TDR Targets

Basic information

Technical information

TDR Targets ID: 147576
Name: N-(6-chloro-2-methoxyacridin-9-yl)-N'-[2-[(6- chloro-2-methoxyacridin-9-yl)amino]ethyl]etha ne-1,2-diamine
MW: 586.511 | Formula: C32H29Cl2N5O2
H donors: 3 H acceptors: 2 LogP: 7.57 Rotable bonds: 10
Rule of 5 violations (Lipinski): 2
SMILES: COc1ccc2c(c1)c(NCCNCCNc1c3cc(OC)ccc3nc3c1ccc(c3)Cl)c1c(n2)cc(cc1)Cl
InChi: 1S/C32H29Cl2N5O2/c1-40-21-5-9-27-25(17-21)31(23-7-3-19(33)15-29(23)38-27)36-13-11-35-12-14-37-32-24-8-4-20(34)16-30(24)39-28-10-6-22(41-2)18-26(28)32/h3-10,15-18,35H,11-14H2,1-2H3,(H,36,38)(H,37,39)
InChiKey: APQIOBDMOGNRCR-UHFFFAOYSA-N

Network

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Target Layer

Model Organisms

Species	Viewmode
Arabidopsis thaliana
Caenorhabditis elegans
Dictyostelium discoideum
Drosophila melanogaster
Escherichia coli
Homo sapiens
Mus musculus
Oryza sativa
Saccharomyces cerevisiae
Schmidtea mediterranea
Other organisms

TDR Pathogens:

Species	Viewmode
Brugia malayi
Chlamydia trachomatis
Echinococcus granulosus
Entamoeba histolytica
Echinococcus multilocularis
Giardia lamblia
Leishmania major
Loa Loa (eye worm)
Mycobacterium leprae
Mycobacterium tuberculosis
Mycobacterium ulcerans
Onchocerca volvulus
Plasmodium falciparum
Plasmodium vivax
Schistosoma mansoni
Trypanosoma brucei
Trypanosoma cruzi
Toxoplasma gondii
Treponema pallidum
Trichomonas vaginalis
Wolbachia endosymbiont of Brugia malayi

Other Pathogens:

Species	Viewmode
Babesia bovis
Candida albicans
Cryptosporidium hominis
Cryptosporidium parvum
Leishmania braziliensis
Leishmania donovani
Leishmania infantum
Leishmania mexicana
Neospora caninum
Plasmodium berghei
Plasmodium knowlesi
Plasmodium yoelii
Schistosoma japonicum
Trypanosoma brucei gambiense
Trypanosoma congolense
Theileria parva

Compound Layer

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Clustering layers

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Synonyms

N-(6-chloro-2-methoxy-acridin-9-yl)-N'-[2-[(6-chloro-2-methoxy-acridin-9-yl)amino]ethyl]ethane-1,2-diamine
N-(6-chloro-2-methoxy-9-acridinyl)-N'-[2-[(6-chloro-2-methoxy-9-acridinyl)amino]ethyl]ethane-1,2-diamine
bis[2-[(6-chloro-2-methoxy-acridin-9-yl)amino]ethyl]amine
(6-chloro-2-methoxy-acridin-9-yl)-[2-[2-[(6-chloro-2-methoxy-acridin-9-yl)amino]ethylamino]ethyl]amine

