Detailed information for compound 344922

Basic information

Technical information
  • TDR Targets ID: 344922
  • Name: 5,7-dihydroxy-8-(3-methylbut-2-enyl)-6-(2-met hylpropanoyl)-4-phenylchromen-2-one
  • MW: 392.444 | Formula: C24H24O5
  • H donors: 2 H acceptors: 4 LogP: 5.58 Rotable bonds: 5
    Rule of 5 violations (Lipinski): 1
  • SMILES: CC(=CCc1c(O)c(C(=O)C(C)C)c(c2c1oc(=O)cc2c1ccccc1)O)C
  • InChi: 1S/C24H24O5/c1-13(2)10-11-16-22(27)20(21(26)14(3)4)23(28)19-17(12-18(25)29-24(16)19)15-8-6-5-7-9-15/h5-10,12,14,27-28H,11H2,1-4H3
  • InChiKey: IWUNXYBEJCJQHB-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 5,7-dihydroxy-8-(3-methylbut-2-enyl)-6-(2-methylpropanoyl)-4-phenyl-chromen-2-one
  • 5,7-dihydroxy-8-(3-methylbut-2-enyl)-6-(2-methyl-1-oxopropyl)-4-phenyl-1-benzopyran-2-one
  • 5,7-dihydroxy-6-isobutyryl-8-(3-methylbut-2-enyl)-4-phenyl-coumarin
  • 4-phenylcoumarin
  • 5,7-dihydroxy-8-(3-methylbut-2-enyl)-6-(2-methyl-1-oxopropyl)-4-phenyl-2-chromenone
  • 16981-20-7
  • NSC 130114
  • 2H-1-Benzopyran-2-one, 5,7-dihydroxy-8-(3-methyl-2-butenyl)-6-(2-methyl-1-oxopropyl)-4-phenyl-
  • Coumarin, 5,7-dihydroxy-6-isobutyryl-8-(3-methyl-2-butenyl)-4-phenyl-
  • Mesuol
  • NSC130114
  • AIDS-257826
  • AIDS257826

