TDR Targets

Basic information

Technical information

TDR Targets ID: 273153
Name: N-[3-(dimethylamino)-4-[(3-fluoroacridin-9-yl )amino]phenyl]methanesulfonamide
MW: 424.491 | Formula: C22H21FN4O2S
H donors: 2 H acceptors: 3 LogP: 4.26 Rotable bonds: 5
Rule of 5 violations (Lipinski): 1
SMILES: Fc1ccc2c(c1)nc1c(c2Nc2ccc(cc2N(C)C)NS(=O)(=O)C)cccc1
InChi: 1S/C22H21FN4O2S/c1-27(2)21-13-15(26-30(3,28)29)9-11-19(21)25-22-16-6-4-5-7-18(16)24-20-12-14(23)8-10-17(20)22/h4-13,26H,1-3H3,(H,24,25)
InChiKey: OMVPIKQULSSHOI-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-[3-(dimethylamino)-4-[(3-fluoro-9-acridinyl)amino]phenyl]methanesulfonamide
N-[3-dimethylamino-4-[(3-fluoroacridin-9-yl)amino]phenyl]methanesulfonamide
N-[3-dimethylamino-4-[(3-fluoro-9-acridinyl)amino]phenyl]methanesulfonamide
106521-47-5
N-(3-(Dimethylamino)-4-((3-fluoro-9-acridinyl)amino)phenyl)methanesulfonamide
Methanesulfonamide, N-(3-(dimethylamino)-4-((3-fluoro-9-acridinyl)amino)phenyl)-

