TDR Targets

Basic information

Technical information

TDR Targets ID: 113193
Name: 2-[5-[4-(2,3-dichlorophenyl)piperazin-1-yl]pe ntyl]isoindole-1,3-dione
MW: 446.37 | Formula: C23H25Cl2N3O2
H donors: 0 H acceptors: 2 LogP: 4.86 Rotable bonds: 7
Rule of 5 violations (Lipinski): 1
SMILES: Clc1cccc(c1Cl)N1CCN(CC1)CCCCCN1C(=O)c2c(C1=O)cccc2
InChi: 1S/C23H25Cl2N3O2/c24-19-9-6-10-20(21(19)25)27-15-13-26(14-16-27)11-4-1-5-12-28-22(29)17-7-2-3-8-18(17)23(28)30/h2-3,6-10H,1,4-5,11-16H2
InChiKey: HZMBQYFOWZCHKD-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

2-[5-[4-(2,3-dichlorophenyl)piperazin-1-yl]pentyl]isoindoline-1,3-dione
2-[5-[4-(2,3-dichlorophenyl)-1-piperazinyl]pentyl]isoindoline-1,3-dione
2-[5-[4-(2,3-dichlorophenyl)piperazino]pentyl]isoindoline-1,3-quinone
2-[5-[4-(2,3-dichlorophenyl)piperazin-1-yl]pentyl]isoindoline-1,3-quinone

Targets

Known targets for this compound

Species	Target name	Source	Bibliographic reference
Homo sapiens	dopamine receptor D3	Starlite/ChEMBL	References
Homo sapiens	dopamine receptor D2	Starlite/ChEMBL	References
Homo sapiens	dopamine receptor D4	Starlite/ChEMBL	References
Rattus norvegicus	Dopamine D2 receptor	Starlite/ChEMBL	References
Rattus norvegicus	Dopamine D3 receptor	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

Species	Potential target	Known druggable target	Length	Alignment span	Identity
Loa Loa (eye worm)	hypothetical protein	Dopamine D3 receptor	446 aa	425 aa	21.4 %
Schistosoma japonicum	ko:K04145 dopamine receptor D2, putative	Dopamine D3 receptor	446 aa	426 aa	28.6 %
Schistosoma mansoni	biogenic amine receptor	Dopamine D3 receptor	446 aa	455 aa	28.6 %
Onchocerca volvulus	RB1-inducible coiled-coil protein 1 homolog	Dopamine D3 receptor	446 aa	478 aa	22.8 %
Onchocerca volvulus		Dopamine D3 receptor	446 aa	462 aa	26.0 %
Onchocerca volvulus		Dopamine D3 receptor	446 aa	434 aa	19.4 %
Brugia malayi	hypothetical protein	dopamine receptor D3	400 aa	392 aa	19.9 %
Onchocerca volvulus	Glycoprotein hormone beta 5 homolog	Dopamine D3 receptor	446 aa	489 aa	22.9 %
Schistosoma mansoni	amine GPCR	Dopamine D3 receptor	446 aa	420 aa	31.4 %
Loa Loa (eye worm)	TYRA-2 protein	Dopamine D3 receptor	446 aa	494 aa	24.3 %
Echinococcus multilocularis	biogenic amine (5HT) receptor	Dopamine D3 receptor	446 aa	499 aa	30.9 %
Echinococcus granulosus	g protein coupled receptor	Dopamine D2 receptor	444 aa	457 aa	21.0 %
Echinococcus multilocularis	g protein coupled receptor	Dopamine D2 receptor	444 aa	465 aa	21.5 %
Schistosoma japonicum	Octopamine receptor, putative	Dopamine D3 receptor	446 aa	501 aa	28.5 %
Echinococcus multilocularis	serotonin receptor	Dopamine D2 receptor	444 aa	428 aa	31.3 %
Schistosoma japonicum	ko:K04145 dopamine receptor D2, putative	Dopamine D3 receptor	446 aa	463 aa	29.8 %
Schistosoma japonicum	ko:K04207 neuropeptide Y receptor Y5, putative	Dopamine D2 receptor	444 aa	386 aa	19.7 %
Schistosoma japonicum	ko:K04136 adrenergic receptor, alpha 1b, putative	Dopamine D2 receptor	444 aa	440 aa	30.0 %
Schistosoma mansoni	biogenic amine (dopamine) receptor	Dopamine D2 receptor	444 aa	494 aa	26.3 %
Echinococcus granulosus	biogenic amine 5HT receptor	Dopamine D2 receptor	444 aa	429 aa	31.7 %
Echinococcus granulosus	alpha 1A adrenergic receptor	Dopamine D3 receptor	446 aa	460 aa	21.1 %
Schistosoma mansoni	muscarinic acetylcholine (GAR) receptor	Dopamine D2 receptor	444 aa	487 aa	23.8 %
Schistosoma mansoni	ancient conserved domain protein 2 (cyclin m2)	Dopamine D3 receptor	446 aa	463 aa	25.5 %
Echinococcus multilocularis	alpha 1A adrenergic receptor	Dopamine D3 receptor	446 aa	473 aa	21.6 %

