TDR Targets

Basic information

Technical information

TDR Targets ID: 32329
Name: 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindo l-3-yl]-N-[(2R)-1-hydroxy-4-methylsulfanylbut an-2-yl]acetamide
MW: 475 | Formula: C24H27ClN2O4S
H donors: 2 H acceptors: 3 LogP: 4.14 Rotable bonds: 11
Rule of 5 violations (Lipinski): 1
SMILES: CSCC[C@@H](NC(=O)Cc1c(C)n(c2c1cc(OC)cc2)C(=O)c1ccc(cc1)Cl)CO
InChi: 1S/C24H27ClN2O4S/c1-15-20(13-23(29)26-18(14-28)10-11-32-3)21-12-19(31-2)8-9-22(21)27(15)24(30)16-4-6-17(25)7-5-16/h4-9,12,18,28H,10-11,13-14H2,1-3H3,(H,26,29)/t18-/m1/s1
InChiKey: PMLQJXADXWPWHU-GOSISDBHSA-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-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-indol-3-yl]-N-[(1R)-1-(hydroxymethyl)-3-methylsulfanyl-propyl]acetamide
2-[1-[(4-chlorophenyl)-oxomethyl]-5-methoxy-2-methyl-3-indolyl]-N-[(1R)-1-(hydroxymethyl)-3-(methylthio)propyl]acetamide
2-[1-(4-chlorophenyl)carbonyl-5-methoxy-2-methyl-indol-3-yl]-N-[(2R)-1-hydroxy-4-methylsulfanyl-butan-2-yl]ethanamide
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-indol-3-yl]-N-[(1R)-1-methylol-3-(methylthio)propyl]acetamide

Targets

Known targets for this compound

Species	Target name	Source	Bibliographic reference
Homo sapiens	prostaglandin-endoperoxide synthase 2 (prostaglandin G/H synthase and cyclooxygenase)	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