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Human immunodeficiency virus 1 Human immunodeficiency virus type 1 reverse transcriptase Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Trypanosoma congolense RNA helicase, putative Get druggable targets OG5_139608 All targets in OG5_139608
Plasmodium yoelii integrase-related Get druggable targets OG5_139608 All targets in OG5_139608
Schistosoma mansoni hypothetical protein Get druggable targets OG5_139608 All targets in OG5_139608
Trypanosoma brucei RNA helicase, putative Get druggable targets OG5_139608 All targets in OG5_139608
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
Leishmania major farnesyl pyrophosphate synthase 0.0422 0.9943 0.9938
Entamoeba histolytica bifunctional short chain isoprenyl diphosphate synthase, putative 0.0169 0.3173 1
Mycobacterium ulcerans geranylgeranyl pyrophosphate synthase 0.0422 0.9943 1
Loa Loa (eye worm) hexokinase 0.0079 0.079 0.079
Plasmodium vivax geranylgeranyl pyrophosphate synthase 0.0422 0.9943 1
Entamoeba histolytica geranylgeranyl pyrophosphate synthase, putative 0.0169 0.3173 1
Trichomonas vaginalis geranylgeranyl diphosphate synthase, putative 0.0422 0.9943 0.5
Echinococcus multilocularis farnesyl pyrophosphate synthase 0.0422 0.9943 0.9938
Loa Loa (eye worm) hexokinase 0.0079 0.079 0.079
Schistosoma mansoni farnesyl pyrophosphate synthase 0.0422 0.9943 0.9938
Leishmania major polyprenyl synthase, putative 0.0424 1 1
Brugia malayi Polyprenyl synthetase family protein 0.0422 0.9943 0.9943
Entamoeba histolytica geranylgeranyl pyrophosphate synthetase, putative 0.0169 0.3173 1
Echinococcus multilocularis decaprenyl diphosphate synthase subunit 1 0.0169 0.3173 0.2587
Echinococcus multilocularis geranylgeranyl pyrophosphate synthase 0.0424 1 1
Echinococcus granulosus decaprenyl diphosphate synthase subunit 1 0.0169 0.3173 0.2587
Chlamydia trachomatis geranylgeranyl pyrophosphate synthase 0.0169 0.3173 0.5
Echinococcus granulosus farnesyl pyrophosphate synthase 0.0422 0.9943 0.9938
Trypanosoma brucei solanesyl-diphosphate synthase, putative 0.0169 0.3173 0.2603
Trypanosoma cruzi solanesyl-diphosphate synthase 0.0169 0.3173 0.2587
Brugia malayi Polyprenyl synthetase family protein 0.0169 0.3173 0.3173
Wolbachia endosymbiont of Brugia malayi geranylgeranyl pyrophosphate synthase 0.0169 0.3173 0.5
Loa Loa (eye worm) geranylgeranyl pyrophosphate synthetase 0.0424 1 1
Toxoplasma gondii polyprenyl synthetase superfamily protein 0.0169 0.3173 0.2603
Wolbachia endosymbiont of Brugia malayi geranylgeranyl pyrophosphate synthase 0.0169 0.3173 0.5
Echinococcus granulosus prenyl decaprenyl diphosphate synthase 0.0169 0.3173 0.2587
Plasmodium falciparum geranylgeranyl pyrophosphate synthase, putative 0.0422 0.9943 1
Plasmodium vivax octaprenyl pyrophosphate synthase, putative 0.0169 0.3173 0.2603
Mycobacterium leprae PROBABLE POLYPRENYL-DIPHOSPHATE SYNTHASE GRCC1 (POLYPRENYL PYROPHOSPHATE SYNTHETASE) 0.0169 0.3173 0.5
Onchocerca volvulus 0.0079 0.079 1
Plasmodium falciparum octaprenyl pyrophosphate synthase 0.0169 0.3173 0.2603
Schistosoma mansoni hypothetical protein 0.01 0.1341 0.0597
Trypanosoma brucei farnesyl pyrophosphate synthase 0.0422 0.9943 1
Treponema pallidum octaprenyl-diphosphate synthase 0.0424 1 1
Brugia malayi hexokinase 0.0079 0.079 0.079
Mycobacterium ulcerans geranylgeranyl pyrophosphate synthase 0.0422 0.9943 1
Trypanosoma cruzi polyprenyl synthase, putative 0.0424 1 1
Onchocerca volvulus 0.0079 0.079 1
Mycobacterium tuberculosis Probable geranylgeranyl pyrophosphate synthetase IdsA2 (ggppsase) (GGPP synthetase) (geranylgeranyl diphosphate synthase) 0.0422 0.9943 1
Echinococcus multilocularis prenyl (decaprenyl) diphosphate synthase 0.0169 0.3173 0.2587
Echinococcus granulosus geranylgeranyl pyrophosphate synthase 0.0424 1 1
Schistosoma mansoni geranylgeranyl pyrophosphate synthase 0.0424 1 1
Schistosoma mansoni glutathione synthetase 0.0169 0.3173 0.2587
Giardia lamblia Farnesyl diphosphate synthase 0.0422 0.9943 0.5
Schistosoma mansoni trans-prenyltransferase 0.0169 0.3173 0.2587
Loa Loa (eye worm) polyprenyl synthetase 0.0169 0.3173 0.3173
Trichomonas vaginalis geranylgeranyl pyrophosphate synthase, putative 0.0422 0.9943 0.5
Trypanosoma cruzi farnesyl pyrophosphate synthase 0.0422 0.9943 0.9938
Trypanosoma cruzi solanesyl-diphosphate synthase, putative 0.0169 0.3173 0.2587
Loa Loa (eye worm) polyprenyl synthetase 0.0422 0.9943 0.9943
Trypanosoma cruzi farnesyl pyrophosphate synthase, putative 0.0422 0.9943 0.9938
Brugia malayi Hexokinase family protein 0.0079 0.079 0.079
Toxoplasma gondii polyprenyl synthetase superfamily protein 0.0422 0.9943 1
Trypanosoma cruzi solanesyl-diphosphate synthase, putative 0.0169 0.3173 0.2587
Loa Loa (eye worm) hypothetical protein 0.0054 0.0116 0.0116
Leishmania major solanesyl-diphosphate synthase, putative 0.0169 0.3173 0.2587
Trypanosoma cruzi polyprenyl synthase, putative 0.0424 1 1
Onchocerca volvulus 0.0079 0.079 1
Loa Loa (eye worm) hexokinase type II 0.0079 0.079 0.079
Trichomonas vaginalis geranylgeranyl pyrophosphate synthase, putative 0.0422 0.9943 0.5
Trypanosoma brucei RNA helicase, putative 0.01 0.1341 0.0601

