Detailed information for compound 1516773

Basic information

Technical information
  • TDR Targets ID: 1516773
  • Name: (2R)-2-(3-chloro-4-methylsulfonylphenyl)-3-[( 1R)-3-oxocyclopentyl]-N-pyrazin-2-ylpropanami de
  • MW: 421.898 | Formula: C19H20ClN3O4S
  • H donors: 1 H acceptors: 6 LogP: 1.21 Rotable bonds: 7
    Rule of 5 violations (Lipinski): 1
  • SMILES: O=C1CC[C@@H](C1)C[C@H](c1ccc(c(c1)Cl)S(=O)(=O)C)C(=O)Nc1cnccn1
  • InChi: 1S/C19H20ClN3O4S/c1-28(26,27)17-5-3-13(10-16(17)20)15(9-12-2-4-14(24)8-12)19(25)23-18-11-21-6-7-22-18/h3,5-7,10-12,15H,2,4,8-9H2,1H3,(H,22,23,25)/t12-,15+/m0/s1
  • InChiKey: XEANIURBPHCHMG-SWLSCSKDSA-N  


Substructure search Similarity search

Network

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Synonyms

  • (2R)-2-(3-chloro-4-methylsulfonyl-phenyl)-3-[(1R)-3-oxocyclopentyl]-N-pyrazin-2-yl-propanamide
  • (2R)-2-(3-chloro-4-methylsulfonylphenyl)-3-[(1R)-3-oxocyclopentyl]-N-(2-pyrazinyl)propanamide
  • (2R)-2-(3-chloro-4-mesyl-phenyl)-3-[(1R)-3-ketocyclopentyl]-N-pyrazin-2-yl-propionamide

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens glucokinase (hexokinase 4) Starlite/ChEMBL References
Homo sapiens peroxisome proliferator-activated receptor delta Starlite/ChEMBL No references
Rattus norvegicus Hexokinase type IV Starlite/ChEMBL No references

