Detailed information for compound 219323

Basic information

Technical information
  • TDR Targets ID: 219323
  • Name: 3-(2,4-difluorophenoxy)-6-methyl-2-(4-methyls ulfonylphenyl)pyran-4-one
  • MW: 392.373 | Formula: C19H14F2O5S
  • H donors: 0 H acceptors: 3 LogP: 3.31 Rotable bonds: 4
    Rule of 5 violations (Lipinski): 1
  • SMILES: Fc1ccc(c(c1)F)Oc1c(=O)cc(oc1c1ccc(cc1)S(=O)(=O)C)C
  • InChi: 1S/C19H14F2O5S/c1-11-9-16(22)19(26-17-8-5-13(20)10-15(17)21)18(25-11)12-3-6-14(7-4-12)27(2,23)24/h3-10H,1-2H3
  • InChiKey: WOBUKGPQDSRSPN-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 3-(2,4-difluorophenoxy)-6-methyl-2-(4-methylsulfonylphenyl)-4-pyranone
  • 3-(2,4-difluorophenoxy)-2-(4-mesylphenyl)-6-methyl-pyran-4-one

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
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Giardia lamblia Ribonuclease H 0.0095 0.0612 0.5
Toxoplasma gondii fatty acid elongase 0.0179 0.1481 0.1288
Loa Loa (eye worm) hypothetical protein 0.0121 0.088 0.088
Schistosoma mansoni elongation of fatty acids protein 1 0.0179 0.1481 0.1485
Leishmania major fatty acid elongase, putative 0.0748 0.7357 1
Echinococcus multilocularis elongation of very long chain fatty acids 0.017 0.139 0.909
Trypanosoma cruzi fatty acid elongase, putative 0.0748 0.7357 1
Leishmania major fatty acid elongase, putative 0.017 0.139 0.1154
Schistosoma mansoni fatty acid acyl transferase-related 0.0179 0.1481 0.1485
Loa Loa (eye worm) MH2 domain-containing protein 0.0093 0.059 0.059
Loa Loa (eye worm) RNA recognition domain-containing protein domain-containing protein 0.0054 0.0186 0.0186
Leishmania major fatty acid elongase, putative 0.0748 0.7357 1
Leishmania major fatty acid elongase, putative 0.017 0.139 0.1154
Loa Loa (eye worm) ELO-9 protein 0.017 0.139 0.139
Leishmania major long chain polyunsaturated fatty acid elongation enzyme-like protein 0.0179 0.1481 0.1288
Onchocerca volvulus 0.017 0.139 1
Schistosoma mansoni tar DNA-binding protein 0.0054 0.0186 0.0187
Onchocerca volvulus 0.017 0.139 1
Onchocerca volvulus Elongation of very long chain fatty acids protein homolog 0.017 0.139 1
Leishmania major fatty acid elongase, putative 0.0748 0.7357 1
Trypanosoma brucei hypothetical protein, conserved 0.0117 0.0846 0.025
Trypanosoma brucei unspecified product 0.0117 0.0846 0.025
Leishmania major fatty acid elongase, putative 0.017 0.139 0.1154
Trypanosoma brucei retrotransposon hot spot protein 4 (RHS4), interrupted 0.0117 0.0846 0.025
Brugia malayi RNA binding protein 0.0054 0.0186 0.0186
Trypanosoma cruzi fatty acid elongase, putative 0.017 0.139 0.1154
Trypanosoma cruzi fatty acid elongase, putative 0.017 0.139 0.1154
Leishmania major fatty acid elongase, putative 0.0179 0.1481 0.1288
Trichomonas vaginalis ribonuclease H1, putative 0.0095 0.0612 0.5
Loa Loa (eye worm) fatty acid elongation protein 3 0.017 0.139 0.139
Onchocerca volvulus Elongation of very long chain fatty acids protein homolog 0.017 0.139 1
Schistosoma mansoni tar DNA-binding protein 0.0054 0.0186 0.0187
Trypanosoma cruzi fatty acid elongase, putative 0.0179 0.1481 0.1288
Schistosoma mansoni phosphoglucomutase 0.0095 0.0612 0.0614
Mycobacterium ulcerans short chain dehydrogenase 0.051 0.4907 0.5
Brugia malayi Iron-sulfur cluster assembly accessory protein 0.0037 0.002 0.002