No druggable targets predicted by sequence similarity

Ranking Plot

Putative Targets List

Species	Potential target	Raw	Global	Species
Echinococcus multilocularis	Tubulin beta 2C chain	0.0513	1	1
Leishmania major	alpha tubulin	0.0379	0.6718	0.6599
Schistosoma mansoni	tubulin subunit alpha	0.0379	0.6718	0.6599
Schistosoma mansoni	tubulin subunit epsilon	0.0274	0.415	0.3938
Plasmodium vivax	tubulin beta chain, putative	0.0513	1	1
Loa Loa (eye worm)	tubulin alpha 2	0.026	0.3801	0.3801
Echinococcus granulosus	Tubulin alpha 1 chain	0.0379	0.6718	0.6599
Echinococcus granulosus	tubulin epsilon chain	0.0274	0.415	0.3938
Echinococcus granulosus	tubulin subunit TubB	0.0379	0.6718	0.6599
Trichomonas vaginalis	tubulin beta chain, putative	0.0379	0.6718	0.6599
Trypanosoma brucei	epsilon tubulin	0.0274	0.415	0.3938
Echinococcus multilocularis	tubulin, beta 4A class IVa	0.0513	1	1
Loa Loa (eye worm)	BEN-1 protein	0.0513	1	1
Echinococcus granulosus	tubulin alpha chain	0.0379	0.6718	0.6599
Leishmania major	alpha tubulin	0.0379	0.6718	0.6599
Leishmania major	beta tubulin	0.0513	1	1
Echinococcus granulosus	tubulin subunit beta	0.0513	1	1
Echinococcus multilocularis	Tubulin beta 2C chain	0.0513	1	1
Brugia malayi	tubulin alpha chain - mouse	0.0379	0.6718	0.6599
Schistosoma mansoni	tubulin subunit beta	0.0513	1	1
Trichomonas vaginalis	tubulin alpha-1 chain, putative	0.0379	0.6718	0.6599
Trypanosoma brucei	beta tubulin	0.0513	1	1
Echinococcus granulosus	Tubulin beta 2C chain	0.0513	1	1
Echinococcus granulosus	beta tubulin	0.0513	1	1
Leishmania major	beta tubulin	0.0513	1	1
Trypanosoma brucei	alpha tubulin	0.0379	0.6718	0.6599
Trypanosoma cruzi	tubulin gamma chain	0.0274	0.415	0.3938
Schistosoma mansoni	tubulin subunit alpha	0.0379	0.6718	0.6599
Echinococcus granulosus	Tubulin alpha 1 chain	0.0379	0.6718	0.6599
Echinococcus granulosus	alpha tubulin	0.0379	0.6718	0.6599
Mycobacterium leprae	cell division protein FtsZ	0.0119	0.0349	0.5
Giardia lamblia	Beta tubulin	0.0513	1	1
Trichomonas vaginalis	tubulin beta chain, putative	0.0379	0.6718	0.6599
Treponema pallidum	cell division protein FtsZ	0.0119	0.0349	0.5
Plasmodium falciparum	tubulin gamma chain	0.0274	0.415	0.3938
Leishmania major	beta tubulin	0.0513	1	1
Trypanosoma cruzi	epsilon tubulin, putative	0.0274	0.415	0.3938
Echinococcus multilocularis	tubulin alpha 1C chain	0.0379	0.6718	0.6599
Schistosoma mansoni	tubulin subunit beta	0.0513	1	1
Brugia malayi	Tubulin alpha-2 chain	0.0379	0.6718	0.6599
Leishmania major	alpha tubulin	0.0379	0.6718	0.6599
Echinococcus granulosus	tubulin alpha chain	0.0379	0.6718	0.6599
Entamoeba histolytica	tubulin alpha chain, putative	0.0379	0.6718	0.4389
Leishmania major	beta tubulin	0.0513	1	1
Echinococcus multilocularis	Tubulin alpha 1 chain	0.0379	0.6718	0.6599
Echinococcus multilocularis	Tubulin alpha 1 chain	0.0379	0.6718	0.6599
Trichomonas vaginalis	tubulin alpha chain, putative	0.0274	0.415	0.3938
Plasmodium falciparum	tubulin beta chain	0.0513	1	1
Leishmania major	beta tubulin	0.0513	1	1
Loa Loa (eye worm)	hypothetical protein	0.0379	0.6718	0.6718
Echinococcus granulosus	beta tubulin	0.0513	1	1
Plasmodium falciparum	tubulin epsilon chain, putative	0.0274	0.415	0.3938
Loa Loa (eye worm)	alpha-tubulin	0.0379	0.6718	0.6718
Loa Loa (eye worm)	alpha-tubulin	0.0379	0.6718	0.6718
Echinococcus multilocularis	tubulin alpha chain	0.0379	0.6718	0.6599
Leishmania major	beta tubulin	0.0513	1	1
Plasmodium falciparum	alpha tubulin 2	0.0379	0.6718	0.6599
Trypanosoma brucei	alpha tubulin	0.0379	0.6718	0.6599
Echinococcus granulosus	Tubulin beta 2C chain	0.0513	1	1
Echinococcus multilocularis	tubulin alpha chain	0.0379	0.6718	0.6599
Leishmania major	beta tubulin	0.0513	1	1
Loa Loa (eye worm)	tubulin alpha chain	0.0379	0.6718	0.6718
Echinococcus granulosus	Tubulin beta 2C chain	0.0513	1	1
Schistosoma mansoni	alpha tubulin	0.0379	0.6718	0.6599
Leishmania major	beta tubulin	0.0513	1	1
Echinococcus granulosus	tubulin alpha chain	0.0379	0.6718	0.6599
Trichomonas vaginalis	tubulin alpha-1 chain, putative	0.0155	0.1233	0.0916
Leishmania major	beta tubulin	0.0513	1	1
Echinococcus multilocularis	tubulin alpha chain	0.0379	0.6718	0.6599
