Detailed information for compound 1124763

Basic information

Technical information
  • TDR Targets ID: 1124763
  • Name: (E)-N-hydroxy-3-[3-[1-(2-morpholin-4-ylethyl) benzimidazol-2-yl]phenyl]prop-2-enamide
  • MW: 392.451 | Formula: C22H24N4O3
  • H donors: 2 H acceptors: 3 LogP: 1.91 Rotable bonds: 7
    Rule of 5 violations (Lipinski): 1
  • SMILES: ONC(=O)/C=C/c1cccc(c1)c1nc2c(n1CCN1CCOCC1)cccc2
  • InChi: 1S/C22H24N4O3/c27-21(24-28)9-8-17-4-3-5-18(16-17)22-23-19-6-1-2-7-20(19)26(22)11-10-25-12-14-29-15-13-25/h1-9,16,28H,10-15H2,(H,24,27)/b9-8+
  • InChiKey: PRFVRQDWLLQIJO-CMDGGOBGSA-N  


Substructure search Similarity search

Network

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Synonyms

  • (E)-3-[3-[1-(2-morpholinoethyl)benzimidazol-2-yl]phenyl]prop-2-enehydroxamic acid
  • (E)-3-[3-[1-(2-morpholinoethyl)-2-benzimidazolyl]phenyl]prop-2-enehydroxamic acid

