TDR Targets

Basic information

Technical information

TDR Targets ID: 309813
Name: 7-amino-2-(2-dimethylaminoethyl)benzo[a]phena lene-1,3-dione
MW: 332.396 | Formula: C21H20N2O2
H donors: 1 H acceptors: 2 LogP: 3.63 Rotable bonds: 3
Rule of 5 violations (Lipinski): 1
SMILES: CN(CCC1C(=O)c2cccc3c2c(C1=O)c1ccccc1c3N)C
InChi: 1S/C21H20N2O2/c1-23(2)11-10-16-20(24)15-9-5-8-14-17(15)18(21(16)25)12-6-3-4-7-13(12)19(14)22/h3-9,16H,10-11,22H2,1-2H3
InChiKey: DCIRJNXFRSTMKD-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

7-azanyl-2-(2-dimethylaminoethyl)benzo[a]phenalene-1,3-dione
7-amino-2-(2-dimethylaminoethyl)benzo[a]phenalene-1,3-quinone

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
Toxoplasma gondii	Kazal-type serine protease inhibitor domain-containing protein	0.0046	0.4902	0.5466
Leishmania major	tyrosyl-DNA phosphodiesterase 1	0.0079	1	1
Brugia malayi	Kazal-type serine protease inhibitor domain containing protein	0.0046	0.4902	0.4902
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.002	0.101	1
Leishmania major	cathepsin L-like protease	0.0077	0.9595	0.955
Onchocerca volvulus		0.0067	0.813	1
Onchocerca volvulus	Cathepsin F homolog	0.002	0.101	0.1242
Loa Loa (eye worm)	sodium-independent organic anion transporter	0.0067	0.813	0.813
Brugia malayi	sodium-independent organic anion transporter family protein	0.0067	0.813	0.813
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.002	0.101	1
Loa Loa (eye worm)	hypothetical protein	0.0046	0.4902	0.4902
Loa Loa (eye worm)	fibroinase	0.002	0.101	0.101
Onchocerca volvulus	Putative organic anion transporter	0.0067	0.813	1
Loa Loa (eye worm)	hypothetical protein	0.0046	0.4902	0.4902
Brugia malayi	Cathepsin L-like precursor	0.002	0.101	0.101
Entamoeba histolytica	cysteine proteinase, putative	0.002	0.101	0.101
Leishmania major	cathepsin L-like protease	0.0077	0.9595	0.955
Brugia malayi	SPARC precursor	0.0046	0.4902	0.4902
Entamoeba histolytica	cysteine proteinase, putative	0.002	0.101	0.101
Loa Loa (eye worm)	cysteine protease	0.002	0.101	0.101
Toxoplasma gondii	Kazal-type serine protease inhibitor domain-containing protein	0.0046	0.4902	0.5466
Brugia malayi	Kazal-type serine protease inhibitor domain containing protein	0.0046	0.4902	0.4902
Leishmania major	cathepsin L-like protease	0.0077	0.9595	0.955
Loa Loa (eye worm)	hypothetical protein	0.0067	0.813	0.813
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.002	0.101	1
Loa Loa (eye worm)	agrin synaptic family protein	0.0046	0.4902	0.4902
Onchocerca volvulus		0.002	0.101	0.1242
Toxoplasma gondii	Kazal-type serine protease inhibitor domain-containing protein	0.0046	0.4902	0.5466
Onchocerca volvulus		0.0067	0.813	1
Loa Loa (eye worm)	papain family cysteine protease containing protein	0.002	0.101	0.101
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.002	0.101	1
Schistosoma mansoni	agrin	0.0046	0.4902	0.4902
Echinococcus granulosus	Solute carrier organic anion transporter family	0.0067	0.813	0.813
Brugia malayi	Cathepsin L-like precursor	0.002	0.101	0.101
Echinococcus granulosus	follistatin	0.0046	0.4902	0.4902
Schistosoma mansoni	cathepsin F (C01 family)	0.002	0.101	0.101
Echinococcus multilocularis	follistatin	0.0046	0.4902	0.4329
Loa Loa (eye worm)	hypothetical protein	0.0067	0.813	0.813
Echinococcus granulosus	tyrosyl DNA phosphodiesterase 1	0.0079	1	1
