Detailed information for compound 261799

Basic information

Technical information
  • TDR Targets ID: 261799
  • Name: 4-(3-hydroxy-4-methoxyphenyl)-5,7-dimethoxych romen-2-one
  • MW: 328.316 | Formula: C18H16O6
  • H donors: 1 H acceptors: 2 LogP: 2.65 Rotable bonds: 4
    Rule of 5 violations (Lipinski): 1
  • SMILES: COc1cc(OC)c2c(c1)oc(=O)cc2c1ccc(c(c1)O)OC
  • InChi: 1S/C18H16O6/c1-21-11-7-15(23-3)18-12(9-17(20)24-16(18)8-11)10-4-5-14(22-2)13(19)6-10/h4-9,19H,1-3H3
  • InChiKey: KOAAZLIOOBKJEK-UHFFFAOYSA-N  


Substructure search Similarity search

Network

Hover on a compound node to display the structore

Synonyms

  • 4-(3-hydroxy-4-methoxy-phenyl)-5,7-dimethoxy-chromen-2-one
  • 4-(3-hydroxy-4-methoxyphenyl)-5,7-dimethoxy-1-benzopyran-2-one
  • 4-(3-hydroxy-4-methoxy-phenyl)-5,7-dimethoxy-coumarin
  • 4-(3-hydroxy-4-methoxyphenyl)-5,7-dimethoxy-2-chromenone