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
Echinococcus granulosus	para nitrobenzyl esterase	0.0365	0.1461	0.1274
Trypanosoma cruzi	trypanothione reductase, putative	0.0135	0.0365	0.2104
Trypanosoma cruzi	dihydroorotate dehydrogenase (fumarate), putative	0.0172	0.0541	0.3253
Loa Loa (eye worm)	hypothetical protein	0.0365	0.1461	0.1461
Onchocerca volvulus		0.0365	0.1461	0.5
Loa Loa (eye worm)	hypothetical protein	0.0365	0.1461	0.1461
Brugia malayi	Carboxylesterase family protein	0.0365	0.1461	0.1461
Brugia malayi	glutathione reductase	0.0389	0.1574	0.1574
Loa Loa (eye worm)	hypothetical protein	0.0365	0.1461	0.1461
Entamoeba histolytica	dihydropyrimidine dehydrogenase, putative	0.0103	0.0214	0.5
Trypanosoma cruzi	dihydrolipoamide dehydrogenase, putative	0.0135	0.0365	0.2104
Brugia malayi	Carboxylesterase family protein	0.2161	1	1
Trypanosoma brucei	dihydroorotate dehydrogenase (fumarate)	0.0172	0.0541	0.1455
Trichomonas vaginalis	dihydroorotate dehydrogenase, putative	0.0103	0.0214	0.12
Plasmodium vivax	glutathione reductase, putative	0.0389	0.1574	1
Schistosoma mansoni	family S9 non-peptidase homologue (S09 family)	0.0365	0.1461	0.1137
Onchocerca volvulus		0.0365	0.1461	0.5
Trichomonas vaginalis	dihydroorotate dehydrogenase, putative	0.0103	0.0214	0.12
Trichomonas vaginalis	glutathione reductase, putative	0.0135	0.0365	0.2271
Mycobacterium tuberculosis	POSSIBLE PARA-NITROBENZYL ESTERASE (FRAGMENT)	0.0365	0.1461	0.9066
Loa Loa (eye worm)	hypothetical protein	0.0365	0.1461	0.1461
Trichomonas vaginalis	spcc417.12 protein, putative	0.0365	0.1461	1
Echinococcus multilocularis	dihydrolipoamide dehydrogenase	0.0135	0.0365	0.0155
Loa Loa (eye worm)	carboxylesterase	0.2161	1	1
Echinococcus multilocularis	para nitrobenzyl esterase	0.0365	0.1461	0.1274
Trypanosoma cruzi	dihydroorotate dehydrogenase, putative	0.0172	0.0541	0.3253
Schistosoma mansoni	acetylcholinesterase	0.0365	0.1461	0.1137
Onchocerca volvulus		0.0365	0.1461	0.5
Schistosoma mansoni	family S9 non-peptidase homologue (S09 family)	0.0365	0.1461	0.1137
Echinococcus granulosus	thioredoxin glutathione reductase	0.0389	0.1574	0.139
Trypanosoma cruzi	dihydrolipoamide dehydrogenase, putative	0.0135	0.0365	0.2104
Trichomonas vaginalis	mercuric reductase, putative	0.0135	0.0365	0.2271
Schistosoma mansoni	BC026374 protein (S09 family)	0.0365	0.1461	0.1137
Wolbachia endosymbiont of Brugia malayi	dihydroorotate dehydrogenase 2	0.0172	0.0541	1
Echinococcus multilocularis	family S9 non peptidase ue (S09 family)	0.0365	0.1461	0.1274
Giardia lamblia	NADH oxidase lateral transfer candidate	0.0135	0.0365	0.5
Trypanosoma cruzi	dihydrolipoamide dehydrogenase, putative	0.0135	0.0365	0.2104
Leishmania major	dihydroorotate dehydrogenase	0.0172	0.0541	0.1455
Trypanosoma cruzi	dihydrolipoyl dehydrogenase, putative	0.0135	0.0365	0.2104
Echinococcus granulosus	neuroligin	0.0365	0.1461	0.1274
Trypanosoma cruzi	dihydrolipoamide dehydrogenase, putative	0.0135	0.0365	0.2104
Echinococcus multilocularis	acetylcholinesterase	0.2161	1	1
Echinococcus multilocularis	BC026374 protein (S09 family)	0.0365	0.1461	0.1274
Loa Loa (eye worm)	hypothetical protein	0.2161	1	1
Mycobacterium tuberculosis	NADPH-dependent mycothiol reductase Mtr	0.0389	0.1574	1
Schistosoma mansoni	memapsin-2 (A01 family)	0.0895	0.3981	0.3753
Mycobacterium tuberculosis	Carboxylesterase LipT	0.0365	0.1461	0.9066
Brugia malayi	Zinc finger, C2H2 type family protein	0.0067	0.0044	0.0044
Plasmodium vivax	thioredoxin reductase, putative	0.0389	0.1574	1
Brugia malayi	Dihydroorotate dehydrogenase, mitochondrial precursor, putative	0.0172	0.0541	0.0541
Brugia malayi	Dihydroorotate dehydrogenase, mitochondrial precursor, putative	0.0172	0.0541	0.0541
Plasmodium falciparum	dihydroorotate dehydrogenase	0.0172	0.0541	0.1455
Loa Loa (eye worm)	hypothetical protein	0.2161	1	1
Echinococcus multilocularis	acetylcholinesterase	0.2161	1	1
Schistosoma mansoni	gliotactin	0.0365	0.1461	0.1137
Brugia malayi	dihydrolipoyl dehydrogenase, mitochondrial precursor, putative	0.0135	0.0365	0.0365
Brugia malayi	Pyridine nucleotide-disulphide oxidoreductase, dimerisation domain containing protein	0.0099	0.0195	0.0195
Mycobacterium tuberculosis	Probable dihydroorotate dehydrogenase PyrD	0.0172	0.0541	0.1455
Brugia malayi	Carboxylesterase family protein	0.0365	0.1461	0.1461
Onchocerca volvulus		0.0365	0.1461	0.5
Brugia malayi	hypothetical protein	0.0365	0.1461	0.1461
Echinococcus multilocularis	thioredoxin glutathione reductase	0.0389	0.1574	0.139
Leishmania major	trypanothione reductase	0.0389	0.1574	1
Plasmodium vivax	dihydroorotate dehydrogenase, mitochondrial precursor, putative	0.0172	0.0541	0.1455
Loa Loa (eye worm)	thioredoxin reductase	0.0389	0.1574	0.1574
Echinococcus granulosus	BC026374 protein S09 family	0.0365	0.1461	0.1274
Loa Loa (eye worm)	acetylcholinesterase 1	0.2161	1	1
Echinococcus granulosus	family S9 non peptidase ue S09 family	0.0365	0.1461	0.1274
Echinococcus multilocularis	neuroligin	0.0365	0.1461	0.1274
Echinococcus granulosus	acetylcholinesterase	0.2161	1	1
Mycobacterium ulcerans	carboxylesterase, LipT	0.0365	0.1461	1
Loa Loa (eye worm)	carboxylesterase	0.0365	0.1461	0.1461
Mycobacterium tuberculosis	POSSIBLE PARA-NITROBENZYL ESTERASE (FRAGMENT)	0.0365	0.1461	0.9066
Toxoplasma gondii	dihydroorotate dehydrogenase reveal, putative	0.0172	0.0541	0.1455
Mycobacterium leprae	Probable dihydroorotate dehydrogenase PyrD	0.0172	0.0541	1
Brugia malayi	Carboxylesterase family protein	0.0365	0.1461	0.1461
Loa Loa (eye worm)	hypothetical protein	0.0365	0.1461	0.1461
Chlamydia trachomatis	dihydrolipoyl dehydrogenase	0.0135	0.0365	0.5
Toxoplasma gondii	thioredoxin reductase	0.0389	0.1574	1
Loa Loa (eye worm)	hypothetical protein	0.0365	0.1461	0.1461
Trypanosoma cruzi	dihydrolipoamide dehydrogenase, putative	0.0135	0.0365	0.2104
Trypanosoma cruzi	dihydrolipoamide dehydrogenase, putative	0.0135	0.0365	0.2104
Schistosoma mansoni	neuroligin 3 (S09 family)	0.0365	0.1461	0.1137
Schistosoma mansoni	dihydroorotate dehydrogenase	0.0172	0.0541	0.0183
Trichomonas vaginalis	carboxylesterase domain containing protein, putative	0.0365	0.1461	1
Echinococcus granulosus	dihydrolipoamide dehydrogenase	0.0135	0.0365	0.0155
Loa Loa (eye worm)	glutathione reductase	0.0389	0.1574	0.1574
Plasmodium falciparum	thioredoxin reductase	0.0389	0.1574	1
Echinococcus granulosus	carboxylesterase 5A	0.2161	1	1
Trypanosoma cruzi	trypanothione reductase, putative	0.0389	0.1574	1
Brugia malayi	alpha keto acid dehydrogenase complex, E3 component, lipoamide dehydrogenase	0.0099	0.0195	0.0195
Trypanosoma cruzi	dihydroorotate dehydrogenase, putative	0.0172	0.0541	0.3253
Schistosoma mansoni	family S9 non-peptidase homologue (S09 family)	0.2161	1	1
Schistosoma mansoni	family S9 non-peptidase homologue (S09 family)	0.0365	0.1461	0.1137
Brugia malayi	Thioredoxin reductase	0.0389	0.1574	0.1574
Trypanosoma brucei	trypanothione reductase	0.0389	0.1574	1
Loa Loa (eye worm)	hypothetical protein	0.0365	0.1461	0.1461
Onchocerca volvulus		0.0365	0.1461	0.5
Mycobacterium ulcerans	dihydroorotate dehydrogenase 2	0.0172	0.0541	0.1605
Echinococcus granulosus	acetylcholinesterase	0.2161	1	1
Treponema pallidum	NADH oxidase	0.0135	0.0365	0.5
Loa Loa (eye worm)	carboxylesterase	0.0365	0.1461	0.1461
Trypanosoma cruzi	dihydrolipoyl dehydrogenase, putative	0.0135	0.0365	0.2104
Plasmodium falciparum	glutathione reductase	0.0389	0.1574	1
Brugia malayi	Carboxylesterase family protein	0.0365	0.1461	0.1461
Echinococcus multilocularis	carboxylesterase 5A	0.2161	1	1