Ranking Plot

Putative Targets List

Species	Potential target	Raw	Global	Species
Trichomonas vaginalis	Clan CA, family C1, papain-like cysteine peptidase	0.0022	0.1093	0.1093
Onchocerca volvulus		0.0022	0.1093	0.1093
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0022	0.1093	0.1093
Trypanosoma cruzi	cysteine peptidase, putative	0.0022	0.1093	0.1093
Trypanosoma brucei	Eukaryotic initiation factor 4A-1	0.008	1	1
Schistosoma mansoni	cathepsin F (C01 family)	0.0022	0.1093	0.1093
Onchocerca volvulus		0.0022	0.1093	0.1093
Toxoplasma gondii	eukaryotic initiation factor-4A, putative	0.008	1	1
Giardia lamblia	Translation initiation factor eIF-4A, putative	0.008	1	0.5
Trypanosoma cruzi	cysteine peptidase, putative	0.0022	0.1093	0.1093
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0022	0.1093	0.1093
Leishmania major	cathepsin L-like protease	0.0022	0.1093	0.0589
Loa Loa (eye worm)	papain family cysteine protease containing protein	0.0022	0.1093	0.1093
Brugia malayi	Cytochrome P450 family protein	0.0027	0.1895	0.1895
Trichomonas vaginalis	Clan CA, family C1, papain-like cysteine peptidase	0.0022	0.1093	0.1093
Trypanosoma brucei	cysteine peptidase, Clan CA, family C1, Cathepsin L-like	0.0022	0.1093	0.0589
Echinococcus multilocularis	cysteine protease	0.0022	0.1093	0.0589
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0022	0.1093	0.1093
Loa Loa (eye worm)	cytochrome P450 family protein	0.0027	0.1895	0.1895
Loa Loa (eye worm)	cytochrome P450 family protein	0.0027	0.1895	0.1895
Onchocerca volvulus		0.0022	0.1093	0.1093
Trichomonas vaginalis	Clan CA, family C1, papain-like cysteine peptidase	0.0022	0.1093	0.1093
Trichomonas vaginalis	Clan CA, family C1, papain-like cysteine peptidase	0.0022	0.1093	0.1093
Onchocerca volvulus	Eukaryotic initiation factor 4A homolog	0.008	1	1
Echinococcus multilocularis	cathepsin L cysteine protease	0.0022	0.1093	0.0589
Trypanosoma brucei	cysteine peptidase, Clan CA, family C1, Cathepsin L-like	0.0022	0.1093	0.0589
Echinococcus multilocularis	cathepsin l cysteine peptidase	0.0022	0.1093	0.0589
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0022	0.1093	0.1093
Entamoeba histolytica	DEAD/DEAH box helicase, putative	0.008	1	1
Entamoeba histolytica	cysteine protease, putative	0.0022	0.1093	0.1093
Trypanosoma cruzi	cruzipain precursor, putative	0.0022	0.1093	0.1093
Trichomonas vaginalis	DEAD box ATP-dependent RNA helicase, putative	0.008	1	1
Onchocerca volvulus	Cathepsin L homolog	0.0022	0.1093	0.1093
Trypanosoma cruzi	cytochrome P450, putative	0.0027	0.1895	0.1895
Trichomonas vaginalis	Clan CA, family C1, papain-like cysteine peptidase	0.0022	0.1093	0.1093
Trypanosoma brucei	cysteine peptidase, Clan CA, family C1, Cathepsin L-like	0.0022	0.1093	0.0589
Echinococcus multilocularis	eukaryotic initiation factor 4A	0.008	1	1
Schistosoma mansoni	hypothetical protein	0.0018	0.0535	0.0535
Loa Loa (eye worm)	hypothetical protein	0.0022	0.1093	0.1093
Brugia malayi	Cytochrome P450 family protein	0.0057	0.6459	0.6459
Toxoplasma gondii	cathepsin CPL	0.0022	0.1093	0.0589
Mycobacterium tuberculosis	Probable cold-shock DeaD-box protein A homolog DeaD (ATP-dependent RNA helicase dead homolog)	0.008	1	1
Echinococcus granulosus	cathepsin l cysteine peptidase	0.0022	0.1093	0.1093