Echinococcus multilocularis	hypothetical protein	0.0379	0.6718	0.6599
Schistosoma mansoni	tubulin subunit beta	0.0513	1	1
Echinococcus granulosus	tubulin alpha	0.0274	0.415	0.3938
Leishmania major	beta tubulin	0.0513	1	1
Trypanosoma brucei	alpha tubulin	0.0379	0.6718	0.6599
Echinococcus multilocularis	Tubulin beta 2C chain	0.0513	1	1
Schistosoma mansoni	tubulin subunit beta	0.0513	1	1
Trypanosoma brucei	epsilon tubulin	0.0274	0.415	0.3938
Leishmania major	beta tubulin	0.0513	1	1
Toxoplasma gondii	beta-1 tubulin, putative	0.0513	1	1
Echinococcus granulosus	tubulin gamma 1 chain	0.0274	0.415	0.3938
Loa Loa (eye worm)	hypothetical protein	0.026	0.3801	0.3801
Plasmodium vivax	tubulin alpha chain, putative	0.0379	0.6718	0.6599
Trichomonas vaginalis	tubulin alpha-1 chain, putative	0.026	0.3801	0.3577
Toxoplasma gondii	alpha tubulin TUBA1	0.0379	0.6718	0.6599
Echinococcus multilocularis	beta tubulin	0.0513	1	1
Echinococcus multilocularis	tubulin epsilon chain	0.0274	0.415	0.3938
Trichomonas vaginalis	tubulin beta chain, putative	0.0379	0.6718	0.6599
Echinococcus multilocularis	tubulin subunit TubB	0.0379	0.6718	0.6599
Plasmodium vivax	tubulin epsilon chain, putative	0.0274	0.415	0.3938
Trichomonas vaginalis	tubulin epsilon chain, putative	0.0513	1	1
Trichomonas vaginalis	tubulin alpha chain, putative	0.0155	0.1233	0.0916
Loa Loa (eye worm)	BEN-1 protein	0.0513	1	1
Leishmania major	beta tubulin	0.0513	1	1
Schistosoma mansoni	alpha tubulin	0.0379	0.6718	0.6599
Loa Loa (eye worm)	tubulin beta-4 chain	0.0513	1	1
Loa Loa (eye worm)	tubulin beta chain	0.0513	1	1
Leishmania major	epsilon tubulin, putative	0.0274	0.415	0.3938
Echinococcus granulosus	peroxisome assembly protein 26	0.0379	0.6718	0.6599
Brugia malayi	alpha-tubulin	0.0379	0.6718	0.6599
Toxoplasma gondii	alpha-tubulin I, putative	0.0379	0.6718	0.6599
Loa Loa (eye worm)	tubulin alpha-3 chain	0.0224	0.2917	0.2917
Trichomonas vaginalis	tubulin gamma chain, putative	0.0513	1	1
Schistosoma mansoni	tubulin subunit beta	0.0513	1	1
Echinococcus granulosus	tubulin beta 4A class IVa	0.0513	1	1
Echinococcus multilocularis	Tubulin beta 2C chain	0.0513	1	1
Leishmania major	alpha tubulin	0.0379	0.6718	0.6599
Trichomonas vaginalis	tubulin, putative	0.0513	1	1
Trichomonas vaginalis	tubulin, putative	0.0155	0.1233	0.0916
Trichomonas vaginalis	tubulin, putative	0.0155	0.1233	0.0916
Schistosoma mansoni	tubulin subunit gamma	0.0274	0.415	0.3938
Echinococcus multilocularis	peroxisome assembly protein 26	0.0379	0.6718	0.6599
Echinococcus multilocularis	tubulin beta 1 chain	0.0513	1	1
Loa Loa (eye worm)	tubulin beta chain	0.0119	0.0349	0.0349
Trypanosoma brucei	alpha tubulin, putative	0.0155	0.1233	0.0916
Trypanosoma cruzi	epsilon tubulin, putative	0.0274	0.415	0.3938
Echinococcus multilocularis	beta tubulin	0.0513	1	1
Brugia malayi	Tubulin alpha chain	0.0379	0.6718	0.6599
Brugia malayi	Tubulin gamma chain	0.0274	0.415	0.3938
Trypanosoma brucei	beta tubulin	0.0274	0.415	0.3938
Echinococcus granulosus	tubulin alpha chain	0.0379	0.6718	0.6599
Trichomonas vaginalis	tubulin beta chain, putative	0.0379	0.6718	0.6599
Echinococcus granulosus	Tubulin alpha 1 chain	0.0379	0.6718	0.6599
Schistosoma mansoni	tubulin subunit alpha	0.0379	0.6718	0.6599
Wolbachia endosymbiont of Brugia malayi	cell division protein FtsZ	0.0119	0.0349	0.5
Toxoplasma gondii	beta-tubulin, putative	0.0513	1	1
Trypanosoma brucei	epsilon tubulin	0.0274	0.415	0.3938
Entamoeba histolytica	tubulin family protein	0.0513	1	1
Echinococcus granulosus	tubulin alpha 1C chain	0.0379	0.6718	0.6599
Echinococcus granulosus	tubulin alpha 3 chain	0.0379	0.6718	0.6599
Leishmania major	alpha tubulin	0.0379	0.6718	0.6599
Loa Loa (eye worm)	hypothetical protein	0.0224	0.2917	0.2917
Giardia lamblia	Alpha-tubulin	0.0379	0.6718	0.6599
Trichomonas vaginalis	tubulin alpha chain, putative	0.0513	1	1
Echinococcus granulosus	tubulin beta 1 chain	0.0513	1	1
Giardia lamblia	Alpha-tubulin	0.0379	0.6718	0.6599
Trichomonas vaginalis	tubulin beta chain, putative	0.0155	0.1233	0.0916
Loa Loa (eye worm)	tubulin beta-2A chain	0.0513	1	1
Plasmodium falciparum	alpha tubulin 1	0.0379	0.6718	0.6599
Brugia malayi	beta-tubulin, identical	0.0513	1	1
