Detailed information for compound 436566

Basic information

Technical information
  • TDR Targets ID: 436566
  • Name: (2E,5E)-2,5-bis[(3,4,5-trimethoxyphenyl)methy lidene]cyclopentan-1-one
  • MW: 440.486 | Formula: C25H28O7
  • H donors: 0 H acceptors: 1 LogP: 4.35 Rotable bonds: 8
    Rule of 5 violations (Lipinski): 1
  • SMILES: COc1cc(/C=C/2\CC/C(=C\c3cc(OC)c(c(c3)OC)OC)/C2=O)cc(c1OC)OC
  • InChi: 1S/C25H28O7/c1-27-19-11-15(12-20(28-2)24(19)31-5)9-17-7-8-18(23(17)26)10-16-13-21(29-3)25(32-6)22(14-16)30-4/h9-14H,7-8H2,1-6H3/b17-9+,18-10+
  • InChiKey: JKCXONUCRFROOH-BEQMOXJMSA-N  


Substructure search Similarity search

Network

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Synonyms

  • (2E,5E)-2,5-bis[(3,4,5-trimethoxyphenyl)methylene]cyclopentanone
  • (2E,5E)-2,5-bis(3,4,5-trimethoxybenzylidene)cyclopentanone
  • 2,5-bis[(3,4,5-trimethoxyphenyl)methylidene]cyclopentan-1-one
  • 2,5-bis[(3,4,5-trimethoxyphenyl)methylene]cyclopentan-1-one
  • (2E,5E)-2,5-bis[(3,4,5-trimethoxyphenyl)methylene]cyclopentan-1-one
  • 2,5-bis[(3,4,5-trimethoxyphenyl)methylene]-1-cyclopentanone
  • (2E,5E)-2,5-bis[(3,4,5-trimethoxyphenyl)methylene]-1-cyclopentanone
  • 2,5-bis(3,4,5-trimethoxybenzylidene)cyclopentan-1-one
  • (2E,5E)-2,5-bis(3,4,5-trimethoxybenzylidene)cyclopentan-1-one
  • T0502-2030
  • MLS000418563
  • SMR000265057

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens geminin, DNA replication inhibitor Starlite/ChEMBL No references
Homo sapiens SMAD family member 2 Starlite/ChEMBL No references
Homo sapiens survival of motor neuron 2, centromeric Starlite/ChEMBL No references
Homo sapiens lamin A/C Starlite/ChEMBL No references
Homo sapiens lysine (K)-specific demethylase 4A Starlite/ChEMBL No references