Schistosoma mansoni	cathepsin F (C01 family)	0.0022	0.1093	0.1093
Loa Loa (eye worm)	cysteine protease	0.0022	0.1093	0.1093
Loa Loa (eye worm)	cytochrome P450 family protein	0.0057	0.6459	0.6459
Trypanosoma cruzi	Lanosterol 14-alpha demethylase	0.0018	0.0535	0.0535
Brugia malayi	Cathepsin L-like precursor	0.0022	0.1093	0.1093
Entamoeba histolytica	cysteine proteinase, putative	0.0022	0.1093	0.1093
Mycobacterium ulcerans	cytochrome P450 185A4 Cyp185A4	0.0027	0.1895	1
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0022	0.1093	0.1093
Loa Loa (eye worm)	Papain cysteine protease/cathepsin propeptide inhibitor-containing protein	0.0022	0.1093	0.1093
Plasmodium vivax	RNA helicase-1, putative	0.008	1	1
Brugia malayi	Papain family cysteine protease containing protein	0.0022	0.1093	0.1093
Echinococcus granulosus	cytochrome P450 2K1	0.0018	0.0535	0.0535
Brugia malayi	cytochrome P450	0.0018	0.0535	0.0535
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0022	0.1093	0.1093
Trypanosoma cruzi	Lanosterol 14-alpha demethylase	0.0018	0.0535	0.0535
Trichomonas vaginalis	DEAD box ATP-dependent RNA helicase, putative	0.008	1	1
Onchocerca volvulus		0.0022	0.1093	0.1093
Trypanosoma cruzi	Eukaryotic initiation factor 4A-1	0.008	1	1
Treponema pallidum	ATP-dependent RNA helicase	0.008	1	0.5
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0022	0.1093	0.1093
Mycobacterium leprae	Conserved hypothetical protein	0.0018	0.0535	0.5
Trypanosoma brucei	cysteine peptidase, Clan CA, family C1, Cathepsin L-like	0.0022	0.1093	0.0589
Trypanosoma brucei	cysteine peptidase, Clan CA, family C1, Cathepsin L-like	0.0022	0.1093	0.0589
Loa Loa (eye worm)	CYP4Cod1	0.0027	0.1895	0.1895
Echinococcus multilocularis	cathepsin l cysteine peptidase	0.0022	0.1093	0.0589
Leishmania major	cysteine peptidase A (CPA)	0.0022	0.1093	0.0589
Echinococcus granulosus	cathepsin L cysteine proteinase	0.0022	0.1093	0.1093
Trypanosoma cruzi	cysteine peptidase, putative	0.0022	0.1093	0.1093
Loa Loa (eye worm)	cytochrome P450	0.0018	0.0535	0.0535
Echinococcus multilocularis	cathepsin L cysteine protease	0.0022	0.1093	0.0589
Trypanosoma brucei	cysteine peptidase, Clan CA, family C1, Cathepsin L-like	0.0022	0.1093	0.0589
Echinococcus multilocularis	cysteine protease	0.0022	0.1093	0.0589
Onchocerca volvulus		0.0022	0.1093	0.1093
Trichomonas vaginalis	Clan CA, family C1, cathepsin L or K-like cysteine peptidase	0.0022	0.1093	0.1093
Trypanosoma cruzi	cytochrome P450, putative	0.0027	0.1895	0.1895
Schistosoma mansoni	DEAD box ATP-dependent RNA helicase	0.008	1	1
Trichomonas vaginalis	Clan CA, family C1, papain-like cysteine peptidase	0.0022	0.1093	0.1093
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0022	0.1093	0.1093
Leishmania major	cytochrome p450-like protein	0.0027	0.1895	0.1437
Leishmania major	eukaryotic initiation factor 4a, putative	0.008	1	1
Trichomonas vaginalis	DEAD box ATP-dependent RNA helicase, putative	0.008	1	1
Loa Loa (eye worm)	fibroinase	0.0022	0.1093	0.1093
Trypanosoma brucei	cysteine peptidase, Clan CA, family C1, Cathepsin L-like	0.0022	0.1093	0.0589
Brugia malayi	Cytochrome P450 family protein	0.0027	0.1895	0.1895
Brugia malayi	Cathepsin L-like precursor	0.0022	0.1093	0.1093
