Detailed information for compound 205734

Basic information

Technical information
  • TDR Targets ID: 205734
  • Name: 4-[4-(oxan-2-yloxymethyl)phenoxy]thieno[2,3-c ]pyridine-2-carboxamide
  • MW: 384.449 | Formula: C20H20N2O4S
  • H donors: 1 H acceptors: 2 LogP: 3.12 Rotable bonds: 6
    Rule of 5 violations (Lipinski): 1
  • SMILES: NC(=O)c1sc2c(c1)c(cnc2)Oc1ccc(cc1)COC1CCCCO1
  • InChi: 1S/C20H20N2O4S/c21-20(23)17-9-15-16(10-22-11-18(15)27-17)26-14-6-4-13(5-7-14)12-25-19-3-1-2-8-24-19/h4-7,9-11,19H,1-3,8,12H2,(H2,21,23)
  • InChiKey: KCKRKRQSCSVZSK-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 4-[4-(tetrahydropyran-2-yloxymethyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide
  • 4-[4-(2-tetrahydropyranyloxymethyl)phenoxy]-2-thieno[2,3-c]pyridinecarboxamide
  • 4-[4-(oxan-2-yloxymethyl)phenoxy]thieno[5,4-c]pyridine-2-carboxamide
  • 4-[4-(tetrahydropyran-2-yloxymethyl)phenoxy]thieno[5,4-c]pyridine-2-carboxamide
  • 4-[4-(2-tetrahydropyranyloxymethyl)phenoxy]-2-thieno[5,4-c]pyridinecarboxamide