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

Ranking Plot

Putative Targets List

Species	Potential target	Raw	Global	Species
Brugia malayi	ecdysteroid receptor	0.0078139	1	0.5
Onchocerca volvulus	Bile acid receptor homolog	0.0078139	1	0.5
Trichomonas vaginalis	NAD(P)H dehydrogenase, putative	0.0068194	0.836054	1
Giardia lamblia	NADPH oxidoreductase, putative	0.0068194	0.836054	0.5
Trichomonas vaginalis	conserved hypothetical protein	0.0068194	0.836054	1
Entamoeba histolytica	modulator of drug activity B homolog, putative	0.00174788	0	0.5
Trichomonas vaginalis	conserved hypothetical protein	0.0068194	0.836054	1
Trichomonas vaginalis	conserved hypothetical protein	0.0068194	0.836054	1
Giardia lamblia	NADPH oxidoreductase, putative	0.0068194	0.836054	0.5
Trichomonas vaginalis	conserved hypothetical protein	0.0068194	0.836054	1
Trichomonas vaginalis	conserved hypothetical protein	0.0068194	0.836054	1
Giardia lamblia	NADPH oxidoreductase, putative	0.0068194	0.836054	0.5
Trichomonas vaginalis	conserved hypothetical protein	0.0068194	0.836054	1
Trichomonas vaginalis	conserved hypothetical protein	0.0068194	0.836054	1
Trichomonas vaginalis	NAD(P)H dehydrogenase, putative	0.0068194	0.836054	1
Trichomonas vaginalis	conserved hypothetical protein	0.0068194	0.836054	1
Entamoeba histolytica	iron-sulfur flavoprotein, putative	0.00174788	0	0.5
Trichomonas vaginalis	conserved hypothetical protein	0.0068194	0.836054	1
Trichomonas vaginalis	conserved hypothetical protein	0.0068194	0.836054	1
Giardia lamblia	NADPH oxidoreductase, putative	0.0068194	0.836054	0.5
Trichomonas vaginalis	conserved hypothetical protein	0.0068194	0.836054	1
Onchocerca volvulus	Bile acid receptor homolog	0.0078139	1	0.5
Trichomonas vaginalis	conserved hypothetical protein	0.0068194	0.836054	1
Brugia malayi	ecdysteroid receptor	0.0078139	1	0.5
Trichomonas vaginalis	conserved hypothetical protein	0.0068194	0.836054	1
Trichomonas vaginalis	conserved hypothetical protein	0.0068194	0.836054	1
Trichomonas vaginalis	conserved hypothetical protein	0.0068194	0.836054	1
Trichomonas vaginalis	NAD(P)H dehydrogenase, putative	0.0068194	0.836054	1
Loa Loa (eye worm)	hypothetical protein	0.0078139	1	0.5
Entamoeba histolytica	modulator of drug activity B homolog, putative	0.00174788	0	0.5
Giardia lamblia	NADPH oxidoreductase, putative	0.0068194	0.836054	0.5
Trichomonas vaginalis	NAD(P)H dehydrogenase, putative	0.0068194	0.836054	1
Entamoeba histolytica	iron-sulfur flavoprotein, putative	0.00174788	0	0.5
Trichomonas vaginalis	conserved hypothetical protein	0.0068194	0.836054	1
Trichomonas vaginalis	conserved hypothetical protein	0.0068194	0.836054	1
Entamoeba histolytica	hypothetical protein	0.00174788	0	0.5
Trichomonas vaginalis	conserved hypothetical protein	0.00507152	0.547911	0.655353
Trichomonas vaginalis	conserved hypothetical protein	0.0068194	0.836054	1
Trichomonas vaginalis	conserved hypothetical protein	0.00507152	0.547911	0.655353
Trichomonas vaginalis	conserved hypothetical protein	0.0068194	0.836054	1
Trichomonas vaginalis	conserved hypothetical protein	0.0068194	0.836054	1
Trichomonas vaginalis	NAD(P)H dehydrogenase, putative	0.0068194	0.836054	1
Trichomonas vaginalis	conserved hypothetical protein	0.0068194	0.836054	1
Trichomonas vaginalis	conserved hypothetical protein	0.0068194	0.836054	1
Entamoeba histolytica	hypothetical protein	0.00174788	0	0.5
Giardia lamblia	NADPH oxidoreductase, putative	0.0068194	0.836054	0.5
Trichomonas vaginalis	conserved hypothetical protein	0.0068194	0.836054	1
Trichomonas vaginalis	conserved hypothetical protein	0.0068194	0.836054	1
Trichomonas vaginalis	conserved hypothetical protein	0.0068194	0.836054	1
Trichomonas vaginalis	NAD(P)H dehydrogenase, putative	0.0068194	0.836054	1
Loa Loa (eye worm)	hypothetical protein	0.0078139	1	0.5
Trichomonas vaginalis	conserved hypothetical protein	0.0068194	0.836054	1

