Detailed information for compound 249553

Basic information

Technical information
  • TDR Targets ID: 249553
  • Name: 5-hydroxy-2-[4-methoxy-3-[2-oxo-2-[4-[(2,3,4- trimethoxyphenyl)methyl]piperazin-1-yl]ethoxy ]phenyl]-7-[2-oxo-2-[4-[(2,3,4-trimethoxyphen yl)methyl]piperazin-1-yl]ethoxy]chromen-4-one
  • MW: 912.977 | Formula: C48H56N4O14
  • H donors: 1 H acceptors: 4 LogP: 4.78 Rotable bonds: 20
    Rule of 5 violations (Lipinski): 2
  • SMILES: COc1ccc(cc1OCC(=O)N1CCN(CC1)Cc1ccc(c(c1OC)OC)OC)c1cc(=O)c2c(o1)cc(cc2O)OCC(=O)N1CCN(CC1)Cc1ccc(c(c1OC)OC)OC
  • InChi: 1S/C48H56N4O14/c1-57-36-11-8-30(22-40(36)65-29-43(56)52-20-16-50(17-21-52)27-32-10-13-38(59-3)48(63-7)46(32)61-5)39-25-35(54)44-34(53)23-33(24-41(44)66-39)64-28-42(55)51-18-14-49(15-19-51)26-31-9-12-37(58-2)47(62-6)45(31)60-4/h8-13,22-25,53H,14-21,26-29H2,1-7H3
  • InChiKey: VBIWWIXVYZBLKW-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 5-hydroxy-2-[4-methoxy-3-[2-oxo-2-[4-[(2,3,4-trimethoxyphenyl)methyl]-1-piperazinyl]ethoxy]phenyl]-7-[2-oxo-2-[4-[(2,3,4-trimethoxyphenyl)methyl]-1-piperazinyl]ethoxy]-1-benzopyran-4-one
  • 5-hydroxy-7-[2-keto-2-[4-(2,3,4-trimethoxybenzyl)piperazino]ethoxy]-2-[3-[2-keto-2-[4-(2,3,4-trimethoxybenzyl)piperazino]ethoxy]-4-methoxy-phenyl]chromone
  • 5-hydroxy-2-[4-methoxy-3-[2-oxo-2-[4-[(2,3,4-trimethoxyphenyl)methyl]-1-piperazinyl]ethoxy]phenyl]-7-[2-oxo-2-[4-[(2,3,4-trimethoxyphenyl)methyl]-1-piperazinyl]ethoxy]-4-chromenone
  • 5-hydroxy-7-[2-keto-2-[4-(2,3,4-trimethoxybenzyl)piperazin-1-yl]ethoxy]-2-[3-[2-keto-2-[4-(2,3,4-trimethoxybenzyl)piperazin-1-yl]ethoxy]-4-methoxy-phenyl]chromone

