Detailed information for compound 29303

Basic information

Technical information
  • TDR Targets ID: 29303
  • Name: 2-[3-chloro-4-[3-[(3-ethyl-7-propyl-1,2-benzo xazol-6-yl)oxy]propylsulfanyl]phenyl]acetic a cid
  • MW: 447.975 | Formula: C23H26ClNO4S
  • H donors: 1 H acceptors: 3 LogP: 6.5 Rotable bonds: 11
    Rule of 5 violations (Lipinski): 1
  • SMILES: CCCc1c(OCCCSc2ccc(cc2Cl)CC(=O)O)ccc2c1onc2CC
  • InChi: 1S/C23H26ClNO4S/c1-3-6-17-20(9-8-16-19(4-2)25-29-23(16)17)28-11-5-12-30-21-10-7-15(13-18(21)24)14-22(26)27/h7-10,13H,3-6,11-12,14H2,1-2H3,(H,26,27)
  • InChiKey: LBEYMGDIPDOUKK-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 2-[3-chloro-4-[3-[(3-ethyl-7-propyl-1,2-benzoxazol-6-yl)oxy]propylthio]phenyl]acetic acid
  • 2-[3-chloro-4-[3-[(3-ethyl-7-propyl-1,2-benzoxazol-6-yl)oxy]propylsulfanyl]phenyl]ethanoic acid
  • 2-[3-chloro-4-[3-(3-ethyl-7-propyl-indoxazen-6-yl)oxypropylthio]phenyl]acetic acid

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens peroxisome proliferator-activated receptor alpha Starlite/ChEMBL References
Homo sapiens peroxisome proliferator-activated receptor gamma Starlite/ChEMBL References
Homo sapiens peroxisome proliferator-activated receptor delta Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Schistosoma japonicum IPR008946,Nuclear receptor, ligand-binding,domain-containing Get druggable targets OG5_137778 All targets in OG5_137778
Schistosoma japonicum ko:K08701 nuclear receptor, subfamily 1, invertebrate, putative Get druggable targets OG5_137778 All targets in OG5_137778
Schistosoma mansoni nuclear hormone receptor superfamily protein-related Get druggable targets OG5_137778 All targets in OG5_137778
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Echinococcus granulosus ecdysone induced protein 78C peroxisome proliferator-activated receptor gamma 477 aa 447 aa 28.2 %
Brugia malayi ecdysteroid receptor peroxisome proliferator-activated receptor alpha 468 aa 397 aa 25.4 %
Brugia malayi ecdysteroid receptor peroxisome proliferator-activated receptor delta 441 aa 369 aa 24.7 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Loa Loa (eye worm) FAD binding domain-containing protein 0.1032 0.484 0.3805
Entamoeba histolytica type A flavoprotein, putative 0.0639 0.167 0.5
Schistosoma mansoni 5-methyl tetrahydrofolate-homocysteine methyltransferase reductase 0.1032 0.484 0.484
Toxoplasma gondii flavodoxin domain-containing protein 0.0829 0.3203 0.5
Trypanosoma cruzi p450 reductase, putative 0.1671 1 1
Echinococcus granulosus NADPH cytochrome P450 reductase 0.1671 1 1
Trypanosoma cruzi cytochrome P450 reductase, putative 0.1671 1 1
Entamoeba histolytica type A flavoprotein, putative 0.0639 0.167 0.5
Trypanosoma cruzi cytochrome P450 reductase, putative 0.1671 1 1
Trichomonas vaginalis NADPH fad oxidoreductase, putative 0.1481 0.8466 0.8159
Leishmania major cytochrome P450 reductase, putative 0.1481 0.8466 0.8159
Echinococcus multilocularis NADPH dependent diflavin oxidoreductase 1 0.1671 1 1
Entamoeba histolytica type A flavoprotein, putative 0.0639 0.167 0.5
Schistosoma mansoni cytochrome P450 reductase 0.1671 1 1
Loa Loa (eye worm) hypothetical protein 0.1671 1 1
Treponema pallidum flavodoxin 0.0639 0.167 0.5
Plasmodium falciparum nitric oxide synthase, putative 0.1671 1 1
Entamoeba histolytica type A flavoprotein, putative 0.0639 0.167 0.5
Entamoeba histolytica type A flavoprotein, putative 0.0639 0.167 0.5
Trypanosoma cruzi NADPH-dependent FMN/FAD containing oxidoreductase, putative 0.1671 1 1
Trypanosoma brucei NADPH--cytochrome P450 reductase, putative 0.1671 1 1
Schistosoma mansoni diflavin oxidoreductase 0.0829 0.3203 0.3203
Trypanosoma brucei NADPH-cytochrome p450 reductase, putative 0.1671 1 1
Plasmodium vivax NADPH-cytochrome p450 reductase, putative 0.1671 1 1
Trypanosoma brucei NADPH--cytochrome P450 reductase, putative 0.1671 1 1
Toxoplasma gondii flavodoxin domain-containing protein 0.0829 0.3203 0.5
Loa Loa (eye worm) FAD binding domain-containing protein 0.1671 1 1
Mycobacterium ulcerans formate dehydrogenase H FdhF 0.1671 1 0.5
Echinococcus granulosus NADPH dependent diflavin oxidoreductase 1 0.1671 1 1
Giardia lamblia Hypothetical protein 0.1481 0.8466 0.5
Giardia lamblia Nitric oxide synthase, inducible 0.1481 0.8466 0.5
Brugia malayi FAD binding domain containing protein 0.1671 1 1
Plasmodium vivax flavodoxin domain containing protein 0.1481 0.8466 0.8159
Chlamydia trachomatis sulfite reductase 0.1032 0.484 0.5
Echinococcus multilocularis NADPH cytochrome P450 reductase 0.1671 1 1
Trypanosoma brucei NADPH-dependent diflavin oxidoreductase 1 0.1671 1 1
Leishmania major p450 reductase, putative 0.1671 1 1
Schistosoma mansoni NADPH flavin oxidoreductase 0.0842 0.3306 0.3306
Brugia malayi FAD binding domain containing protein 0.1032 0.484 0.3805
Trichomonas vaginalis sulfite reductase, putative 0.1671 1 1
Leishmania major NADPH-cytochrome p450 reductase-like protein 0.1671 1 1