Trichomonas vaginalis	Clan CA, family C1, cathepsin L or K-like cysteine peptidase	0.002	0.101	1
Trichomonas vaginalis	Clan CA, family C1, papain-like cysteine peptidase	0.002	0.101	1
Echinococcus granulosus	cathepsin l cysteine peptidase	0.002	0.101	0.101
Plasmodium falciparum	cysteine proteinase falcipain 3	0.002	0.101	0.5
Onchocerca volvulus		0.0067	0.813	1
Trichomonas vaginalis	Clan CA, family C1, papain-like cysteine peptidase	0.002	0.101	1
Trypanosoma cruzi	MFS transporter, putative	0.0067	0.813	0.792
Trypanosoma cruzi	tyrosyl-DNA Phosphodiesterase (Tdp1), putative	0.0079	1	1
Loa Loa (eye worm)	hypothetical protein	0.0046	0.4902	0.4902
Loa Loa (eye worm)	hypothetical protein	0.0067	0.813	0.813
Trypanosoma cruzi	cysteine peptidase, putative	0.0077	0.9595	0.955
Echinococcus granulosus	organic anion transporting polypeptide 30B	0.0067	0.813	0.813
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.002	0.101	1
Onchocerca volvulus		0.002	0.101	0.1242
Toxoplasma gondii	protease inhibitor PI2	0.0046	0.4902	0.5466
Schistosoma mansoni	organic anion transporter	0.0067	0.813	0.813
Loa Loa (eye worm)	hypothetical protein	0.0067	0.813	0.813
Brugia malayi	Cathepsin L-like precursor	0.002	0.101	0.101
Onchocerca volvulus		0.002	0.101	0.1242
Brugia malayi	secreted modular calcium-binding protein 1	0.0046	0.4902	0.4902
Entamoeba histolytica	cysteine protease, putative	0.002	0.101	0.101
Loa Loa (eye worm)	hypothetical protein	0.0067	0.813	0.813
Onchocerca volvulus		0.002	0.101	0.1242
Echinococcus multilocularis	Solute carrier organic anion transporter family	0.0067	0.813	0.792
Loa Loa (eye worm)	hypothetical protein	0.002	0.101	0.101
Brugia malayi	hypothetical protein	0.0067	0.813	0.813
Trypanosoma cruzi	tyrosyl-DNA Phosphodiesterase (Tdp1), putative	0.0079	1	1
Brugia malayi	sodium-independent organic anion transporter family protein	0.0067	0.813	0.813
Plasmodium falciparum	cysteine proteinase falcipain 2a	0.002	0.101	0.5
Brugia malayi	hypothetical protein	0.0067	0.813	0.813
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.002	0.101	1
Schistosoma mansoni	organic anion transporter	0.0067	0.813	0.813
Onchocerca volvulus		0.0067	0.813	1
Trypanosoma cruzi	cysteine peptidase, putative	0.0077	0.9595	0.955
Onchocerca volvulus		0.002	0.101	0.1242
Onchocerca volvulus		0.0067	0.813	1
Loa Loa (eye worm)	Papain cysteine protease/cathepsin propeptide inhibitor-containing protein	0.002	0.101	0.101
Onchocerca volvulus	Cathepsin L homolog	0.002	0.101	0.1242
Loa Loa (eye worm)	hypothetical protein	0.0067	0.813	0.813
Echinococcus multilocularis	agrin	0.0046	0.4902	0.4329
Plasmodium falciparum	cysteine proteinase falcipain 2b	0.002	0.101	0.5
Onchocerca volvulus	Putative organic anion transporter	0.0067	0.813	1
Loa Loa (eye worm)	kazal-type serine protease inhibitor domain-containing protein	0.0046	0.4902	0.4902
Trichomonas vaginalis	Clan CA, family C1, papain-like cysteine peptidase	0.002	0.101	1
Brugia malayi	Cathepsin L-like precursor	0.002	0.101	0.101
Loa Loa (eye worm)	hypothetical protein	0.0046	0.4902	0.4902
Trichomonas vaginalis	Clan CA, family C1, papain-like cysteine peptidase	0.002	0.101	1
Trichomonas vaginalis	Clan CA, family C1, papain-like cysteine peptidase	0.002	0.101	1
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.002	0.101	1