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens histone deacetylase 8 Starlite/ChEMBL References
Homo sapiens histone deacetylase 6 Starlite/ChEMBL References
Homo sapiens histone deacetylase 1 Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Leishmania mexicana histone deacetylase, putative Get druggable targets OG5_126654 All targets in OG5_126654
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_126654 All targets in OG5_126654
Leishmania braziliensis histone deacetylase, putative Get druggable targets OG5_126654 All targets in OG5_126654
Leishmania major histone deacetylase, putative Get druggable targets OG5_126654 All targets in OG5_126654
Cryptosporidium hominis histone deacetylase Get druggable targets OG5_126742 All targets in OG5_126742
Plasmodium yoelii histone deacetylase Get druggable targets OG5_126742 All targets in OG5_126742
Babesia bovis histone deacetylase Get druggable targets OG5_126742 All targets in OG5_126742
Trypanosoma brucei gambiense histone deacetylase, putative Get druggable targets OG5_126654 All targets in OG5_126654
Leishmania major histone deacetylase, putative Get druggable targets OG5_126654 All targets in OG5_126654
Trypanosoma cruzi histone deacetylase 1, putative Get druggable targets OG5_126742 All targets in OG5_126742
Trypanosoma brucei gambiense histone deacetylase 1,histone deacetylase-like 1 protein, putative Get druggable targets OG5_126742 All targets in OG5_126742
Babesia bovis histone deacetylase, putative Get druggable targets OG5_126654 All targets in OG5_126654
Plasmodium falciparum histone deacetylase, putative Get druggable targets OG5_126654 All targets in OG5_126654
Schistosoma mansoni histone deacetylase 4 5 Get druggable targets OG5_126654 All targets in OG5_126654
Plasmodium falciparum histone deacetylase 2 Get druggable targets OG5_126654 All targets in OG5_126654
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_126654 All targets in OG5_126654
Trypanosoma congolense histone deacetylase 4 Get druggable targets OG5_126654 All targets in OG5_126654
Leishmania mexicana histone deacetylase, putative Get druggable targets OG5_126654 All targets in OG5_126654
Leishmania mexicana histone deacetylase, putative Get druggable targets OG5_126742 All targets in OG5_126742
Schistosoma mansoni histone deacetylase 4 5 Get druggable targets OG5_126654 All targets in OG5_126654
Echinococcus granulosus histone deacetylase Get druggable targets OG5_126654 All targets in OG5_126654
Plasmodium vivax histone deacetylase 2, putative Get druggable targets OG5_126654 All targets in OG5_126654
Theileria parva hypothetical protein Get druggable targets OG5_126654 All targets in OG5_126654
Neospora caninum hypothetical protein Get druggable targets OG5_126742 All targets in OG5_126742
Brugia malayi Histone deacetylase family protein Get druggable targets OG5_126654 All targets in OG5_126654
Schistosoma japonicum Histone deacetylase 4, putative Get druggable targets OG5_126654 All targets in OG5_126654
Leishmania mexicana histone deacetylase, putative Get druggable targets OG5_126742 All targets in OG5_126742
Candida albicans strong similarity to S. cerevisiae HDA1 (YNL021W) class II histone deacetylase HDA1 complex subunit Get druggable targets OG5_126654 All targets in OG5_126654
Neospora caninum histone deacetylase, putative Get druggable targets OG5_126742 All targets in OG5_126742
Echinococcus multilocularis histone deacetylase 3 Get druggable targets OG5_126742 All targets in OG5_126742
Schistosoma japonicum Histone deacetylase 6, putative Get druggable targets OG5_126654 All targets in OG5_126654
Trichomonas vaginalis histone deacetylase, putative Get druggable targets OG5_126742 All targets in OG5_126742
Leishmania donovani histone deacetylase, putative Get druggable targets OG5_126742 All targets in OG5_126742
Schistosoma japonicum Histone deacetylase 10, putative Get druggable targets OG5_126654 All targets in OG5_126654
Cryptosporidium hominis hypothetical protein Get druggable targets OG5_126654 All targets in OG5_126654
