3246 0.4684
Leishmania major trypanothione reductase 0.008 0.3365 0.4881
Entamoeba histolytica phosphofructokinase, putative 0.0134 0.6458 1
Brugia malayi dihydrolipoyl dehydrogenase, mitochondrial precursor, putative 0.0028 0.0415 0.0446
Mycobacterium leprae PROBABLE NADH DEHYDROGENASE NDH 0.0125 0.5902 0.8371
Brugia malayi 6-phosphofructokinase 0.0134 0.6458 0.6934
Plasmodium vivax glutathione reductase, putative 0.008 0.3365 1
Schistosoma mansoni 6-phosphofructokinase 0.0134 0.6458 0.635
Mycobacterium tuberculosis Probable dehydrogenase 0.0125 0.5902 0.8371
Mycobacterium tuberculosis NAD(P)H quinone reductase LpdA 0.0145 0.7051 1
Mycobacterium tuberculosis Probable 6-phosphofructokinase PfkA (phosphohexokinase) (phosphofructokinase) 0.0134 0.6458 0.9159
Echinococcus multilocularis transfer RNA-Lys 0.0041 0.1159 0.1231
Trichomonas vaginalis phosphofructokinase, putative 0.0134 0.6458 1
Schistosoma mansoni DNA topoisomerase type I 0.0078 0.3246 0.304
Plasmodium falciparum ATP-dependent 6-phosphofructokinase 0.0036 0.0906 0.1665
Trichomonas vaginalis phosphofructokinase, putative 0.0036 0.0906 0.0813
Toxoplasma gondii endonuclease IV APN 0.0077 0.3219 0.9506
Echinococcus multilocularis DNA topoisomerase 1 0.0078 0.3246 0.4684
Mycobacterium tuberculosis Putative ferredoxin reductase 0.0125 0.5902 0.8371
Trypanosoma cruzi ATP-dependent 6-phosphofructokinase, glycosomal 0.0134 0.6458 1
Loa Loa (eye worm) hypoxia-induced factor 1 0.017 0.8503 0.913
Plasmodium falciparum apurinic/apyrimidinic endonuclease Apn1, putative 0.0077 0.3219 0.9506
Mycobacterium leprae PROBABLE ENDONUCLEASE IV END (ENDODEOXYRIBONUCLEASE IV) (APURINASE) 0.0077 0.3219 0.4565
Chlamydia trachomatis endonuclease IV 0.0077 0.3219 1
Mycobacterium tuberculosis Probable soluble pyridine nucleotide transhydrogenase SthA (STH) (NAD(P)(+) transhydrogenase [B-specific]) (nicotinamide nucleot 0.0028 0.0415 0.0589
Plasmodium vivax thioredoxin reductase, putative 0.008 0.3365 1
Mycobacterium ulcerans putative regulatory protein 0.0041 0.1159 0.1795
Leishmania major ATP-dependent phosphofructokinase 0.0134 0.6458 1
Schistosoma mansoni 6-phosphofructokinase 0.0134 0.6458 0.635
Trichomonas vaginalis phosphofructokinase, putative 0.0134 0.6458 1
Trypanosoma cruzi DNA topoisomerase IB, large subunit, putative 0.0078 0.3246 0.4684
Loa Loa (eye worm) hypothetical protein 0.0185 0.9313 1
Echinococcus multilocularis 6 phosphofructokinase 0.0134 0.6458 1
Toxoplasma gondii thioredoxin reductase 0.008 0.3365 1
Brugia malayi Thioredoxin reductase 0.008 0.3365 0.3613
Mycobacterium tuberculosis NADPH-dependent mycothiol reductase Mtr 0.008 0.3365 0.4772
Mycobacterium leprae DIHYDROLIPOAMIDE DEHYDROGENASE LPD (LIPOAMIDE REDUCTASE (NADH)) (LIPOYL DEHYDROGENASE) (DIHYDROLIPOYL DEHYDROGENASE) (DIAPHORASE 0.0145 0.7051 1
Mycobacterium ulcerans endonuclease IV 0.0077 0.3219 0.4984
