Detailed information for compound 184560

Basic information

Technical information
  • TDR Targets ID: 184560
  • Name: 8-(2-Chloro-3,4,5-Trimethoxy-Benzyl)-2-Fluoro -9-Pent-4-Ylnyl-9h-Purin-6-Ylamine
  • MW: 433.864 | Formula: C20H21ClFN5O3
  • H donors: 1 H acceptors: 3 LogP: 3.51 Rotable bonds: 8
    Rule of 5 violations (Lipinski): 1
  • SMILES: C#CCCCn1c(Cc2cc(OC)c(c(c2Cl)OC)OC)nc2c1nc(F)nc2N
  • InChi: 1S/C20H21ClFN5O3/c1-5-6-7-8-27-13(24-15-18(23)25-20(22)26-19(15)27)10-11-9-12(28-2)16(29-3)17(30-4)14(11)21/h1,9H,6-8,10H2,2-4H3,(H2,23,25,26)
  • InChiKey: KCIOVTSUEXGUFJ-UHFFFAOYSA-N  


Substructure search Similarity search

Network

Hover on a compound node to display the structore

Synonyms

  • 8-[(2-chloro-3,4,5-trimethoxyphenyl)methyl]-2-fluoro-9-pent-4-ynylpurin-6-amine
  • 8-[(2-chloro-3,4,5-trimethoxy-phenyl)methyl]-2-fluoro-9-pent-4-ynyl-purin-6-amine
  • 8-[(2-chloro-3,4,5-trimethoxyphenyl)methyl]-2-fluoro-9-pent-4-ynyl-6-purinamine
  • [8-(2-chloro-3,4,5-trimethoxy-benzyl)-2-fluoro-9-pent-4-ynyl-purin-6-yl]amine
  • 8-(2-Chloro-3,4,5-trimethoxybenzyl)-2-fluoro-9-(pent-4-ynyl)-9H-purin-6-amine
  • NChemBio.2007.10-comp3
  • PU1