Trypanosoma brucei histone deacetylase 4 Get druggable targets OG5_126654 All targets in OG5_126654
Echinococcus multilocularis histone deacetylase Get druggable targets OG5_126654 All targets in OG5_126654
Trichomonas vaginalis histone deacetylase, putative Get druggable targets OG5_126742 All targets in OG5_126742
Plasmodium yoelii hypothetical protein Get druggable targets OG5_126654 All targets in OG5_126654
Schistosoma japonicum Histone deacetylase 10, putative Get druggable targets OG5_126654 All targets in OG5_126654
Trichomonas vaginalis histone deacetylase 1, 2 ,3, putative Get druggable targets OG5_126742 All targets in OG5_126742
Echinococcus granulosus histone deacetylase 6 Get druggable targets OG5_126654 All targets in OG5_126654
Trypanosoma cruzi histone deacetylase, putative Get druggable targets OG5_126654 All targets in OG5_126654
Trichomonas vaginalis histone deacetylase, putative Get druggable targets OG5_126742 All targets in OG5_126742
Schistosoma japonicum ko:K01463 Hdac3 [EC:3.5.1.-], putative Get druggable targets OG5_126742 All targets in OG5_126742
Trypanosoma congolense histone deacetylase, putative Get druggable targets OG5_126654 All targets in OG5_126654
Trypanosoma cruzi histone deacetylase 1, putative Get druggable targets OG5_126742 All targets in OG5_126742
Theileria parva histone deacetylase, putative Get druggable targets OG5_126654 All targets in OG5_126654
Leishmania braziliensis histone deacetylase, putative Get druggable targets OG5_126742 All targets in OG5_126742
Leishmania infantum histone deacetylase, putative Get druggable targets OG5_126654 All targets in OG5_126654
Schistosoma mansoni histone deacetylase Get druggable targets OG5_126742 All targets in OG5_126742
Candida albicans one of two distinct genes with strong similarity to S. cerevisiae RPD3 (YNL330C) SIN3 histone deacetylase complex component Get druggable targets OG5_126742 All targets in OG5_126742
Echinococcus granulosus histone deacetylase 6 Get druggable targets OG5_126654 All targets in OG5_126654
Leishmania donovani histone deacetylase, putative Get druggable targets OG5_126742 All targets in OG5_126742
Echinococcus granulosus histone deacetylase 6 Get druggable targets OG5_126654 All targets in OG5_126654
Trichomonas vaginalis histone deacetylase 1, 2 ,3, putative Get druggable targets OG5_126742 All targets in OG5_126742
Toxoplasma gondii histone deacetylase HDAC2 Get druggable targets OG5_126742 All targets in OG5_126742
Leishmania donovani histone deacetylase, putative Get druggable targets OG5_126654 All targets in OG5_126654
Neospora caninum hypothetical protein Get druggable targets OG5_126654 All targets in OG5_126654
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_126742 All targets in OG5_126742
Schistosoma japonicum IPR000286,Histone deacetylase superfamily;IPR013838,Beta tubulin, autoregulation binding site,domain-containing Get druggable targets OG5_126654 All targets in OG5_126654
Toxoplasma gondii histone deacetylase HDAC1 Get druggable targets OG5_126654 All targets in OG5_126654
Trypanosoma brucei histone deacetylase, putative Get druggable targets OG5_126654 All targets in OG5_126654
Plasmodium yoelii Histone deacetylase family, putative Get druggable targets OG5_126654 All targets in OG5_126654
Leishmania infantum histone deacetylase, putative Get druggable targets OG5_126742 All targets in OG5_126742
Trypanosoma congolense histone deacetylase-like 1 protein, putative Get druggable targets OG5_126742 All targets in OG5_126742
Echinococcus granulosus histone deacetylase 1 Get druggable targets OG5_126742 All targets in OG5_126742
Trypanosoma cruzi histone deacetylase, putative Get druggable targets OG5_126654 All targets in OG5_126654
Leishmania major histone deacetylase, putative Get druggable targets OG5_126742 All targets in OG5_126742
Trypanosoma congolense histone deacetylase 4 Get druggable targets OG5_126654 All targets in OG5_126654