Leishmania major fatty acid elongase, putative 0.017 0.139 0.1154
Loa Loa (eye worm) fatty acid elongation protein 3 0.0748 0.7357 0.7357
Schistosoma mansoni tar DNA-binding protein 0.0054 0.0186 0.0187
Brugia malayi fatty acid elongation protein 3 0.017 0.139 0.139
Brugia malayi RNase H family protein 0.0095 0.0612 0.0612
Loa Loa (eye worm) fatty acid elongation protein 3 0.017 0.139 0.139
Leishmania major fatty acid elongase, putative 0.017 0.139 0.1154
Trypanosoma brucei Fatty acid elongase 0.017 0.139 0.0831
Schistosoma mansoni elongation of fatty acids protein 1 0.017 0.139 0.1394
Loa Loa (eye worm) TAR-binding protein 0.0054 0.0186 0.0186
Schistosoma mansoni hypothetical protein 0.0131 0.0992 0.0995
Brugia malayi MH2 domain containing protein 0.0093 0.059 0.059
Toxoplasma gondii integral membrane protein, GNS1/SUR4 family protein, putative 0.0748 0.7357 1
Schistosoma mansoni tar DNA-binding protein 0.0054 0.0186 0.0187
Echinococcus granulosus survival motor neuron protein 1 0.0184 0.1529 1
Trypanosoma brucei Fatty acid elongase 0.0748 0.7357 0.7208
Trypanosoma cruzi fatty acid elongase, putative 0.0748 0.7357 1
Schistosoma mansoni tar DNA-binding protein 0.0054 0.0186 0.0187
Trypanosoma brucei Fatty acid elongase 0.017 0.139 0.0831
Schistosoma mansoni survival motor neuron protein 0.0037 0.002 0.002
Brugia malayi fatty acid elongation protein 3 0.017 0.139 0.139
Onchocerca volvulus Ribonuclease H1 homolog 0.0095 0.0612 0.4321
Echinococcus granulosus ribonuclease H1 0.0095 0.0612 0.4001
Mycobacterium tuberculosis Probable oxidoreductase 0.051 0.4907 0.5
Loa Loa (eye worm) RNA binding protein 0.0054 0.0186 0.0186
Leishmania major fatty acid elongase, putative 0.017 0.139 0.1154
Echinococcus multilocularis ribonuclease H1 0.0095 0.0612 0.4001
Echinococcus multilocularis geminin 0.0131 0.0992 0.6486
Plasmodium vivax long chain polyunsaturated fatty acid elongation enzyme, putative 0.0179 0.1481 0.0152
Plasmodium falciparum fatty acid elongation protein, GNS1/SUR4 family, putative 0.0748 0.7357 1
Brugia malayi Fatty acid elongation protein 3 0.0748 0.7357 0.7357
Leishmania major fatty acid elongase, putative 0.017 0.139 0.1154
Brugia malayi TAR-binding protein 0.0054 0.0186 0.0186
Schistosoma mansoni elongation of fatty acids protein 1 0.017 0.139 0.1394
Loa Loa (eye worm) fatty acid elongation protein 3 0.017 0.139 0.139
Schistosoma mansoni phosphoglucomutase 0.0095 0.0612 0.0614
Schistosoma mansoni hypothetical protein 0.1001 0.997 1
Trypanosoma brucei RNA helicase, putative 0.1001 0.997 1
Loa Loa (eye worm) hypothetical protein 0.0184 0.1529 0.1529
Onchocerca volvulus Elongation of very long chain fatty acids protein 5 homolog 0.017 0.139 1
Brugia malayi sulfakinin receptor protein 0.0121 0.088 0.088
Brugia malayi Hypothetical 34.1 kDa protein C40H1.4 in chromosome III 0.017 0.139 0.139
Schistosoma mansoni phosphoglucomutase 0.0095 0.0612 0.0614
Echinococcus granulosus tar DNA binding protein 0.0054 0.0186 0.1218
Echinococcus granulosus geminin 0.0131 0.0992 0.6486
Echinococcus multilocularis survival motor neuron protein 1 0.0184 0.1529 1
Trypanosoma cruzi fatty acid elongase, putative 0.0179 0.1481 0.1288
Brugia malayi hypothetical protein 0.0184 0.1529 0.1529
Loa Loa (eye worm) hypothetical protein 0.017 0.139 0.139