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
Loa Loa (eye worm) hypothetical protein 0.0089926 0.0302521 0.0302521
Trypanosoma cruzi metallo-peptidase, Clan MF, Family M17 0.0105517 0.0570724 0.0599135
Echinococcus multilocularis leucyl aminopeptidase 0.0105517 0.0570724 0.0570724
Echinococcus multilocularis Peptidase M1, membrane alanine aminopeptidase, N terminal 0.0160209 0.151161 0.151161
Schistosoma mansoni PwLAP aminopeptidase (M17 family) 0.0105517 0.0570724 0.0570724
Leishmania major aspartyl aminopeptidase, putative,metallo-peptidase, Clan MH, Family M20 0.0089926 0.0302521 0.00382243
Schistosoma mansoni aspartyl aminopeptidase (M18 family) 0.0089926 0.0302521 0.0302521
Trypanosoma brucei metallo-peptidase, Clan MF, Family M17 0.0105517 0.0570724 0.0327902
Plasmodium vivax M1-family alanyl aminopeptidase, putative 0.0393478 0.552454 0.584173
Echinococcus granulosus puromycin sensitive aminopeptidase 0.0160209 0.151161 0.137549
Schistosoma mansoni aspartyl aminopeptidase (M18 family) 0.0089926 0.0302521 0.0302521
Trypanosoma brucei aspartyl aminopeptidase, putative 0.0089926 0.0302521 0.00382243
Loa Loa (eye worm) hypothetical protein 0.00878688 0.0267131 0.0267131
Trypanosoma cruzi metallo-peptidase, Clan MH, Family M20 0.0089926 0.0302521 0.0317581
Schistosoma mansoni aminopeptidase PILS (M01 family) 0.0160209 0.151161 0.151161
Echinococcus multilocularis puromycin sensitive aminopeptidase 0.0160209 0.151161 0.151161
Echinococcus granulosus leukotriene A 4 hydrolase 0.0653633 1 1
Wolbachia endosymbiont of Brugia malayi leucyl aminopeptidase 0.0611018 0.926689 0.5
Loa Loa (eye worm) hypothetical protein 0.0337397 0.455978 0.455978
Echinococcus multilocularis baculoviral IAP repeat containing protein 0.00815157 0.0157838 0.0157838
Brugia malayi Peptidase family M1 containing protein 0.00878688 0.0267131 0.0184818
Trypanosoma brucei pyroglutamyl-peptidase I, putative 0.0626068 0.95258 1
Plasmodium vivax M18 aspartyl aminopeptidase, putative 0.0089926 0.0302521 0.00393239
Echinococcus granulosus puromycin sensitive aminopeptidase 0.0160209 0.151161 0.137549
Trypanosoma cruzi metallo-peptidase, Clan MA(E) Family M1 0.00878688 0.0267131 0.0280429
Leishmania major aminopeptidase, putative,metallo-peptidase, Clan MF, Family M17 0.0105517 0.0570724 0.0327902
Trypanosoma cruzi metallo-peptidase, Clan MF, Family M17 0.0105517 0.0570724 0.0599135
Echinococcus granulosus leucyl aminopeptidase 0.0105517 0.0570724 0.0419508
Echinococcus multilocularis puromycin sensitive aminopeptidase 0.0160209 0.151161 0.151161
Brugia malayi TATA binding protein associated factor 0.00878688 0.0267131 0.0184818
Brugia malayi hypothetical protein 0.0333114 0.44861 0.731922
Brugia malayi hypothetical protein 0.00878688 0.0267131 0.0184818
Schistosoma mansoni inhibitor of apoptosis protein 0.00815157 0.0157838 0.0157838
Schistosoma mansoni inhibitor of apoptosis (iap) domain family member 0.00815157 0.0157838 0.0157838
Trypanosoma cruzi aminopeptidase, putative 0.00878688 0.0267131 0.0280429
Trypanosoma cruzi metallo-peptidase, Clan MF, Family M17, putative 0.046214 0.670573 0.703955
Brugia malayi Aminopeptidase W07G4.4 in chromosome V 0.0105517 0.0570724 0.0698204
Schistosoma mansoni aminopeptidase A (M01 family) 0.00878688 0.0267131 0.0267131
Plasmodium falciparum M18 aspartyl aminopeptidase 0.0089926 0.0302521 0.00549662
Echinococcus granulosus ankyrin repeat domain containing protein 17 0.0105517 0.0570724 0.0419508
