Detailed information for compound 64852

Basic information

Technical information
  • TDR Targets ID: 64852
  • Name: 2-(4-hydroxyphenyl)-3-methyl-1-[[4-(2-piperid in-1-ylethoxy)phenyl]methyl]indol-5-ol
  • MW: 456.576 | Formula: C29H32N2O3
  • H donors: 2 H acceptors: 2 LogP: 5.77 Rotable bonds: 7
    Rule of 5 violations (Lipinski): 1
  • SMILES: Oc1ccc2c(c1)c(C)c(n2Cc1ccc(cc1)OCCN1CCCCC1)c1ccc(cc1)O
  • InChi: 1S/C29H32N2O3/c1-21-27-19-25(33)11-14-28(27)31(29(21)23-7-9-24(32)10-8-23)20-22-5-12-26(13-6-22)34-18-17-30-15-3-2-4-16-30/h5-14,19,32-33H,2-4,15-18,20H2,1H3
  • InChiKey: JICOGKJOQXTAIP-UHFFFAOYSA-N  


Substructure search Similarity search

Network

Hover on a compound node to display the structore

Synonyms

  • 2-(4-hydroxyphenyl)-3-methyl-1-[[4-[2-(1-piperidyl)ethoxy]phenyl]methyl]indol-5-ol
  • 2-(4-hydroxyphenyl)-3-methyl-1-[[4-[2-(1-piperidyl)ethoxy]phenyl]methyl]-5-indolol
  • 2-(4-hydroxyphenyl)-3-methyl-1-[4-(2-piperidinoethoxy)benzyl]indol-5-ol
  • 2-(4-hydroxyphenyl)-3-methyl-1-(4-(2-piperidin-1-yl-ethoxy)-benzyl)-1H-indol-5-ol
  • 198480-55-6
  • 2-(p-Hydroxyphenyl)-3-methyl-1-(p-(2-piperidinoethoxy)benzyl)indol-5-ol
  • Pipendoxifene [INN]
  • ERA-923
  • Pipendoxifene