Plasmodium vivax 6-phosphofructokinase, putative 0.0036 0.0906 0.1665
Echinococcus multilocularis n acetylated alpha linked acidic dipeptidase 2 0.0039 0.1055 0.1058
Trypanosoma brucei DNA topoisomerase IB, large subunit 0.0078 0.3246 0.4684
Trichomonas vaginalis phosphofructokinase, putative 0.0134 0.6458 1
Loa Loa (eye worm) 6-phosphofructokinase 0.0134 0.6458 0.6934
Trypanosoma brucei ATP-dependent 6-phosphofructokinase, glycosomal 0.0134 0.6458 1
Trichomonas vaginalis phosphofructokinase, putative 0.0134 0.6458 1
Brugia malayi DNA-(Apurinic or apyrimidinic site) lyase 0.0077 0.3219 0.3456
Mycobacterium tuberculosis Dihydrolipoamide dehydrogenase LpdC (lipoamide reductase (NADH)) (lipoyl dehydrogenase) (dihydrolipoyl dehydrogenase) (diaphoras 0.0145 0.7051 1
Treponema pallidum diphosphate--fructose-6-phosphate 1-phosphotransferase 0.0134 0.6458 1
Giardia lamblia Pyrophosphate-fructose 6-phosphate 1-phosphotransferase alpha subunit 0.0036 0.0906 1
Brugia malayi 6-phosphofructokinase 0.0134 0.6458 0.6934
Loa Loa (eye worm) phosphofructokinase 0.0134 0.6458 0.6934
Schistosoma mansoni aryl hydrocarbon receptor 0.0055 0.197 0.1726
Toxoplasma gondii phosphofructokinase domain-containing protein 0.0036 0.0906 0.1665
Plasmodium vivax 6-phosphofructokinase, putative 0.0036 0.0906 0.1665
Mycobacterium ulcerans dihydrolipoamide dehydrogenase, LpdB 0.0028 0.0415 0.0643
Schistosoma mansoni DNA topoisomerase type I 0.0078 0.3246 0.304
Trypanosoma cruzi trypanothione reductase, putative 0.008 0.3365 0.4881
Chlamydia trachomatis fructose-6-phosphate phosphotransferase 0.0036 0.0906 0.1752
Trichomonas vaginalis phosphofructokinase, putative 0.0036 0.0906 0.0813
Loa Loa (eye worm) 6-phosphofructokinase 0.0134 0.6458 0.6934
Schistosoma mansoni dihydrolipoamide dehydrogenase 0.0028 0.0415 0.0124
Plasmodium falciparum ATP-dependent 6-phosphofructokinase 0.0036 0.0906 0.1665
Brugia malayi DNA topoisomerase I 0.0078 0.3246 0.3485
Mycobacterium tuberculosis Probable nitrite reductase [NAD(P)H] large subunit [FAD flavoprotein] NirB 0.0125 0.5902 0.8371
Trichomonas vaginalis 6-phosphofructokinase, putative 0.0036 0.0906 0.0813
Entamoeba histolytica phosphofructokinase, putative 0.0134 0.6458 1
Wolbachia endosymbiont of Brugia malayi dihydrolipoamide dehydrogenase E3 component 0.0028 0.0415 0.5
Trichomonas vaginalis phosphofructokinase, putative 0.0036 0.0906 0.0813
Mycobacterium leprae PROBABLE 6-PHOSPHOFRUCTOKINASE PFKA (PHOSPHOHEXOKINASE) (PHOSPHOFRUCTOKINASE) 0.0134 0.6458 0.9159
Schistosoma mansoni single-minded 0.0055 0.197 0.1726
Trichomonas vaginalis phosphofructokinase, putative 0.0036 0.0906 0.0813
Loa Loa (eye worm) hypothetical protein 0.004 0.1108 0.119
Brugia malayi hypothetical protein 0.0185 0.9313 1
Leishmania major DNA topoisomerase IB, large subunit 0.0078 0.3246 0.4684