Loa Loa (eye worm) hypothetical protein 0.00815157 0.0157838 0.0157838
Brugia malayi cytosol aminopeptidase 0.0105517 0.0570724 0.0698204
Onchocerca volvulus 0.0160209 0.151161 0.228927
Onchocerca volvulus 0.00878688 0.0267131 0.0184818
Trichomonas vaginalis Clan MA, family M1, aminopeptidase N-like metallopeptidase 0.0160209 0.151161 1
Loa Loa (eye worm) hypothetical protein 0.00878688 0.0267131 0.0267131
Mycobacterium ulcerans aminopeptidase N PepN 0.0160209 0.151161 0.138279
Echinococcus granulosus aspartyl aminopeptidase 0.0089926 0.0302521 0.0147004
Loa Loa (eye worm) hypothetical protein 0.0089926 0.0302521 0.0302521
Echinococcus granulosus puromycin sensitive aminopeptidase 0.00878688 0.0267131 0.0111046
Loa Loa (eye worm) leukotriene A4 hydrolase 0.0653633 1 1
Loa Loa (eye worm) TATA binding protein associated factor 0.00878688 0.0267131 0.0267131
Echinococcus multilocularis inhibitor of apoptosis protein 0.00815157 0.0157838 0.0157838
Trypanosoma cruzi Aminopeptidase M1, putative 0.0160209 0.151161 0.158686
Echinococcus multilocularis puromycin sensitive aminopeptidase 0.0160209 0.151161 0.151161
Trypanosoma cruzi cytosolic leucyl aminopeptidase, putative 0.046214 0.670573 0.703955
Trypanosoma cruzi aminopeptidase, putative 0.0160209 0.151161 0.158686
Onchocerca volvulus 0.0425266 0.60714 1
Trypanosoma brucei metallo-peptidase, Clan MA(E) Family M1 0.0160209 0.151161 0.134412
Brugia malayi Peptidase family M1 containing protein 0.0425266 0.60714 1
Mycobacterium ulcerans leucyl aminopeptidase 0.0611018 0.926689 1
Plasmodium falciparum M1-family alanyl aminopeptidase 0.0393478 0.552454 0.816546
Trypanosoma cruzi pyroglutamyl-peptidase I, putative 0.0626068 0.95258 1
Echinococcus multilocularis leucyl aminopeptidase 0.0105517 0.0570724 0.0570724
Schistosoma mansoni Tata binding protein associated factor (M01 family) 0.00878688 0.0267131 0.0267131
Leishmania major cytosolic leucyl aminopeptidase,metallo-peptidase, Clan MF, Family M17 0.046214 0.670573 0.695414
Trypanosoma brucei Aminopeptidase M1, putative 0.0160209 0.151161 0.134412
Schistosoma mansoni leukotriene A4 hydrolase (M01 family) 0.0653633 1 1
Toxoplasma gondii leucyl aminopeptidase LAP 0.0611018 0.926689 1
Leishmania major aminopeptidase-like protein,metallo-peptidase, Clan MA(E), Family M1 0.0160209 0.151161 0.134412
Leishmania major aminopeptidase, putative,metallo-peptidase, Clan MA(E), Family M1 0.0160209 0.151161 0.134412
Schistosoma mansoni leucine aminopeptidase 0.0105517 0.0570724 0.0570724
Trichomonas vaginalis Clan MH, family M18, aspartyl aminopeptidase-like metallopeptidase 0.0089926 0.0302521 0.028438
Trichomonas vaginalis Clan MA, family M1, aminopeptidase N-like metallopeptidase 0.0160209 0.151161 1
Trypanosoma brucei aspartyl aminopeptidase, putative 0.0089926 0.0302521 0.00382243
Trypanosoma cruzi Cysteine peptidase, Clan CF, family C15 0.0626068 0.95258 1
Trypanosoma cruzi aspartyl aminopeptidase, putative 0.0089926 0.0302521 0.0317581
Leishmania major aminopeptidase, putative,metallo-peptidase, Clan MF, Family M17 0.0105517 0.0570724 0.0327902
Trypanosoma cruzi puromycin-sensitive aminopeptidase-like protein, putative 0.00878688 0.0267131 0.0280429
Echinococcus multilocularis aspartyl aminopeptidase 0.0089926 0.0302521 0.0302521
Entamoeba histolytica aminopeptidase, putative 0.0160209 0.151161 1
Trichomonas vaginalis Clan MH, family M18, aspartyl aminopeptidase-like metallopeptidase 0.0089926 0.0302521 0.028438
