Detailed information for compound 227479

Basic information

Technical information
  • TDR Targets ID: 227479
  • Name: 5-cyclopropyl-2-(2-dimethylaminoethyl)-7-(2,6 -dimethylpyridin-4-yl)-6,8-difluoropyrazolo[4 ,3-c]quinolin-3-one
  • MW: 437.485 | Formula: C24H25F2N5O
  • H donors: 0 H acceptors: 2 LogP: 3.56 Rotable bonds: 5
    Rule of 5 violations (Lipinski): 1
  • SMILES: CN(CCn1nc2c(c1=O)cn(c1c2cc(F)c(c1F)c1cc(C)nc(c1)C)C1CC1)C
  • InChi: 1S/C24H25F2N5O/c1-13-9-15(10-14(2)27-13)20-19(25)11-17-22-18(24(32)31(28-22)8-7-29(3)4)12-30(16-5-6-16)23(17)21(20)26/h9-12,16H,5-8H2,1-4H3
  • InChiKey: PGJDQMYHNOXAEZ-UHFFFAOYSA-N  


Substructure search Similarity search

Network

Hover on a compound node to display the structore

Synonyms

  • 5-cyclopropyl-2-(2-dimethylaminoethyl)-7-(2,6-dimethyl-4-pyridyl)-6,8-difluoro-pyrazolo[4,3-c]quinolin-3-one
  • 5-cyclopropyl-2-(2-dimethylaminoethyl)-7-(2,6-dimethyl-4-pyridyl)-6,8-difluoro-3-pyrazolo[4,3-c]quinolinone
  • 5-cyclopropyl-2-(2-dimethylaminoethyl)-7-(2,6-dimethylpyridin-4-yl)-6,8-difluoro-pyrazolo[4,3-c]quinolin-3-one
  • 5-cyclopropyl-2-(2-dimethylaminoethyl)-7-(2,6-dimethylpyridin-4-yl)-6,8-difluoropyrazolo[4,5-c]quinolin-3-one
  • 5-cyclopropyl-2-(2-dimethylaminoethyl)-7-(2,6-dimethyl-4-pyridyl)-6,8-difluoro-pyrazolo[4,5-c]quinolin-3-one
  • 5-cyclopropyl-2-(2-dimethylaminoethyl)-7-(2,6-dimethyl-4-pyridyl)-6,8-difluoro-3-pyrazolo[4,5-c]quinolinone
  • 5-cyclopropyl-2-(2-dimethylaminoethyl)-7-(2,6-dimethylpyridin-4-yl)-6,8-difluoro-pyrazolo[4,5-c]quinolin-3-one

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens topoisomerase (DNA) II beta 180kDa Starlite/ChEMBL No references