Activities

Activity type	Activity value	Assay description	Source	Reference
Activity (functional)		Antimicrobial activity against Trypanosoma cruzi amastigotes assessed as increase in survival time of J774 cells at 5 uM	ChEMBL.	17371810
Activity (functional)		Antimicrobial activity against Schistosoma mansoni assessed as worm vitality at 3 uM after 4 hrs	ChEMBL.	17371810
Activity (functional)		Antimicrobial activity against Schistosoma mansoni assessed as worm vitality at 1 uM after 4 hrs	ChEMBL.	17371810
Activity (functional)		Antimicrobial activity against Schistosoma mansoni assessed as worm vitality at 6 uM after 4 hrs	ChEMBL.	17371810
Activity (functional)		Antileishmanial activity against Leishmania major MHOM/IL/81/FE/BNI amastigotes after 48 hrs at 1 uM	ChEMBL.	17371810
Activity (functional)	0	Antimicrobial activity against Schistosoma mansoni assessed as worm vitality at 6 uM after 4 hrs	ChEMBL.	17371810
Activity (functional)	0	Antimicrobial activity against Trypanosoma cruzi amastigotes assessed as increase in survival time of J774 cells at 5 uM	ChEMBL.	17371810
Activity (functional)	0	Antimicrobial activity against Schistosoma mansoni assessed as worm vitality at 3 uM after 4 hrs	ChEMBL.	17371810
Activity (functional)	0	Antimicrobial activity against Schistosoma mansoni assessed as worm vitality at 1 uM after 4 hrs	ChEMBL.	17371810
Activity (functional)	0	Antileishmanial activity against Leishmania major MHOM/IL/81/FE/BNI amastigotes after 48 hrs at 1 uM	ChEMBL.	17371810
Activity (ADMET)	0	Cytotoxicity against BALB/c mouse peritoneal macrophages at 10 uM after 48 hrs hrs	ChEMBL.	17371810
Activity (functional)	= 0 %	Antimicrobial activity against Trichomonas vaginalis G3 assessed as parasite death at 10 uM after 24 hrs	ChEMBL.	17371810
Activity (functional)	= 0 %	Antimicrobial activity against Trichomonas vaginalis G3 assessed as parasite death at 10 uM after 24 hrs	ChEMBL.	17371810
Activity (functional)	= 47 %	Antileishmanial activity against Leishmania donovani MHOM/SD/00/1S-2D promastigotes assessed as parasite death at 10 uM after 72 hrs	ChEMBL.	17371810
Activity (functional)	= 47 %	Antileishmanial activity against Leishmania donovani MHOM/SD/00/1S-2D promastigotes assessed as parasite death at 10 uM after 72 hrs	ChEMBL.	17371810
Activity (functional)	= 100 %	Antimicrobial activity against Trypanosoma brucei brucei clone 427-221a at 1.56 uM	ChEMBL.	17371810
Activity (ADMET)	= 100 %	Toxicity against human MRC5 cells at 3.13 uM	ChEMBL.	17371810
Activity (ADMET)	= 100 %	Toxicity against human MRC5 cells at 3.13 uM	ChEMBL.	17371810
Activity (functional)	= 100 %	Antimicrobial activity against Trypanosoma brucei brucei clone 427-221a at 1.56 uM	ChEMBL.	17371810
Cytotoxicity (functional)	%	In Vitro evaluation of the compound for the percentage of activity towards L. infantum at 3.13 microM Concentration; Toxic upon mouse primary peritoneal macrophages	ChEMBL.	10893302
Cytotoxicity (functional)	%	In Vitro evaluation of the compound for the percentage of activity towards T. cruzi at 3.13 microM Concentration; Toxic upon mouse primary peritoneal macrophages	ChEMBL.	10893302
Cytotoxicity (functional)	%	Percentage of activity against T. cruzi at 12.5 microM; Toxic upon mouse primary peritoneal macrophages	ChEMBL.	10893302
Cytotoxicity (functional)	%	In Vitro evaluation of the compound for the percentage of activity towards T. cruzi at 6.25 microM Concentration; Toxic upon mouse primary peritoneal macrophages	ChEMBL.	10893302
