TDR Targets

Basic information

Technical information

TDR Targets ID: 416251
Name: 5-[2-bromoethyl(2-chloroethyl)amino]-2,4-dini trobenzamide
MW: 395.594 | Formula: C11H12BrClN4O5
H donors: 1 H acceptors: 5 LogP: 1.93 Rotable bonds: 8
Rule of 5 violations (Lipinski): 1
SMILES: ClCCN(c1cc(C(=O)N)c(cc1[N+](=O)[O-])[N+](=O)[O-])CCBr
InChi: 1S/C11H12BrClN4O5/c12-1-3-15(4-2-13)9-5-7(11(14)18)8(16(19)20)6-10(9)17(21)22/h5-6H,1-4H2,(H2,14,18)
InChiKey: YIBANNNXXGVGBK-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

5-[2-bromoethyl(2-chloroethyl)amino]-2,4-dinitro-benzamide
5-(2-bromoethyl-(2-chloroethyl)amino)-2,4-dinitrobenzamide
5-(2-bromoethyl-(2-chloroethyl)amino)-2,4-dinitro-benzamide

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
Mycobacterium ulcerans	zinc metalloprotease	0.0479	1	1
Mycobacterium tuberculosis	Probable zinc metalloprotease Zmp1	0.0479	1	1
Schistosoma mansoni	family M13 non-peptidase homologue (M13 family)	0.0117	0.2043	0.2043
Loa Loa (eye worm)	hypothetical protein	0.0479	1	1
Echinococcus multilocularis	endothelin converting enzyme 1	0.0479	1	1
Loa Loa (eye worm)	hypothetical protein	0.0363	0.7438	0.7438
Schistosoma mansoni	family S9 non-peptidase homologue (S09 family)	0.014	0.2555	0.2555
Echinococcus granulosus	acetylcholinesterase	0.014	0.2555	0.2555
Echinococcus granulosus	guanine nucleotide binding protein Gs subunit	0.0044	0.045	0.045
Schistosoma mansoni	endothelin-converting enzyme-like 1 (damage-induced neuronal endopeptidase)	0.0117	0.2043	0.2043
Schistosoma mansoni	hypothetical protein	0.0125	0.2226	0.2226
Echinococcus granulosus	acetylcholinesterase	0.014	0.2555	0.2555
Loa Loa (eye worm)	hypothetical protein	0.0354	0.7255	0.7255
Schistosoma mansoni	family M13 unassigned peptidase (M13 family)	0.0117	0.2043	0.2043
Loa Loa (eye worm)	hypothetical protein	0.0354	0.7255	0.7255
Brugia malayi	peptidase family M13 containing protein	0.0117	0.2043	0.2043
Loa Loa (eye worm)	hypothetical protein	0.0363	0.7438	0.7438
Echinococcus granulosus	carboxylesterase 5A	0.014	0.2555	0.2555
Loa Loa (eye worm)	hypothetical protein	0.0363	0.7438	0.7438
Schistosoma mansoni	family M13 unassigned peptidase (M13 family)	0.0242	0.4788	0.4788
Onchocerca volvulus		0.0237	0.4692	1
Loa Loa (eye worm)	hypothetical protein	0.014	0.2555	0.2555
Loa Loa (eye worm)	hypothetical protein	0.0237	0.4692	0.4692
Schistosoma mansoni	family M13 unassigned peptidase (M13 family)	0.0242	0.4788	0.4788
Echinococcus multilocularis	guanine nucleotide binding protein G(s) subunit	0.0044	0.045	0.045
Echinococcus granulosus	endothelin converting enzyme 1	0.0479	1	1
Brugia malayi	Carboxylesterase family protein	0.014	0.2555	0.2555
Toxoplasma gondii	peptidase family M13 protein	0.0479	1	0.5
Schistosoma mansoni	hypothetical protein	0.0125	0.2226	0.2226
Loa Loa (eye worm)	peptidase family M13 containing protein	0.0354	0.7255	0.7255