Mycobacterium tuberculosis Probable reductase 0.0125 0.5902 0.8371
Loa Loa (eye worm) glutathione reductase 0.008 0.3365 0.3613
Mycobacterium ulcerans 6-phosphofructokinase 0.0134 0.6458 1
Brugia malayi PAS domain containing protein 0.0055 0.197 0.2115
Wolbachia endosymbiont of Brugia malayi dihydrolipoamide dehydrogenase E3 component 0.0028 0.0415 0.5
Brugia malayi glutathione reductase 0.008 0.3365 0.3613
Echinococcus granulosus thioredoxin glutathione reductase 0.008 0.3365 0.4881
Mycobacterium ulcerans dihydrolipoamide dehydrogenase 0.0028 0.0415 0.0643
Mycobacterium tuberculosis Probable membrane NADH dehydrogenase NdhA 0.0125 0.5902 0.8371
Treponema pallidum diphosphate--fructose-6-phosphate 1-phosphotransferase 0.0036 0.0906 0.0813
Loa Loa (eye worm) hypothetical protein 0.0026 0.0349 0.0375
Toxoplasma gondii phosphofructokinase PFKII 0.0036 0.0906 0.1665
Mycobacterium tuberculosis Probable NADH dehydrogenase Ndh 0.0125 0.5902 0.8371
Brugia malayi hypoxia-induced factor 1 0.017 0.8503 0.913
Trypanosoma brucei trypanothione reductase 0.008 0.3365 0.4881
Echinococcus granulosus 6 phosphofructokinase 0.0134 0.6458 1
Loa Loa (eye worm) hypothetical protein 0.0036 0.0908 0.0975
Schistosoma mansoni DNA topoisomerase type I 0.0078 0.3246 0.304
Echinococcus multilocularis thioredoxin glutathione reductase 0.008 0.3365 0.4881
Mycobacterium tuberculosis Probable endonuclease IV End (endodeoxyribonuclease IV) (apurinase) 0.0077 0.3219 0.4565
Loa Loa (eye worm) hypothetical protein 0.0077 0.3219 0.3456
Echinococcus granulosus single minded 2 0.0041 0.1159 0.1231
Trichomonas vaginalis phosphofructokinase, putative 0.0036 0.0906 0.0813
Entamoeba histolytica phosphofructokinase, putative 0.0134 0.6458 1
Plasmodium falciparum topoisomerase I 0.0078 0.3246 0.9597
Loa Loa (eye worm) thioredoxin reductase 0.008 0.3365 0.3613
Chlamydia trachomatis fructose-6-phosphate phosphotransferase 0.0036 0.0906 0.1752
Trichomonas vaginalis phosphofructokinase, putative 0.0036 0.0906 0.0813
Plasmodium vivax apurinic/apyrimidinic endonuclease Apn1, putative 0.0077 0.3219 0.9506
Plasmodium vivax topoisomerase I, putative 0.0078 0.3246 0.9597
Loa Loa (eye worm) DNA topoisomerase I 0.0078 0.3246 0.3485
Brugia malayi phosphofructokinase 0.0134 0.6458 0.6934
Mycobacterium tuberculosis Probable oxidoreductase 0.0145 0.7051 1
Mycobacterium ulcerans flavoprotein disulfide reductase 0.0028 0.0415 0.0643
Toxoplasma gondii 6-phosphofructokinase 0.0036 0.0906 0.1665
Plasmodium falciparum thioredoxin reductase 0.008 0.3365 1

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 0.23 uM Inhibition of human C-C chemokine receptor type 2 ChEMBL. 14698169
IC50 (binding) = 0.23 uM Inhibition of human C-C chemokine receptor type 2 ChEMBL. 14698169

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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