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Loa Loa (eye worm) intermediate filament tail domain-containing protein Get druggable targets OG5_128723 All targets in OG5_128723
Plasmodium yoelii hypothetical protein Get druggable targets OG5_127917 All targets in OG5_127917
Brugia malayi MH2 domain containing protein Get druggable targets OG5_131716 All targets in OG5_131716
Schistosoma japonicum expressed protein Get druggable targets OG5_128723 All targets in OG5_128723
Brugia malayi jmjC domain containing protein Get druggable targets OG5_127917 All targets in OG5_127917
Loa Loa (eye worm) 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
Schistosoma japonicum JmjC domain-containing histone demethylation protein 3C, putative Get druggable targets OG5_127917 All targets in OG5_127917
Loa Loa (eye worm) MH2 domain-containing protein Get druggable targets OG5_131716 All targets in OG5_131716
Schistosoma japonicum expressed protein Get druggable targets OG5_127917 All targets in OG5_127917
Echinococcus multilocularis Transcription factor, JmjC domain containing protein Get druggable targets OG5_127917 All targets in OG5_127917
Echinococcus multilocularis cytoplasmic intermediate filament protein Get druggable targets OG5_128723 All targets in OG5_128723
Brugia malayi hypothetical protein Get druggable targets OG5_132873 All targets in OG5_132873
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 japonicum Intermediate filament protein ifa-1, putative Get druggable targets OG5_128723 All targets in OG5_128723
Echinococcus granulosus survival motor neuron protein 1 Get druggable targets OG5_132873 All targets in OG5_132873
Echinococcus multilocularis lamin dm0 Get druggable targets OG5_128723 All targets in OG5_128723
Schistosoma japonicum Probable JmjC domain-containing histone demethylation protein 3B, putative Get druggable targets OG5_127917 All targets in OG5_127917
Echinococcus multilocularis musashi Get druggable targets OG5_128723 All targets in OG5_128723
Onchocerca volvulus Get druggable targets OG5_128723 All targets in OG5_128723
Schistosoma mansoni jumonji domain containing protein Get druggable targets OG5_127917 All targets in OG5_127917
Echinococcus granulosus jumonji domain containing protein Get druggable targets OG5_127917 All targets in OG5_127917
Echinococcus granulosus Transcription factor JmjC domain containing protein Get druggable targets OG5_127917 All targets in OG5_127917
Candida albicans one of two closely related potential jumonji-like transcription factor genes similar to S. cerevisiae RPH1 (YER169W) damage-resp Get druggable targets OG5_127917 All targets in OG5_127917
Echinococcus granulosus lamin Get druggable targets OG5_128723 All targets in OG5_128723
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_132873 All targets in OG5_132873
Schistosoma japonicum expressed protein Get druggable targets OG5_128723 All targets in OG5_128723
Candida albicans one of two closely related potential jumonji-like transcription factor genes similar to S. cerevisiae RPH1 (YER169W) damage-resp Get druggable targets OG5_127917 All targets in OG5_127917
Brugia malayi intermediate filament protein Get druggable targets OG5_128723 All targets in OG5_128723
Candida albicans one of two closely related potential jumonji-like transcription factor genes similar to S. cerevisiae RPH1 (YER169W) damage-resp Get druggable targets OG5_127917 All targets in OG5_127917
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
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
Echinococcus multilocularis jumonji domain containing protein Get druggable targets OG5_127917 All targets in OG5_127917
Loa Loa (eye worm) transcription factor SMAD2 Get druggable targets OG5_131716 All targets in OG5_131716
Schistosoma mansoni intermediate filament proteins Get druggable targets OG5_128723 All targets in OG5_128723
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_127917 All targets in OG5_127917
Candida albicans one of two closely related potential jumonji-like transcription factor genes similar to S. cerevisiae RPH1 (YER169W) damage-resp Get druggable targets OG5_127917 All targets in OG5_127917
Echinococcus granulosus cytoplasmic 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
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_128723 All targets in OG5_128723
Echinococcus granulosus lamin dm0 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
Echinococcus multilocularis lamin Get druggable targets OG5_128723 All targets in OG5_128723
Echinococcus multilocularis survival motor neuron protein 1 Get druggable targets OG5_132873 All targets in OG5_132873
Schistosoma japonicum expressed protein Get druggable targets OG5_127917 All targets in OG5_127917
Loa Loa (eye worm) jmjC domain-containing protein Get druggable targets OG5_127917 All targets in OG5_127917
Schistosoma mansoni lamin 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
Brugia malayi Hypothetical 65.5 kDa Trp-Asp repeats containing protein F02E8.5 inchromosome X geminin, DNA replication inhibitor 209 aa 176 aa 27.8 %
Brugia malayi MH2 domain containing protein SMAD family member 2 467 aa 405 aa 31.6 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Schistosoma mansoni DNA polymerase gamma 0.0131071 0.347691 1
Trypanosoma cruzi mitochondrial DNA polymerase beta, putative 0.0321173 1 1
Leishmania major mitochondrial DNA polymerase beta 0.0321173 1 1
Trypanosoma cruzi mitochondrial DNA polymerase beta-PAK, putative 0.0153674 0.425251 0.392054
Trypanosoma cruzi mitochondrial DNA polymerase beta-PAK, putative 0.0055645 0.0888775 0.0362505
Mycobacterium ulcerans hypothetical protein 0.0167498 0.472688 0.5
Plasmodium vivax DNA polymerase alpha, putative 0.0046789 0.0584892 0.5
Loa Loa (eye worm) hypothetical protein 0.0131071 0.347691 1
Onchocerca volvulus DNA polymerase alpha catalytic subunit homolog 0.00912281 0.210976 0.5
Echinococcus granulosus DNA polymerase subunit gamma 0.0131071 0.347691 1
Brugia malayi DNA polymerase I family protein 0.0131071 0.347691 1
Echinococcus multilocularis hypothetical protein 0.0131071 0.347691 1
Schistosoma mansoni DNA polymerase alpha catalytic subunit 0.00614846 0.108915 0.313254
Giardia lamblia DNA polymerase alpha subunit A 0.00590789 0.10066 0.5
Toxoplasma gondii hypothetical protein 0.00523718 0.0776459 1
Trypanosoma cruzi mitochondrial DNA polymerase beta, putative 0.0321173 1 1
Mycobacterium tuberculosis Conserved hypothetical protein 0.0167498 0.472688 0.5
Trypanosoma brucei mitochondrial DNA polymerase beta-PAK 0.0153674 0.425251 0.392054
Trypanosoma brucei mitochondrial DNA polymerase beta 0.0321173 1 1