Targets

Known targets for this compound

No curated genes were found associated with this compound

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
Trypanosoma cruzi tubulin delta chain 0.0382831 0.5309 0.506714
Leishmania major alpha tubulin 0.0421261 0.633293 0.614387
Brugia malayi Tubulin alpha chain 0.0421261 0.633293 0.614387
Trichomonas vaginalis tubulin gamma chain, putative 0.0558891 1 1
Leishmania major beta tubulin 0.0558891 1 1
Trypanosoma brucei beta tubulin 0.0558891 1 1
Echinococcus multilocularis tubulin alpha 3 chain 0.0421261 0.633293 0.614387
Trichomonas vaginalis tubulin beta chain, putative 0.0421261 0.633293 0.633293
Schistosoma mansoni tubulin subunit beta 0.0558891 1 1
Loa Loa (eye worm) alpha-tubulin isotype 2 0.0277094 0.249167 0.210456
Leishmania major alpha tubulin 0.0421261 0.633293 0.614387
Echinococcus multilocularis hypothetical protein 0.0421261 0.633293 0.614387
Leishmania major alpha tubulin 0.0421261 0.633293 0.614387
Echinococcus granulosus alpha tubulin 0.0421261 0.633293 0.614387
Toxoplasma gondii alpha tubulin TUBA1 0.0421261 0.633293 0.614387
Trypanosoma brucei beta tubulin 0.0558891 1 1
Toxoplasma gondii tubulin/FtsZ family, GTPase domain-containing protein 0.0314426 0.348639 0.315056
Schistosoma mansoni tubulin subunit epsilon 0.03532 0.451948 0.423692
Echinococcus granulosus tubulin subunit TubB 0.0421261 0.633293 0.614387
Leishmania major beta tubulin 0.0558891 1 1
Loa Loa (eye worm) tubulin beta-2A chain 0.0558891 1 1
Echinococcus multilocularis beta tubulin 0.0558891 1 1
Schistosoma mansoni tubulin subunit beta 0.0558891 1 1
Brugia malayi tubulin alpha-2 chain 0.0421261 0.633293 0.614387
Leishmania major beta tubulin 0.0558891 1 1
Loa Loa (eye worm) tubulin alpha 2 0.0277094 0.249167 0.210456
Plasmodium vivax tubulin beta chain, putative 0.0558891 1 1
Echinococcus granulosus tubulin alpha 1C chain 0.0421261 0.633293 0.614387
Trichomonas vaginalis tubulin alpha-1 chain, putative 0.0421261 0.633293 0.633293
Echinococcus multilocularis tubulin alpha 0.0314426 0.348639 0.315056
Echinococcus granulosus Tubulin beta 2C chain 0.0558891 1 1
Echinococcus multilocularis Tubulin beta 2C chain 0.0558891 1 1
Echinococcus multilocularis Tubulin alpha 1 chain 0.0421261 0.633293 0.614387
Echinococcus multilocularis tubulin alpha chain 0.0421261 0.633293 0.614387
Echinococcus granulosus peroxisome assembly protein 26 0.0421261 0.633293 0.614387
Echinococcus granulosus Tubulin beta 2C chain 0.0558891 1 1
Echinococcus multilocularis tubulin gamma 1 chain 0.0353837 0.453645 0.425476
Giardia lamblia Beta tubulin 0.0558891 1 1
Echinococcus multilocularis Tubulin beta 2C chain 0.0558891 1 1
Echinococcus granulosus tubulin beta 4A class IVa 0.0558891 1 1
Trypanosoma cruzi epsilon tubulin, putative 0.03532 0.451948 0.423692
Echinococcus granulosus beta tubulin 0.0558891 1 1
Toxoplasma gondii beta-1 tubulin, putative 0.0558891 1 1
Leishmania major beta tubulin 0.0558891 1 1
Echinococcus multilocularis tubulin epsilon chain 0.03532 0.451948 0.423692
Echinococcus granulosus Tubulin beta 2C chain 0.0558891 1 1
Loa Loa (eye worm) hypothetical protein 0.0277094 0.249167 0.210456
Leishmania major beta tubulin 0.0558891 1 1
Trypanosoma cruzi tubulin delta chain 0.0382831 0.5309 0.506714
Brugia malayi tubulin alpha chain - mouse 0.0421261 0.633293 0.614387
Trypanosoma cruzi zeta tubulin, putative 0.0541589 0.9539 0.951523
Trichomonas vaginalis tubulin alpha-1 chain, putative 0.0251002 0.179649 0.179649
Trypanosoma brucei beta tubulin 0.0558891 1 1
Echinococcus granulosus tubulin alpha chain 0.0421261 0.633293 0.614387
Leishmania major alpha tubulin 0.0421261 0.633293 0.614387
Leishmania major zeta tubulin, putative 0.0541589 0.9539 0.951523
Echinococcus multilocularis peroxisome assembly protein 26 0.0421261 0.633293 0.614387
Loa Loa (eye worm) hypothetical protein 0.0251002 0.179649 0.137353
Plasmodium falciparum tubulin gamma chain 0.0353837 0.453645 0.425476
Echinococcus granulosus beta tubulin 0.0558891 1 1
Echinococcus multilocularis tubulin, beta 4A class IVa 0.0558891 1 1
Plasmodium vivax tubulin epsilon chain, putative 0.03532 0.451948 0.423692
Giardia lamblia Alpha-tubulin 0.0421261 0.633293 0.328813
Toxoplasma gondii alpha-tubulin I, putative 0.0421261 0.633293 0.614387
Leishmania major beta tubulin 0.0558891 1 1
Trypanosoma brucei epsilon tubulin 0.0314426 0.348639 0.315056