Schistosoma mansoni	neprilysin-2 (M13 family)	0.0242	0.4788	0.4788
Loa Loa (eye worm)	peptidase family M13 containing protein	0.0354	0.7255	0.7255
Schistosoma mansoni	Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein)	0.0044	0.045	0.045
Loa Loa (eye worm)	hypothetical protein	0.0479	1	1
Loa Loa (eye worm)	hypothetical protein	0.0354	0.7255	0.7255
Schistosoma mansoni	family M13 unassigned peptidase (M13 family)	0.0117	0.2043	0.2043
Schistosoma mansoni	family M13 unassigned peptidase (M13 family)	0.0479	1	1
Echinococcus multilocularis	acetylcholinesterase	0.014	0.2555	0.2555
Brugia malayi	Carboxylesterase family protein	0.014	0.2555	0.2555
Loa Loa (eye worm)	hypothetical protein	0.0354	0.7255	0.7255
Loa Loa (eye worm)	hypothetical protein	0.014	0.2555	0.2555
Trichomonas vaginalis	spcc417.12 protein, putative	0.0024	0	0.5
Brugia malayi	Hypothetical zinc metalloproteinase T16A9.4	0.0479	1	1
Loa Loa (eye worm)	carboxylesterase	0.014	0.2555	0.2555
Schistosoma mansoni	family M13 unassigned peptidase (M13 family)	0.0125	0.2226	0.2226
Schistosoma mansoni	Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein)	0.0044	0.045	0.045
Echinococcus multilocularis	guanine nucleotide binding protein G(s) subunit	0.0044	0.045	0.045
Schistosoma mansoni	endothelin-converting enzyme-related	0.0117	0.2043	0.2043
Mycobacterium leprae	probable zinc metalloprotease	0.0479	1	0.5
Schistosoma mansoni	hypothetical protein	0.0125	0.2226	0.2226
Brugia malayi	GTP-binding regulatory protein Gs alpha-S chain, putative	0.0044	0.045	0.045
Trichomonas vaginalis	carboxylesterase domain containing protein, putative	0.0024	0	0.5
Loa Loa (eye worm)	hypothetical protein	0.0363	0.7438	0.7438
Schistosoma mansoni	hypothetical protein	0.0125	0.2226	0.2226
Schistosoma mansoni	neprilysin	0.0125	0.2226	0.2226
Echinococcus multilocularis	acetylcholinesterase	0.014	0.2555	0.2555
Loa Loa (eye worm)	hypothetical protein	0.0479	1	1
Loa Loa (eye worm)	GTP-binding regulatory protein Gs alpha-S chain	0.0044	0.045	0.045
Schistosoma mansoni	family M13 non-peptidase homologue (M13 family)	0.0242	0.4788	0.4788
Loa Loa (eye worm)	zinc metallopeptidase 4	0.0117	0.2043	0.2043
Schistosoma mansoni	Nep2 peptidase (M13 family)	0.0242	0.4788	0.4788
Loa Loa (eye worm)	hypothetical protein	0.0363	0.7438	0.7438
Schistosoma mansoni	family M13 unassigned peptidase (M13 family)	0.0117	0.2043	0.2043
Schistosoma mansoni	hypothetical protein	0.0125	0.2226	0.2226
Schistosoma mansoni	Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein)	0.0044	0.045	0.045
Schistosoma mansoni	hypothetical protein	0.0125	0.2226	0.2226
Echinococcus granulosus	guanine nucleotide binding protein Gs subunit	0.0044	0.045	0.045
Loa Loa (eye worm)	acetylcholinesterase 1	0.014	0.2555	0.2555
Loa Loa (eye worm)	hypothetical protein	0.0363	0.7438	0.7438
Echinococcus multilocularis	carboxylesterase 5A	0.014	0.2555	0.2555