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens vascular cell adhesion molecule 1 Starlite/ChEMBL References
Homo sapiens selectin E Starlite/ChEMBL References
Homo sapiens intercellular adhesion molecule 1 Starlite/ChEMBL References
Trypanosoma cruzi trypanothione reductase, putative Curated by TDR Targets References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Plasmodium yoelii glutathione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Leishmania infantum trypanothione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Trypanosoma brucei trypanothione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Neospora caninum MGC84926 protein, related Get druggable targets OG5_126785 All targets in OG5_126785
Candida albicans similar to S. cerevisiae GLR1 (YPL091W) glutathione oxidoreductase Get druggable targets OG5_126785 All targets in OG5_126785
Trypanosoma cruzi trypanothione reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Theileria parva thioredoxin reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Plasmodium vivax glutathione reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Plasmodium berghei thioredoxin reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Plasmodium knowlesi thioredoxin reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Babesia bovis thiodoxin reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Neospora caninum Glutathione reductase, related Get druggable targets OG5_126785 All targets in OG5_126785
Echinococcus multilocularis thioredoxin glutathione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Brugia malayi Thioredoxin reductase Get druggable targets OG5_126785 All targets in OG5_126785
Plasmodium falciparum glutathione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Leishmania major trypanothione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Trypanosoma congolense trypanothione reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Loa Loa (eye worm) thioredoxin reductase Get druggable targets OG5_126785 All targets in OG5_126785
Brugia malayi glutathione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Leishmania mexicana trypanothione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Candida albicans similar to S. cerevisiae GLR1 (YPL091W) glutathione oxidoreductase Get druggable targets OG5_126785 All targets in OG5_126785
Cryptosporidium hominis thioredoxin reductase Get druggable targets OG5_126785 All targets in OG5_126785
Leishmania braziliensis trypanothione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Trypanosoma brucei gambiense trypanothione reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Plasmodium falciparum thioredoxin reductase Get druggable targets OG5_126785 All targets in OG5_126785
Plasmodium knowlesi glutathione reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Cryptosporidium parvum thioredoxin reductase 1 Get druggable targets OG5_126785 All targets in OG5_126785
Plasmodium berghei glutathione reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Leishmania donovani trypanothione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Plasmodium vivax thioredoxin reductase, putative Get druggable targets OG5_126785 All targets in OG5_126785
Plasmodium yoelii thioredoxin reductase Get druggable targets OG5_126785 All targets in OG5_126785
Mycobacterium tuberculosis NADPH-dependent mycothiol reductase Mtr Get druggable targets OG5_126785 All targets in OG5_126785
Toxoplasma gondii thioredoxin reductase Get druggable targets OG5_126785 All targets in OG5_126785
Echinococcus granulosus thioredoxin glutathione reductase Get druggable targets OG5_126785 All targets in OG5_126785
Schistosoma japonicum ko:K00384 thioredoxin reductase (NADPH) [EC1.8.1.9], putative Get druggable targets OG5_126785 All targets in OG5_126785
Loa Loa (eye worm) glutathione reductase Get druggable targets OG5_126785 All targets in OG5_126785
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Plasmodium falciparum dihydrolipoyl dehydrogenase, apicoplast trypanothione reductase, putative 492 aa 548 aa 21.5 %
Echinococcus granulosus c4b binding protein beta chain selectin E 610 aa 551 aa 22.1 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Mycobacterium tuberculosis Conserved protein 0.0035 0.0993 0.0452
Mycobacterium ulcerans hypothetical protein 0.0035 0.0993 1
Echinococcus multilocularis beta LACTamase domain containing family member 0.0035 0.0993 0.1417
Loa Loa (eye worm) TK/KIN16 protein kinase 0.0015 0.0032 0.0032
Schistosoma mansoni cell adhesion molecule 0.0015 0.0032 0.0055
Chlamydia trachomatis dihydrolipoyl dehydrogenase 0.0026 0.057 0.5
Plasmodium vivax dihydrolipoyl dehydrogenase, mitochondrial, putative 0.0026 0.057 0.1966
Echinococcus granulosus guanine nucleotide binding protein Gs subunit 0.0045 0.1441 0.2057
Toxoplasma gondii NADPH-glutathione reductase 0.0026 0.057 0.1966
