TDR Targets

Basic information

Technical information

TDR Targets ID: 346831
Name: 1-[(4-hydroxyphenyl)methyl]-5-[(2S)-2-(phenox ymethyl)pyrrolidin-1-yl]sulfonylindole-2,3-di one
MW: 492.544 | Formula: C26H24N2O6S
H donors: 1 H acceptors: 5 LogP: 3.41 Rotable bonds: 7
Rule of 5 violations (Lipinski): 1
SMILES: Oc1ccc(cc1)CN1C(=O)C(=O)c2c1ccc(c2)S(=O)(=O)N1CCC[C@H]1COc1ccccc1
InChi: 1S/C26H24N2O6S/c29-20-10-8-18(9-11-20)16-27-24-13-12-22(15-23(24)25(30)26(27)31)35(32,33)28-14-4-5-19(28)17-34-21-6-2-1-3-7-21/h1-3,6-13,15,19,29H,4-5,14,16-17H2/t19-/m0/s1
InChiKey: KYJSQQPQAAKFQY-IBGZPJMESA-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

1-[(4-hydroxyphenyl)methyl]-5-[(2S)-2-(phenoxymethyl)pyrrolidin-1-yl]sulfonyl-indoline-2,3-dione
1-[(4-hydroxyphenyl)methyl]-5-[[(2S)-2-(phenoxymethyl)-1-pyrrolidinyl]sulfonyl]indoline-2,3-dione
1-[(4-hydroxyphenyl)methyl]-5-[(2S)-2-(phenoxymethyl)pyrrolidin-1-yl]sulfonyl-indole-2,3-dione
1-(4-hydroxybenzyl)-5-[(2S)-2-(phenoxymethyl)pyrrolidino]sulfonyl-isatin
1-(4-hydroxybenzyl)-5-[(2S)-2-(phenoxymethyl)pyrrolidin-1-yl]sulfonyl-isatin

Targets

Known targets for this compound

Species	Target name	Source	Bibliographic reference
Homo sapiens	caspase 6, apoptosis-related cysteine peptidase	Starlite/ChEMBL	References
Homo sapiens	caspase 7, apoptosis-related cysteine peptidase	Starlite/ChEMBL	References
Homo sapiens	caspase 3, apoptosis-related cysteine peptidase	Starlite/ChEMBL	References
Homo sapiens	caspase 1, apoptosis-related cysteine peptidase	Starlite/ChEMBL	References

Predicted pathogen targets for this compound

By orthology

Species	Potential target	Known druggable target/s	Ortholog Group
Echinococcus multilocularis	caspase 3, apoptosis cysteine peptidase	Get druggable targets OG5_130238	All targets in OG5_130238
Schistosoma japonicum	ko:K04397 caspase 7, apoptosis-related cysteine protease, putative	Get druggable targets OG5_130238	All targets in OG5_130238
Echinococcus granulosus	caspase	Get druggable targets OG5_130238	All targets in OG5_130238
Schistosoma mansoni	caspase-3 (C14 family)	Get druggable targets OG5_130238	All targets in OG5_130238
Echinococcus multilocularis	caspase 3	Get druggable targets OG5_130238	All targets in OG5_130238
Echinococcus granulosus	caspase 3 apoptosis cysteine peptidase	Get druggable targets OG5_130238	All targets in OG5_130238
Schistosoma mansoni	caspase-7 (C14 family)	Get druggable targets OG5_130238	All targets in OG5_130238
Echinococcus multilocularis	caspase	Get druggable targets OG5_130238	All targets in OG5_130238
Schistosoma japonicum	ko:K02187 caspase 3, apoptosis-related cysteine protease, putative	Get druggable targets OG5_130238	All targets in OG5_130238
Echinococcus granulosus	caspase 3	Get druggable targets OG5_130238	All targets in OG5_130238

By sequence similarity to non orthologous known druggable targets

Species	Potential target	Known druggable target	Length	Alignment span	Identity
Echinococcus granulosus	caspase 8	caspase 1, apoptosis-related cysteine peptidase	383 aa	312 aa	26.6 %
Brugia malayi	Cell death protein 3 precursor	caspase 6, apoptosis-related cysteine peptidase	293 aa	270 aa	34.4 %
Brugia malayi	Cell death protein 3 precursor	caspase 3, apoptosis-related cysteine peptidase	277 aa	253 aa	38.7 %
Brugia malayi	Cell death protein 3 precursor	caspase 7, apoptosis-related cysteine peptidase	303 aa	256 aa	37.1 %