Plasmodium vivax M17 leucyl aminopeptidase, putative 0.0611018 0.926689 1
Mycobacterium tuberculosis Probable aminopeptidase PepB 0.0611018 0.926689 1
Leishmania major aminopeptidase, putative,metallo-peptidase, Clan MF, Family M17 0.0105517 0.0570724 0.0327902
Loa Loa (eye worm) hypothetical protein 0.0265057 0.33153 0.33153
Trichomonas vaginalis Clan MH, family M18, aspartyl aminopeptidase-like metallopeptidase 0.0089926 0.0302521 0.028438
Echinococcus granulosus puromycin sensitive aminopeptidase 0.00878688 0.0267131 0.0111046
Echinococcus multilocularis leucine aminopeptidase protein 0.0611018 0.926689 0.926689
Loa Loa (eye worm) aminopeptidase N 0.0160209 0.151161 0.151161
Echinococcus granulosus puromycin sensitive aminopeptidase 0.0160209 0.151161 0.137549
Schistosoma mansoni cytosol alanyl aminopeptidase (M01 family) 0.0160209 0.151161 0.151161
Plasmodium falciparum M17 leucyl aminopeptidase 0.046214 0.670573 1
Leishmania major pyroglutamyl-peptidase I (C15 family) 0.0626068 0.95258 1
Echinococcus granulosus aminopeptidase N 0.0425266 0.60714 0.600839
Brugia malayi Aminopeptidase ZK353.6 in chromosome III 0.0105517 0.0570724 0.0698204
Echinococcus multilocularis aminopeptidase N 0.0425266 0.60714 0.60714
Loa Loa (eye worm) aminopeptidase in chromosome V 0.0105517 0.0570724 0.0570724
Brugia malayi Ubiquitin carboxyl-terminal hydrolase family protein 0.0105517 0.0570724 0.0698204
Echinococcus granulosus leucyl aminopeptidase 0.0105517 0.0570724 0.0419508
Brugia malayi Peptidase family M1 containing protein 0.0160209 0.151161 0.228927
Trypanosoma brucei Aminopeptidase M1, putative 0.0160209 0.151161 0.134412
Schistosoma mansoni hypothetical protein 0.00815157 0.0157838 0.0157838
Loa Loa (eye worm) peptidase family M1 containing protein 0.0352925 0.482691 0.482691
Echinococcus granulosus puromycin sensitive aminopeptidase 0.0160209 0.151161 0.137549
Trypanosoma cruzi metallo-peptidase, clan MA(E), family M1, putative 0.00878688 0.0267131 0.0280429
Trypanosoma cruzi puromycin-sensitive aminopeptidase-like protein, putative 0.00878688 0.0267131 0.0280429
Echinococcus multilocularis puromycin sensitive aminopeptidase 0.0160209 0.151161 0.151161
Loa Loa (eye worm) hypothetical protein 0.00815157 0.0157838 0.0157838
Loa Loa (eye worm) aspartyl aminopeptidase 0.0089926 0.0302521 0.0302521
Trypanosoma brucei metallo-peptidase, Clan MF, Family M17 0.046214 0.670573 0.695414
Mycobacterium leprae Probable cytosol aminopeptidase PepB 0.0611018 0.926689 1
Chlamydia trachomatis cytosol aminopeptidase 0.0611018 0.926689 0.5
Brugia malayi hypothetical protein 0.0160209 0.151161 0.228927
Loa Loa (eye worm) hypothetical protein 0.00878688 0.0267131 0.0267131
Brugia malayi Aspartyl aminopeptidase 0.0089926 0.0302521 0.0244665
Echinococcus multilocularis leucyl aminopeptidase 0.0105517 0.0570724 0.0570724
Trypanosoma cruzi metallo-peptidase, clan MA(E), family M1, putative 0.0160209 0.151161 0.158686
Echinococcus multilocularis puromycin sensitive aminopeptidase 0.0160209 0.151161 0.151161
Echinococcus granulosus leucine aminopeptidase protein 0.0611018 0.926689 0.925513
Echinococcus multilocularis leukotriene A 4 hydrolase 0.0653633 1 1
Trypanosoma brucei aminopeptidase, putative 0.0105517 0.0570724 0.0327902
Trypanosoma brucei metallo-peptidase, Clan MF, Family M17 0.0105517 0.0570724 0.0327902
Loa Loa (eye worm) aminopeptidase in chromosome III 0.0105517 0.0570724 0.0570724