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens heat shock protein 90kDa alpha (cytosolic), class A member 1 Starlite/ChEMBL References
Homo sapiens heat shock protein 90kDa alpha (cytosolic), class B member 1 Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Echinococcus multilocularis endoplasmin Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania braziliensis heat shock protein 83-1 Get druggable targets OG5_126623 All targets in OG5_126623
Trypanosoma cruzi heat shock protein 85, putative Get druggable targets OG5_126623 All targets in OG5_126623
Plasmodium yoelii heat shock 90 kDa protein homolog Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania major heat shock protein 83-1 Get druggable targets OG5_126623 All targets in OG5_126623
Trypanosoma brucei gambiense Heat shock protein 83, putative Get druggable targets OG5_126623 All targets in OG5_126623
Giardia lamblia Heat shock protein HSP 90-alpha Get druggable targets OG5_126623 All targets in OG5_126623
Trypanosoma cruzi heat shock protein 85, putative Get druggable targets OG5_126623 All targets in OG5_126623
Trypanosoma cruzi heat shock protein 85, putative Get druggable targets OG5_126623 All targets in OG5_126623
Entamoeba histolytica heat shock protein 90, putative Get druggable targets OG5_126623 All targets in OG5_126623
Trypanosoma brucei gambiense Heat shock protein 83, putative Get druggable targets OG5_126623 All targets in OG5_126623
Entamoeba histolytica heat shock protein 90, putative Get druggable targets OG5_126623 All targets in OG5_126623
Trypanosoma cruzi heat shock protein 85, putative Get druggable targets OG5_126623 All targets in OG5_126623
Loa Loa (eye worm) heat shock protein 90 Get druggable targets OG5_126623 All targets in OG5_126623
Mycobacterium tuberculosis Probable chaperone protein HtpG (heat shock protein) (HSP90 family protein) (high temperature protein G) Get druggable targets OG5_126623 All targets in OG5_126623
Neospora caninum HSP90, related Get druggable targets OG5_126623 All targets in OG5_126623
Toxoplasma gondii heat shock protein HSP90 Get druggable targets OG5_126623 All targets in OG5_126623
Plasmodium berghei heat shock protein 90, putative Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania major heat shock protein 83-1 Get druggable targets OG5_126623 All targets in OG5_126623
Trypanosoma congolense heat shock protein 90, putative Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania donovani heat shock protein 83-1 Get druggable targets OG5_126623 All targets in OG5_126623
Wolbachia endosymbiont of Brugia malayi heat shock protein 90 Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania major heat shock protein 83-1 Get druggable targets OG5_126623 All targets in OG5_126623
Cryptosporidium parvum Hsp90 Get druggable targets OG5_126623 All targets in OG5_126623
Trichomonas vaginalis heat shock protein, putative Get druggable targets OG5_126623 All targets in OG5_126623
Trypanosoma congolense Heat shock protein 83, putative Get druggable targets OG5_126623 All targets in OG5_126623
Trypanosoma brucei gambiense lipophosphoglycan biosynthetic protein, putative,heat shock protein 90, putative,glucose regulated protein 94, putative Get druggable targets OG5_126623 All targets in OG5_126623
Schistosoma japonicum Heat shock protein 83, putative Get druggable targets OG5_126623 All targets in OG5_126623
Candida albicans heat shock protein Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania major heat shock protein 83-1 Get druggable targets OG5_126623 All targets in OG5_126623
Schistosoma japonicum Heat shock protein HSP 90-beta, putative Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania major heat shock protein 83-1 Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania major heat shock protein 83-1 Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania braziliensis heat shock protein 83-1 Get druggable targets OG5_126623 All targets in OG5_126623
Candida albicans hypothetical protein Get druggable targets OG5_126623 All targets in OG5_126623
Toxoplasma gondii heat shock protein 90, putative Get druggable targets OG5_126623 All targets in OG5_126623
Brugia malayi Endoplasmin precursor Get druggable targets OG5_126623 All targets in OG5_126623
Schistosoma mansoni endoplasmin Get druggable targets OG5_126623 All targets in OG5_126623
Echinococcus granulosus heat shock protein Get druggable targets OG5_126623 All targets in OG5_126623
Echinococcus granulosus heat shock protein 90 Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania mexicana lipophosphoglycan biosynthetic protein, putative,heat shock protein 90, putative,glucose regulated protein 94, putative Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania major heat shock protein 83-1 Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania major heat shock protein 83-1 Get druggable targets OG5_126623 All targets in OG5_126623