Ranking Plot

Putative Targets List

Species	Potential target	Raw	Global	Species
Mycobacterium tuberculosis	Probable inosine-5'-monophosphate dehydrogenase GuaB2 (imp dehydrogenase) (inosinic acid dehydrogenase) (inosinate dehydrogenase	0.016	0.3627	1
Plasmodium vivax	inosine-5'-monophosphate dehydrogenase, putative	0.015	0.3173	1
Trypanosoma cruzi	inosine-5'-monophosphate dehydrogenase, putative	0.016	0.3627	1
Trichomonas vaginalis	Clan CD, family C14, metacaspase-like cysteine peptidase	0.0118	0.1607	0.5
Loa Loa (eye worm)	IMP dehydrogenase 1	0.016	0.3627	0.8495
Mycobacterium leprae	Probable inosine-5'-monophosphate dehydrogenase GuaB2 (IMP dehydrogenase) (IMPDH) (IMPD)	0.016	0.3627	1
Schistosoma mansoni	caspase-7 (C14 family)	0.0293	1	1
Trypanosoma cruzi	GMP reductase	0.016	0.3627	1
Leishmania major	inosine-5-monophosphate dehydrogenase	0.016	0.3627	1
Echinococcus granulosus	caspase 3	0.0176	0.4384	0.3309
Echinococcus granulosus	caspase 2	0.0167	0.3984	0.2833
Echinococcus multilocularis	caspase	0.0293	1	1
Trypanosoma cruzi	inosine-5'-monophosphate dehydrogenase, putative	0.016	0.3627	1
Trichomonas vaginalis	conserved hypothetical protein	0.0118	0.1607	0.5
Echinococcus granulosus	caspase	0.0293	1	1
Echinococcus multilocularis	caspase 2	0.0167	0.3984	0.2833
Echinococcus multilocularis	caspase 3, apoptosis cysteine peptidase	0.0293	1	1
Schistosoma mansoni	caspase-3 (C14 family)	0.0293	1	1
Onchocerca volvulus	Cell death protein 3 homolog	0.0167	0.3984	0.5
Trypanosoma cruzi	GMP reductase	0.016	0.3627	1
Schistosoma mansoni	caspase-7 (C14 family)	0.0167	0.3984	0.2833
Trichomonas vaginalis	Clan CD, family C14, metacaspase-like cysteine peptidase	0.0118	0.1607	0.5
Trichomonas vaginalis	Clan CD, family C14, metacaspase-like cysteine peptidase	0.0118	0.1607	0.5
Trichomonas vaginalis	conserved hypothetical protein	0.0118	0.1607	0.5
Trypanosoma brucei	inosine-5'-monophosphate dehydrogenase	0.016	0.3627	1
Trichomonas vaginalis	conserved hypothetical protein	0.0118	0.1607	0.5
Mycobacterium ulcerans	inosine 5'-monophosphate dehydrogenase	0.016	0.3627	1
Trichomonas vaginalis	Clan CD, family C14, metacaspase-like cysteine peptidase	0.0118	0.1607	0.5
Trichomonas vaginalis	conserved hypothetical protein	0.0118	0.1607	0.5
Schistosoma mansoni	inosine-5-monophosphate dehydrogenase	0.016	0.3627	0.2406
Trypanosoma brucei	GMP reductase	0.016	0.3627	1
Trichomonas vaginalis	conserved hypothetical protein	0.0118	0.1607	0.5
Loa Loa (eye worm)	hypothetical protein	0.0167	0.3984	1
Echinococcus multilocularis	inosine 5' monophosphate dehydrogenase 2	0.016	0.3627	0.2406
Trichomonas vaginalis	conserved hypothetical protein	0.0118	0.1607	0.5
Echinococcus granulosus	inosine 5' monophosphate dehydrogenase 2	0.016	0.3627	0.2406
Leishmania major	guanosine monophosphate reductase	0.016	0.3627	1
Brugia malayi	Cell death protein 3 precursor	0.0167	0.3984	1
Wolbachia endosymbiont of Brugia malayi	IMP dehydrogenase	0.016	0.3627	0.5
Trypanosoma cruzi	inosine-5'-monophosphate dehydrogenase, putative	0.016	0.3627	1
Trichomonas vaginalis	Clan CD, family C14, metacaspase-like cysteine peptidase	0.0118	0.1607	0.5
Plasmodium falciparum	inosine-5'-monophosphate dehydrogenase	0.015	0.3173	1
Trichomonas vaginalis	Clan CD, family C14, metacaspase-like cysteine peptidase	0.0118	0.1607	0.5
Toxoplasma gondii	IMP dehydrogenas	0.016	0.3627	1
Echinococcus multilocularis	caspase 3	0.0176	0.4384	0.3309
Trichomonas vaginalis	Clan CD, family C14, metacaspase-like cysteine peptidase	0.0118	0.1607	0.5
Trichomonas vaginalis	Clan CD, family C14, metacaspase-like cysteine peptidase	0.0118	0.1607	0.5
Trichomonas vaginalis	Clan CD, family C14, metacaspase-like cysteine peptidase	0.0118	0.1607	0.5
Brugia malayi	inosine-5'-monophosphate dehydrogenase family protein	0.016	0.3627	0.8495