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Echinococcus granulosus hexokinase Get druggable targets OG5_126743 All targets in OG5_126743
Babesia bovis hexokinase Get druggable targets OG5_126743 All targets in OG5_126743
Candida albicans similar to D.occidentalis hexokinase HXK which is able to phosphorylate glucose and fructose Get druggable targets OG5_126743 All targets in OG5_126743
Echinococcus multilocularis hexokinase Get druggable targets OG5_126743 All targets in OG5_126743
Onchocerca volvulus Get druggable targets OG5_126743 All targets in OG5_126743
Echinococcus granulosus hexokinase type 2 Get druggable targets OG5_126743 All targets in OG5_126743
Echinococcus multilocularis hexokinase Get druggable targets OG5_126743 All targets in OG5_126743
Echinococcus multilocularis hexokinase type 2 Get druggable targets OG5_126743 All targets in OG5_126743
Brugia malayi hexokinase Get druggable targets OG5_126743 All targets in OG5_126743
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_126743 All targets in OG5_126743
Candida albicans one of four closely related hexokinase-like genes similar to P.angusta GLK1 and to S. cerevisiae Glucokinase GLK1 (YCL040W) Get druggable targets OG5_126743 All targets in OG5_126743
Toxoplasma gondii hexokinase Get druggable targets OG5_126743 All targets in OG5_126743
Echinococcus granulosus hexokinase Get druggable targets OG5_126743 All targets in OG5_126743
Brugia malayi Hexokinase family protein Get druggable targets OG5_126743 All targets in OG5_126743
Candida albicans one of four closely related hexokinase-like genes similar to P.angusta GLK1 and to S. cerevisiae GLK1 (YCL040W) Get druggable targets OG5_126743 All targets in OG5_126743
Plasmodium yoelii hexokinase Get druggable targets OG5_126743 All targets in OG5_126743
Plasmodium falciparum hexokinase Get druggable targets OG5_126743 All targets in OG5_126743
Entamoeba histolytica hexokinase 1 Get druggable targets OG5_126743 All targets in OG5_126743
Candida albicans one of four closely related hexokinase-like genes similar to P.angusta GLK1 and to S. cerevisiae Glucokinase GLK1 (YCL040W) Get druggable targets OG5_126743 All targets in OG5_126743
Trypanosoma cruzi hexokinase, putative Get druggable targets OG5_126743 All targets in OG5_126743
Trypanosoma brucei gambiense hexokinase, putative Get druggable targets OG5_126743 All targets in OG5_126743
Trypanosoma brucei gambiense hexokinase, putative Get druggable targets OG5_126743 All targets in OG5_126743
Trypanosoma brucei hexokinase, putative Get druggable targets OG5_126743 All targets in OG5_126743
Cryptosporidium hominis hexokinase i Get druggable targets OG5_126743 All targets in OG5_126743
Leishmania major hexokinase, putative Get druggable targets OG5_126743 All targets in OG5_126743
Plasmodium berghei hexokinase, putative Get druggable targets OG5_126743 All targets in OG5_126743
Onchocerca volvulus Get druggable targets OG5_126743 All targets in OG5_126743
Entamoeba histolytica hexokinase 2 Get druggable targets OG5_126743 All targets in OG5_126743
Leishmania donovani hexokinase, putative Get druggable targets OG5_126743 All targets in OG5_126743
Neospora caninum cDNA FLJ57348, highly similar to Homo sapiens hexokinase domain containing 1 (HKDC1), mRNA, related Get druggable targets OG5_126743 All targets in OG5_126743
Echinococcus multilocularis hexokinase Get druggable targets OG5_126743 All targets in OG5_126743
Loa Loa (eye worm) hexokinase type II Get druggable targets OG5_126743 All targets in OG5_126743
Trypanosoma cruzi hexokinase, putative Get druggable targets OG5_126743 All targets in OG5_126743
Loa Loa (eye worm) hexokinase Get druggable targets OG5_126743 All targets in OG5_126743
Plasmodium vivax hexokinase, putative Get druggable targets OG5_126743 All targets in OG5_126743
Loa Loa (eye worm) hexokinase Get druggable targets OG5_126743 All targets in OG5_126743
Candida albicans one of four closely related hexokinase-like genes similar to P.angusta GLK1 and to S. cerevisiae Glucokinase GLK1 (YCL040W) Get druggable targets OG5_126743 All targets in OG5_126743
Leishmania mexicana hexokinase, putative Get druggable targets OG5_126743 All targets in OG5_126743
Trypanosoma brucei hexokinase Get druggable targets OG5_126743 All targets in OG5_126743