Activities

Activity type Activity value Assay description Source Reference
Cell death (functional) = 22.5 % Toxicity of compound against human MT-2 cell line at the concentration of 50 uM ChEMBL. 16137881
Cell death (functional) = 22.5 % Toxicity of compound against human MT-2 cell line at the concentration of 50 uM ChEMBL. 16137881
GI50 (functional) = 0.1 ug ml-1 Cytotoxicity against human SF268 cells ChEMBL. 15787438
GI50 (functional) = 0.2 ug ml-1 Cytotoxicity against human MCF7 cells ChEMBL. 15787438
GI50 (functional) = 0.3 ug ml-1 Cytotoxicity against human H460 cells ChEMBL. 15787438
IC50 (binding) uM Inhibitory concentration against recombinant human immunodeficiency virus 1 reverse transcriptase; NT= not tested ChEMBL. 16137881
IC50 (binding) 0 uM Inhibitory concentration against recombinant human immunodeficiency virus 1 reverse transcriptase; NT= not tested ChEMBL. 16137881
IC50 (functional) = 1.3 uM Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced NO production incubated for 10 mins prior to LPS-challenge measured after 18 hrs by Griess method ChEMBL. 22831798
IC50 (binding) = 2.5 uM Inhibitory concentration against recombinant human immunodeficiency virus 1 reverse transcriptase ChEMBL. 16137881
IC50 (binding) = 2.5 uM Inhibitory concentration against recombinant human immunodeficiency virus 1 reverse transcriptase ChEMBL. 16137881
Inhibition (binding) Inhibition of STAT1 phosphorylation in LPS-induced mouse RAW264.7 cells incubated for 10 mins prior to LPS-challenge measured after 30 mins by Western blot analysis ChEMBL. 22831798
Inhibition (functional) U 0 % Anti-HIV activity (at 50 uM) against human HeLa cells through a HeLa-Tet-ON assay; U= unspecific ChEMBL. 16137881
Inhibition (functional) 0 % Anti-HIV activity (at 25 uM) against human HeLa-Tat-Luc cells transfected with HIV-1 LTR activated by Tat protein; NT= not tested ChEMBL. 16137881
Inhibition (functional) S 0 % Anti-HIV activity (at 50 uM) against human HeLa cells through a HeLa-Tet-ON assay; U= specific ChEMBL. 16137881
Inhibition (functional) = 11.5 % Anti-HIV activity (at 25 uM) against human HeLa-Tat-Luc cells transfected with HIV-1 LTR activated by Tat protein ChEMBL. 16137881
Inhibition (functional) = 11.5 % Anti-HIV activity (at 25 uM) against human HeLa-Tat-Luc cells transfected with HIV-1 LTR activated by Tat protein ChEMBL. 16137881
Inhibition (functional) = 33.7 % Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced NO production at 1 uM incubated for 10 mins prior to LPS-challenge measured after 18 hrs by Griess method relative to control ChEMBL. 22831798
Inhibition (functional) = 67.1 % Anti-HIV activity (at 25 uM) against Jurkat-derived 5.1 cell line stably transfected with HIV-LTR activated by TNF alpha ChEMBL. 16137881
Inhibition (functional) = 71 % Anti-HIV activity (at 25 uM) against Jurkat-derived 5.1 cell line stably transfected with HIV-LTR activated by TNF alpha ChEMBL. 16137881
Inhibition (functional) = 71.3 % Anti-HIV activity (at 50 uM) against human HeLa-Tat-Luc cells transfected with HIV-1 LTR activated by Tat protein ChEMBL. 16137881
Inhibition (functional) = 71.3 % Anti-HIV activity (at 50 uM) against human HeLa-Tat-Luc cells transfected with HIV-1 LTR activated by Tat protein ChEMBL. 16137881
Inhibition (functional) = 77.9 % Anti-HIV activity (at 50 uM) against Jurkat-derived 5.1 cell line stably transfected with HIV-LTR activated by TNF alpha ChEMBL. 16137881

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Mus musculus ChEMBL23 22831798

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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