Cytotoxicity (functional)	%	Percentage of activity against L. infantum at 12.5 microM Concentration; Toxic upon mouse primary peritoneal macrophages	ChEMBL.	10893302
Cytotoxicity (functional)	%	In Vitro evaluation of the compound for the percentage of activity towards L. infantum at 1.56 microM Concentration; Toxic upon mouse primary peritoneal macrophages	ChEMBL.	10893302
Cytotoxicity (functional)	%	Percentage of activity against L. infantum at 6.25 microM; Toxic upon mouse primary peritoneal macrophages	ChEMBL.	10893302
Cytotoxicity (functional)	%	In Vitro evaluation of the compound for the percentage of activity towards T. cruzi at 1.56 microM Concentration; Toxic upon mouse primary peritoneal macrophages	ChEMBL.	10893302
Cytotoxicity (functional)	T 0 %	Percentage of activity against T. cruzi at 12.5 microM; Toxic upon mouse primary peritoneal macrophages	ChEMBL.	10893302
Cytotoxicity (functional)	T 0 %	In Vitro evaluation of the compound for the percentage of activity towards T. cruzi at 6.25 microM Concentration; Toxic upon mouse primary peritoneal macrophages	ChEMBL.	10893302
Cytotoxicity (functional)	T 0 %	In Vitro evaluation of the compound for the percentage of activity towards T. cruzi at 3.13 microM Concentration; Toxic upon mouse primary peritoneal macrophages	ChEMBL.	10893302
Cytotoxicity (functional)	T 0 %	In Vitro evaluation of the compound for the percentage of activity towards T. cruzi at 1.56 microM Concentration; Toxic upon mouse primary peritoneal macrophages	ChEMBL.	10893302
Cytotoxicity (functional)	T 0 %	Percentage of activity against L. infantum at 12.5 microM Concentration; Toxic upon mouse primary peritoneal macrophages	ChEMBL.	10893302
Cytotoxicity (functional)	T 0 %	Percentage of activity against L. infantum at 6.25 microM; Toxic upon mouse primary peritoneal macrophages	ChEMBL.	10893302
Cytotoxicity (functional)	T 0 %	In Vitro evaluation of the compound for the percentage of activity towards L. infantum at 3.13 microM Concentration; Toxic upon mouse primary peritoneal macrophages	ChEMBL.	10893302
Cytotoxicity (functional)	T 0 %	In Vitro evaluation of the compound for the percentage of activity towards L. infantum at 1.56 microM Concentration; Toxic upon mouse primary peritoneal macrophages	ChEMBL.	10893302
Cytotoxicity (functional)	= 100 %	Cytotoxicity on MRC-5 cells at 25 microM	ChEMBL.	10893302
Cytotoxicity (functional)	= 100 %	Cytotoxicity on MRC-5 cells at 12.5 microM	ChEMBL.	10893302
Cytotoxicity (functional)	= 100 %	Cytotoxicity on MRC-5 cells at 6.25 microM	ChEMBL.	10893302
Cytotoxicity (functional)	= 100 %	Cytotoxicity on MRC-5 cells at 3.13 microM	ChEMBL.	10893302
Cytotoxicity (functional)	= 100 %	Percentage of activity against T. brucei at 12.5 microM	ChEMBL.	10893302
Cytotoxicity (functional)	= 100 %	Percentage of activity against T. brucei at 6.25 microM	ChEMBL.	10893302
Cytotoxicity (functional)	= 100 %	Percentage of activity against T. brucei at 3.13 microM	ChEMBL.	10893302
Cytotoxicity (functional)	= 100 %	Percentage of activity against T. brucei at 1.56 microM	ChEMBL.	10893302
Cytotoxicity (functional)	= 100 %	Cytotoxicity on MRC-5 cells at 25 microM	ChEMBL.	10893302
Cytotoxicity (functional)	= 100 %	Cytotoxicity on MRC-5 cells at 12.5 microM	ChEMBL.	10893302
Cytotoxicity (functional)	= 100 %	Cytotoxicity on MRC-5 cells at 6.25 microM	ChEMBL.	10893302
