Detailed information for compound 83147

Basic information

Technical information
  • TDR Targets ID: 83147
  • Name: 5-[(E)-2-(4-methoxyphenyl)ethenyl]benzene-1,3 -diol
  • MW: 242.27 | Formula: C15H14O3
  • H donors: 2 H acceptors: 2 LogP: 3.45 Rotable bonds: 3
    Rule of 5 violations (Lipinski): 1
  • SMILES: COc1ccc(cc1)/C=C/c1cc(O)cc(c1)O
  • InChi: 1S/C15H14O3/c1-18-15-6-4-11(5-7-15)2-3-12-8-13(16)10-14(17)9-12/h2-10,16-17H,1H3/b3-2+
  • InChiKey: IHVRWFJGOIWMGC-NSCUHMNNSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 5-[(E)-2-(4-methoxyphenyl)vinyl]benzene-1,3-diol
  • 5-[(E)-2-(4-methoxyphenyl)vinyl]resorcinol
  • 3,5-dihydroxy-4'-methoxystilbene
  • 5-[2-(4-methoxyphenyl)ethenyl]benzene-1,3-diol
  • 5-[2-(4-methoxyphenyl)vinyl]benzene-1,3-diol
  • 5-[2-(4-methoxyphenyl)vinyl]resorcinol
  • KBioGR_002190
  • NCGC00094628-01
  • KBioSS_001953
  • Spectrum2_000046
  • Spectrum_001473
  • KBio2_004521
  • SpecPlus_000119
  • SPBio_000171
  • BSPBio_003527
  • KBio2_001953
  • SDCCGMLS-0066773.P001
  • KBio2_007089
  • Spectrum3_001927
  • KBio1_001159
  • KBio3_002754
  • Spectrum4_001745
  • QTL1_000070
  • BML 233
  • Deoxyrhapontigenin
  • Desoxyrhapontigenin
  • DivK1c_006215
  • Spectrum5_000570

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens lamin A/C Starlite/ChEMBL No references
Homo sapiens arachidonate 12-lipoxygenase Starlite/ChEMBL No references
Homo sapiens cytochrome P450, family 1, subfamily A, polypeptide 1 Starlite/ChEMBL No references
Homo sapiens prostaglandin-endoperoxide synthase 2 (prostaglandin G/H synthase and cyclooxygenase) Starlite/ChEMBL References
Mus musculus RAR-related orphan receptor gamma Starlite/ChEMBL No references
Homo sapiens cytochrome P450, family 1, subfamily B, polypeptide 1 Starlite/ChEMBL No references