Schistosoma mansoni endoplasmin Get druggable targets OG5_126623 All targets in OG5_126623
Schistosoma japonicum IPR003367,Thrombospondin type 3 repeat;IPR002048,Calcium-binding EF-hand,domain-containing Get druggable targets OG5_126623 All targets in OG5_126623
Babesia bovis hsp90 protein Get druggable targets OG5_126623 All targets in OG5_126623
Schistosoma japonicum Heat shock protein HSP 90-alpha, putative Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania mexicana heat shock protein 83-1 Get druggable targets OG5_126623 All targets in OG5_126623
Trichomonas vaginalis heat shock protein, putative Get druggable targets OG5_126623 All targets in OG5_126623
Mycobacterium ulcerans heat shock protein 90 Get druggable targets OG5_126623 All targets in OG5_126623
Echinococcus multilocularis heat shock protein 90 Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania major heat shock protein 83-1 Get druggable targets OG5_126623 All targets in OG5_126623
Treponema pallidum heat shock protein 90 Get druggable targets OG5_126623 All targets in OG5_126623
Trypanosoma congolense heat shock protein 90, putative Get druggable targets OG5_126623 All targets in OG5_126623
Cryptosporidium hominis heat shock protein 83 Get druggable targets OG5_126623 All targets in OG5_126623
Trichomonas vaginalis heat shock protein, putative Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania braziliensis heat shock protein 83-1 Get druggable targets OG5_126623 All targets in OG5_126623
Trypanosoma brucei heat shock protein, putative Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania major lipophosphoglycan biosynthetic protein, putative,heat shock protein 90, putative,glucose regulated protein 94, putative Get druggable targets OG5_126623 All targets in OG5_126623
Trypanosoma cruzi heat shock protein 90, putative Get druggable targets OG5_126623 All targets in OG5_126623
Plasmodium vivax heat shock protein 86, putative Get druggable targets OG5_126623 All targets in OG5_126623
Trypanosoma brucei gambiense heat shock protein 83,heat shock protein Get druggable targets OG5_126623 All targets in OG5_126623
Plasmodium falciparum heat shock protein 90 Get druggable targets OG5_126623 All targets in OG5_126623
Echinococcus granulosus heat shock protein 90 Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania infantum heat shock protein 83-1 Get druggable targets OG5_126623 All targets in OG5_126623
Schistosoma mansoni heat shock protein Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania major heat shock protein 83-1 Get druggable targets OG5_126623 All targets in OG5_126623
Mycobacterium leprae PROBABLE CHAPERONE PROTEIN HTPG (HEAT SHOCK PROTEIN) (HSP90 FAMILY PROTEIN) (HIGH TEMPERATURE PROTEIN G) Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania mexicana heat shock protein 83-1 Get druggable targets OG5_126623 All targets in OG5_126623
Trypanosoma brucei heat shock protein, putative Get druggable targets OG5_126623 All targets in OG5_126623
Trypanosoma brucei heat shock protein, putative Get druggable targets OG5_126623 All targets in OG5_126623
Loa Loa (eye worm) endoplasmin Get druggable targets OG5_126623 All targets in OG5_126623
Trichomonas vaginalis heat shock protein, putative Get druggable targets OG5_126623 All targets in OG5_126623
Echinococcus granulosus endoplasmin Get druggable targets OG5_126623 All targets in OG5_126623
Echinococcus multilocularis heat shock protein 90 Get druggable targets OG5_126623 All targets in OG5_126623
Trypanosoma brucei heat shock protein 90, putative Get druggable targets OG5_126623 All targets in OG5_126623
Trypanosoma cruzi heat shock protein 90, putative Get druggable targets OG5_126623 All targets in OG5_126623
Trypanosoma brucei heat shock protein 90, putative Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania major heat shock protein 83-1 Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania infantum heat shock protein 83-1 Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania infantum heat shock protein 83-1 Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania major heat shock protein 83-1 Get druggable targets OG5_126623 All targets in OG5_126623
Trypanosoma cruzi Heat shock protein 83, putative Get druggable targets OG5_126623 All targets in OG5_126623
Giardia lamblia Heat shock protein HSP 90-alpha Get druggable targets OG5_126623 All targets in OG5_126623
Plasmodium knowlesi heat shock protein 90, putative Get druggable targets OG5_126623 All targets in OG5_126623
Trypanosoma brucei heat shock protein, putative Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania major heat shock protein 83-1 Get druggable targets OG5_126623 All targets in OG5_126623