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Onchocerca volvulus DNA topoisomerase 2 homolog Get druggable targets OG5_127113 All targets in OG5_127113
Candida albicans DNA topoisomerase II similar to S. cerevisiae TOP2 (YNL088W) Get druggable targets OG5_127113 All targets in OG5_127113
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_127113 All targets in OG5_127113
Trypanosoma cruzi DNA topoisomerase II, putative Get druggable targets OG5_127113 All targets in OG5_127113
Trichomonas vaginalis DNA topoisomerase II, putative Get druggable targets OG5_127113 All targets in OG5_127113
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_127113 All targets in OG5_127113
Onchocerca volvulus DNA topoisomerase 2 homolog Get druggable targets OG5_127113 All targets in OG5_127113
Plasmodium vivax DNA topoisomerase II, putative Get druggable targets OG5_127113 All targets in OG5_127113
Leishmania infantum DNA topoisomerase ii Get druggable targets OG5_127113 All targets in OG5_127113
Trypanosoma congolense DNA topoisomerase II, putative Get druggable targets OG5_127113 All targets in OG5_127113
Trypanosoma brucei DNA topoisomerase II beta, putative Get druggable targets OG5_127113 All targets in OG5_127113
Giardia lamblia DNA topoisomerase II Get druggable targets OG5_127113 All targets in OG5_127113
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_127113 All targets in OG5_127113
Entamoeba histolytica DNA topoisomerase II, putative Get druggable targets OG5_127113 All targets in OG5_127113
Chlamydia trachomatis DNA gyrase subunit B Get druggable targets OG5_127113 All targets in OG5_127113
Toxoplasma gondii DNA topoisomerase 2, putative Get druggable targets OG5_127113 All targets in OG5_127113
Plasmodium yoelii DNA topoisomerase II, putative Get druggable targets OG5_127113 All targets in OG5_127113
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_127113 All targets in OG5_127113
Neospora caninum hypothetical protein Get druggable targets OG5_127113 All targets in OG5_127113
Brugia malayi DNA gyrase/topoisomerase IV, A subunit family protein Get druggable targets OG5_127113 All targets in OG5_127113
Onchocerca volvulus Putative DNA topoisomerase 2, mitochondrial Get druggable targets OG5_127113 All targets in OG5_127113
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_127113 All targets in OG5_127113
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_127113 All targets in OG5_127113
Leishmania braziliensis DNA topoisomerase ii Get druggable targets OG5_127113 All targets in OG5_127113
Plasmodium berghei DNA topoisomerase 2, putative Get druggable targets OG5_127113 All targets in OG5_127113
Babesia bovis DNA topoisomerase II, putative Get druggable targets OG5_127113 All targets in OG5_127113
Cryptosporidium hominis DNA topoisomerase II Get druggable targets OG5_127113 All targets in OG5_127113
Candida albicans DNA topoisomerase II similar to S. cerevisiae TOP2 (YNL088W) Get druggable targets OG5_127113 All targets in OG5_127113
Leishmania mexicana DNA topoisomerase ii Get druggable targets OG5_127113 All targets in OG5_127113
Brugia malayi Probable DNA topoisomerase II Get druggable targets OG5_127113 All targets in OG5_127113
Brugia malayi DNA topoisomerase II, alpha isozyme Get druggable targets OG5_127113 All targets in OG5_127113
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_127113 All targets in OG5_127113
Plasmodium falciparum DNA topoisomerase 2 Get druggable targets OG5_127113 All targets in OG5_127113
Schistosoma japonicum ko:K03164 DNA topoisomerase II, putative Get druggable targets OG5_127113 All targets in OG5_127113
Trypanosoma congolense DNA topoisomerase II, putative Get druggable targets OG5_127113 All targets in OG5_127113
Echinococcus multilocularis DNA topoisomerase 2 alpha Get druggable targets OG5_127113 All targets in OG5_127113
Trypanosoma brucei DNA topoisomerase II alpha, putative Get druggable targets OG5_127113 All targets in OG5_127113
Schistosoma mansoni DNA topoisomerase II Get druggable targets OG5_127113 All targets in OG5_127113
Schistosoma japonicum expressed protein Get druggable targets OG5_127113 All targets in OG5_127113
Plasmodium knowlesi DNA topoisomerase 2, putative Get druggable targets OG5_127113 All targets in OG5_127113
Leishmania donovani DNA topoisomerase ii Get druggable targets OG5_127113 All targets in OG5_127113
Cryptosporidium parvum DNA topoisomerase II Get druggable targets OG5_127113 All targets in OG5_127113