Activities

Activity type Activity value Assay description Source Reference
CC50 = 0.873 uM NOVARTIS: Cytotoxicity against human hepatocellular carcinoma cell line (Huh7) ChEMBL. 18579783
CC50 (functional) = 19 uM Cytotoxicity against HSC2 cells ChEMBL. 17383883
CC50 (functional) = 19 uM Cytotoxicity against HSC2 cells ChEMBL. 17383883
CC50 (functional) = 21 uM Cytotoxicity against human HL60 cells ChEMBL. 17383883
CC50 (functional) = 21 uM Cytotoxicity against human HL60 cells ChEMBL. 17383883
CC50 (functional) = 58 uM Cytotoxicity against HSC4 cells ChEMBL. 17383883
CC50 (functional) = 58 uM Cytotoxicity against HSC4 cells ChEMBL. 17383883
CC50 (functional) = 89 uM Cytotoxicity against HSC3 cells ChEMBL. 17383883
CC50 (functional) = 89 uM Cytotoxicity against HSC3 cells ChEMBL. 17383883
CC50 (ADMET) = 240 uM Cytotoxicity against HGF cells ChEMBL. 17383883
CC50 (ADMET) = 247 uM Cytotoxicity against HPC cells ChEMBL. 17383883
CC50 (ADMET) = 281 uM Cytotoxicity against HPLF cells ChEMBL. 17383883
EC50 (functional) = 0.457 uM NOVARTIS: Inhibition of Plasmodium falciparum W2 (drug-resistant) proliferation in erythrocyte-based infection assay ChEMBL. 18579783
EC50 (functional) = 0.458 uM NOVARTIS: Inhibition of Plasmodium falciparum 3D7 (drug-susceptible) proliferation in erythrocyte-based infection assay ChEMBL. 18579783
IC50 (functional) = 16.42 uM Cytotoxicity against human PC3 cells after 72 hrs by MTT assay ChEMBL. 22551677
Inhibition (binding) Inhibition of 17beta-HSD3 in human testis microsomes at 100 uM ChEMBL. 20346654
Inhibition (binding) = 5 % Inhibition of 11beta-HSD2 in human kidney microsomes using [3H]-cortisol as substrate assessed as formation of cortisone at 100 uM after 30 mins by radiometric analysis relative to control ChEMBL. 23800686
Inhibition (binding) = 9 % Inhibition of 11beta-HSD2 in rat kidney microsomes using [3H]-CORT as substrate assessed as formation of 11-DHC at 100 uM after 30 mins by radiometric analysis relative to control ChEMBL. 23800686
Inhibition (binding) = 11 % Inhibition of 17beta-HSD3 in Sprague-Dawley rat laydig cells at 100 uM ChEMBL. 20346654
Inhibition (binding) = 12 % Inhibition of 11beta-HSD1 in rat testis microsomes using [3H]-11-DHC as substrate assessed as formation of CORT at 100 uM after 60 to 90 mins by radiometric analysis relative to control ChEMBL. 23800686
Inhibition (binding) = 16 % Inhibition of 11beta-HSD1 in human liver microsomes using [3H]-cortisone as substrate assessed as formation of cortisol at 100 uM after 60 to 90 mins by radiometric analysis relative to control ChEMBL. 23800686
Inhibition (binding) = 18 % Inhibition of 11beta-HSD1 in Sprague-Dawley rat leydig cells at 100 uM relative to control ChEMBL. 23800686
Inhibition (binding) = 31 % Inhibition of human 11beta-HSD1 transfected in CHOP cells at 100 uM relative to control ChEMBL. 23800686
Potency (functional) = 0.1413 um PUBCHEM_BIOASSAY: qHTS Assay for Modulators of Lamin A Splicing. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 2.0787 uM PUBCHEM_BIOASSAY: Primary qHTS for delayed death inhibitors of the malarial parasite plastid, 96 hour incubation. (Class of assay: confirmatory) [Related pubchem assays (depositor defined):AID488745, AID488752, AID488774, AID504848, AID504850] ChEMBL. No reference