Activities

Activity type	Activity value	Assay description	Source	Reference
Activity (functional)	= 3.4 uM	Clonogenic survival of 3% V79 NTRpuro cells in co-cultures with 97% V79 NTRoua after 5 hrs by MCL assay	ChEMBL.	17326614
Activity (functional)	= 8.2 uM	Clonogenic survival of 97% V79 NTRoua cells in co-cultures with 3% V79 NTRpuro cells after 5 hrs by MCL assay	ChEMBL.	17326614
Activity (functional)	> 300 uM	Clonogenic survival of V79 NTRoua cells after 5 hrs by MCL assay	ChEMBL.	17326614
IC50 (functional)	= 0.1 uM	Antiproliferative activity against mouse EMT6 NTRpuro cells after 18 hrs	ChEMBL.	17326614
IC50 (functional)	= 0.1 uM	Antiproliferative activity against mouse EMT6 NTRpuro cells after 18 hrs	ChEMBL.	17326614
IC50 (functional)	= 0.59 uM	Antiproliferative activity against chinese hamster V79 NTRpuro cells after 18 hrs	ChEMBL.	17326614
IC50 (functional)	= 0.69 uM	Antiproliferative activity against human WiDr NTRneo cells after 18 hrs	ChEMBL.	17326614
IC50 (functional)	= 0.69 uM	Antiproliferative activity against human WiDr NTRneo cells after 18 hrs	ChEMBL.	17326614
IC50 (functional)	= 0.84 uM	Antiproliferative activity against human Skov3 NTRneo cells after 18 hrs	ChEMBL.	17326614
IC50 (functional)	= 139 uM	Antiproliferative activity against chinese hamster wildtype V79 NTR-ve cells after 18 hrs	ChEMBL.	17326614
IC50 (functional)	= 150 uM	Antiproliferative activity against mouse wild type EMT6 NTR-ve cells after 18 hrs	ChEMBL.	17326614
IC50 (functional)	= 150 uM	Antiproliferative activity against human wild type WiDr NTR-ve cells after 18 hrs	ChEMBL.	17326614
IC50 (functional)	= 150 uM	Antiproliferative activity against mouse wild type EMT6 NTR-ve cells after 18 hrs	ChEMBL.	17326614
IC50 (functional)	= 150 uM	Antiproliferative activity against human wild type WiDr NTR-ve cells after 18 hrs	ChEMBL.	17326614
IC50 (functional)	= 226 uM	Antiproliferative activity against human wild type Skov3 NTR-ve cells after 18 hrs	ChEMBL.	17326614
LCK (functional)	> 3.02	Antitumor activity against mixed mouse EMT6/EMT6 NTRpuro cells injected in CD1 nude mouse assessed as cell kill at 237 umol/kg, ip in DMSO after 18 hrs	ChEMBL.	17326614
LogP (ADMET)	= 1.61	Partition coefficient of the compound at pH 7.4 by shake-flask method	ChEMBL.	17326614
MTD (ADMET)	= 237 umol/Kg	Toxicity in ip dosed CD1 nude mouse in DMSO	ChEMBL.	17326614
MTD (ADMET)	= 237 umol/Kg	Toxicity in ip dosed CD1 nude mouse in DMSO	ChEMBL.	17326614
Ratio IC50 (functional)	= 236	Selectivity ratio of IC50 for WiDr NTR-ve cells to IC50 for WiDr NTRneo cells	ChEMBL.	17326614
Ratio IC50 (functional)	= 237	Selectivity ratio of IC50 for V79 NTR-ve cells to IC50 for V79 NTRpuro cells	ChEMBL.	17326614
Ratio IC50 (functional)	= 280	Selectivity ratio of IC50 for Skov3 NTR-ve cells to IC50 for Skov3 NTRneo cells	ChEMBL.	17326614
Ratio IC50 (functional)	= 2190	Selectivity ratio of IC50 for EMT6 NTR-ve cells to IC50 forEMT6 NTRpuro cells	ChEMBL.	17326614
Solubility	= 0.63 mM	Solubility in alpha MEM	ChEMBL.	17326614
Stabilty	= 62 %	Stability in alpha MEM at 37 degC after 24 hrs	ChEMBL.	17326614

Phenotypes

Whole-cell/tissue/organism interactions

Species name	Source	Reference	Is orphan
Mus musculus	ChEMBL23	17326614
Homo sapiens	ChEMBL23	17326614

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: CHEMBL222417
PubChem: 10023618

Bibliographic References

1 literature reference was collected for this gene.

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Detailed information for compound 416251