Trichomonas vaginalis tubulin epsilon chain, putative 0.0421261 0.633293 0.633293
Trichomonas vaginalis tubulin beta chain, putative 0.0421261 0.633293 0.633293
Echinococcus multilocularis tubulin alpha chain 0.0421261 0.633293 0.614387
Leishmania major alpha tubulin 0.0421261 0.633293 0.614387
Loa Loa (eye worm) beta-tubulin 0.0558891 1 1
Trypanosoma cruzi alpha tubulin, putative 0.0421261 0.633293 0.614387
Leishmania major beta tubulin 0.0558891 1 1
Echinococcus multilocularis tubulin alpha chain 0.0421261 0.633293 0.614387
Echinococcus granulosus tubulin alpha 3 chain 0.0421261 0.633293 0.614387
Loa Loa (eye worm) tubulin beta-1 chain 0.0558891 1 1
Trypanosoma brucei zeta tubulin 0.0541589 0.9539 0.951523
Leishmania major beta tubulin 0.0558891 1 1
Leishmania major epsilon tubulin, putative 0.03532 0.451948 0.423692
Trypanosoma brucei beta tubulin 0.0558891 1 1
Echinococcus multilocularis tubulin alpha chain 0.0421261 0.633293 0.614387
Trypanosoma cruzi tubulin gamma chain 0.0353837 0.453645 0.425476
Trypanosoma brucei tubulin gamma chain 0.0353837 0.453645 0.425476
Trichomonas vaginalis tubulin beta chain, putative 0.0421261 0.633293 0.633293
Loa Loa (eye worm) BEN-1 protein 0.0558891 1 1
Echinococcus multilocularis beta tubulin 0.0558891 1 1
Loa Loa (eye worm) tubulin alpha 2 0.0277094 0.249167 0.210456
Leishmania major beta tubulin 0.0558891 1 1
Brugia malayi beta-tubulin, identical 0.0558891 1 1
Trypanosoma brucei epsilon tubulin 0.03532 0.451948 0.423692
Leishmania major beta tubulin 0.0558891 1 1
Echinococcus granulosus tubulin alpha 1C chain 0.0421261 0.633293 0.614387
Trypanosoma brucei alpha tubulin 0.0421261 0.633293 0.614387
Echinococcus granulosus Tubulin beta 2C chain 0.0558891 1 1
Trichomonas vaginalis tubulin beta chain, putative 0.0421261 0.633293 0.633293
Brugia malayi alpha-tubulin 0.0421261 0.633293 0.614387
Trypanosoma brucei alpha tubulin 0.0421261 0.633293 0.614387
Trichomonas vaginalis tubulin alpha chain, putative 0.0314426 0.348639 0.348639
Echinococcus granulosus tubulin epsilon chain 0.03532 0.451948 0.423692
Schistosoma mansoni alpha tubulin 0.0421261 0.633293 0.614387
Trypanosoma brucei alpha tubulin 0.0421261 0.633293 0.614387
Loa Loa (eye worm) tubulin alpha-2 chain 0.0421261 0.633293 0.614387
Echinococcus granulosus tubulin gamma 1 chain 0.0353837 0.453645 0.425476
Plasmodium vivax tubulin alpha chain, putative 0.0421261 0.633293 0.614387
Trichomonas vaginalis tubulin alpha-1 chain, putative 0.0277094 0.249167 0.249167
Trichomonas vaginalis tubulin gamma chain, putative 0.03532 0.451948 0.451948
Trypanosoma brucei alpha tubulin 0.0421261 0.633293 0.614387
Plasmodium falciparum alpha tubulin 2 0.0421261 0.633293 0.614387
Loa Loa (eye worm) tubulin gamma chain 0.0353837 0.453645 0.425476
Entamoeba histolytica tubulin family protein 0.0558891 1 1
Echinococcus multilocularis tubulin subunit beta 0.0558891 1 1
Echinococcus multilocularis tubulin subunit TubB 0.0421261 0.633293 0.614387
Echinococcus granulosus tubulin alpha chain 0.0421261 0.633293 0.614387
Trichomonas vaginalis tubulin beta chain, putative 0.0421261 0.633293 0.633293
Loa Loa (eye worm) tubulin alpha-3 chain 0.0251002 0.179649 0.137353
Brugia malayi Tubulin beta-1 chain 0.0558891 1 1
Leishmania major beta tubulin 0.0558891 1 1
Echinococcus multilocularis Tubulin alpha 1 chain 0.0421261 0.633293 0.614387
Trypanosoma cruzi beta tubulin, putative 0.0558891 1 1
Leishmania major beta tubulin 0.0558891 1 1
Echinococcus granulosus tubulin alpha 3 chain 0.0421261 0.633293 0.614387
Schistosoma mansoni tubulin subunit beta 0.0558891 1 1
Echinococcus multilocularis tubulin alpha 1C chain 0.0421261 0.633293 0.614387
Echinococcus multilocularis Tubulin beta 2C chain 0.0558891 1 1
Schistosoma mansoni alpha tubulin 0.0421261 0.633293 0.614387
Leishmania major alpha tubulin 0.0421261 0.633293 0.614387
Loa Loa (eye worm) alpha-tubulin 0.0421261 0.633293 0.614387
Loa Loa (eye worm) tubulin beta chain 0.0558891 1 1
Schistosoma mansoni tubulin subunit beta 0.0558891 1 1
Echinococcus granulosus tubulin alpha chain 0.0421261 0.633293 0.614387
Leishmania major alpha tubulin 0.0421261 0.633293 0.614387
Schistosoma mansoni tubulin subunit alpha 0.0421261 0.633293 0.614387
Loa Loa (eye worm) BEN-1 protein 0.0558891 1 1
Trypanosoma brucei tubulin delta chain 0.0382831 0.5309 0.506714
Schistosoma mansoni tubulin subunit gamma 0.0353837 0.453645 0.425476