Leishmania major DNA topoisomerase ii Get druggable targets OG5_127113 All targets in OG5_127113
Trypanosoma brucei gambiense DNA topoisomerase II, putative Get druggable targets OG5_127113 All targets in OG5_127113
Loa Loa (eye worm) TOPoisomerase family member Get druggable targets OG5_127113 All targets in OG5_127113
Trypanosoma brucei gambiense DNA topoisomerase II, putative Get druggable targets OG5_127113 All targets in OG5_127113
Trypanosoma cruzi DNA topoisomerase II, putative Get druggable targets OG5_127113 All targets in OG5_127113
Theileria parva DNA topoisomerase II, putative Get druggable targets OG5_127113 All targets in OG5_127113
Echinococcus granulosus DNA topoisomerase 2 alpha Get druggable targets OG5_127113 All targets in OG5_127113
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
Brugia malayi Nuclear hormone receptor family member nhr-19 0.0056 0.0564 0.0597
Onchocerca volvulus DNA topoisomerase 2 homolog 0.0056 0.0572 0.0572
Echinococcus multilocularis ecdysone induced protein 78C 0.0056 0.0564 0.0702
Brugia malayi nuclear receptor NHR-88 0.0056 0.0564 0.0597
Echinococcus granulosus Nuclear hormone receptor family member nhr 41 0.0056 0.0564 0.0656
Loa Loa (eye worm) hypothetical protein 0.0034 0.0152 0.0162
Brugia malayi steroid hormone receptor 0.0056 0.0564 0.0597
Loa Loa (eye worm) nuclear Hormone Receptor family member 0.0056 0.0564 0.0597
Brugia malayi Nuclear hormone receptor family member nhr-14 0.0056 0.0564 0.0597
Brugia malayi hypothetical protein 0.0029 0.006 0.0064
Trichomonas vaginalis DNA topoisomerase II, putative 0.0078 0.098 0.5
Brugia malayi Nuclear hormone receptor family member nhr-49 0.0056 0.0564 0.0597
Brugia malayi Nuclear hormone receptor family member nhr-25 0.0056 0.0564 0.0597
Onchocerca volvulus 0.0056 0.0564 0.0564
Entamoeba histolytica DNA topoisomerase II, putative 0.0078 0.098 0.5
Brugia malayi Probable DNA topoisomerase II 0.0078 0.098 0.1039
Echinococcus multilocularis nuclear receptor 2DBD gamma 0.0056 0.0564 0.0702
Brugia malayi DNA topoisomerase II, alpha isozyme 0.0078 0.098 0.1039
Schistosoma mansoni retinoid-x-receptor (RXR) 0.0056 0.0564 0.0656
Schistosoma mansoni nuclear hormone receptor nor-1/nor-2 0.0056 0.0564 0.0656
Schistosoma mansoni retinoic acid receptor RXR 0.0476 0.8596 1
Echinococcus multilocularis DNA topoisomerase 2 alpha 0.0078 0.098 0.122
Brugia malayi Nuclear hormone receptor family member nhr-1 0.0056 0.0564 0.0597
Brugia malayi Nuclear hormone receptor-like 1 0.0056 0.0564 0.0597
Brugia malayi Nuclear hormone receptor family member nhr-19 0.0056 0.0564 0.0597
Loa Loa (eye worm) nuclear hormone receptor family member nhr-41 0.0056 0.0564 0.0597
Leishmania major DNA topoisomerase ii 0.007 0.0831 1
Echinococcus granulosus FTZ F1 alpha 0.0056 0.0564 0.0656
Loa Loa (eye worm) hypothetical protein 0.0029 0.006 0.0064
Schistosoma mansoni FTZ-F1 nuclear receptor-like protein 0.0056 0.0564 0.0656
Loa Loa (eye worm) nuclear hormone receptor family member nhr-31 0.0056 0.0564 0.0597
Brugia malayi Nuclear hormone receptor family member nhr-40 0.0056 0.0564 0.0597
Schistosoma mansoni retinoid-x-receptor (RXR) 0.0029 0.006 0.007
Echinococcus granulosus nuclear receptor 2DBD gamma 0.0056 0.0564 0.0656
Schistosoma mansoni steroid hormone receptor ad4bp 0.0056 0.0564 0.0656
Brugia malayi Nuclear hormone receptor family member nhr-3 0.0056 0.0564 0.0597
Brugia malayi Nuclear hormone receptor-like 1 0.0029 0.006 0.0064
Onchocerca volvulus DNA topoisomerase 2 homolog 0.0056 0.0572 0.0572
Loa Loa (eye worm) hypothetical protein 0.0052 0.0492 0.0521
Loa Loa (eye worm) hypothetical protein 0.0056 0.0564 0.0597
Plasmodium vivax DNA topoisomerase II, putative 0.0078 0.098 0.5
Brugia malayi Nuclear hormone receptor family member nhr-41 0.0056 0.0564 0.0597
Brugia malayi nuclear receptor RXR 0.0029 0.006 0.0064
Loa Loa (eye worm) hypothetical protein 0.0056 0.0564 0.0597
Loa Loa (eye worm) hypothetical protein 0.0029 0.006 0.0064
Brugia malayi Nuclear hormone receptor family member nhr-31 0.0056 0.0564 0.0597
Echinococcus granulosus nuclear receptor 2DBD gamma 0.0056 0.0564 0.0656
Echinococcus multilocularis FTZ F1 nuclear receptor protein 0.0056 0.0564 0.0702
Echinococcus multilocularis thyroid hormone receptor alpha 0.0056 0.0564 0.0702
Echinococcus granulosus COUP TF:Svp nuclear hormone receptor 0.0056 0.0564 0.0656
Echinococcus granulosus retinoic acid receptor rxr beta a 0.0476 0.8596 1
Onchocerca volvulus Protein ultraspiracle homolog 0.0056 0.0564 0.0564