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.002	0.101	1
Toxoplasma gondii	Kazal-type serine protease inhibitor domain-containing protein	0.0046	0.4902	0.5466
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.002	0.101	1
Trichomonas vaginalis	Clan CA, family C1, papain-like cysteine peptidase	0.002	0.101	1
Brugia malayi	Papain family cysteine protease containing protein	0.002	0.101	0.101
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.002	0.101	1
Onchocerca volvulus		0.0046	0.4902	0.603
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.002	0.101	1
Onchocerca volvulus		0.002	0.101	0.1242
Echinococcus multilocularis	tyrosyl DNA phosphodiesterase 1	0.0079	1	1
Echinococcus granulosus	cathepsin L cysteine proteinase	0.002	0.101	0.101
Brugia malayi	sodium-independent organic anion transporter family protein	0.0067	0.813	0.813
Trichomonas vaginalis	Clan CA, family C1, papain-like cysteine peptidase	0.002	0.101	1
Echinococcus multilocularis	expressed protein	0.0046	0.4902	0.4329
Schistosoma mansoni	tyrosyl-DNA phosphodiesterase	0.0079	1	1
Echinococcus multilocularis	organic anion transporting polypeptide 30B	0.0067	0.813	0.792
Loa Loa (eye worm)	ctsf protein	0.002	0.101	0.101
Echinococcus multilocularis	transcription factor Dp 1	0.0046	0.4927	0.4357
Trypanosoma brucei	tyrosyl-DNA Phosphodiesterase (Tdp1), putative	0.0079	1	1
Schistosoma mansoni	cathepsin F (C01 family)	0.002	0.101	0.101
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.002	0.101	1
Onchocerca volvulus	Cathepsin L homolog	0.002	0.101	0.1242
Schistosoma mansoni	follistatin	0.0046	0.4902	0.4902
Plasmodium vivax	vivapain-2	0.002	0.101	0.5
Onchocerca volvulus		0.002	0.101	0.1242
Brugia malayi	Cathepsin L-like precursor	0.002	0.101	0.101
Trichomonas vaginalis	Clan CA, family C1, papain-like cysteine peptidase	0.002	0.101	1
Loa Loa (eye worm)	tyrosyl-DNA phosphodiesterase	0.0079	1	1
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.002	0.101	1
Trypanosoma cruzi	major cysteine proteinase, putative	0.006	0.7104	0.6779
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.002	0.101	1
Trypanosoma cruzi	cysteine peptidase, clan CA, family C1, cathepsin L-like, putative	0.007	0.8585	0.8426
Onchocerca volvulus	Putative organic anion transporter	0.0067	0.813	1
Echinococcus granulosus	transcription factor Dp 1	0.0046	0.4927	0.4927
Trichomonas vaginalis	Clan CA, family C1, papain-like cysteine peptidase	0.002	0.101	1
Trypanosoma cruzi	cysteine peptidase, putative	0.0077	0.9595	0.955
Loa Loa (eye worm)	hypothetical protein	0.0067	0.813	0.813
Brugia malayi	Cathepsin L-like precursor	0.002	0.101	0.101
Brugia malayi	Kazal-type serine protease inhibitor domain containing protein	0.0046	0.4902	0.4902
Trichomonas vaginalis	Clan CA, family C1, cathepsin L or K-like cysteine peptidase	0.002	0.101	1
Echinococcus granulosus	cathepsin l1	0.002	0.101	0.101
Entamoeba histolytica	tyrosyl-DNA phosphodiesterase, putative	0.0079	1	1
Toxoplasma gondii	transporter, major facilitator family protein	0.0067	0.813	1
Trypanosoma cruzi	cruzipain precursor, putative	0.0077	0.9595	0.955
Plasmodium vivax	vivapain-2	0.002	0.101	0.5
Brugia malayi	prostaglandin transporter	0.0067	0.813	0.813
Brugia malayi	Kazal-type serine protease inhibitor domain containing protein	0.0046	0.4902	0.4902
Echinococcus granulosus	agrin	0.0046	0.4902	0.4902