Giardia lamblia Alpha-tubulin 0.0421261 0.633293 0.328813
Giardia lamblia Beta tubulin 0.0558891 1 1
Echinococcus granulosus Tubulin alpha 1 chain 0.0421261 0.633293 0.614387
Toxoplasma gondii tubulin/FtsZ family, GTPase domain-containing protein 0.0382831 0.5309 0.506714
Trypanosoma cruzi epsilon tubulin, putative 0.03532 0.451948 0.423692
Echinococcus granulosus tubulin beta 1 chain 0.0558891 1 1
Schistosoma mansoni tubulin subunit beta 0.0558891 1 1
Trichomonas vaginalis tubulin alpha chain, putative 0.0558891 1 1
Loa Loa (eye worm) alpha-tubulin 0.0421261 0.633293 0.614387
Loa Loa (eye worm) tubulin alpha chain 0.0421261 0.633293 0.614387
Loa Loa (eye worm) tubulin alpha chain 0.0421261 0.633293 0.614387
Trichomonas vaginalis tubulin beta chain, putative 0.0558891 1 1
Schistosoma mansoni tubulin subunit beta 0.0558891 1 1
Echinococcus granulosus tubulin alpha chain 0.0421261 0.633293 0.614387
Echinococcus granulosus tubulin subunit beta 0.0558891 1 1
Leishmania major alpha tubulin 0.0421261 0.633293 0.614387
Trichomonas vaginalis tubulin epsilon chain, putative 0.0421261 0.633293 0.633293
Entamoeba histolytica tubulin family protein 0.0558891 1 1
Trypanosoma brucei zeta tubulin, putative 0.0541589 0.9539 0.951523
Echinococcus granulosus Tubulin beta 2C chain 0.0558891 1 1
Schistosoma mansoni alpha tubulin 0.0421261 0.633293 0.614387
Giardia lamblia Beta tubulin 0.0558891 1 1
Loa Loa (eye worm) tubulin beta-4 chain 0.0558891 1 1
Echinococcus granulosus tubulin alpha 0.0314426 0.348639 0.315056
Plasmodium vivax tubulin alpha chain, putative 0.0421261 0.633293 0.614387
Echinococcus multilocularis Tubulin alpha 1 chain 0.0421261 0.633293 0.614387
Toxoplasma gondii beta-tubulin, putative 0.0558891 1 1
Schistosoma mansoni tubulin subunit alpha 0.0421261 0.633293 0.614387
Entamoeba histolytica tubulin alpha chain, putative 0.0421261 0.633293 0.328813
Echinococcus multilocularis Tubulin beta 2C chain 0.0558891 1 1
Trichomonas vaginalis tubulin epsilon chain, putative 0.0558891 1 1
Plasmodium falciparum tubulin epsilon chain, putative 0.03532 0.451948 0.423692
Trypanosoma brucei beta tubulin 0.0314426 0.348639 0.315056
Plasmodium vivax tubulin gamma chain, putative 0.0353837 0.453645 0.425476
Echinococcus multilocularis tubulin alpha 1C chain 0.0421261 0.633293 0.614387
Brugia malayi Tubulin gamma chain 0.0353837 0.453645 0.425476
Trichomonas vaginalis tubulin gamma chain, putative 0.0353837 0.453645 0.453645
Echinococcus multilocularis tubulin beta 1 chain 0.0558891 1 1
Echinococcus multilocularis tubulin alpha 3 chain 0.0421261 0.633293 0.614387
Leishmania major alpha tubulin 0.0421261 0.633293 0.614387
Leishmania major beta tubulin 0.0558891 1 1
Trypanosoma brucei epsilon tubulin 0.03532 0.451948 0.423692
Echinococcus multilocularis Tubulin beta 2C chain 0.0558891 1 1
Leishmania major beta tubulin 0.0558891 1 1
Loa Loa (eye worm) hypothetical protein 0.0421261 0.633293 0.614387
Leishmania major alpha tubulin 0.0421261 0.633293 0.614387
Trichomonas vaginalis tubulin beta chain, putative 0.0421261 0.633293 0.633293
Echinococcus granulosus Tubulin alpha 1 chain 0.0421261 0.633293 0.614387
Echinococcus multilocularis tubulin alpha chain 0.0421261 0.633293 0.614387
Leishmania major beta tubulin 0.0558891 1 1
Leishmania major beta tubulin 0.0558891 1 1
Echinococcus granulosus Tubulin alpha 1 chain 0.0421261 0.633293 0.614387
Brugia malayi Tubulin alpha-2 chain 0.0421261 0.633293 0.614387
Brugia malayi Tubulin alpha-2 chain 0.0421261 0.633293 0.614387
Schistosoma mansoni tubulin subunit alpha 0.0421261 0.633293 0.614387
Leishmania major gamma-tubulin 0.0353837 0.453645 0.425476
Trichomonas vaginalis tubulin epsilon chain, putative 0.0558891 1 1
Plasmodium falciparum alpha tubulin 1 0.0421261 0.633293 0.614387
Entamoeba histolytica tubulin alpha-1 chain 0.0421261 0.633293 0.328813
Echinococcus granulosus tubulin alpha chain 0.0421261 0.633293 0.614387
Trypanosoma cruzi zeta tubulin, putative 0.0541589 0.9539 0.951523
Leishmania major beta tubulin 0.0558891 1 1
Toxoplasma gondii beta tubulin 0.0558891 1 1
Leishmania major alpha tubulin 0.0421261 0.633293 0.614387
Leishmania major alpha tubulin 0.0421261 0.633293 0.614387
Plasmodium falciparum tubulin beta chain 0.0558891 1 1
Leishmania major beta tubulin 0.0558891 1 1
Leishmania major delta tubulin, putative 0.0382831 0.5309 0.506714
Trichomonas vaginalis tubulin, putative 0.0558891 1 1