Cytotoxicity (functional)	= 100 %	Cytotoxicity on MRC-5 cells at 3.13 microM	ChEMBL.	10893302
Cytotoxicity (functional)	= 100 %	Percentage of activity against T. brucei at 12.5 microM	ChEMBL.	10893302
Cytotoxicity (functional)	= 100 %	Percentage of activity against T. brucei at 6.25 microM	ChEMBL.	10893302
Cytotoxicity (functional)	= 100 %	Percentage of activity against T. brucei at 3.13 microM	ChEMBL.	10893302
Cytotoxicity (functional)	= 100 %	Percentage of activity against T. brucei at 1.56 microM	ChEMBL.	10893302
EC50 (functional)	= 63 nM	Antimalarial activity against chloroquine-resistant Plasmodium falciparum FcB1R after 72 hrs	ChEMBL.	17371810
EC50 (functional)	= 63 nM	Antimalarial activity against chloroquine-resistant Plasmodium falciparum FcB1R after 72 hrs	ChEMBL.	17371810
EC50 (functional)	= 218 nM	Antimicrobial activity against Trypanosoma brucei brucei clone 427-221a after 48 hrs	ChEMBL.	17371810
EC50 (functional)	= 218 nM	Antimicrobial activity against Trypanosoma brucei brucei clone 427-221a after 48 hrs	ChEMBL.	17371810
EC50 (functional)	= 618 nM	Antimicrobial activity against chloroquine-sensitive Plasmodium falciparum 3D7 after 72 hrs	ChEMBL.	17371810
EC50 (functional)	= 618 nM	Antimicrobial activity against chloroquine-sensitive Plasmodium falciparum 3D7 after 72 hrs	ChEMBL.	17371810
EC50 (functional)	= 791 nM	Antimicrobial activity against chloroquine-resistant Plasmodium falciparum W2 after 72 hrs	ChEMBL.	17371810
EC50 (functional)	= 791 nM	Antimicrobial activity against chloroquine-resistant Plasmodium falciparum W2 after 72 hrs	ChEMBL.	17371810
EC50 (ADMET)	= 9470 nM	Cytotoxicity against human HL60 cells	ChEMBL.	17371810
EC50 (ADMET)	= 9470 nM	Cytotoxicity against human HL60 cells	ChEMBL.	17371810
EC50 (functional)	= 5 uM	Antimicrobial activity against Entamoeba histolytica HM1 IMSS tropozoits after 48 hrs	ChEMBL.	17371810
EC50 (functional)	= 5 uM	Antimicrobial activity against Entamoeba histolytica HM1 IMSS tropozoits after 48 hrs	ChEMBL.	17371810
IC50 (functional)	= 63 nM	In vitro sensitivity of Plasmodium falciparum FcB1R Strain	ChEMBL.	10893302
IC50 (functional)	= 63 nM	In vitro sensitivity of Plasmodium falciparum FcB1R Strain	ChEMBL.	10893302
MIC (functional)	= 10000 nM	Antimicrobial activity against Trypanosoma brucei brucei clone 427-221a after 48 hrs	ChEMBL.	17371810
MIC (ADMET)	> 10000 nM	Cytotoxicity against human HL60 cells	ChEMBL.	17371810
MIC (ADMET)	> 10000 nM	Cytotoxicity against human HL60 cells	ChEMBL.	17371810
MIC (functional)	= 10000 nM	Antimicrobial activity against Trypanosoma brucei brucei clone 427-221a after 48 hrs	ChEMBL.	17371810
Ratio (functional)	> 1	Selectivity index, ratio of MIC for HL60 cells to MIC for Trypanosoma brucei brucei clone 427-221a	ChEMBL.	17371810
Ratio EC50 (functional)	= 43	Selectivity index, ratio of EC50 for HL60 cells to EC50 for Trypanosoma brucei brucei clone 427-221a	ChEMBL.	17371810

Phenotypes

Whole-cell/tissue/organism interactions

Species name	Source	Reference
Trypanosoma brucei gambiense		17371810
Plasmodium falciparum	ChEMBL23	10893302
Entamoeba histolytica	ChEMBL23	17371810
Homo sapiens	ChEMBL23	17371810

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

ChEMBL: CHEMBL90969
PubChem: 10579215

Bibliographic References

2 literature references were collected for this gene.

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Detailed information for compound 147576