Trypanosoma brucei heat shock protein, putative Get druggable targets OG5_126623 All targets in OG5_126623
Trypanosoma brucei Heat shock protein 83, putative Get druggable targets OG5_126623 All targets in OG5_126623
Plasmodium yoelii heat shock protein 90 Get druggable targets OG5_126623 All targets in OG5_126623
Echinococcus multilocularis heat shock protein Get druggable targets OG5_126623 All targets in OG5_126623
Candida albicans heat shock protein Get druggable targets OG5_126623 All targets in OG5_126623
Theileria parva heat shock protein 90 Get druggable targets OG5_126623 All targets in OG5_126623
Trypanosoma cruzi heat shock protein 90, putative Get druggable targets OG5_126623 All targets in OG5_126623
Trypanosoma brucei heat shock protein, putative Get druggable targets OG5_126623 All targets in OG5_126623
Schistosoma mansoni heat shock protein Get druggable targets OG5_126623 All targets in OG5_126623
Trypanosoma brucei heat shock protein, putative Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania infantum lipophosphoglycan biosynthetic protein, putative,heat shock protein 90, putative,glucose regulated protein 94, putative Get druggable targets OG5_126623 All targets in OG5_126623
Plasmodium knowlesi endoplasmin, putative Get druggable targets OG5_126623 All targets in OG5_126623
Giardia lamblia Grp94/Hsp90 Get druggable targets OG5_126623 All targets in OG5_126623
Brugia malayi heat shock protein 90 Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania major heat shock protein 83-1 Get druggable targets OG5_126623 All targets in OG5_126623
Plasmodium vivax endoplasmin, putative Get druggable targets OG5_126623 All targets in OG5_126623
Neospora caninum HSP90-like protein, related Get druggable targets OG5_126623 All targets in OG5_126623
Echinococcus granulosus heat shock protein heat shock protein 90 alpha Get druggable targets OG5_126623 All targets in OG5_126623
Trypanosoma brucei heat shock protein, putative Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania braziliensis lipophosphoglycan biosynthetic protein, putative,heat shock protein 90, putative,glucose regulated protein 94, putative Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania major heat shock protein 83-1 Get druggable targets OG5_126623 All targets in OG5_126623
Schistosoma japonicum ko:K04079 molecular chaperone HtpG, putative Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania major heat shock protein 83-1 Get druggable targets OG5_126623 All targets in OG5_126623
Schistosoma japonicum ko:K09487 heat shock protein 90kDa beta, putative Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania donovani heat shock protein 90, putative Get druggable targets OG5_126623 All targets in OG5_126623
Leishmania major heat shock protein 83-1 Get druggable targets OG5_126623 All targets in OG5_126623
Plasmodium yoelii putative heat shock protein 81-2 Get druggable targets OG5_126623 All targets in OG5_126623
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Plasmodium falciparum heat shock protein 90, putative heat shock protein 90kDa alpha (cytosolic), class B member 1 724 aa 725 aa 35.6 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Plasmodium falciparum eukaryotic initiation factor 4A 0.0135 1 1
Trypanosoma cruzi Eukaryotic initiation factor 4A-1 0.0135 1 1
Trypanosoma cruzi Eukaryotic initiation factor 4A-1 0.0135 1 1
Echinococcus multilocularis eukaryotic initiation factor 4A III 0.0135 1 1
Echinococcus multilocularis eukaryotic initiation factor 4A 0.0135 1 1
Leishmania major eukaryotic initiation factor 4a, putative 0.0135 1 1
Echinococcus granulosus eukaryotic initiation factor 4A 0.0135 1 1
Echinococcus granulosus eukaryotic initiation factor 4A III 0.0135 1 1
Onchocerca volvulus Eukaryotic initiation factor 4A homolog 0.0135 1 0.5
Trichomonas vaginalis DEAD box ATP-dependent RNA helicase, putative 0.0135 1 1
Schistosoma mansoni DEAD box ATP-dependent RNA helicase 0.0135 1 1
Treponema pallidum ATP-dependent RNA helicase 0.0135 1 0.5
Leishmania major eukaryotic initiation factor 4a, putative 0.0135 1 1
Trichomonas vaginalis DEAD box ATP-dependent RNA helicase, putative 0.0135 1 1
Giardia lamblia Translation initiation factor eIF-4A, putative 0.0135 1 1
Trypanosoma brucei Eukaryotic initiation factor 4A-1 0.0135 1 1
Loa Loa (eye worm) hypothetical protein 0.0135 1 1
Trichomonas vaginalis DEAD box ATP-dependent RNA helicase, putative 0.0135 1 1
Toxoplasma gondii eukaryotic initiation factor-4A, putative 0.0135 1 1
Schistosoma mansoni DEAD box ATP-dependent RNA helicase 0.0135 1 1
Mycobacterium tuberculosis Probable cold-shock DeaD-box protein A homolog DeaD (ATP-dependent RNA helicase dead homolog) 0.0135 1 0.5
Plasmodium vivax RNA helicase-1, putative 0.0135 1 1
Entamoeba histolytica DEAD/DEAH box helicase, putative 0.0135 1 1

