Detailed information for compound 557821

Basic information

Technical information
  • TDR Targets ID: 557821
  • Name: 4-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-9-[(2S ,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymeth yl)tetrahydropyran-2-yl]oxy-1H-benzo[f]isoben zofuran-3-one
  • MW: 542.488 | Formula: C27H26O12
  • H donors: 4 H acceptors: 5 LogP: 1.82 Rotable bonds: 6
    Rule of 5 violations (Lipinski): 2
  • SMILES: OC[C@H]1O[C@@H](Oc2c3COC(=O)c3c(c3c2cc(OC)c(c3)OC)c2ccc3c(c2)OCO3)[C@@H]([C@H]([C@@H]1O)O)O
  • InChi: 1S/C27H26O12/c1-33-16-6-12-13(7-17(16)34-2)25(39-27-24(31)23(30)22(29)19(8-28)38-27)14-9-35-26(32)21(14)20(12)11-3-4-15-18(5-11)37-10-36-15/h3-7,19,22-24,27-31H,8-10H2,1-2H3/t19-,22-,23+,24-,27+/m1/s1
  • InChiKey: BJGIWVGXMRUMNA-WBYCZGBQSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 4-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-9-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-tetrahydropyranyl]oxy]-1H-benzo[f]isobenzofuran-3-one
  • 4-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-9-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1H-benzo[f][2]benzofuran-3-one
  • 4-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-9-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methylol-tetrahydropyran-2-yl]oxy-1H-benzo[f]isobenzofuran-3-one
  • cleistanthin B
  • 4-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-9-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1H-benzo[f][2]benzoxol-3-one
  • 30021-77-3
  • Naphtho(2,3-c)furan-1(3H)-one, 9-(1,3-benzodioxol-5-yl)-4-(beta-D-glucopyranosyloxy)-6,7-dimethoxy-
  • 9-(1,3-Benzodioxol-5-yl)-4-(beta-D-glucopyranosyloxy)-6,7-dimethoxynaphtho(2,3-c)furan-1(3H)-one
  • Clei B

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
Echinococcus multilocularis Hepatocellular carcinoma associated antigen 59 0.150623 0.753721 1
Loa Loa (eye worm) hypothetical protein 0.150623 0.753721 0.752205
Brugia malayi Protein kinase domain containing protein 0.196834 1 1
Trypanosoma cruzi arginine N-methyltransferase, putative 0.013973 0.0254443 0.5
Schistosoma mansoni hypothetical protein 0.0200335 0.0577439 0.0766117
Schistosoma mansoni microtubule-associated protein tau 0.0478696 0.206097 0.273439
Trypanosoma brucei Protein arginine N-methyltransferase 1 catalytic subunit 0.013973 0.0254443 0.5
Schistosoma mansoni hypothetical protein 0.0200335 0.0577439 0.0766117
Echinococcus multilocularis microtubule associated protein 2 0.0478696 0.206097 0.213157
Echinococcus granulosus microtubule associated protein 2 0.0478696 0.206097 0.213157
Toxoplasma gondii hypothetical protein 0.150623 0.753721 0.5
Trypanosoma cruzi arginine N-methyltransferase, putative 0.013973 0.0254443 0.5
Entamoeba histolytica hypothetical protein 0.013973 0.0254443 0.5
Onchocerca volvulus 0.150623 0.753721 1
Loa Loa (eye worm) TK/ALK protein kinase 0.1967 0.999288 1
Brugia malayi Hepatocellular carcinoma-associated antigen 59 family protein 0.150623 0.753721 0.747291
Entamoeba histolytica arginine N-methyltransferase protein, putative 0.013973 0.0254443 0.5
Loa Loa (eye worm) hypothetical protein 0.0199514 0.0573064 0.0494694
Echinococcus granulosus Hepatocellular carcinoma associated antigen 59 0.150623 0.753721 1
Onchocerca volvulus 0.150623 0.753721 1
Plasmodium vivax hypothetical protein, conserved 0.150623 0.753721 0.5
Loa Loa (eye worm) hypothetical protein 0.013973 0.0254443 0.0173182
Plasmodium falciparum conserved protein, unknown function 0.150623 0.753721 0.5
Brugia malayi Amyloid A4 extracellular domain containing protein 0.0253111 0.0858712 0.0620045
Loa Loa (eye worm) hypothetical protein 0.150623 0.753721 0.752205
Loa Loa (eye worm) hypothetical protein 0.175769 0.887738 0.887437
Loa Loa (eye worm) hypothetical protein 0.0200335 0.0577439 0.0499109
Brugia malayi hypothetical protein 0.0200335 0.0577439 0.0331428
Loa Loa (eye worm) hypothetical protein 0.0200335 0.0577439 0.0499109
Loa Loa (eye worm) hypothetical protein 0.0200335 0.0577439 0.0499109
Schistosoma mansoni hypothetical protein 0.150623 0.753721 1

Activities

Activity type Activity value Assay description Source Reference
CC50 (functional) = 0.784 uM Huh7 cytotoxicity for Pf inhibitors Novartis-GNF Malaria Box. No reference
CC50 = 0.784 uM NOVARTIS: Cytotoxicity against human hepatocellular carcinoma cell line (Huh7) ChEMBL. 18579783
EC50 (functional) = 0.0743 uM PF proliferation inhibition 3D7 Novartis-GNF Malaria Box. No reference
EC50 (functional) = 0.0743 uM NOVARTIS: Inhibition of Plasmodium falciparum 3D7 (drug-susceptible) proliferation in erythrocyte-based infection assay ChEMBL. 18579783
EC50 (functional) = 0.12 uM W2 Pf proliferation inhibition Novartis-GNF Malaria Box. No reference
EC50 (functional) = 0.12 uM NOVARTIS: Inhibition of Plasmodium falciparum W2 (drug-resistant) proliferation in erythrocyte-based infection assay ChEMBL. 18579783
IC50 (functional) = 2.44 uM Cytotoxicity against human MCF7 cells after 72 hrs by sulforhodamine B and MTT assay ChEMBL. 22119124
IC50 (functional) = 9.67 uM Cytotoxicity against human HCT116 cells after 72 hrs by sulforhodamine B and MTT assay ChEMBL. 22119124
IC50 (functional) > 10 uM Cytotoxicity against human KB cells after 72 hrs by sulforhodamine B and MTT assay ChEMBL. 22119124
IC50 (functional) > 10 uM Cytotoxicity against human HT-29 cells ChEMBL. 24937209
IFI promiscuity index = 0.1236 IFI promiscuity index Novartis-GNF Malaria Box. No reference
Inhibition (binding) Inhibition of human topoisomerase 2-mediated decatenation of kinetoplast DNA at 100 uM after 15 mins by agarose gel electrophoresis ChEMBL. 22119124

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Plasmodium falciparum ChEMBL23 18579783
Homo sapiens ChEMBL23 22119124

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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