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Brugia malayi Intermediate filament tail domain containing protein Get druggable targets OG5_128723 All targets in OG5_128723
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_128723 All targets in OG5_128723
Echinococcus granulosus intermediate filament protein Get druggable targets OG5_128723 All targets in OG5_128723
Echinococcus multilocularis cytoplasmic intermediate filament protein Get druggable targets OG5_128723 All targets in OG5_128723
Echinococcus granulosus lamin Get druggable targets OG5_128723 All targets in OG5_128723
Loa Loa (eye worm) intermediate filament protein Get druggable targets OG5_128723 All targets in OG5_128723
Echinococcus granulosus cytoplasmic intermediate filament protein Get druggable targets OG5_128723 All targets in OG5_128723
Schistosoma japonicum Lamin-C, putative Get druggable targets OG5_128723 All targets in OG5_128723
Onchocerca volvulus Get druggable targets OG5_128723 All targets in OG5_128723
Schistosoma mansoni intermediate filament proteins Get druggable targets OG5_128723 All targets in OG5_128723
Echinococcus multilocularis lamin dm0 Get druggable targets OG5_128723 All targets in OG5_128723
Schistosoma japonicum expressed protein Get druggable targets OG5_128723 All targets in OG5_128723
Schistosoma mansoni lamin Get druggable targets OG5_128723 All targets in OG5_128723
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_128723 All targets in OG5_128723
Schistosoma mansoni lamin Get druggable targets OG5_128723 All targets in OG5_128723
Schistosoma japonicum expressed protein Get druggable targets OG5_128723 All targets in OG5_128723
Schistosoma japonicum Intermediate filament protein ifa-1, putative Get druggable targets OG5_128723 All targets in OG5_128723
Brugia malayi intermediate filament protein Get druggable targets OG5_128723 All targets in OG5_128723
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_128723 All targets in OG5_128723
Onchocerca volvulus Get druggable targets OG5_128723 All targets in OG5_128723
Echinococcus multilocularis musashi Get druggable targets OG5_128723 All targets in OG5_128723
Echinococcus granulosus lamin dm0 Get druggable targets OG5_128723 All targets in OG5_128723
Echinococcus multilocularis lamin Get druggable targets OG5_128723 All targets in OG5_128723
Schistosoma japonicum ko:K07611 lamin, putative Get druggable targets OG5_128723 All targets in OG5_128723
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_128723 All targets in OG5_128723
Loa Loa (eye worm) intermediate filament tail domain-containing protein Get druggable targets OG5_128723 All targets in OG5_128723
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_128723 All targets in OG5_128723
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Echinococcus granulosus arachidonate 5 lipoxygenase arachidonate 12-lipoxygenase 663 aa 662 aa 22.8 %
Brugia malayi Cytochrome P450 family protein cytochrome P450, family 1, subfamily A, polypeptide 1 512 aa 505 aa 26.7 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Echinococcus multilocularis arachidonate 5 lipoxygenase 0.0067 1 1
Onchocerca volvulus Peroxidasin homolog 0.0032 0.3225 0.9064
Loa Loa (eye worm) hypothetical protein 0.0032 0.3225 0.953
Loa Loa (eye worm) hypothetical protein 0.0032 0.3225 0.953
Loa Loa (eye worm) hypothetical protein 0.0032 0.3225 0.953
Schistosoma mansoni peroxidasin 0.0032 0.3225 0.1852
Brugia malayi Peroxidasin 0.0032 0.3225 0.9458
Onchocerca volvulus Peroxidase homolog 0.0032 0.3225 0.9064
Brugia malayi hypothetical protein 0.0024 0.1686 0.4209
Loa Loa (eye worm) hypothetical protein 0.0032 0.3225 0.953
Onchocerca volvulus Dual oxidase homolog 0.0032 0.3225 0.9064
Loa Loa (eye worm) hypothetical protein 0.0032 0.3225 0.953
Loa Loa (eye worm) hypothetical protein 0.0016 0.0116 0.0342
Echinococcus granulosus Polycystic kidney disease protein 0.0024 0.1686 0.1588