Echinococcus granulosus guanine nucleotide binding protein Gs subunit 0.0045 0.1441 0.2057
Brugia malayi beta-lactamase family protein 0.0035 0.0993 0.0993
Brugia malayi Hypothetical 52.5 kDa protein ZK945.1 in chromosome II, putative 0.0035 0.0993 0.0993
Loa Loa (eye worm) hypothetical protein 0.0035 0.0993 0.0993
Trichomonas vaginalis alpha-glucosidase, putative 0.0036 0.1038 1
Trypanosoma cruzi trypanothione reductase, putative 0.0076 0.2898 1
Loa Loa (eye worm) follicle stimulating hormone receptor 0.0228 1 1
Brugia malayi dihydrolipoyl dehydrogenase, mitochondrial precursor, putative 0.0026 0.057 0.057
Brugia malayi alpha keto acid dehydrogenase complex, E3 component, lipoamide dehydrogenase 0.0019 0.0242 0.0242
Toxoplasma gondii pyruvate dehydrogenase complex subunit PDH-E3II 0.0026 0.057 0.1966
Brugia malayi Immunoglobulin I-set domain containing protein 0.0015 0.0032 0.0032
Treponema pallidum NADH oxidase 0.0026 0.057 0.5
Trypanosoma brucei glucosidase, putative 0.0036 0.1038 0.201
Wolbachia endosymbiont of Brugia malayi dihydrolipoamide dehydrogenase E3 component 0.0026 0.057 0.5
Mycobacterium tuberculosis NADPH-dependent mycothiol reductase Mtr 0.0076 0.2898 0.2488
Trichomonas vaginalis neutral alpha-glucosidase ab precursor, putative 0.0036 0.1038 1
Echinococcus granulosus neurotracting:lsamp:neurotrimin:obcam 0.0015 0.0032 0.0046
Schistosoma mansoni Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein) 0.0045 0.1441 0.2427
Plasmodium falciparum dihydrolipoyl dehydrogenase, mitochondrial 0.0026 0.057 0.1966
Giardia lamblia NADH oxidase lateral transfer candidate 0.0026 0.057 0.5
Schistosoma mansoni Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein) 0.0045 0.1441 0.2427
Brugia malayi beta-lactamase 0.0035 0.0993 0.0993
Plasmodium vivax dihydrolipoyl dehydrogenase, apicoplast, putative 0.0026 0.057 0.1966
Mycobacterium tuberculosis Possible conserved lipoprotein LpqK 0.0035 0.0993 0.0452
Echinococcus multilocularis neutral alpha glucosidase AB 0.0036 0.1038 0.1481
Trypanosoma cruzi hypothetical protein, conserved 0.0036 0.1038 0.201
Echinococcus multilocularis lysosomal alpha glucosidase 0.0164 0.7008 1
Loa Loa (eye worm) hypothetical protein 0.0035 0.0993 0.0993
Trypanosoma cruzi hypothetical protein, conserved 0.0035 0.0993 0.1818
Echinococcus granulosus thioredoxin glutathione reductase 0.0076 0.2898 0.4136
Brugia malayi glutathione reductase 0.0076 0.2898 0.2898
Echinococcus multilocularis guanine nucleotide binding protein G(s) subunit 0.0045 0.1441 0.2057
Loa Loa (eye worm) beta-lactamase 0.0035 0.0993 0.0993
Plasmodium falciparum dihydrolipoyl dehydrogenase, apicoplast 0.0026 0.057 0.1966
Leishmania major trypanothione reductase 0.0076 0.2898 1
Trypanosoma brucei trypanothione reductase 0.0076 0.2898 1
Loa Loa (eye worm) hypothetical protein 0.0015 0.0032 0.0032
Brugia malayi Glycosyl hydrolases family 31 protein 0.0164 0.7008 0.7008
Onchocerca volvulus 0.0035 0.0993 0.2632
Mycobacterium ulcerans esterase/lipase LipP 0.0035 0.0993 1
Trichomonas vaginalis D-aminoacylase, putative 0.0035 0.0993 0.9045
Echinococcus multilocularis dihydrolipoamide dehydrogenase 0.0026 0.057 0.0813
Trypanosoma brucei hypothetical protein, conserved 0.0035 0.0993 0.1818
Plasmodium vivax thioredoxin reductase, putative 0.0076 0.2898 1
Trichomonas vaginalis alpha-glucosidase, putative 0.0036 0.1038 1
Loa Loa (eye worm) hypothetical protein 0.0018 0.0167 0.0167
Loa Loa (eye worm) hypothetical protein 0.0022 0.036 0.036
Loa Loa (eye worm) hypothetical protein 0.0016 0.0075 0.0075
Brugia malayi GTP-binding regulatory protein Gs alpha-S chain, putative 0.0045 0.1441 0.1441
Schistosoma mansoni family S12 unassigned peptidase (S12 family) 0.0035 0.0993 0.1672
Trichomonas vaginalis penicillin-binding protein, putative 0.0035 0.0993 0.9045
Trichomonas vaginalis penicillin-binding protein, putative 0.0035 0.0993 0.9045
Mycobacterium ulcerans fusion of enoyl-CoA hydratase, EchA21 and lipase, LipE 0.0035 0.0993 1
Echinococcus granulosus roundabout 2 0.0018 0.0167 0.0238
Trichomonas vaginalis D-aminoacylase, putative 0.0035 0.0993 0.9045
Wolbachia endosymbiont of Brugia malayi dihydrolipoamide dehydrogenase E3 component 0.0026 0.057 0.5
Loa Loa (eye worm) hypothetical protein 0.0018 0.0167 0.0167
Brugia malayi Thioredoxin reductase 0.0076 0.2898 0.2898
Trichomonas vaginalis alpha-glucosidase, putative 0.0036 0.1038 1
Echinococcus multilocularis guanine nucleotide binding protein G(s) subunit 0.0045 0.1441 0.2057
Echinococcus multilocularis lysosomal alpha glucosidase 0.0164 0.7008 1
Loa Loa (eye worm) thioredoxin reductase 0.0076 0.2898 0.2898
Trichomonas vaginalis sucrase-isomaltase, putative 0.0036 0.1038 1
Toxoplasma gondii glycosyl hydrolase, family 31 protein 0.0036 0.1038 0.3581
Schistosoma mansoni Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein) 0.0045 0.1441 0.2427