Activities

Activity type Activity value Assay description Source Reference
AUC (ADMET) = 0.62 ug hr ml-1 Dose-normalized AUC was determined by po administration (10 mg/kg) of the compound in fasted male Sprague-Dawley rats ChEMBL. 12657263
Clp (ADMET) = 17.6 ml min-1 kg-1 Clearance was determined by iv administration (1.5 mg/kg) of the compound in fasted male Sprague-Dawley rats ChEMBL. 12657263
Corr (functional) = 29 % In vivo plasma glucose in Zucker diabetic fatty rat after 11 days at 30 mg/kg/day ChEMBL. 12657263
Corr (functional) = 33 % In vivo plasma glucose in db/db mouse after 11 days at 100 mg/kg/day ChEMBL. 12657263
Corr (functional) = 33 % In vivo plasma glucose in db/db mouse after 11 days at 100 mg/kg/day ChEMBL. 12657263
Corr (functional) = 66 % In vivo plasma glucose in Zucker diabetic fatty rat after 11 days at 100 mg/kg/day ChEMBL. 12657263
Dec (functional) = -14 % In vivo plasma free fatty acid in Zucker diabetic fatty rat after 11 days at 30 mg/kg/day ChEMBL. 12657263
Dec (functional) = 42 % In vivo plasma triglyceride in Zucker diabetic fatty rat after 11 days at 30 mg/kg/day ChEMBL. 12657263
Dec (functional) = 52 % In vivo plasma triglyceride in Zucker diabetic fatty rat after 11 days at 100 mg/kg/day ChEMBL. 12657263
Dec (functional) = 67 % In vivo plasma triglyceride in db/db mouse after 11 days at 100 mg/kg/day ChEMBL. 12657263
Dec (functional) = 67 % In vivo plasma triglyceride in db/db mouse after 11 days at 100 mg/kg/day ChEMBL. 12657263
Dec (functional) = 70 % In vivo plasma free fatty acid in Zucker diabetic fatty rat after 11 days at 100 mg/kg/day ChEMBL. 12657263
EC50 (binding) = 11 nM Transcriptional activation by human PPAR delta ChEMBL. 12657263
EC50 (binding) = 11 nM Transcriptional activation by human PPAR delta ChEMBL. 12657263
EC50 (binding) = 19 nM Transcriptional activation by human PPAR gamma ChEMBL. 12657263
EC50 (binding) = 19 nM Transcriptional activation by human PPAR gamma ChEMBL. 12657263
EC50 (binding) = 247 nM Transcriptional activation by human PPAR alpha ChEMBL. 12657263
EC50 (binding) = 247 nM Transcriptional activation by human PPAR alpha ChEMBL. 12657263
EC50 (binding) = 0.012 uM Agonist activity at human PPARdelta ligand binding domain expressed in human 293T cells co-transfected with Gal4-DBD by luciferase transactivation assay ChEMBL. 19928766
EC50 (binding) = 0.1 uM Agonist activity at human PPARgamma ligand binding domain expressed in human 293T cells co-transfected with Gal4-DBD by luciferase transactivation assay ChEMBL. 19928766
EC50 (binding) = 1.3 uM Agonist activity at human PPARalpha ligand binding domain expressed in human 293T cells co-transfected with Gal4-DBD by luciferase transactivation assay ChEMBL. 19928766
F (ADMET) = 50 % Oral bioavailability in rat (Sprague-Dawley) (fasted male) (dose 10 mg/kg) ChEMBL. 12657263
IC50 (functional) = 6.244 Agonist activity at PPARalpha ChEMBL. 22564380
IC50 (functional) = 6.959 Agonist activity at PPARgamma ChEMBL. 22564380
IC50 (functional) = 8.398 Agonist activity at PPARdelta ChEMBL. 22564380
IC50 (binding) = 4 nM In vitro binding affinity for human PPAR delta in SPA ChEMBL. 12657263
IC50 (binding) = 4 nM In vitro binding affinity for human PPAR delta in SPA ChEMBL. 12657263
IC50 (binding) = 110 nM In vitro binding affinity for human PPAR gamma in SPA ChEMBL. 12657263
IC50 (binding) = 110 nM In vitro binding affinity for human PPAR gamma in SPA ChEMBL. 12657263
IC50 (functional) = 110 nM Displacement of radio-labeled full agonist from PPARgamma receptor ChEMBL. 21482446
IC50 (binding) = 570 nM In vitro binding affinity for human PPAR alpha in SPA ChEMBL. 12657263
IC50 (binding) = 570 nM In vitro binding affinity for human PPAR alpha in SPA ChEMBL. 12657263
T1/2 (ADMET) = 1 hr Half-life was determined by iv administration (1.5 mg/kg) of the compound in fasted male Sprague-Dawley rats ChEMBL. 12657263

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

Bibliographic References

4 literature references were collected for this gene.

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