Leishmania infantum hexokinase, putative Get druggable targets OG5_126743 All targets in OG5_126743
Theileria parva hexokinase, putative Get druggable targets OG5_126743 All targets in OG5_126743
Trypanosoma brucei hexokinase Get druggable targets OG5_126743 All targets in OG5_126743
Cryptosporidium parvum hexokinase Get druggable targets OG5_126743 All targets in OG5_126743
Echinococcus granulosus hexokinase Get druggable targets OG5_126743 All targets in OG5_126743
Candida albicans similar to D.occidentalis hexokinase HXK which is able to phosphorylate glucose and fructose Get druggable targets OG5_126743 All targets in OG5_126743
Treponema pallidum hexokinase (hxk) Get druggable targets OG5_126743 All targets in OG5_126743
Leishmania major hexokinase, putative Get druggable targets OG5_126743 All targets in OG5_126743
Schistosoma mansoni hexokinase Get druggable targets OG5_126743 All targets in OG5_126743
Candida albicans one of four closely related hexokinase-like genes similar to P.angusta GLK1 and to S. cerevisiae Glucokinase GLK1 (YCL040W) Get druggable targets OG5_126743 All targets in OG5_126743
Leishmania braziliensis hexokinase, putative Get druggable targets OG5_126743 All targets in OG5_126743
Onchocerca volvulus Get druggable targets OG5_126743 All targets in OG5_126743
Leishmania mexicana hexokinase, putative Get druggable targets OG5_126743 All targets in OG5_126743
Candida albicans one of four closely related hexokinase-like genes similar to P.angusta GLK1 and to S. cerevisiae Glucokinase GLK1 (YCL040W) Get druggable targets OG5_126743 All targets in OG5_126743
Leishmania infantum hexokinase, putative Get druggable targets OG5_126743 All targets in OG5_126743
Candida albicans one of four closely related hexokinase-like genes similar to P.angusta GLK1 and to S. cerevisiae Glucokinase GLK1 (YCL040W) Get druggable targets OG5_126743 All targets in OG5_126743
Plasmodium knowlesi hexokinase, putative Get druggable targets OG5_126743 All targets in OG5_126743
Schistosoma japonicum ko:K00844 hexokinase [EC2.7.1.1], putative Get druggable targets OG5_126743 All targets in OG5_126743
Trypanosoma congolense hexokinase Get druggable targets OG5_126743 All targets in OG5_126743
Theileria parva hexokinase, putative Get druggable targets OG5_126743 All targets in OG5_126743
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Onchocerca volvulus Hexokinase type IV   465 aa 458 aa 42.4 %
Brugia malayi ecdysteroid receptor peroxisome proliferator-activated receptor delta 441 aa 369 aa 24.7 %
Candida albicans N-acetylglucosamine kinase Hexokinase type IV   465 aa 393 aa 22.6 %
Brugia malayi Hexokinase family protein Hexokinase type IV   465 aa 472 aa 29.2 %
Brugia malayi Hexokinase family protein glucokinase (hexokinase 4) 465 aa 470 aa 30.0 %
Onchocerca volvulus Hexokinase type IV   465 aa 453 aa 40.4 %
Candida albicans N-acetylglucosamine kinase Hexokinase type IV   465 aa 393 aa 22.6 %
Onchocerca volvulus Hexokinase type IV   465 aa 456 aa 45.0 %
Onchocerca volvulus Putative electron transfer flavoprotein subunit alpha, mitochondrial Hexokinase type IV   465 aa 460 aa 45.0 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Schistosoma mansoni peroxidasin 0.0073 0.3395 0.3395
Brugia malayi hypothetical protein 0.008 0.3743 0.3743
Onchocerca volvulus 0.0121 0.6021 0.6021
Brugia malayi hypothetical protein 0.0043 0.1734 0.1734
Loa Loa (eye worm) hypothetical protein 0.0073 0.3395 0.3395
Loa Loa (eye worm) hypothetical protein 0.0061 0.2717 0.2717
Onchocerca volvulus Peroxidase homolog 0.0073 0.3395 0.3395
Loa Loa (eye worm) blistered cuticle protein 3 0.0073 0.3395 0.3395
Brugia malayi Animal haem peroxidase family protein 0.0073 0.3395 0.3395
Loa Loa (eye worm) hypothetical protein 0.0131 0.6605 0.6605
Onchocerca volvulus 0.0073 0.3395 0.3395
Brugia malayi Voltage-gated potassium channel, EAG (KCNH1)-related. C. elegans egl-2 ortholog 0.0013 0.0039 0.0039
Loa Loa (eye worm) hypothetical protein 0.0073 0.3395 0.3395
Loa Loa (eye worm) hypothetical protein 0.0073 0.3395 0.3395
Echinococcus multilocularis potassium voltage gated channel subfamily H 0.0045 0.1795 0.1795
Onchocerca volvulus Peroxidasin homolog 0.0073 0.3395 0.3395
Brugia malayi Peroxidasin 0.0073 0.3395 0.3395
Brugia malayi Blistered cuticle protein 3 0.0073 0.3395 0.3395