Activities

Activity type Activity value Assay description Source Reference
Activity (functional) = 72 % Antitumor activity in human MCF7 cells xenografted mouse assessed as reduction of tumor burden at 200 mg/kg, ip administered alternative days ChEMBL. 19017562
EC50 (binding) = 1200 nM Displacement of cy3B-GM from Hsp90alpha ChEMBL. 16797988
EC50 (binding) = 1200 nM Displacement of cy3B-GM from Hsp90alpha ChEMBL. 16797988
EC50 (functional) = 0.17 uM Effective concentration against heat shock protein HSP90-alpha in SKBr3 cells ChEMBL. 15828828
EC50 (functional) = 0.17 uM Effective concentration against heat shock protein HSP90-alpha in SKBr3 cells ChEMBL. 15828828
EC50 (functional) = 0.23 uM Effective concentration against heat shock protein HSP90-alpha in MDA-MB-468 cells ChEMBL. 15828828
EC50 (functional) = 0.23 uM Effective concentration against heat shock protein HSP90-alpha in MDA-MB-468 cells ChEMBL. 15828828
GI50 (functional) = 3.9 uM Cellular activity of the compound against human colon tumour cell line, HCT116 ChEMBL. 14698151
GI50 (functional) = 3.9 uM Cellular activity of the compound against human colon tumour cell line, HCT116 ChEMBL. 14698151
IC50 (functional) = -5.7 Antiproliferative activity evaluated against MCF-7 cell line ChEMBL. 14741278
IC50 (binding) = 0.66 uM Displacement of GM-cy3B from Hsp90 in human SKBR3 cells after 24 hrs by fluorescence polarization assay ChEMBL. 24548207
IC50 (functional) = 1.2 uM Antiproliferative activity against human MCF7 cells by MTS assay ChEMBL. 17488003
IC50 (functional) = 1.2 uM Antiproliferative activity against human MCF7 cells by MTS assay ChEMBL. 17488003
IC50 (functional) = 1.5 uM Inhibition of Hsp90 protein as degradation of HER2 kinase in SKBr3 cells ChEMBL. 15828828
IC50 (functional) = 1.5 uM Inhibition of Hsp90 protein as degradation of HER2 kinase in SKBr3 cells ChEMBL. 15828828
IC50 (binding) = 1.7 uM Inhibition of human recombinant HSP90 in MCF7 cells assessed as Her2 degradation ChEMBL. 17488003
IC50 (binding) = 1.7 uM Inhibition of human recombinant HSP90 in MCF7 cells assessed as Her2 degradation ChEMBL. 17488003
IC50 (functional) = 1.8 uM Inhibitory concentration against SKBr3 cell line ChEMBL. 15828828
IC50 (functional) = 1.8 uM Inhibitory concentration against SKBr3 cell line ChEMBL. 15828828
IC50 (binding) = 2.5 uM Binding affinity to human recombinant HSP90 in MCF7 cell lysates assessed as inhibition of biotinylated-geldanamycin binding ChEMBL. 17488003
IC50 (binding) = 2.5 uM Binding affinity to human recombinant HSP90 in MCF7 cell lysates assessed as inhibition of biotinylated-geldanamycin binding ChEMBL. 17488003
IC50 (binding) = 6 uM Binding affinity to human recombinant HSP90 assessed as inhibition of biotinylated-geldanamycin binding ChEMBL. 17488003
IC50 (binding) = 6 uM Binding affinity to human recombinant HSP90 assessed as inhibition of biotinylated-geldanamycin binding ChEMBL. 17488003
IC50 (binding) = 7 uM Selectivity for HSP90 in MCF7 cells over HSP90 in NDF cells ChEMBL. 17488003
IC50 (binding) = 18 uM Binding affinity to HSP90 in human NDF cell lysates assessed as inhibition of biotinylated-geldanamycin binding ChEMBL. 17488003
IC50 (binding) = 18 uM Binding affinity to HSP90 in human NDF cell lysates assessed as inhibition of biotinylated-geldanamycin binding ChEMBL. 17488003
IC50 (binding) = 30 uM Inhibition of ATP-ase activity in human colon tumour cell line (HCT116) ChEMBL. 14698151
IC50 (binding) = 30 uM Inhibition of ATP-ase activity in human colon tumour cell line (HCT116) ChEMBL. 14698151
Log IC50 (functional) = 5.7 Antiproliferative activity evaluated against MCF-7 cell line ChEMBL. 14741278

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Homo sapiens ChEMBL23 14741278

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

6 literature references were collected for this gene.

If you have references for this compound, please enter them in a user comment (below) or Contact us.