Brugia malayi hypothetical protein 0.0024 0.1686 0.4209
Echinococcus multilocularis lipoxygenase domain containing protein 0.0024 0.1686 0.1588
Echinococcus multilocularis peroxidasin 0.0032 0.3225 0.3146
Loa Loa (eye worm) hypothetical protein 0.0033 0.3384 1
Brugia malayi Blistered cuticle protein 3 0.0032 0.3225 0.9458
Onchocerca volvulus Peroxidasin homolog 0.0032 0.3225 0.9064
Schistosoma mansoni lamin 0.0033 0.3384 0.2043
Brugia malayi Animal haem peroxidase family protein 0.0032 0.3225 0.9458
Loa Loa (eye worm) intermediate filament protein 0.0033 0.3384 1
Brugia malayi Animal haem peroxidase family protein 0.0032 0.3225 0.9458
Loa Loa (eye worm) hypothetical protein 0.0024 0.1686 0.4981
Echinococcus granulosus lipoxygenase domain containing protein 0.0024 0.1686 0.1588
Loa Loa (eye worm) cytoplasmic intermediate filament protein 0.0017 0.0451 0.1333
Plasmodium vivax multidomain scavenger receptor, putative 0.0024 0.1686 0.5
Loa Loa (eye worm) hypothetical protein 0.0032 0.3225 0.953
Echinococcus granulosus peroxidasin 0.0032 0.3225 0.3146
Loa Loa (eye worm) hypothetical protein 0.0032 0.3225 0.953
Echinococcus granulosus RUN 0.0024 0.1686 0.1588
Brugia malayi Doublecortin family protein 0.0024 0.1686 0.4209
Loa Loa (eye worm) hypothetical protein 0.0032 0.3225 0.953
Echinococcus granulosus lamin 0.0033 0.3384 0.3307
Schistosoma mansoni intermediate filament proteins 0.0033 0.3384 0.2043
Echinococcus multilocularis lipoxygenase domain containing protein 0.0024 0.1686 0.1588
Echinococcus granulosus lipoxygenase domain containing protein 0.0024 0.1686 0.1588
Loa Loa (eye worm) hypothetical protein 0.0024 0.1686 0.4981
Loa Loa (eye worm) animal heme peroxidase 0.0032 0.3225 0.953
Loa Loa (eye worm) hypothetical protein 0.0032 0.3225 0.953
Onchocerca volvulus 0.0033 0.3384 1
Loa Loa (eye worm) intermediate filament tail domain-containing protein 0.0033 0.3384 1
Echinococcus multilocularis RUN 0.0024 0.1686 0.1588
Loa Loa (eye worm) blistered cuticle protein 3 0.0032 0.3225 0.953
Loa Loa (eye worm) animal heme peroxidase 0.0032 0.3225 0.953
Onchocerca volvulus 0.0032 0.3225 0.9064
Brugia malayi Animal haem peroxidase family protein 0.0032 0.3225 0.9458
Loa Loa (eye worm) hypothetical protein 0.0032 0.3225 0.953
Echinococcus granulosus intermediate filament protein 0.0033 0.3384 0.3307
Onchocerca volvulus Chorion peroxidase homolog 0.0032 0.3225 0.9064
Loa Loa (eye worm) hypothetical protein 0.0032 0.3225 0.953
Echinococcus multilocularis lamin 0.0033 0.3384 0.3307
Onchocerca volvulus 0.0033 0.3384 1
Onchocerca volvulus Peroxidase homolog 0.0032 0.3225 0.9064
Loa Loa (eye worm) animal heme peroxidase 0.0032 0.3225 0.953
Brugia malayi intermediate filament protein 0.0033 0.3384 1
Onchocerca volvulus 0.0032 0.3225 0.9064
Loa Loa (eye worm) doublecortin family protein 0.0024 0.1686 0.4981
Brugia malayi Animal haem peroxidase family protein 0.0032 0.3225 0.9458
Brugia malayi Intermediate filament tail domain containing protein 0.0033 0.3384 1
Loa Loa (eye worm) hypothetical protein 0.0032 0.3225 0.953
Schistosoma mansoni lipoxygenase 0.0067 1 1
Echinococcus multilocularis musashi 0.0033 0.3384 0.3307
Loa Loa (eye worm) hypothetical protein 0.0032 0.3225 0.953
Brugia malayi Animal haem peroxidase family protein 0.0032 0.3225 0.9458
Echinococcus multilocularis lamin dm0 0.0033 0.3384 0.3307
Schistosoma mansoni peroxidasin 0.0032 0.3225 0.1852
Echinococcus multilocularis Polycystic kidney disease protein 0.0024 0.1686 0.1588
Loa Loa (eye worm) hypothetical protein 0.0032 0.3269 0.9658
Brugia malayi hypothetical protein 0.0032 0.3225 0.9458
Loa Loa (eye worm) animal heme peroxidase 0.0032 0.3225 0.953
Echinococcus granulosus lamin dm0 0.0033 0.3384 0.3307
Onchocerca volvulus 0.0032 0.3225 0.9064
Plasmodium falciparum LCCL domain-containing protein 0.0024 0.1686 0.5
Schistosoma mansoni lamin 0.0033 0.3384 0.2043
Loa Loa (eye worm) hypothetical protein 0.0032 0.3225 0.953