Echinococcus multilocularis	tubulin alpha 3 chain	0.0379	0.6718	0.6599
Leishmania major	alpha tubulin	0.0379	0.6718	0.6599
Leishmania major	gamma-tubulin	0.0274	0.415	0.3938
Echinococcus multilocularis	Tubulin beta 2C chain	0.0513	1	1
Leishmania major	alpha tubulin	0.0379	0.6718	0.6599
Echinococcus multilocularis	tubulin alpha 1C chain	0.0379	0.6718	0.6599
Toxoplasma gondii	beta tubulin	0.0513	1	1
Leishmania major	alpha tubulin	0.0379	0.6718	0.6599
Echinococcus granulosus	tubulin alpha 3 chain	0.0379	0.6718	0.6599
Trichomonas vaginalis	tubulin epsilon chain, putative	0.0513	1	1
Trichomonas vaginalis	tubulin alpha chain, putative	0.0155	0.1233	0.0916
Leishmania major	alpha tubulin	0.0379	0.6718	0.6599
Onchocerca volvulus		0.0155	0.1233	0.5
Trichomonas vaginalis	tubulin epsilon chain, putative	0.0379	0.6718	0.6599
Loa Loa (eye worm)	tubulin gamma chain	0.0274	0.415	0.415
Leishmania major	beta tubulin	0.0513	1	1
Trichomonas vaginalis	tubulin alpha-1 chain, putative	0.0224	0.2917	0.2661
Leishmania major	alpha tubulin	0.0379	0.6718	0.6599
Giardia lamblia	Beta tubulin	0.0513	1	1
Loa Loa (eye worm)	tubulin beta-1 chain	0.0513	1	1
Schistosoma mansoni	tubulin subunit beta	0.0513	1	1
Loa Loa (eye worm)	tubulin alpha chain	0.0379	0.6718	0.6718
Leishmania major	alpha tubulin	0.0379	0.6718	0.6599
Trypanosoma brucei	alpha tubulin	0.0379	0.6718	0.6599
Leishmania major	beta tubulin	0.0513	1	1
Trichomonas vaginalis	tubulin beta chain, putative	0.0379	0.6718	0.6599
Trypanosoma brucei	beta tubulin	0.0513	1	1
Leishmania major	beta tubulin	0.0513	1	1
Trypanosoma brucei	tubulin gamma chain	0.0274	0.415	0.3938
Echinococcus multilocularis	tubulin alpha chain	0.0379	0.6718	0.6599
Mycobacterium ulcerans	cell division protein FtsZ	0.0119	0.0349	0.5
Trichomonas vaginalis	tubulin gamma chain, putative	0.0274	0.415	0.3938
Giardia lamblia	Beta tubulin	0.0513	1	1
Trichomonas vaginalis	tubulin alpha chain, putative	0.0155	0.1233	0.0916
Echinococcus multilocularis	tubulin alpha 3 chain	0.0379	0.6718	0.6599
Echinococcus granulosus	Tubulin beta 2C chain	0.0513	1	1
Trichomonas vaginalis	tubulin epsilon chain, putative	0.0379	0.6718	0.6599
Trichomonas vaginalis	tubulin gamma chain, putative	0.0274	0.415	0.3938
Trypanosoma brucei	beta tubulin	0.0513	1	1
Echinococcus granulosus	Tubulin beta 2C chain	0.0513	1	1
Giardia lamblia	Gamma tubulin	0.0274	0.415	0.3938
Echinococcus granulosus	tubulin alpha 1C chain	0.0379	0.6718	0.6599
Schistosoma mansoni	alpha tubulin	0.0379	0.6718	0.6599
Plasmodium vivax	tubulin alpha chain, putative	0.0379	0.6718	0.6599
Plasmodium vivax	tubulin gamma chain, putative	0.0274	0.415	0.3938
Loa Loa (eye worm)	tubulin alpha-2 chain	0.0379	0.6718	0.6718
Brugia malayi	tubulin alpha-2 chain	0.0379	0.6718	0.6599
Echinococcus granulosus	tubulin alpha chain	0.0379	0.6718	0.6599
Leishmania major	alpha tubulin	0.0379	0.6718	0.6599
Brugia malayi	Tubulin beta chain	0.0155	0.1233	0.0916
Echinococcus multilocularis	tubulin gamma 1 chain	0.0274	0.415	0.3938
Loa Loa (eye worm)	beta-tubulin	0.0513	1	1
Toxoplasma gondii	tubulin/FtsZ family, GTPase domain-containing protein	0.0274	0.415	0.3938
Trichomonas vaginalis	tubulin beta chain, putative	0.0379	0.6718	0.6599
Trypanosoma brucei	beta tubulin	0.0513	1	1
Echinococcus multilocularis	tubulin alpha chain	0.0379	0.6718	0.6599
Brugia malayi	Tubulin alpha-2 chain	0.0379	0.6718	0.6599
Loa Loa (eye worm)	alpha-tubulin isotype 2	0.026	0.3801	0.3801
Trichomonas vaginalis	tubulin beta chain, putative	0.0513	1	1
Mycobacterium tuberculosis	Cell division protein FtsZ	0.0119	0.0349	0.5
Trypanosoma cruzi	beta tubulin, putative	0.0513	1	1
Echinococcus multilocularis	tubulin subunit beta	0.0513	1	1
Leishmania major	beta tubulin	0.0513	1	1
Leishmania major	beta tubulin	0.0513	1	1
Echinococcus multilocularis	tubulin alpha	0.0274	0.415	0.3938
Echinococcus multilocularis	Tubulin alpha 1 chain	0.0379	0.6718	0.6599
Loa Loa (eye worm)	tubulin alpha 2	0.026	0.3801	0.3801
Entamoeba histolytica	tubulin family protein	0.0513	1	1
Leishmania major	beta tubulin	0.0513	1	1
Trypanosoma cruzi	alpha tubulin, putative	0.0379	0.6718	0.6599
Entamoeba histolytica	tubulin alpha-1 chain	0.0379	0.6718	0.4389