Activities

Activity type	Activity value	Assay description	Source	Reference
D50 (functional)	j 0 mg kg-1 day-1	Compound was evaluated in vivo against P388 cells and measured as D50 which is the dose to provide an average %ILS of 50% was determined; An ILS 50% could not be reached at any dose	ChEMBL.	3560159
D50 (functional)	j 0 mg kg-1 day-1	In vivo antitumor activity against Lewis lung carcinoma cells expressed as D50 which is the dose to provide an average %ILS of 50%; An ILS 50% could not be reached at any dose	ChEMBL.	3560159
IC50 (functional)	= 77 nM	In vitro inhibitory activity against Murine leukemia (L1210)	ChEMBL.	3560159
IC50 (functional)	= 77 nM	In vitro inhibitory activity against Murine leukemia (L1210)	ChEMBL.	3560159
IC50 (functional)	= 770 nM	In vitro for the inhibition of human colon tumor (HCT-8) cells.	ChEMBL.	3560159
IC50 (functional)	= 770 nM	In vitro for the inhibition of human colon tumor (HCT-8) cells.	ChEMBL.	3560159
ILSmax (functional)	0 %	In vivo antitumor activity against Lewis lung carcinoma cells expressed as percent increase in lifespan at an optimal dose of 45 mg/kg/day; Inactive	ChEMBL.	3560159
ILSmax (functional)	= 42 %	In vivo antitumor activity against P388 cells expressed as percent increase in lifespan at an optimal dose of 65 mg/kg/day	ChEMBL.	3560159
ILSmax (functional)	= 42 %	In vivo antitumor activity against P388 cells expressed as percent increase in lifespan at an optimal dose of 65 mg/kg/day	ChEMBL.	3560159
Log K (binding)	= 5.5	Binding constant (log K) for DNA by ethidium bromide displacement	ChEMBL.	3560159
Ratio (functional)	= 10	Ratio of IC50 of HCT-8 to IC50 of L1210 cell lines	ChEMBL.	3560159

Phenotypes

Whole-cell/tissue/organism interactions

Species name	Source	Reference	Is orphan
Homo sapiens	ChEMBL23	3560159
Mus musculus	ChEMBL23	3560159

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

PubChem: 149724

Bibliographic References

1 literature reference was collected for this gene.

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Detailed information for compound 273153