Trypanosoma brucei	cysteine peptidase, Clan CA, family C1, Cathepsin L-like	0.0022	0.1093	0.0589
Trypanosoma cruzi	Eukaryotic initiation factor 4A-1	0.008	1	1
Trypanosoma brucei	cysteine peptidase, Clan CA, family C1, Cathepsin L-like	0.0022	0.1093	0.0589
Brugia malayi	Cathepsin L-like precursor	0.0022	0.1093	0.1093
Schistosoma mansoni	cytochrome P450	0.0018	0.0535	0.0535
Trypanosoma cruzi	cytochrome p450-like protein, putative	0.0018	0.0535	0.0535
Leishmania major	cathepsin L-like protease	0.0022	0.1093	0.0589
Entamoeba histolytica	cysteine proteinase, putative	0.0022	0.1093	0.1093
Loa Loa (eye worm)	ctsf protein	0.0022	0.1093	0.1093
Leishmania major	cathepsin L-like protease	0.0022	0.1093	0.0589
Brugia malayi	Cathepsin L-like precursor	0.0022	0.1093	0.1093
Echinococcus granulosus	cathepsin l1	0.0022	0.1093	0.1093
Echinococcus multilocularis	eukaryotic initiation factor 4A III	0.008	1	1
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0022	0.1093	0.1093
Trichomonas vaginalis	Clan CA, family C1, cathepsin L or K-like cysteine peptidase	0.0022	0.1093	0.1093
Onchocerca volvulus	Cathepsin F homolog	0.0022	0.1093	0.1093
Echinococcus granulosus	eukaryotic initiation factor 4A III	0.008	1	1
Trypanosoma brucei	cysteine peptidase, Clan CA, family C1, Cathepsin L-like	0.0022	0.1093	0.0589
Trichomonas vaginalis	Clan CA, family C1, papain-like cysteine peptidase	0.0022	0.1093	0.1093
Loa Loa (eye worm)	hypothetical protein	0.008	1	1
Leishmania major	cathepsin L-like protease	0.0022	0.1093	0.0589
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0022	0.1093	0.1093
Leishmania major	cathepsin L-like protease	0.0022	0.1093	0.0589
Leishmania major	cathepsin L-like protease	0.0022	0.1093	0.0589
Brugia malayi	Cathepsin L-like precursor	0.0022	0.1093	0.1093
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0022	0.1093	0.1093
Trypanosoma cruzi	cysteine peptidase, putative	0.0022	0.1093	0.1093
Echinococcus granulosus	eukaryotic initiation factor 4A	0.008	1	1
Leishmania major	cathepsin L-like protease	0.0022	0.1093	0.0589
Trichomonas vaginalis	Clan CA, family C1, papain-like cysteine peptidase	0.0022	0.1093	0.1093
Schistosoma mansoni	DEAD box ATP-dependent RNA helicase	0.008	1	1
Trypanosoma brucei	cytochrome P450, putative	0.0027	0.1895	0.1437
Brugia malayi	Cytochrome P450 family protein	0.0018	0.0535	0.0535
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0022	0.1093	0.1093
Trichomonas vaginalis	Clan CA, family C1, papain-like cysteine peptidase	0.0022	0.1093	0.1093
Onchocerca volvulus		0.0022	0.1093	0.1093
Brugia malayi	Cathepsin L-like precursor	0.0022	0.1093	0.1093
Onchocerca volvulus		0.0022	0.1093	0.1093
Onchocerca volvulus	Cathepsin L homolog	0.0022	0.1093	0.1093
Trypanosoma brucei	cysteine peptidase, Clan CA, family C1, Cathepsin L-like	0.0022	0.1093	0.0589
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0022	0.1093	0.1093
Leishmania major	cathepsin L-like protease	0.0022	0.1093	0.0589
Leishmania major	eukaryotic initiation factor 4a, putative	0.008	1	1
Plasmodium falciparum	eukaryotic initiation factor 4A	0.008	1	1
Mycobacterium leprae	putative cytochrome p450	0.0018	0.0535	0.5
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0022	0.1093	0.1093