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens estrogen receptor 2 (ER beta) Starlite/ChEMBL References
Homo sapiens estrogen receptor 1 Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
No druggable targets predicted by orthology data
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Loa Loa (eye worm) hypothetical protein estrogen receptor 2 (ER beta) 495 aa 418 aa 25.8 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Brugia malayi Ligand-binding domain of nuclear hormone receptor family protein 0.0016 0.5 0.5
Echinococcus multilocularis FTZ F1 alpha 0.0016 0.5 0.5
Echinococcus granulosus nuclear receptor 2DBD gamma 0.0016 0.5 0.5
Loa Loa (eye worm) nuclear hormone receptor family member nhr-41 0.0016 0.5 0.5
Brugia malayi Nuclear hormone receptor family member nhr-19 0.0016 0.5 0.5
Schistosoma mansoni nuclear hormone receptor nor-1/nor-2 0.0016 0.5 0.5
Loa Loa (eye worm) nuclear hormone receptor family member nhr-40 0.0016 0.5 0.5
Echinococcus granulosus FTZ F1 alpha 0.0016 0.5 0.5
Echinococcus granulosus Nuclear hormone receptor family member nhr 41 0.0016 0.5 0.5
Loa Loa (eye worm) nuclear hormone receptor family member nhr-14 0.0016 0.5 0.5
Echinococcus multilocularis thyroid hormone receptor alpha 0.0016 0.5 0.5
Brugia malayi nuclear receptor NHR-88 0.0016 0.5 0.5
Loa Loa (eye worm) hypothetical protein 0.0016 0.5 0.5
Echinococcus multilocularis nuclear receptor 2DBD gamma 0.0016 0.5 0.5
Loa Loa (eye worm) hypothetical protein 0.0016 0.5 0.5
Schistosoma mansoni photoreceptor-specific nuclear receptor related 0.0016 0.5 0.5
Brugia malayi Nuclear hormone receptor-like 1 0.0016 0.5 0.5
Echinococcus granulosus nuclear receptor 2DBD gamma 0.0016 0.5 0.5
Onchocerca volvulus Steroid hormone receptor family member cnr14 homolog 0.0016 0.5 0.5
Echinococcus multilocularis ecdysone induced protein 78C 0.0016 0.5 0.5
Brugia malayi Nuclear hormone receptor family member nhr-14 0.0016 0.5 0.5
Brugia malayi Steroid receptor seven-up type 2 0.0016 0.5 0.5
Schistosoma mansoni FTZ-F1 nuclear receptor-like protein 0.0016 0.5 0.5
Brugia malayi Nuclear hormone receptor family member nhr-19 0.0016 0.5 0.5
Schistosoma mansoni nuclear hormone receptor 0.0016 0.5 0.5
Loa Loa (eye worm) hypothetical protein 0.0016 0.5 0.5
Schistosoma mansoni nuclear receptor 2DBD-gamma 0.0016 0.5 0.5
Loa Loa (eye worm) nuclear Hormone Receptor family member 0.0016 0.5 0.5
Brugia malayi Ligand-binding domain of nuclear hormone receptor family protein 0.0016 0.5 0.5
Loa Loa (eye worm) nuclear hormone receptor family member nhr-49 0.0016 0.5 0.5
Schistosoma mansoni Tr4/Tr2 (homologue) 0.0016 0.5 0.5
Loa Loa (eye worm) hypothetical protein 0.0016 0.5 0.5
Echinococcus multilocularis nuclear receptor 2DBD gamma 0.0016 0.5 0.5
Echinococcus granulosus ecdysone induced protein 78C 0.0016 0.5 0.5
Brugia malayi Nuclear hormone receptor family member nhr-40 0.0016 0.5 0.5
Brugia malayi Nuclear hormone receptor family member nhr-1 0.0016 0.5 0.5
Brugia malayi nuclear hormone receptor 0.0016 0.5 0.5
Brugia malayi steroid hormone receptor 0.0016 0.5 0.5
Onchocerca volvulus 0.0016 0.5 0.5
Echinococcus granulosus hepatocyte nuclear factor 4 alpha 0.0016 0.5 0.5
Onchocerca volvulus Bile acid receptor homolog 0.0016 0.5 0.5
Brugia malayi Nuclear hormone receptor family member nhr-3 0.0016 0.5 0.5
Echinococcus multilocularis hepatocyte nuclear factor 4 alpha 0.0016 0.5 0.5
Echinococcus multilocularis Nuclear hormone receptor family member nhr 41 0.0016 0.5 0.5
Schistosoma mansoni retinoid-x-receptor (RXR) 0.0016 0.5 0.5
Schistosoma mansoni steroid hormone receptor ad4bp 0.0016 0.5 0.5
Brugia malayi Nuclear hormone receptor family member nhr-49 0.0016 0.5 0.5
Loa Loa (eye worm) nuclear hormone receptor family member nhr-31 0.0016 0.5 0.5
Echinococcus granulosus FTZ F1 nuclear receptor protein 0.0016 0.5 0.5
Brugia malayi Nuclear hormone receptor family member nhr-25 0.0016 0.5 0.5
Brugia malayi photoreceptor-specific nuclear receptor 0.0016 0.5 0.5
Echinococcus granulosus COUP TF:Svp nuclear hormone receptor 0.0016 0.5 0.5
Schistosoma mansoni coup transcription factor 0.0016 0.5 0.5
Schistosoma mansoni thyroid hormone receptor 0.0016 0.5 0.5
Schistosoma mansoni RAR-like nuclear receptor 0.0016 0.5 0.5
Loa Loa (eye worm) steroid hormone receptor 0.0016 0.5 0.5
Echinococcus granulosus retinoic acid receptor rxr beta a 0.0016 0.5 0.5
Loa Loa (eye worm) hypothetical protein 0.0016 0.5 0.5
Brugia malayi Nuclear hormone receptor family member nhr-41 0.0016 0.5 0.5
Loa Loa (eye worm) hypothetical protein 0.0016 0.5 0.5
Loa Loa (eye worm) hypothetical protein 0.0016 0.5 0.5
Loa Loa (eye worm) nuclear hormone receptor family member nhr-1 0.0016 0.5 0.5
Echinococcus multilocularis FTZ F1 nuclear receptor protein 0.0016 0.5 0.5
Onchocerca volvulus Protein ultraspiracle homolog 0.0016 0.5 0.5
Schistosoma mansoni thyroid hormone receptor 0.0016 0.5 0.5
Brugia malayi Nuclear hormone receptor family member nhr-25 0.0016 0.5 0.5
Brugia malayi Nuclear hormone receptor family member nhr-31 0.0016 0.5 0.5
Echinococcus multilocularis COUP TF:Svp nuclear hormone receptor 0.0016 0.5 0.5
Loa Loa (eye worm) hypothetical protein 0.0016 0.5 0.5
Schistosoma mansoni retinoic acid receptor RXR 0.0016 0.5 0.5