Potency (functional) 2.6169 uM PUBCHEM_BIOASSAY: Primary qHTS for delayed death inhibitors of the malarial parasite plastid, 48 hour incubation. (Class of assay: confirmatory) [Related pubchem assays (depositor defined):AID488752, AID488774, AID504848, AID504850] ChEMBL. No reference
Potency (functional) 4.6109 uM PubChem BioAssay. A quantitative high throughput screen for small molecules that induce DNA re-replication in SW480 colon adenocarcinoma cells. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 5.8048 uM PubChem BioAssay. A quantitative high throughput screen for small molecules that induce DNA re-replication in MCF 10a normal breast cells. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 7.0795 uM PUBCHEM_BIOASSAY: qHTS for Inhibitors of TGF-b. (Class of assay: confirmatory) [Related pubchem assays (depositor defined):AID588856, AID588860] ChEMBL. No reference
Potency (functional) = 11.2202 um PUBCHEM_BIOASSAY: qHTS Assay for Enhancers of SMN2 Splice Variant Expression. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 19.9526 uM PUBCHEM_BIOASSAY: qHTS Assay for Inhibitors of JMJD2A-Tudor Domain. (Class of assay: confirmatory) [Related pubchem assays (depositor defined):AID504402] ChEMBL. No reference
Potency (functional) 20.5962 uM PUBCHEM_BIOASSAY: qHTS screen for small molecules that inhibit ELG1-dependent DNA repair in human embryonic kidney (HEK293T) cells expressing luciferase-tagged ELG1. (Class of assay: confirmatory) [Related pubchem assays (depositor defined):AID493107, AID493125] ChEMBL. No reference
Potency (functional) 22.3872 uM PubChem BioAssay. qHTS of PTHR Inhibitors: Primary Screen. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) = 25.1189 um PUBCHEM_BIOASSAY: qHTS Assay for Promiscuous and Specific Inhibitors of Cruzain (without detergent). (Class of assay: confirmatory) [Related pubchem assays: 2158 (Confirmation qHTS Assay for Inhibitors of Cruzain), 2249 (Probe Development Summary of Promiscuous Inhibitors (Artifacts) of Cruzain), 2161 (qHTS Assay for Inhibitors of Papain: Counterscreen for Cruzain Assay), 1478 (qHTS Assay for Promiscuous and Specific Inhibitors of Cruzain (with detergent))] ChEMBL. No reference
Potency (functional) 28.1838 uM PubChem BioAssay. Inhibitors of USP1/UAF1: Primary Screen. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 35.4813 uM PUBCHEM_BIOASSAY: qHTS Assay for Inhibitors of RanGTP induced Rango (Ran-regulated importin-beta cargo) - Importin beta complex dissociation. (Class of assay: confirmatory) [Related pubchem assays (depositor defined):AID540262] ChEMBL. No reference
Potency (functional) 75.6863 uM PubChem BioAssay. qHTS Assay to Find Inhibitors of Pin1. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 89.1251 uM PUBCHEM_BIOASSAY: qHTS for Inhibitors of Polymerase Iota. (Class of assay: confirmatory) [Related pubchem assays (depositor defined):AID588623] ChEMBL. No reference
Potency (functional) 89.1251 uM PUBCHEM_BIOASSAY: qHTS Assay for Inhibitors of Rango (Ran-regulated importin-beta cargo) - Importin beta complex formation. (Class of assay: confirmatory) [Related pubchem assays (depositor defined):AID540273] ChEMBL. No reference

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Homo sapiens ChEMBL23 22551677
Plasmodium falciparum ChEMBL23 18579783

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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