Activities

Activity type	Activity value	Assay description	Source	Reference
IC50 (binding)	= 0.25 uM	Inhibitory concentration against human prostaglandin G/H synthase 2	ChEMBL.	11965379
IC50 (binding)	= 0.25 uM	Inhibition of human COX2	ChEMBL.	17656360
IC50 (binding)	= 0.25 uM	Inhibitory concentration against human prostaglandin G/H synthase 2	ChEMBL.	11965379
IC50 (binding)	= 0.25 uM	Inhibition of human COX2	ChEMBL.	17656360
IC50 (binding)	= 51 uM	Inhibitory concentration against prostaglandin G/H synthase 1	ChEMBL.	11965379
IC50 (binding)	= 51 uM	Inhibition of ovine COX1	ChEMBL.	17656360
IC50 (binding)	= 51 uM	Inhibitory concentration against prostaglandin G/H synthase 1	ChEMBL.	11965379
IC50 (binding)	= 51 uM	Inhibition of ovine COX1	ChEMBL.	17656360
Ratio (binding)	= 200	Ratio of inhibitory concentration of prostaglandin G/H synthase 1 to prostaglandin G/H synthase 2	ChEMBL.	11965379
Ratio (binding)	= 200	Ratio of inhibitory concentration of prostaglandin G/H synthase 1 to prostaglandin G/H synthase 2	ChEMBL.	11965379

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: CHEMBL432260
PubChem: 24825530

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 32329