Schistosoma mansoni transcription factor LCR-F1 0.0043 0.1734 0.1734
Schistosoma mansoni voltage-gated potassium channel 0.0013 0.0039 0.0039
Onchocerca volvulus Chorion peroxidase homolog 0.0073 0.3395 0.3395
Onchocerca volvulus Peroxidasin homolog 0.0073 0.3395 0.3395
Echinococcus multilocularis voltage gated potassium channel 0.0013 0.0039 0.0039
Echinococcus granulosus potassium voltage gated channel subfamily H 0.0045 0.1795 0.1795
Brugia malayi Animal haem peroxidase family protein 0.0073 0.3395 0.3395
Onchocerca volvulus Peroxidase homolog 0.0073 0.3395 0.3395
Loa Loa (eye worm) hypothetical protein 0.0073 0.3395 0.3395
Loa Loa (eye worm) hypothetical protein 0.0073 0.3395 0.3395
Trichomonas vaginalis voltage and ligand gated potassium channel, putative 0.0042 0.1632 0.5
Loa Loa (eye worm) hypothetical protein 0.0073 0.3395 0.3395
Brugia malayi Animal haem peroxidase family protein 0.0073 0.3395 0.3395
Loa Loa (eye worm) hypothetical protein 0.0073 0.3395 0.3395
Echinococcus multilocularis Basic leucine zipper (bZIP) transcription 0.0043 0.1734 0.1734
Loa Loa (eye worm) animal heme peroxidase 0.0073 0.3395 0.3395
Onchocerca volvulus 0.008 0.3743 0.3743
Echinococcus multilocularis potassium voltage gated channel subfamily H 0.0013 0.0039 0.0039
Brugia malayi Animal haem peroxidase family protein 0.0073 0.3395 0.3395
Loa Loa (eye worm) hexokinase 0.0121 0.6021 0.6021
Loa Loa (eye worm) hypothetical protein 0.0061 0.2717 0.2717
Loa Loa (eye worm) animal heme peroxidase 0.0073 0.3395 0.3395
Trichomonas vaginalis voltage and ligand gated potassium channel, putative 0.0042 0.1632 0.5
Schistosoma mansoni voltage-gated potassium channel 0.0013 0.0039 0.0039
Loa Loa (eye worm) hypothetical protein 0.0099 0.4797 0.4797
Loa Loa (eye worm) hypothetical protein 0.0073 0.3395 0.3395
Brugia malayi Hexokinase family protein 0.006 0.2626 0.2626
Schistosoma mansoni jun-related protein 0.0082 0.3897 0.3897
Onchocerca volvulus Dual oxidase homolog 0.0073 0.3395 0.3395
Brugia malayi hypothetical protein 0.0073 0.3395 0.3395
Loa Loa (eye worm) hypothetical protein 0.0073 0.3395 0.3395
Loa Loa (eye worm) hypothetical protein 0.0073 0.3395 0.3395
Loa Loa (eye worm) hypothetical protein 0.0073 0.3395 0.3395
Schistosoma mansoni voltage-gated potassium channel 0.0049 0.2022 0.2022
Brugia malayi Voltage-gated potassium channel, HERG (KCNH2)-related. C. elegans unc-103 ortholog 0.0045 0.1795 0.1795
Loa Loa (eye worm) animal heme peroxidase 0.0073 0.3395 0.3395
Echinococcus multilocularis Basic leucine zipper (bZIP) transcription factor 0.0101 0.4951 0.4951
Loa Loa (eye worm) hypothetical protein 0.0073 0.3395 0.3395
Echinococcus granulosus Basic leucine zipper bZIP transcription factor 0.0101 0.4951 0.4951
Onchocerca volvulus Hexokinase homolog 0.0121 0.6021 0.6021
Loa Loa (eye worm) hypothetical protein 0.0073 0.3395 0.3395
Schistosoma mansoni voltage-gated potassium channel 0.0049 0.2022 0.2022
Onchocerca volvulus 0.0073 0.3395 0.3395
Echinococcus granulosus voltage gated potassium channel 0.0013 0.0039 0.0039
Echinococcus granulosus potassium voltage gated channel subfamily H 0.0013 0.0039 0.0039
Loa Loa (eye worm) hypothetical protein 0.0073 0.3395 0.3395
Loa Loa (eye worm) voltage and ligand gated potassium channel 0.0045 0.1795 0.1795
Schistosoma mansoni hypothetical protein 0.0082 0.3897 0.3897
Brugia malayi bZIP transcription factor family protein 0.0101 0.4951 0.4951
Brugia malayi Animal haem peroxidase family protein 0.0073 0.3395 0.3395
Echinococcus granulosus Basic leucine zipper bZIP transcription 0.0043 0.1734 0.1734
Brugia malayi hexokinase type II 0.0061 0.2717 0.2717
Schistosoma mansoni peroxidasin 0.0073 0.3395 0.3395
Echinococcus multilocularis jun protein 0.0101 0.4951 0.4951
Onchocerca volvulus 0.0073 0.3395 0.3395
Loa Loa (eye worm) hypothetical protein 0.0013 0.0039 0.0039
Loa Loa (eye worm) hexokinase 0.006 0.2626 0.2626
Echinococcus granulosus jun protein 0.0101 0.4951 0.4951
Echinococcus multilocularis peroxidasin 0.0073 0.3395 0.3395
Brugia malayi Hexokinase family protein 0.0121 0.6021 0.6021
Schistosoma mansoni hypothetical protein 0.0043 0.1734 0.1734
Loa Loa (eye worm) animal heme peroxidase 0.0073 0.3395 0.3395
Loa Loa (eye worm) hypothetical protein 0.0039 0.1468 0.1468
Echinococcus granulosus peroxidasin 0.0073 0.3395 0.3395