Onchocerca volvulus Putative DNA topoisomerase 2, mitochondrial 0.0056 0.0572 0.0572
Loa Loa (eye worm) hypothetical protein 0.0034 0.0152 0.0162
Brugia malayi nuclear hormone receptor 0.0056 0.0564 0.0597
Schistosoma mansoni ecdysone-induced protein 78c (dr-78) 0.0029 0.006 0.007
Toxoplasma gondii DNA topoisomerase 2, putative 0.0078 0.098 0.5
Trypanosoma brucei DNA topoisomerase II beta, putative 0.007 0.0831 1
Schistosoma mansoni coup transcription factor 0.0056 0.0564 0.0656
Loa Loa (eye worm) nuclear hormone receptor family member nhr-40 0.0056 0.0564 0.0597
Brugia malayi photoreceptor-specific nuclear receptor 0.0056 0.0564 0.0597
Brugia malayi ecdysteroid receptor 0.0056 0.0564 0.0597
Loa Loa (eye worm) hypothetical protein 0.0029 0.006 0.0064
Plasmodium falciparum DNA topoisomerase 2 0.0078 0.098 1
Brugia malayi DNA gyrase/topoisomerase IV, A subunit family protein 0.0078 0.098 0.1039
Brugia malayi Nuclear hormone receptor family member nhr-25 0.0056 0.0564 0.0597
Schistosoma mansoni nuclear receptor 2DBD-gamma 0.0056 0.0564 0.0656
Loa Loa (eye worm) nuclear hormone receptor family member nhr-1 0.0056 0.0564 0.0597
Echinococcus multilocularis nuclear receptor subfamily 1 group D 0.0029 0.006 0.0075
Echinococcus multilocularis FTZ F1 alpha 0.0056 0.0564 0.0702
Trypanosoma cruzi DNA topoisomerase II, putative 0.007 0.0831 1
Schistosoma mansoni RAR-like nuclear receptor 0.0056 0.0564 0.0656
Loa Loa (eye worm) hypothetical protein 0.0029 0.006 0.0064
Onchocerca volvulus Bile acid receptor homolog 0.0056 0.0564 0.0564
Loa Loa (eye worm) hypothetical protein 0.0056 0.0564 0.0597
Echinococcus multilocularis Nuclear hormone receptor family member nhr 41 0.0056 0.0564 0.0702
Brugia malayi nuclear hormone receptor 0.052 0.9436 1
Echinococcus multilocularis retinoic acid receptor rxr beta a retinoic acid receptor rxr alpha a retinoic acid receptor rxr alpha 0.0446 0.8032 1
Loa Loa (eye worm) hypothetical protein 0.0052 0.0492 0.0521
Brugia malayi Ligand-binding domain of nuclear hormone receptor family protein 0.0056 0.0564 0.0597
Schistosoma mansoni thyroid hormone receptor 0.0056 0.0564 0.0656
Loa Loa (eye worm) hypothetical protein 0.0493 0.8933 0.9467
Loa Loa (eye worm) hypothetical protein 0.0056 0.0564 0.0597
Trypanosoma brucei DNA topoisomerase II alpha, putative 0.007 0.0831 1
Loa Loa (eye worm) hypothetical protein 0.0056 0.0564 0.0597
Schistosoma mansoni DNA topoisomerase II 0.0078 0.098 0.114
Echinococcus multilocularis nuclear receptor 2DBD gamma 0.0056 0.0564 0.0702
Schistosoma mansoni Tr4/Tr2 (homologue) 0.0056 0.0564 0.0656
Schistosoma mansoni photoreceptor-specific nuclear receptor related 0.0056 0.0564 0.0656
Echinococcus granulosus ecdysone induced protein 78C 0.0056 0.0564 0.0656
Brugia malayi Ligand-binding domain of nuclear hormone receptor family protein 0.0056 0.0564 0.0597
Brugia malayi Steroid receptor seven-up type 2 0.0056 0.0564 0.0597
Loa Loa (eye worm) nuclear receptor nhr-7B 0.052 0.9436 1
Schistosoma mansoni thyroid hormone receptor 0.0056 0.0564 0.0656
Loa Loa (eye worm) steroid hormone receptor 0.0056 0.0564 0.0597
Brugia malayi Nuclear hormone receptor-like 1 0.0029 0.006 0.0064
Schistosoma mansoni nuclear hormone receptor 0.0056 0.0564 0.0656
Chlamydia trachomatis DNA gyrase subunit B 0.0042 0.0302 0.5
Echinococcus granulosus nuclear receptor subfamily 1 group D 0.0029 0.006 0.007
Loa Loa (eye worm) nuclear hormone receptor family member nhr-14 0.0056 0.0564 0.0597
Brugia malayi hypothetical protein 0.0029 0.006 0.0064
Trypanosoma cruzi DNA topoisomerase II, putative 0.007 0.0831 1
Echinococcus granulosus hepatocyte nuclear factor 4 alpha 0.0056 0.0564 0.0656
Loa Loa (eye worm) hypothetical protein 0.0056 0.0564 0.0597
Echinococcus granulosus FTZ F1 nuclear receptor protein 0.0056 0.0564 0.0656
Loa Loa (eye worm) hypothetical protein 0.0029 0.006 0.0064
Echinococcus multilocularis hepatocyte nuclear factor 4 alpha 0.0056 0.0564 0.0702
Giardia lamblia DNA topoisomerase II 0.0074 0.0915 0.5
Echinococcus granulosus DNA topoisomerase 2 alpha 0.0078 0.098 0.114
Loa Loa (eye worm) hypothetical protein 0.0056 0.0564 0.0597
Loa Loa (eye worm) hypothetical protein 0.0056 0.0564 0.0597
Loa Loa (eye worm) nuclear hormone receptor family member nhr-49 0.0056 0.0564 0.0597
Loa Loa (eye worm) TOPoisomerase family member 0.0078 0.098 0.1039
Loa Loa (eye worm) nuclear hormone receptor-like 1 0.0029 0.006 0.0064
Echinococcus multilocularis COUP TF:Svp nuclear hormone receptor 0.0056 0.0564 0.0702