Activities

Activity type Activity value Assay description Source Reference
Activity (functional) > 2 Agonist activity at PPARalpha in rat H4IIEC3 cells assessed as luciferase activity 100 uM after 24 hrs ChEMBL. 18272370
Activity (binding) 0 Induction of quinone reductase in mouse mutant Hepa 1c1c7c1 cells at 12.5 uM after 24 hrs relative to control ChEMBL. 17316918
Activity (functional) > 2 Agonist activity at PPARalpha in rat H4IIEC3 cells assessed as luciferase activity 100 uM after 24 hrs ChEMBL. 18272370
Activity (functional) = 2.49 ABTS radical scavenging activity assessed as trolox equivalent antioxidant capacity ChEMBL. 17316918
Activity (functional) = 87 % Cytotoxicity against mouse Hepa 1c1c7 cells assessed as cell viability at 12.5 uM after 24 hrs by MTT assay ChEMBL. 17316918
Activity (binding) = 1.14 uM Induction of quinone reductase activity in mouse Hepa 1c1c7 cells at 12.5 uM after 24 hrs relative to control ChEMBL. 17316918
Activity (binding) > 20 uM Induction of NQO1 activity in mouse Hepa1c1c7 cells assessed as concentration required to twofold increase of NQO1 activity at IC50 concentration relative to control ChEMBL. 21215623
EC50 (binding) = 48.6 Antioxidant activity of the compound was determined as the effective concentration to achieve 50% bioeffectivity value of 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) ChEMBL. 12749887
ED50 (functional) = 28.9 ug ml-1 In vitro inhibition of P388 (murine leukaemia) cell proliferation. ChEMBL. 12036362
ED50 (functional) = 28.9 ug ml-1 In vitro inhibition of P388 (murine leukaemia) cell proliferation. ChEMBL. 12036362
GI50 (functional) = 2.7 ug ml-1 In vitro growth inhibition of DU-145 (human prostate carcinoma) cell line. ChEMBL. 12036362
GI50 (functional) = 2.7 ug ml-1 In vitro growth inhibition of DU-145 (human prostate carcinoma) cell line. ChEMBL. 12036362
GI50 (functional) = 3.1 ug ml-1 In vitro growth inhibition of central nervous system SF-268 cell line. ChEMBL. 12036362
GI50 (functional) = 3.1 ug ml-1 In vitro growth inhibition of central nervous system SF-268 cell line. ChEMBL. 12036362
GI50 (functional) = 3.4 ug ml-1 Cell growth inhibition of breast MCF-7 cells, expressed as 50% reduction in the net protein increase ChEMBL. 12036362
GI50 (functional) = 3.4 ug ml-1 Cell growth inhibition of breast MCF-7 cells, expressed as 50% reduction in the net protein increase ChEMBL. 12036362
GI50 (functional) = 3.8 ug ml-1 In vitro growth inhibition of KM20L2 cell line. ChEMBL. 12036362
GI50 (functional) = 3.8 ug ml-1 In vitro growth inhibition of KM20L2 cell line. ChEMBL. 12036362
GI50 (functional) = 6.3 ug ml-1 In vitro growth inhibition of BXPC-3 (human pancreatic adenocarcinoma) cell line. ChEMBL. 12036362
GI50 (functional) = 6.3 ug ml-1 In vitro growth inhibition of BXPC-3 (human pancreatic adenocarcinoma) cell line. ChEMBL. 12036362
GI50 (functional) = 6.8 ug ml-1 In vitro growth inhibition of NCI-H460 (human non-small cell lung carcinoma) cell line. ChEMBL. 12036362
IC50 (binding) = 0.8 uM Inhibition of human recombinant CYP1B1 after 15 mins by 7-ethoxyresorufin-O-deethylation-based spectrofluorimetry ChEMBL. No reference
IC50 (binding) = 19.6 uM Inhibition of COX2 ChEMBL. 18487053
IC50 (functional) = 24.5 uM Cytotoxicity against human HT-29 cells after 3 days by [3H]thymidine incorporation assay ChEMBL. 20627379
IC50 (binding) = 25.8 uM Inhibition of COX1 ChEMBL. 18487053
IC50 (functional) > 30 uM Compound was tested for inhibitory activity against nitric oxide production in LPS-activated mouse peritoneal macrophages (*,showed cytotoxicity at 100 microM) ChEMBL. 10714491
IC50 (functional) > 30 uM Compound was tested for inhibitory activity against nitric oxide production in LPS-activated mouse peritoneal macrophages (*,showed cytotoxicity at 100 microM) ChEMBL. 10714491
IC50 (functional) > 30 uM Cytotoxicity against human Caco-2 cells after 3 days by [3H]thymidine incorporation assay ChEMBL. 20627379
IC50 (functional) > 50 uM Inhibitory concentration of the compound required for antiproliferative activity against human MDA-MB-231 cells ChEMBL. 16250636
IC50 (functional) > 50 uM Inhibitory concentration of the compound required for antiproliferative activity against human MDA-MB-231 cells ChEMBL. 16250636
Inhibition (binding) Inhibitory activity of the compound against yeast alpha-glucosidase; active ChEMBL. 15203173
Inhibition (binding) 0 Inhibitory activity of the compound against yeast alpha-glucosidase; active ChEMBL. 15203173
Inhibition (functional) = 13 % Compound (at 30 microM) was tested for inhibition against nitric oxide production in LPS-activated mouse peritoneal macrophages ChEMBL. 10714491
Inhibition (functional) = 13 % Compound (at 30 microM) was tested for inhibition against nitric oxide production in LPS-activated mouse peritoneal macrophages ChEMBL. 10714491
Inhibition (ADMET) = 134.9879015 % Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM ChEMBL. 23571415
Inhibition (ADMET) = 300.1818701 % Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM ChEMBL. 23571415
Ki (ADMET) = 0.16 uM Inhibition of CYP1A1 (unknown origin) ChEMBL. No reference
Ki (binding) = 2.1 uM Inhibition of CYP1B1 (unknown origin) ChEMBL. No reference
MIC (functional) = 264.5 uM Antibacterial activity against Helicobacter pylori ATCC43504 by agar dilution method ChEMBL. 17883259
MIC95 (functional) = 150 ug ml-1 Antifungal activity against Candida albicans SC5314 ATCC MYA-2876 assessed as growth inhibition after 48 hrs by broth microdilution method ChEMBL. 25014026
Potency (functional) = 1.4125 um PUBCHEM_BIOASSAY: qHTS for inhibitors of ROR gamma transcriptional activity. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) = 3.5481 um PUBCHEM_BIOASSAY: VP16 counterscreen qHTS for inhibitors of ROR gamma transcriptional activity. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) = 11.2202 um PUBCHEM_BIOASSAY: qHTS Assay for Modulators of Lamin A Splicing. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) = 19.9526 um PUBCHEM_BIOASSAY: qHTS Assay for Inhibitors of 12-hLO (12-human lipoxygenase). (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) = 22.3872 um PUBCHEM_BIOASSAY: qHTS Assay for Inhibitors of Human Jumonji Domain Containing 2E (JMJD2E). (Class of assay: confirmatory) ChEMBL. No reference

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

10 literature references were collected for this gene.

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