TDR Targets

Basic information

Technical information

TDR Targets ID: 448035
Name: 3-[[2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl indol-3-yl]acetyl]amino]propyl nitrate
MW: 459.88 | Formula: C22H22ClN3O6
H donors: 1 H acceptors: 4 LogP: 4.38 Rotable bonds: 11
Rule of 5 violations (Lipinski): 1
SMILES: COc1ccc2c(c1)c(CC(=O)NCCCO[N+](=O)[O-])c(n2C(=O)c1ccc(cc1)Cl)C
InChi: 1S/C22H22ClN3O6/c1-14-18(13-21(27)24-10-3-11-32-26(29)30)19-12-17(31-2)8-9-20(19)25(14)22(28)15-4-6-16(23)7-5-15/h4-9,12H,3,10-11,13H2,1-2H3,(H,24,27)
InChiKey: LDTKUCHYCAUAFT-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

3-[[2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-indol-3-yl]acetyl]amino]propyl nitrate
nitric acid 3-[[2-[1-[(4-chlorophenyl)-oxomethyl]-5-methoxy-2-methyl-3-indolyl]-1-oxoethyl]amino]propyl ester
3-[2-[1-(4-chlorophenyl)carbonyl-5-methoxy-2-methyl-indol-3-yl]ethanoylamino]propyl nitrate
nitric acid 3-[[2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-indol-3-yl]acetyl]amino]propyl ester

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
Homo sapiens	prostaglandin-endoperoxide synthase 1 (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
Brugia malayi	cathepsin B-like cysteine proteinase	0.3334	0.2898	1
Schistosoma mansoni	cathepsin B-like peptidase (C01 family)	0.3334	0.2898	0.2898
Plasmodium falciparum	plasmepsin VII	0.0421	0	0.5
Onchocerca volvulus		0.0421	0	0.5
Toxoplasma gondii	cathepsin B	0.11	0.0676	1
Trypanosoma cruzi	cysteine peptidase C (CPC), putative	0.3334	0.2898	1
Plasmodium falciparum	plasmepsin VI	0.0421	0	0.5
Plasmodium falciparum	plasmepsin X	0.0421	0	0.5
Plasmodium falciparum	plasmepsin I	0.0421	0	0.5
Plasmodium vivax	aspartyl proteinase, putative	0.0421	0	0.5
Trypanosoma brucei	cysteine peptidase C (CPC)	0.11	0.0676	0.5
Plasmodium falciparum	plasmepsin IX	0.0421	0	0.5
Loa Loa (eye worm)	cathepsin B	0.11	0.0676	0.2333
Echinococcus multilocularis	cathepsin b	0.3334	0.2898	1
Onchocerca volvulus		0.0421	0	0.5
Schistosoma mansoni	cathepsin B-like peptidase (C01 family)	0.11	0.0676	0.0676
Plasmodium falciparum	plasmepsin IV	0.0421	0	0.5
Plasmodium vivax	aspartyl protease, putative	0.0421	0	0.5
Schistosoma mansoni	cathepsin B-like peptidase (C01 family)	0.3334	0.2898	0.2898
Echinococcus granulosus	cathepsin b	0.3334	0.2898	1
Loa Loa (eye worm)	hypothetical protein	0.3334	0.2898	1
Echinococcus granulosus	cathepsin b	0.3334	0.2898	1
Trichomonas vaginalis	Clan CA, family C1, cathepsin B-like cysteine peptidase	0.11	0.0676	1
Plasmodium vivax	aspartyl protease, putative	0.0421	0	0.5
Giardia lamblia	Cathepsin B precursor	0.11	0.0676	0.5
Giardia lamblia	Cathepsin B precursor	0.11	0.0676	0.5
Giardia lamblia	Cathepsin B precursor	0.11	0.0676	0.5
Plasmodium falciparum	plasmepsin V	0.0421	0	0.5
Schistosoma mansoni	cathepsin B-like peptidase (C01 family)	0.3334	0.2898	0.2898
Plasmodium vivax	plasmepsin V, putative	0.0421	0	0.5
Schistosoma mansoni	SmCB2 peptidase (C01 family)	0.3334	0.2898	0.2898
Plasmodium falciparum	plasmepsin II	0.0421	0	0.5
Plasmodium falciparum	plasmepsin VIII, putative	0.0421	0	0.5
Echinococcus multilocularis	cathepsin b	0.3334	0.2898	1
Plasmodium vivax	aspartyl proteinase, putative	0.0421	0	0.5
Plasmodium vivax	aspartyl protease, putative	0.0421	0	0.5
Leishmania major	cysteine peptidase C (CPC),CPC cysteine peptidase, Clan CA, family C1, Cathepsin B-like	0.11	0.0676	0.5
Plasmodium falciparum	plasmepsin III	0.0421	0	0.5
Plasmodium vivax	plasmepsin IV, putative	0.0421	0	0.5