Activities

Activity type Activity value Assay description Source Reference
EC50 (binding) = 0.93 uM Inhibition of calf thymus DNA/ethidium bromide complex formation. ChEMBL. No reference
EC50 (binding) = 0.93 uM Inhibition of calf thymus DNA/ethidium bromide complex formation. ChEMBL. No reference
EC50 (binding) = 2.6 uM Compound was tested for topoisomerase II inhibition in purified HeLa cells by SDS/K+ precipitation method ChEMBL. No reference
EC50 (binding) = 2.6 uM Compound was tested for topoisomerase II inhibition in purified HeLa cells by SDS/K+ precipitation method ChEMBL. No reference
IC50 (functional) = 0.26 uM In vitro cytotoxicity was evaluated following 1 hour transient exposure of P388 mouse leukemia cells to the compound ChEMBL. No reference
IC50 (functional) = 0.26 uM In vitro cytotoxicity was evaluated following 1 hour transient exposure of P388 mouse leukemia cells to the compound ChEMBL. No reference
MTD (functional) = 34 mg kg-1 In vivo antitumor activity was measured as the maximum dose tolerated by murine when administered intravenously ChEMBL. No reference
MTD (functional) = 34 mg kg-1 In vivo antitumor activity was measured as the maximum dose tolerated by murine when administered intravenously ChEMBL. No reference
T/C (functional) = 8 % Tested for tumor growth inhibition in mice ChEMBL. No reference
T/C (functional) = 8 % Tested for tumor growth inhibition in mice ChEMBL. No reference

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Mus musculus ChEMBL23

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

No literature references available for this target.

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