Activities

Activity type Activity value Assay description Source Reference
(binding) 0 Inhibitory activity against Topoisomerase I ChEMBL. 16040242
Activity (binding) Modulation of BCRP in human HCT116 cells assessed as intracellular accumulation of mitoxantrone at 10 uM after 30 mins by flow-cytometry ChEMBL. 21488686
Activity (binding) Modulation of P-gp in human K562 cells assessed as intracellular accumulation of daunorubicin at 30 uM after 30 mins by flow-cytometry ChEMBL. 21488686
Activity (functional) = 33 % Cell cycle arrest in drug-resistant human HCT116 cells overexpressing BCRP assessed as accumulation at G2/M phase at 0.1 uM after 24 hrs by FACS-flow cytometry (Rvb = 30 +/- 4 %) ChEMBL. 21488686
Activity (functional) = 33 % Cell cycle arrest in drug-resistant human HCT116 cells overexpressing BCRP assessed as accumulation at G2/M phase at 10 uM after 24 hrs by FACS-flow cytometry (Rvb = 30 +/- 4 %) ChEMBL. 21488686
Activity (functional) = 35 % Cell cycle arrest in drug-sensitive human K562 cells assessed as accumulation at G2/M phase at 0.1 uM after 24 hrs by FACS-flow cytometry (Rvb = 23 +/- 2 %) ChEMBL. 21488686
Activity (functional) = 35 % Cell cycle arrest in drug-resistant human K562 cells overexpressing P-gp assessed as accumulation at G2/M phase at 0.1 uM after 24 hrs by FACS-flow cytometry (Rvb = 18 +/- 2 %) ChEMBL. 21488686
Activity (functional) = 35 % Cell cycle arrest in drug-sensitive human K562 cells assessed as accumulation at G2/M phase at 10 uM after 24 hrs by FACS-flow cytometry (Rvb = 23 +/- 2 %) ChEMBL. 21488686
Activity (functional) = 35 % Cell cycle arrest in drug-resistant human K562 cells overexpressing P-gp assessed as accumulation at G2/M phase at 10 uM after 24 hrs by FACS-flow cytometry (Rvb = 18 +/- 2 %) ChEMBL. 21488686
Activity (functional) = 44 % Cell cycle arrest in drug-sensitive human HCT116 cells assessed as accumulation at G2/M phase at 0.1 uM after 24 hrs by FACS-flow cytometry (Rvb = 32+/- 3 %) ChEMBL. 21488686
Activity (functional) = 44 % Cell cycle arrest in drug-sensitive human HCT116 cells assessed as accumulation at G2/M phase at 10 uM after 24 hrs by FACS-flow cytometry (Rvb = 32+/- 3 %) ChEMBL. 21488686
IC50 (functional) = 88 nM Cytotoxicity against human HBL100 cells after 72 hrs by MTT assay ChEMBL. 21488686
IC50 (functional) = 88 nM Cytotoxicity against drug-resistant human K562 cells overexpressing P-gp after 48 hrs by MTT assay ChEMBL. 21488686
IC50 (functional) = 100 nM Cytotoxicity against drug-sensitive human K562 cells after 48 hrs by MTT assay ChEMBL. 21488686
IC50 (functional) = 210 nM Cytotoxicity against drug-sensitive human HCT116 cells after 48 hrs by MTT assay ChEMBL. 21488686
IC50 (functional) = 310 nM Cytotoxicity against drug-resistant human HCT116 cells overexpressing BCRP after 48 hrs by MTT assay ChEMBL. 21488686
IC50 (functional) = 0.083 uM Inhibitory activity of the compound was determined against CEM human leukemia cell line ChEMBL. 14640552
IC50 (functional) = 0.083 uM Inhibitory activity of the compound was determined against CEM human leukemia cell line ChEMBL. 14640552
IC50 (functional) = 0.083 uM Cytotoxicity against human CEM cells ChEMBL. 19914747
IC50 (functional) = 0.083 uM Cytotoxicity against human CEM cells assessed as cell growth inhibition measured after 72 hrs by CellTiter-96 AQueous one solution cell proliferation assay ChEMBL. 27155469
IC50 (functional) = 0.12 uM Cytotoxic activity against human non-small lung carcinoma cell line H460 ChEMBL. 16040242
IC50 (functional) = 0.12 uM Cytotoxic activity against human non-small lung carcinoma cell line H460 ChEMBL. 16040242
IC50 (ADMET) < 15 uM Cytotoxicity against human THP1 cells assessed as cell viability after 72 hrs by Alamar blue assay ChEMBL. 19914747
IC50 (functional) > 15 uM Antileishmanial activity against Leishmania donovani MHOM/IN/80/DD8 amastigotes infected in human THP1 cells assessed as decrease of infected macrophages after 72 hrs by Giemsa staining ChEMBL. 19914747
IC50 (functional) > 15 uM Antileishmanial activity against Leishmania donovani MHOM/IN/80/DD8 promastigotes assessed as parasite viability after 48 hrs by Alamar blue assay ChEMBL. 19914747
IC50 (functional) > 15 uM Antiplasmodial activity against multidrug-resistant Plasmodium falciparum W2 infected human erythrocytes after 48 hrs by flow cytometry ChEMBL. 19914747

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Plasmodium falciparum ChEMBL23 19914747
Leishmania donovani ChEMBL23 19914747
Homo sapiens ChEMBL23 14640552

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

3 literature references were collected for this gene.

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