Brugia malayi Pyridine nucleotide-disulphide oxidoreductase, dimerisation domain containing protein 0.0019 0.0242 0.0242
Schistosoma mansoni alpha-glucosidase 0.0141 0.5939 1
Leishmania major hypothetical protein, conserved 0.0035 0.0993 0.1818
Mycobacterium leprae Probable lipase LipE 0.0035 0.0993 1
Loa Loa (eye worm) glycosyl hydrolase family 31 protein 0.0164 0.7008 0.7008
Trichomonas vaginalis alpha-glucosidase, putative 0.0036 0.1038 1
Onchocerca volvulus 0.0095 0.3773 1
Onchocerca volvulus 0.0035 0.0993 0.2632
Trichomonas vaginalis neutral alpha-glucosidase ab precursor, putative 0.0036 0.1038 1
Mycobacterium tuberculosis Probable esterase/lipase LipP 0.0035 0.0993 0.0452
Mycobacterium tuberculosis Probable esterase LipL 0.0035 0.0993 0.0452
Trichomonas vaginalis maltase-glucoamylase, putative 0.0036 0.1038 1
Trypanosoma cruzi hypothetical protein, conserved 0.0035 0.0993 0.1818
Mycobacterium tuberculosis Probable hydrolase 0.0035 0.0993 0.0452
Onchocerca volvulus 0.0035 0.0993 0.2632
Loa Loa (eye worm) beta-LACTamase domain containing family member 0.0035 0.0993 0.0993
Leishmania major alpha glucosidase II subunit, putative 0.0036 0.1038 0.201
Plasmodium vivax hypothetical protein, conserved 0.0035 0.0993 0.3427
Echinococcus granulosus beta LACTamase domain containing family member 0.0035 0.0993 0.1417
Echinococcus granulosus neutral alpha glucosidase AB 0.0036 0.1038 0.1481
Mycobacterium tuberculosis Probable lipase LipE 0.0035 0.0993 0.0452
Loa Loa (eye worm) hypothetical protein 0.0035 0.0993 0.0993
Echinococcus multilocularis roundabout 2 0.0018 0.0167 0.0238
Trichomonas vaginalis alpha-glucosidase, putative 0.0036 0.1038 1
Toxoplasma gondii ABC1 family protein 0.0035 0.0993 0.3427
Trichomonas vaginalis D-aminoacylase, putative 0.0035 0.0993 0.9045
Schistosoma mansoni dihydrolipoamide dehydrogenase 0.0026 0.057 0.096
Mycobacterium tuberculosis Conserved protein 0.0035 0.0993 0.0452
Trichomonas vaginalis esterase, putative 0.0035 0.0993 0.9045
Mycobacterium tuberculosis Conserved protein 0.0035 0.0993 0.0452
Brugia malayi GCC2 and GCC3 family protein 0.0022 0.036 0.036
Mycobacterium tuberculosis Probable lipase LipD 0.0035 0.0993 0.0452
Brugia malayi beta-lactamase family protein 0.0035 0.0993 0.0993
Loa Loa (eye worm) glutathione reductase 0.0076 0.2898 0.2898
Mycobacterium tuberculosis Probable conserved lipoprotein 0.0035 0.0993 0.0452
Toxoplasma gondii thioredoxin reductase 0.0076 0.2898 1
Loa Loa (eye worm) hypothetical protein 0.0035 0.0993 0.0993
Loa Loa (eye worm) glycosyl hydrolase family 31 protein 0.0036 0.1038 0.1038
Schistosoma mansoni alpha glucosidase 0.0036 0.1038 0.1747
Mycobacterium leprae conserved hypothetical protein 0.0035 0.0993 1
Mycobacterium ulcerans lipase LipD 0.0035 0.0993 1
Mycobacterium tuberculosis Possible penicillin-binding protein 0.0226 0.9927 1
Echinococcus granulosus lysosomal alpha glucosidase 0.0164 0.7008 1
Plasmodium falciparum thioredoxin reductase 0.0076 0.2898 1
Trypanosoma cruzi hypothetical protein, conserved 0.0036 0.1038 0.201
Schistosoma mansoni alpha-glucosidase 0.0141 0.5939 1
Loa Loa (eye worm) hypothetical protein 0.0035 0.0993 0.0993
Loa Loa (eye worm) hypothetical protein 0.0035 0.0993 0.0993
Mycobacterium ulcerans beta-lactamase 0.0035 0.0993 1
Entamoeba histolytica glycosyl hydrolase, family 31 protein 0.0036 0.1038 0.5
Plasmodium vivax glutathione reductase, putative 0.0076 0.2898 1
Plasmodium falciparum thioredoxin reductase 0.0026 0.057 0.1966
Plasmodium falciparum glutathione reductase 0.0026 0.057 0.1966
Schistosoma mansoni family S12 unassigned peptidase (S12 family) 0.0035 0.0993 0.1672
Echinococcus multilocularis thioredoxin glutathione reductase 0.0076 0.2898 0.4136
Entamoeba histolytica glycosyl hydrolase, family 31 protein 0.0036 0.1038 0.5
Echinococcus granulosus dihydrolipoamide dehydrogenase 0.0026 0.057 0.0813
Brugia malayi Glycosyl hydrolases family 31 protein 0.0036 0.1038 0.1038
Plasmodium falciparum glutathione reductase 0.0076 0.2898 1
Loa Loa (eye worm) GTP-binding regulatory protein Gs alpha-S chain 0.0045 0.1441 0.1441

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 1.4 nM Inhibition of intercellular adhesion molecule-1 (ICAM1) in human endothelial cells ChEMBL. 11585452
IC50 (binding) = 1.4 nM Inhibition of intercellular adhesion molecule-1 (ICAM1) in human endothelial cells ChEMBL. 11585452
IC50 (binding) = 2 nM Inhibition of selectin E in human endothelial cells ChEMBL. 11585452
IC50 (binding) = 2 nM Inhibition of selectin E in human endothelial cells ChEMBL. 11585452
IC50 (binding) > 1000 nM Inhibition of VCAM-1 in human endothelial cells ChEMBL. 11585452
IC50 (binding) > 1000 nM Inhibition of VCAM-1 in human endothelial cells ChEMBL. 11585452

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

1 literature reference was collected for this gene.

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