Activities

Activity type	Activity value	Assay description	Source	Reference
IC50 (binding)	= 7.87	Inhibition of caspase3	ChEMBL.	22503362
IC50 (binding)	= 8.2 nM	Inhibition of caspase 3	ChEMBL.	17154501
IC50 (binding)	= 8.2 nM	Inhibition of caspase 3	ChEMBL.	17154501
IC50 (binding)	= 13.5 nM	Inhibitory activity against caspase 3 using Ac-DEVD-AMC substrate	ChEMBL.	16302804
IC50 (binding)	= 13.5 nM	Inhibitory activity against caspase 3 using Ac-DEVD-AMC substrate	ChEMBL.	16302804
IC50 (binding)	= 44 nM	Inhibitory activity against caspase 7 using Ac-DEVD-AMC substrate	ChEMBL.	16302804
IC50 (binding)	= 44 nM	Inhibitory activity against caspase 7 using Ac-DEVD-AMC substrate	ChEMBL.	16302804
IC50 (binding)	= 52.7 nM	Inhibition of caspase 7	ChEMBL.	17154501
IC50 (binding)	= 52.7 nM	Inhibition of caspase 7	ChEMBL.	17154501
IC50 (binding)	> 5000 nM	Inhibitory activity against caspase 1 using Ac-YVAD-AMC substrate	ChEMBL.	16302804
IC50 (binding)	> 5000 nM	Inhibitory activity against caspase 6 using Ac-VEID-AMC substrate	ChEMBL.	16302804
IC50 (binding)	> 5000 nM	Inhibitory activity against caspase 1 using Ac-YVAD-AMC substrate	ChEMBL.	16302804
IC50 (binding)	> 5000 nM	Inhibitory activity against caspase 6 using Ac-VEID-AMC substrate	ChEMBL.	16302804
IC50 (binding)	> 25000 nM	Inhibition of caspase 1	ChEMBL.	17154501
IC50 (binding)	> 25000 nM	Inhibition of caspase 1	ChEMBL.	17154501
IC50 (binding)	> 50000 nM	Inhibitory activity against caspase 8 using Ac-IETD-AMC substrate	ChEMBL.	16302804
IC50 (binding)	> 50000 nM	Inhibitory activity against caspase 8 using Ac-IETD-AMC substrate	ChEMBL.	16302804
IC50 (binding)	> 500000 nM	Inhibition of caspase 6	ChEMBL.	17154501
IC50 (binding)	> 500000 nM	Inhibition of caspase 8	ChEMBL.	17154501
IC50 (binding)	> 500000 nM	Inhibition of caspase 6	ChEMBL.	17154501
IC50 (binding)	> 500000 nM	Inhibition of caspase 8	ChEMBL.	17154501
Ki (binding)	= 4 nM	Binding affinity to human caspase 3	ChEMBL.	17154501
Ki (binding)	= 4 nM	Binding affinity to human caspase 3	ChEMBL.	17154501

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: CHEMBL200927
PubChem: 11712912

Bibliographic References

3 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 346831