Activities

Activity type	Activity value	Assay description	Source	Reference
Cardiotoxicity (ADMET)	= 1951 nM	Cardiotoxicity was measured by using Neonatal rat heart myocyte assay	ChEMBL.	7699715
IC50 (functional)	= 5.4 nM	Anti-tumor activity against murine L1210 sensitive cell line by using MTT assay	ChEMBL.	7699715
IC50 (functional)	= 5.4 nM	Anti-tumor activity against murine L1210 sensitive cell line by using MTT assay	ChEMBL.	7699715
IC50 (functional)	= 6.8 nM	Anti-tumor activity against murine L1210 resistant cell line by using MTT assay	ChEMBL.	7699715
IC50 (functional)	= 6.8 nM	Anti-tumor activity against murine L1210 resistant cell line by using MTT assay	ChEMBL.	7699715
IC50 (functional)	= 12 nM	Anti-tumor activity against human OVCAR3 ovarian cancer cell lines by using MTT assay	ChEMBL.	7699715
IC50 (functional)	= 12 nM	Anti-tumor activity against human OVCAR3 ovarian cancer cell lines by using MTT assay	ChEMBL.	7699715
IC50 (functional)	= 15 nM	Anti-tumor activity against human UACC375 melanoma cell lines by using MTT assay	ChEMBL.	7699715
ILS (functional)	= 31 %	The percent increase in life span of compound was measured against P388 Leukemia cells in mice at at a dose of 8 mg/kg on days 1,5 and 9	ChEMBL.	7699715
ILS (functional)	= 31 %	The percent increase in life span of compound was measured against P388 Leukemia cells in mice at at a dose of 8 mg/kg on days 1,5 and 9	ChEMBL.	7699715
ILS (functional)	= 46 %	The percent increase in life span of compound was measured against P388 Leukemia in mice at at a dose of 10 mg/kg on days 1,5 and 9	ChEMBL.	7699715
ILS (functional)	= 46 %	The percent increase in life span of compound was measured against P388 Leukemia in mice at at a dose of 12 mg/kg on days 1,5 and 9	ChEMBL.	7699715
ILS (functional)	= 46 %	The percent increase in life span of compound was measured against P388 Leukemia in mice at at a dose of 10 mg/kg on days 1,5 and 9	ChEMBL.	7699715
ILS (functional)	= 46 %	The percent increase in life span of compound was measured against P388 Leukemia in mice at at a dose of 12 mg/kg on days 1,5 and 9	ChEMBL.	7699715
Toxicity ratio (ADMET)	= 177	Toxicity ratio of quotient of the IC50 in myocytes divided by the average IC50 for three tumor cell lines	ChEMBL.	7699715

Phenotypes

Whole-cell/tissue/organism interactions

Species name	Source	Reference	Is orphan
Homo sapiens	ChEMBL23	7699715
Mus musculus	ChEMBL23	7699715

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: CHEMBL174780
PubChem: 11724327

Bibliographic References

1 literature reference was collected for this gene.

If you have references for this compound, please enter them in a user comment (below) or Contact us.

Detailed information for compound 309813