Activities

Activity type Activity value Assay description Source Reference
Activity (functional) = 2.83 mM Antihyperglycemic effect in fasted C57BL/6J mouse assessed as reduction in blood glucose level at 45 mg/kg, po measured after 4 hrs by glucometry analysis ChEMBL. 26685731
Activity (binding) = 0.18 uM Activation of human recombinant glucokinase assessed as concentration required for 1.5 fold increase in enzymatic activity ChEMBL. 22809456
EC50 (binding) = 100 nM Activation of rat glucokinase ChEMBL. No reference
EC50 (binding) = 364 nM Activation of recombinant human glucokinase assessed as formation of glucose-6-phosphate by G6PDH/NADP coupled assay ChEMBL. No reference
EC50 (binding) = 364 nM Activation of recombinant human glucokinase assessed as formation of glucose-6-phosphate by G6PDH/NADP coupled assay LITERATURE. No reference
EC50 (binding) = 1.42 uM Activation of human recombinant glucokinase using 6.5 mM glucose by spectrophotometry ChEMBL. 19435665
EC50 (binding) = 6.32 uM Activation of recombinant human glucokinase assessed as NADPH formation using glucose as substrate incubated for 30 mins in presence of NADP+ and glucose 6-phosphate dehydrogenase ChEMBL. 26685731
Emax (binding) = 148 % Activation of human recombinant glucokinase using 6.5 mM glucose by spectrophotometry relative to control ChEMBL. 19435665
Emax (binding) = 716.4 % Activation of recombinant human glucokinase assessed as NADPH formation using glucose as substrate incubated for 30 mins in presence of NADP+ and glucose 6-phosphate dehydrogenase relative to control ChEMBL. 26685731
K (binding) = 43.9 10'-3/s Binding affinity to biotinylated human recombinant glucokinase expressed in Escherichia coli assessed as off rate constant for activator-enzyme binding kinetics by SPR method ChEMBL. No reference
K (binding) = 2.05 10'5/M/s Binding affinity to biotinylated human recombinant glucokinase expressed in Escherichia coli assessed as on rate constant for activator-enzyme binding kinetics by SPR method ChEMBL. No reference
Kd (binding) = 218.4 nM Binding affinity to biotinylated human recombinant glucokinase expressed in Escherichia coli assessed as dissociation rate constant by SPR method ChEMBL. No reference
Potency (functional) 8.7076 uM PubChem BioAssay: Tox21. qHTS assay to identify small molecule antagonists of the peroxisome proliferator-activated receptor delta (PPARd) signaling pathway. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 24.3365 uM PubChem BioAssay: Tox21. qHTS assay for small molecule agonists of the antioxidant response element (ARE) signaling pathway. (Class of assay: confirmatory) ChEMBL. No reference
PPB (ADMET) = 50 % Plasma protein binding in mouse ChEMBL. 22809456
PPB (ADMET) = 50 % Plasma protein binding in human ChEMBL. 22809456
Stabilty (ADMET) = 35 % Metabolic stability in human hepatocytes after 3 hrs by LC-MS/MS analysis ChEMBL. 24900686
T1/2 (binding) = 15.8 s Binding affinity to biotinylated human recombinant glucokinase expressed in Escherichia coli assessed as dissociation half life by SPR method ChEMBL. No reference

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

3 literature references were collected for this gene.

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