Activities

Activity type	Activity value	Assay description	Source	Reference
Activity (functional)	0	Increase in nitrite plus nitrate levels in Sprague-Dawley rat at 45 umol/kg, po	ChEMBL.	17994684
Activity (functional)	= 71 %	Antiinflammatory activity against Sprague-Dawley rat carrageenan air-pouch model assessed as reduction of prostaglandin E2 at 45 umol/kg, po	ChEMBL.	17994684
Activity (ADMET)	= 85 %	Gastric sparing effect in Sprague-Dawley rat assessed as reduction of aspirin-induced gastric damage at 45 umol/kg, po	ChEMBL.	17994684
Activity (ADMET)	= 98 %	Toxicity in Sprague-Dawley rat assessed as reduction of gastric lesion score at 45 umol/kg, po	ChEMBL.	17994684
Activity (functional)	= 99 %	Antiinflammatory activity against intrapouch dosed Sprague-Dawley rat carrageenan air-pouch model assessed as reduction of prostaglandin E2 at 45 umol/kg	ChEMBL.	17994684
IC50 (binding)	= 1.2 uM	Inhibition of COX2 in human whole blood assessed as effect on LPS-induced thromboxane B2 production	ChEMBL.	17994684
IC50 (binding)	= 1.2 uM	Inhibition of COX2 in human whole blood assessed as effect on LPS-induced thromboxane B2 production	ChEMBL.	17994684
IC50 (binding)	= 6 uM	Inhibition of COX1 in human whole blood assessed as effect on A23187-induced thromboxane B2 production	ChEMBL.	17994684
IC50 (binding)	= 6 uM	Inhibition of COX1 in human whole blood assessed as effect on A23187-induced thromboxane B2 production	ChEMBL.	17994684
Inhibition (binding)	= 0 %	Inhibition of COX1 in human whole blood assessed as effect on A23187-induced thromboxane B2 production at 100 uM relative to control	ChEMBL.	17994684
Inhibition (binding)	= 0 %	Inhibition of COX1 in human whole blood assessed as effect on A23187-induced thromboxane B2 production at 100 uM relative to control	ChEMBL.	17994684
Inhibition (binding)	= 1 %	Inhibition of COX2 in human whole blood assessed as effect on LPS-induced thromboxane B2 production at 30 uM relative to control	ChEMBL.	17994684
Inhibition (binding)	= 1 %	Inhibition of COX2 in human whole blood assessed as effect on LPS-induced thromboxane B2 production at 30 uM relative to control	ChEMBL.	17994684
Inhibition (binding)	= 3 %	Inhibition of COX2 in human whole blood assessed as effect on LPS-induced thromboxane B2 production at 10 uM relative to control	ChEMBL.	17994684
Inhibition (binding)	= 3 %	Inhibition of COX2 in human whole blood assessed as effect on LPS-induced thromboxane B2 production at 10 uM relative to control	ChEMBL.	17994684
Inhibition (binding)	= 7 %	Inhibition of COX1 in human whole blood assessed as effect on A23187-induced thromboxane B2 production at 30 uM relative to control	ChEMBL.	17994684
Inhibition (binding)	= 7 %	Inhibition of COX1 in human whole blood assessed as effect on A23187-induced thromboxane B2 production at 30 uM relative to control	ChEMBL.	17994684
Inhibition (binding)	= 13 %	Inhibition of COX2 in human whole blood assessed as effect on LPS-induced thromboxane B2 production at 3 uM relative to control	ChEMBL.	17994684
Inhibition (binding)	= 13 %	Inhibition of COX2 in human whole blood assessed as effect on LPS-induced thromboxane B2 production at 3 uM relative to control	ChEMBL.	17994684
Inhibition (binding)	= 31 %	Inhibition of COX1 in human whole blood assessed as effect on A23187-induced thromboxane B2 production at 10 uM relative to control	ChEMBL.	17994684
Inhibition (binding)	= 31 %	Inhibition of COX1 in human whole blood assessed as effect on A23187-induced thromboxane B2 production at 10 uM relative to control	ChEMBL.	17994684
Inhibition (binding)	= 65 %	Inhibition of COX1 in human whole blood assessed as effect on A23187-induced thromboxane B2 production at 3 uM relative to control	ChEMBL.	17994684
Inhibition (binding)	= 65 %	Inhibition of COX2 in human whole blood assessed as effect on LPS-induced thromboxane B2 production at 1 uM relative to control	ChEMBL.	17994684
Inhibition (binding)	= 65 %	Inhibition of COX1 in human whole blood assessed as effect on A23187-induced thromboxane B2 production at 3 uM relative to control	ChEMBL.	17994684
Inhibition (binding)	= 65 %	Inhibition of COX2 in human whole blood assessed as effect on LPS-induced thromboxane B2 production at 1 uM relative to control	ChEMBL.	17994684
Inhibition (binding)	= 70 %	Inhibition of COX2 in human whole blood assessed as effect on LPS-induced thromboxane B2 production at 0.3 uM relative to control	ChEMBL.	17994684
Inhibition (binding)	= 70 %	Inhibition of COX2 in human whole blood assessed as effect on LPS-induced thromboxane B2 production at 0.3 uM relative to control	ChEMBL.	17994684
Inhibition (binding)	= 77 %	Inhibition of COX1 in human whole blood assessed as effect on A23187-induced thromboxane B2 production at 1 uM relative to control	ChEMBL.	17994684
Inhibition (binding)	= 77 %	Inhibition of COX1 in human whole blood assessed as effect on A23187-induced thromboxane B2 production at 1 uM relative to control	ChEMBL.	17994684
Inhibition (binding)	= 88 %	Inhibition of COX2 in human whole blood assessed as effect on LPS-induced thromboxane B2 production at 0.1 uM relative to control	ChEMBL.	17994684
Inhibition (binding)	= 88 %	Inhibition of COX2 in human whole blood assessed as effect on LPS-induced thromboxane B2 production at 0.1 uM relative to control	ChEMBL.	17994684
Ratio IC50 (binding)	= 5	Selectivity for human COX2 over human COX1	ChEMBL.	17994684

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: CHEMBL237021
PubChem: 11178642

Bibliographic References

1 literature reference was collected for this gene.

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Detailed information for compound 448035