Activities

Activity type Activity value Assay description Source Reference
IC50 (functional) = 0.18 uM Antiplasmodial activity against Plasmodium falciparum D6 ChEMBL. 17166718
IC50 (functional) = 0.18 uM Antiplasmodial activity against Plasmodium falciparum D6 ChEMBL. 17166718
IC50 (ADMET) = 1 uM Cytotoxicity against MRC5 cells ChEMBL. 17166718
IC50 (ADMET) = 1 uM Cytotoxicity against MRC5 cells ChEMBL. 17166718
IC50 (functional) = 2 uM Ability to potentiate DOX cytotoxicity on K562/DOX MDR cells. Cell survival was assayed by MTT conversion ChEMBL. 9986718
IC50 (functional) = 2 uM Ability to potentiate DOX cytotoxicity on K562/DOX MDR cells. Cell survival was assayed by MTT conversion ChEMBL. 9986718
Modulation factor (functional) = 1 Modulation factor : IC50(DOX alone)/IC50(DOX+modulator) ChEMBL. 9986718
Relative JC-1 accumulation (functional) = 53 Pgp transport inhibitory activity at 10 microM was measured by JC-1 accumulation assay method using JC-1 as substrate ChEMBL. 9986718
Relative JC-1 accumulation (functional) = 22 Pgp transport inhibitory activity at 1 microM was measured by JC-1 accumulation assay method using JC-1 as substrate ChEMBL. 9986718
Relative JC-1 accumulation (functional) = 53 Pgp transport inhibitory activity at 10 microM was measured by JC-1 accumulation assay method using JC-1 as substrate ChEMBL. 9986718
Relative JC-1 accumulation (functional) = 60 Pgp transport inhibitory activity at 5 microM was measured by JC-1 accumulation assay method using JC-1 as substrate ChEMBL. 9986718

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Plasmodium falciparum ChEMBL23 17166718
Homo sapiens ChEMBL23 17166718

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

2 literature references were collected for this gene.

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