Candida albicans one of two distinct genes with strong similarity to S. cerevisiae RPD3 (YNL330C) SIN3 histone deacetylase complex component Get druggable targets OG5_126742 All targets in OG5_126742
Candida albicans one of two distinct genes with strong similarity to S. cerevisiae RPD3 (YNL330C) SIN3 histone deacetylase complex component Get druggable targets OG5_126742 All targets in OG5_126742
Trypanosoma brucei histone deacetylase 1 Get druggable targets OG5_126742 All targets in OG5_126742
Schistosoma mansoni histone deacetylase hda2 Get druggable targets OG5_126654 All targets in OG5_126654
Loa Loa (eye worm) histone deacetylase Get druggable targets OG5_126654 All targets in OG5_126654
Brugia malayi Histone deacetylase 1 Get druggable targets OG5_126742 All targets in OG5_126742
Candida albicans strong similarity to S. cerevisiae HDA1 (YNL021W) class II histone deacetylase HDA1 complex subunit Get druggable targets OG5_126654 All targets in OG5_126654
Plasmodium berghei histone deacetylase, putative Get druggable targets OG5_126654 All targets in OG5_126654
Plasmodium knowlesi histone deacetylase 2, putative Get druggable targets OG5_126654 All targets in OG5_126654
Cryptosporidium parvum histone deacetylase HDA2/Rpd3p Get druggable targets OG5_126742 All targets in OG5_126742
Trichomonas vaginalis histone deacetylase 1, 2 ,3, putative Get druggable targets OG5_126742 All targets in OG5_126742
Schistosoma japonicum Histone deacetylase 4, putative Get druggable targets OG5_126654 All targets in OG5_126654
Schistosoma mansoni histone deacetylase Get druggable targets OG5_126742 All targets in OG5_126742
Cryptosporidium parvum RPD3/HD1 histone deacetylase Get druggable targets OG5_126742 All targets in OG5_126742
Loa Loa (eye worm) histone deacetylase 7A Get druggable targets OG5_126654 All targets in OG5_126654
Schistosoma japonicum Histone deacetylase 6, putative Get druggable targets OG5_126654 All targets in OG5_126654
Echinococcus granulosus histone deacetylase 7 Get druggable targets OG5_126654 All targets in OG5_126654
Leishmania infantum histone deacetylase, putative Get druggable targets OG5_126654 All targets in OG5_126654
Schistosoma japonicum ko:K06067 histone deacetylase 1/2, putative Get druggable targets OG5_126742 All targets in OG5_126742
Entamoeba histolytica histone deacetylase, putative Get druggable targets OG5_126742 All targets in OG5_126742
Echinococcus multilocularis histone deacetylase 6 Get druggable targets OG5_126654 All targets in OG5_126654
Echinococcus multilocularis histone deacetylase 6 Get druggable targets OG5_126654 All targets in OG5_126654
Plasmodium vivax histone deacetylase 1, putative Get druggable targets OG5_126742 All targets in OG5_126742
Plasmodium knowlesi histone deacetylase 1, putative Get druggable targets OG5_126742 All targets in OG5_126742
Brugia malayi histone deacetylase 3 (HD3) Get druggable targets OG5_126742 All targets in OG5_126742
Toxoplasma gondii histone deacetylase HDAC3 Get druggable targets OG5_126742 All targets in OG5_126742
Leishmania donovani histone deacetylase, putative Get druggable targets OG5_126654 All targets in OG5_126654
Echinococcus multilocularis histone deacetylase 1 Get druggable targets OG5_126742 All targets in OG5_126742
Theileria parva hypothetical protein Get druggable targets OG5_126654 All targets in OG5_126654
Giardia lamblia Histone deacetylase Get druggable targets OG5_126742 All targets in OG5_126742
Plasmodium falciparum histone deacetylase 1 Get druggable targets OG5_126742 All targets in OG5_126742
Trichomonas vaginalis histone deacetylase, putative Get druggable targets OG5_126742 All targets in OG5_126742
Leishmania major histone deacetylase, putative Get druggable targets OG5_126742 All targets in OG5_126742
Trypanosoma brucei histone deacetylase 3 Get druggable targets OG5_126654 All targets in OG5_126654
Schistosoma japonicum hypothetical protein Get druggable targets OG5_126654 All targets in OG5_126654
Echinococcus granulosus histone deacetylase 3 Get druggable targets OG5_126742 All targets in OG5_126742