Activities

Activity type	Activity value	Assay description	Source	Reference
Ki (binding)	= 5.6 nM	Binding affinity towards rat Dopamine receptor D3 in Sf9 cells expressing in recombinant baculovirus (Bv) using [125I]-IABN as radioligand	ChEMBL.	12798330
Ki (binding)	= 5.6 nM	Binding affinity towards rat Dopamine receptor D3 in Sf9 cells expressing in recombinant baculovirus (Bv) using [125I]-IABN as radioligand	ChEMBL.	12798330
Ki (binding)	= 7.8 nM	Binding affinity at dopamine receptor D3	ChEMBL.	11543687
Ki (binding)	= 7.8 nM	Binding affinity at dopamine receptor D3	ChEMBL.	11543687
Ki (binding)	= 11 nM	Binding affinity at human dopamine receptor D2	ChEMBL.	11543687
Ki (binding)	= 11 nM	Binding affinity at human dopamine receptor D2	ChEMBL.	11543687
Ki (binding)	= 86.4 nM	Binding affinity towards rat Dopamine receptor D2 in Sf9 cells expressing in recombinant baculovirus (Bv) using [125I]-IABN as radioligand	ChEMBL.	12798330
Ki (binding)	= 86.4 nM	Binding affinity towards rat Dopamine receptor D2 in Sf9 cells expressing in recombinant baculovirus (Bv) using [125I]-IABN as radioligand	ChEMBL.	12798330
Ki (binding)	= 105 nM	Binding affinity at human dopamine receptor D4	ChEMBL.	11543687
Ki (binding)	= 105 nM	Binding affinity at human dopamine receptor D4	ChEMBL.	11543687
logD	= 5.91	Calculated partition coefficient (clogD)	ChEMBL.	12798330
Ratio (binding)	= 1.4	Ratio between binding affinity towards human D2 and D3 receptors	ChEMBL.	11543687
Ratio (binding)	= 13	Ratio between binding affinity towards human D4 and D3 receptors	ChEMBL.	11543687
Ratio (binding)	= 15	Ratio of binding affinities of D2 receptor to D3 receptor	ChEMBL.	12798330

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

ChEMBL: CHEMBL306672
PubChem: 10983150

Bibliographic References

2 literature references were 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 113193