Trypanosoma cruzi fatty acid elongase, putative 0.017 0.139 0.1154
Echinococcus granulosus elongation of very long chain fatty acids 0.017 0.139 0.909
Trypanosoma brucei Long chain fatty acyl elongase 0.0179 0.1481 0.0929
Loa Loa (eye worm) transcription factor SMAD2 0.0093 0.059 0.059
Trypanosoma cruzi fatty acid elongase, putative 0.0748 0.7357 1
Loa Loa (eye worm) GNS1/SUR4 family protein 0.0748 0.7357 0.7357
Brugia malayi hypothetical protein 0.0121 0.088 0.088
Echinococcus multilocularis elongation of very long chain fatty acids 0.0179 0.1481 0.9684
Plasmodium vivax GNS1/SUR4 domain containing protein 0.0748 0.7357 1
Trypanosoma cruzi fatty acid elongase, putative 0.0748 0.7357 1
Brugia malayi RNase H family protein 0.0095 0.0612 0.0612
Treponema pallidum ribonuclease H (rnhA) 0.0095 0.0612 0.5
Trypanosoma brucei ingi protein (ORF1) 0.0117 0.0846 0.025
Schistosoma mansoni hypothetical protein 0.0131 0.0992 0.0995
Loa Loa (eye worm) GNS1/SUR4 family protein 0.1003 1 1
Wolbachia endosymbiont of Brugia malayi ribonuclease HI 0.0095 0.0612 0.5
Brugia malayi fatty acid elongation protein 3 0.017 0.139 0.139
Echinococcus granulosus elongation of very long chain fatty acids 0.0179 0.1481 0.9684
Brugia malayi RNA recognition motif domain containing protein 0.0054 0.0186 0.0186
Plasmodium falciparum long chain fatty acid elongation enzyme, putative 0.0748 0.7357 1
Leishmania major fatty acid elongase, putative 0.017 0.139 0.1154
Trypanosoma brucei ingi protein (ORF1) 0.0117 0.0846 0.025
Brugia malayi RNase H family protein 0.0095 0.0612 0.0612
Toxoplasma gondii GNS1/SUR4 family protein 0.0748 0.7357 1
Schistosoma mansoni elongation of fatty acids protein 1 0.0179 0.1481 0.1485
Leishmania major fatty acid elongase, putative 0.017 0.139 0.1154
Schistosoma mansoni hypothetical protein 0.0037 0.002 0.002
Trypanosoma cruzi fatty acid elongase, putative 0.017 0.139 0.1154
Trypanosoma brucei elongation of very long chain fatty acids protein, putative 0.0179 0.1481 0.0929
Echinococcus multilocularis tar DNA binding protein 0.0054 0.0186 0.1218
Brugia malayi GNS1/SUR4 family protein 0.0748 0.7357 0.7357
Brugia malayi fatty acid elongation protein 3 0.017 0.139 0.139

Activities

Activity type Activity value Assay description Source Reference
AUC (ADMET) = 9216 ng.hr/ml AUC in Wistar rat at 1 mg/kg, po ChEMBL. 16647258
AUC (ADMET) = 18646 ng.hr/ml AUC in Wistar rat after administration as its prodrug at 1 mg/kg, po ChEMBL. 16647258
AUC (ADMET) = 90.2 ug hr ml-1 Area under curve of the compound was determined after 10 mg/kg oral administration in rat at 0-24 hr ChEMBL. 15239665
Binding (binding) = 98.4 Compound was tested for human plasma protein binding ChEMBL. 15239665
Cmax (ADMET) = 1507 ng/ml Cmax in Wistar rat at 1 mg/kg, po ChEMBL. 16647258
Cmax (ADMET) = 2959 ng/ml Cmax in Wistar rat after administration as its prodrug at 1 mg/kg, po ChEMBL. 16647258
Cmax (ADMET) = 6.8 ug ml-1 Cmax of the compound was determined after 10 mg/kg oral administration in rat ChEMBL. 15239665
ED50 (functional) = 0.015 mg kg-1 Compound was tested in vivo for adjuvant arthritis in rat ChEMBL. 15239665
ED50 (functional) = 0.7 mg kg-1 Effective dose in the yeast-induced pyresis model in rat ChEMBL. 15239665
ED50 (functional) = 0.7 mg kg-1 Inhibition of yeast-induced pyresis in Wistar rat ChEMBL. 16647258