Loa Loa (eye worm) histone deacetylase 1 Get druggable targets OG5_126742 All targets in OG5_126742
Cryptosporidium hominis histone deacetylase Get druggable targets OG5_126742 All targets in OG5_126742
Leishmania braziliensis histone deacetylase, putative Get druggable targets OG5_126654 All targets in OG5_126654
Leishmania infantum histone deacetylase, putative Get druggable targets OG5_126742 All targets in OG5_126742
Leishmania braziliensis histone deacetylase, putative Get druggable targets OG5_126742 All targets in OG5_126742
Echinococcus multilocularis histone deacetylase 7 Get druggable targets OG5_126654 All targets in OG5_126654
Plasmodium berghei histone deacetylase 2, putative Get druggable targets OG5_126654 All targets in OG5_126654
Echinococcus multilocularis histone deacetylase 6 Get druggable targets OG5_126654 All targets in OG5_126654
Brugia malayi Histone deacetylase family protein Get druggable targets OG5_126654 All targets in OG5_126654
Plasmodium berghei histone deacetylase 1, putative Get druggable targets OG5_126742 All targets in OG5_126742
Cryptosporidium parvum histone deactylase of possible bacterial origin with ankyrin repeats at the N-terminus Get druggable targets OG5_126654 All targets in OG5_126654
Candida albicans one of two distinct genes with strong similarity to S. cerevisiae RPD3 (YNL330C) SIN3 histone deacetylase complex component Get druggable targets OG5_126742 All targets in OG5_126742
Trypanosoma cruzi histone deacetylase, putative Get druggable targets OG5_126654 All targets in OG5_126654
Trichomonas vaginalis histone deacetylase, putative Get druggable targets OG5_126742 All targets in OG5_126742
Plasmodium vivax histone deacetylase, putative Get druggable targets OG5_126654 All targets in OG5_126654
Loa Loa (eye worm) histone deacetylase 3 Get druggable targets OG5_126742 All targets in OG5_126742
Theileria parva histone deacetylase, putative Get druggable targets OG5_126742 All targets in OG5_126742
Plasmodium knowlesi histone deacetylase, putative Get druggable targets OG5_126654 All targets in OG5_126654
Brugia malayi histone deacetylase 1 (HD1) Get druggable targets OG5_126742 All targets in OG5_126742
Trichomonas vaginalis histone deacetylase, putative Get druggable targets OG5_126742 All targets in OG5_126742
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Plasmodium falciparum histone deacetylase 1 histone deacetylase 8 286 aa 241 aa 44.8 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Loa Loa (eye worm) histone deacetylase 3 0.0113 0.2336 0.2336
Echinococcus multilocularis histone deacetylase 6 0.01 0.1939 0.1314
Treponema pallidum fructose-bisphosphate aldolase 0.0282 0.7305 0.5
Echinococcus multilocularis histone deacetylase 3 0.0113 0.2336 0.1741
Leishmania major histone deacetylase, putative 0.0113 0.2336 1
Trypanosoma cruzi histone deacetylase 1, putative 0.0113 0.2336 1
Toxoplasma gondii histone deacetylase HDAC1 0.0092 0.172 0.619
Brugia malayi histone deacetylase 1 (HD1) 0.0113 0.2336 0.1741
Mycobacterium leprae Probable fructose bisphosphate aldolase Fba 0.0138 0.3057 0.5
Brugia malayi Histone deacetylase family protein 0.0092 0.172 0.1078
Mycobacterium tuberculosis Probable fructose-bisphosphate aldolase Fba 0.0138 0.3057 0.5
Entamoeba histolytica fructose-1,6-bisphosphate aldolase, putative 0.0282 0.7305 1
Trichomonas vaginalis fructose-bisphosphate aldolase, putative 0.0282 0.7305 1
Onchocerca volvulus Histone deacetylase 10 homolog 0.0058 0.072 0.5
Trypanosoma cruzi histone deacetylase, putative 0.0092 0.172 0.619
Trichomonas vaginalis fructose-bisphosphate aldolase, putative 0.0282 0.7305 1
Trichomonas vaginalis fructose-bisphosphate aldolase, putative 0.0282 0.7305 1
Echinococcus granulosus histone deacetylase 7 0.0092 0.172 0.1078
Echinococcus multilocularis histone deacetylase 1 0.0113 0.2336 0.1741
Entamoeba histolytica fructose-1,6-bisphosphate aldolase, putative 0.0282 0.7305 1
Trypanosoma cruzi histone deacetylase, putative 0.0092 0.172 0.619
Mycobacterium ulcerans fructose-bisphosphate aldolase 0.0138 0.3057 0.5
Trichomonas vaginalis fructose-bisphosphate aldolase, putative 0.0282 0.7305 1
Loa Loa (eye worm) hypothetical protein 0.0058 0.072 0.072
Echinococcus multilocularis MAP kinase activated protein kinase 2 0.0374 1 1
Brugia malayi Histone deacetylase 1 0.0113 0.2336 0.1741
Brugia malayi histone deacetylase 3 (HD3) 0.0113 0.2336 0.1741
Leishmania major histone deacetylase, putative 0.0113 0.2336 1
Echinococcus multilocularis histone deacetylase 6 0.0092 0.172 0.1078
Schistosoma mansoni histone deacetylase 0.0113 0.2336 0.1741
Loa Loa (eye worm) histone deacetylase 7A 0.0092 0.172 0.172
Schistosoma mansoni histone deacetylase 4 5 0.0092 0.172 0.1078
Trichomonas vaginalis fructose-bisphosphate aldolase, putative 0.0282 0.7305 1
Echinococcus multilocularis histone deacetylase 6 0.0092 0.172 0.1078
Echinococcus granulosus histone deacetylase 1 0.0113 0.2336 0.1741
Loa Loa (eye worm) hypothetical protein 0.0041 0.0219 0.0219
Trypanosoma cruzi histone deacetylase 1, putative 0.0113 0.2336 1
Trichomonas vaginalis fructose-bisphosphate aldolase, putative 0.0282 0.7305 1
Echinococcus multilocularis histone deacetylase 0.0092 0.172 0.1078
Echinococcus granulosus histone deacetylase 6 0.0092 0.172 0.1078
Trypanosoma brucei histone deacetylase, putative 0.0092 0.172 0.619
Echinococcus granulosus MAP kinase activated protein kinase 2 0.0374 1 1
Loa Loa (eye worm) hypothetical protein 0.0113 0.2336 0.2336
Echinococcus granulosus histone deacetylase 0.0092 0.172 0.1078
Trypanosoma brucei histone deacetylase 4 0.0092 0.172 0.619
Trypanosoma brucei histone deacetylase 3 0.0092 0.172 0.619
Schistosoma mansoni serine/threonine protein kinase 0.0374 1 1
Loa Loa (eye worm) histone deacetylase 11 0.0058 0.072 0.072
Echinococcus granulosus histone deacetylase 6 0.0092 0.172 0.1078
Loa Loa (eye worm) camk/mapkapk/mapkapk protein kinase 0.0374 1 1
Trichomonas vaginalis fructose-bisphosphate aldolase, putative 0.0282 0.7305 1
Echinococcus multilocularis histone deacetylase 7 0.0092 0.172 0.1078
Loa Loa (eye worm) histone deacetylase 0.0092 0.172 0.172
Trypanosoma brucei histone deacetylase 1 0.0113 0.2336 1
Brugia malayi Histone deacetylase family protein 0.0092 0.172 0.1078
Plasmodium vivax histone deacetylase, putative 0.0092 0.172 0.619
Plasmodium vivax histone deacetylase 2, putative 0.0092 0.172 0.619
Trypanosoma cruzi histone deacetylase, putative 0.0092 0.172 0.619
Toxoplasma gondii histone deacetylase HDAC2 0.0113 0.2336 1
Loa Loa (eye worm) histone deacetylase 1 0.0113 0.2336 0.2336
Schistosoma mansoni histone deacetylase 0.0113 0.2336 0.1741
Echinococcus granulosus histone deacetylase 6 0.01 0.1939 0.1314
Schistosoma mansoni histone deacetylase 4 5 0.0092 0.172 0.1078
Plasmodium falciparum histone deacetylase 1 0.0113 0.2336 1
Giardia lamblia Fructose-bisphosphate aldolase 0.0282 0.7305 1
Echinococcus granulosus histone deacetylase 3 0.0113 0.2336 0.1741
Trichomonas vaginalis fructose-bisphosphate aldolase, putative 0.0282 0.7305 1
Plasmodium vivax histone deacetylase 1, putative 0.0113 0.2336 1
Toxoplasma gondii histone deacetylase HDAC3 0.0113 0.2336 1
Schistosoma mansoni histone deacetylase hda2 0.01 0.1939 0.1314

Activities

Activity type Activity value Assay description Source Reference
EC50 (functional) = 1.2 uM Cytotoxicity against human HL60 cells assessed as NADH level after 72 hrs by MTS cells ChEMBL. 20392637
EC50 (functional) = 5 uM Cytotoxicity against human PC3 cells assessed as NADH level after 72 hrs by MTS cells ChEMBL. 20392637
EC50 (functional) = 25 uM Cytotoxicity against human A549 cells assessed as NADH level after 72 hrs by MTS cells ChEMBL. 20392637
IC50 (binding) = 50 nM Inhibition of human recombinant HDAC2 ChEMBL. 20392637
IC50 (binding) = 160 nM Inhibition of human recombinant HDAC6 ChEMBL. 20392637
IC50 (binding) = 400 nM Inhibition of human recombinant HDAC8 ChEMBL. 20392637

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Homo sapiens ChEMBL23 20392637

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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