IC50 (binding) = 4.6517 Inhibitory concentration for Cyclooxygenase-1 (Prostaglandin G/H synthase 1) in human whole blood ChEMBL. 15603946
IC50 (binding) = 7.0969 Inhibitory concentration for Cyclooxygenase-2 (Prostaglandin G/H synthase 2) in human whole blood ChEMBL. 15603946
IC50 (binding) = 0.08 uM Inhibition concentration against cyclooxygenase-2(COX-2) in human whole blood ChEMBL. 15239665
IC50 (binding) = 0.08 uM Inhibition of COX2 in human whole blood ChEMBL. 16647258
IC50 (binding) = 0.08 uM Inhibition concentration against cyclooxygenase-2(COX-2) in human whole blood ChEMBL. 15239665
IC50 (binding) = 0.08 uM Inhibition of COX2 in human whole blood ChEMBL. 16647258
IC50 (binding) = 22.3 uM Inhibition concentration against cyclooxygenase-1 (COX-1) in human whole blood ChEMBL. 15239665
IC50 (binding) = 22.3 uM Inhibition concentration against cyclooxygenase-1 (COX-1) in human whole blood ChEMBL. 15239665
Inhibition (functional) = 68 % Inhibition of adjuvant-induced arthritis in Wistar rat at 0.1 mg/kg, po ChEMBL. 16647258
Inhibition (functional) = 69 % In vivo inhibition of hyperalgesia in rat at 3 mg/kg ChEMBL. 15239665
Log IC50 (binding) = 4.6517 Inhibitory concentration for Cyclooxygenase-1 (Prostaglandin G/H synthase 1) in human whole blood ChEMBL. 15603946
Log IC50 (binding) = 7.0969 Inhibitory concentration for Cyclooxygenase-2 (Prostaglandin G/H synthase 2) in human whole blood ChEMBL. 15603946
Ratio (binding) = 279 Ratio of inhibitory activity of the compound against cyclooxygenase- (COX-1) to that of cyclooxygenase- (COX-2) ChEMBL. 15239665
Ratio (binding) = 279 Ratio of inhibitory activity of the compound against cyclooxygenase- (COX-1) to that of cyclooxygenase- (COX-2) ChEMBL. 15239665
Ratio AUC (ADMET) = 14 Ratio AUC for prodrug to the parent compound in Wistar rat at 1 mg/kg, po ChEMBL. 16647258
Selectivity (binding) = 2.4456 Ratio of pIC50 value against Cyclooxygenase-1 (Prostaglandin G/H synthase 1) and Cyclooxygenase-2 (Prostaglandin G/H synthase 2) ChEMBL. 15603946
Selectivity (binding) = 2.4456 Ratio of pIC50 value against Cyclooxygenase-1 (Prostaglandin G/H synthase 1) and Cyclooxygenase-2 (Prostaglandin G/H synthase 2) ChEMBL. 15603946
Selectivity ratio (binding) = 279 Selectivity ratio for COX2 over COX1 in human whole blood ChEMBL. 16647258
Selectivity ratio (binding) = 279 Selectivity ratio for COX2 over COX1 in human whole blood ChEMBL. 16647258
Solubility = 7 ug ml-1 Solubility in PBS at pH 7.2, 37 degC after 24 hrs ChEMBL. 16647258
Solubility = 9 ug ml-1 Solubility in simulated gastric fluid at pH 1.8, 37 degC after 24 hrs ChEMBL. 16647258
Stabilty (ADMET) = 2 % Metabolic stability in human liver microsomes at 5 uM after 30 min at 30 degC ChEMBL. 16647258
Stabilty (ADMET) = 26 % Metabolic stability in rat liver microsomes at 5 uM after 30 min at 30 degC ChEMBL. 16647258
T1/2 (ADMET) = 4.5 hr Half life of the compound was determined after 10 mg/kg oral administration in rat ChEMBL. 15239665
Tmax (ADMET) = 1 hr Tmax in Wistar rat at 1 mg/kg, po ChEMBL. 16647258
Tmax (ADMET) = 2.3 hr Tmax in Wistar rat after administration as its prodrug at 1 mg/kg, po ChEMBL. 16647258

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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