Activities

Activity type Activity value Assay description Source Reference
AUC (ADMET) = 7 microg.hr/mL AUC in 17-beta estradiol pellets supplemented nu/nu mouse xenografted with tamoxifen-resistant human MCF7 cells at 100 mg/kg/day, po administered for 4 weeks measured on day 28 ChEMBL. 25879485
EC50 (binding) = 0.0001 uM Induction of estrogen receptor-alpha degradation in human MCF7 cells after 4 hrs by in-cell western assay ChEMBL. 25879485
Efficacy (binding) = 87 % Induction of estrogen receptor-alpha degradation in human MCF7 cells at 5.12 x 10'-12 to 10'-5 M after 4 hrs by in-cell western assay relative to fulvestrant ChEMBL. 25879485
Efficacy (functional) = 89 % Cytotoxicity against human MCF7 cells assessed as cell viability at 0.000005 to 10 uM after 5 days by CellTiter-Glo assay relative to fulvestrant ChEMBL. 25879485
Emax (binding) = 83 % Induction of estrogen receptor-alpha degradation in human MCF7 cells at 5.12 x 10'-12 to 10'-5 M after 4 hrs by in-cell western assay relative to control ChEMBL. 25879485
IC50 (binding) Displacement of [3H]-E2 from estrogen receptor-beta (unknown origin) by scintillation counting analysis ChEMBL. 25879485
IC50 (functional) = 1.5 nM In vitro antagonist effect on estrogen receptor alpha transcriptional activation in MCF-7 cells against 10 pM 17-beta-estradiol ChEMBL. 11356100
IC50 (functional) = 1.5 nM In vitro antagonist effect on estrogen receptor alpha transcriptional activation in MCF-7 cells against 10 pM 17-beta-estradiol ChEMBL. 11356100
IC50 (binding) = 14 nM In vitro inhibition of [3H]-17-beta-estradiol binding to human estrogen receptor alpha ChEMBL. 11356100
IC50 (binding) = 14 nM In vitro inhibition of [3H]-17-beta-estradiol binding to human estrogen receptor alpha ChEMBL. 11356100
IC50 (binding) = 40 nM In vitro inhibitory concentration against [3H]-17-beta-estradiol binding to human estrogen receptor 2 ChEMBL. 11356100
IC50 (binding) = 40 nM In vitro inhibitory concentration against [3H]-17-beta-estradiol binding to human estrogen receptor 2 ChEMBL. 11356100
IC50 (binding) = 60 nM BindingDB_Patents: Binding Assay. The competition assay was performed in a 96-well plate (polystyrene*) which binds <2.0% of the total input [3H]-17beta-estradiol and each data point was gathered in triplicate. 100 uG/100 uL of the receptor preparation was aliquoted per well. A saturating dose of 2.5 nM [3H]17beta-estradiol+competitor (or buffer) in a 50 uL volume was added in the preliminary competition when 100x and 500x competitor were evaluated, only 0.8 nM [3H]17beta-estradiol was used. The plate was incubated at room temperature for 2.5 h. At the end of this incubation period 150 uL of ice-cold dextran coated charcoal (5% activated charcoal coated with 0.05% 69K dextran) was added to each well and the plate was immediately centrifuged at 99 g for 5 minutes at 4 C. 200 uL of the supernatant solution was then removed for scintillation counting. Samples were counted to 2% or 10 minutes, whichever occurs first. ChEMBL. No reference
IC50 (binding) = 60 nM BindingDB_Patents: Binding Assay. The competition assay was performed in a 96-well plate (polystyrene*) which binds <2.0% of the total input [3H]-17beta-estradiol and each data point was gathered in triplicate. 100 uG/100 uL of the receptor preparation was aliquoted per well. A saturating dose of 2.5 nM [3H]17beta-estradiol+competitor (or buffer) in a 50 uL volume was added in the preliminary competition when 100x and 500x competitor were evaluated, only 0.8 nM [3H]17beta-estradiol was used. The plate was incubated at room temperature for 2.5 h. At the end of this incubation period 150 uL of ice-cold dextran coated charcoal (5% activated charcoal coated with 0.05% 69K dextran) was added to each well and the plate was immediately centrifuged at 99 g for 5 minutes at 4 C. 200 uL of the supernatant solution was then removed for scintillation counting. Samples were counted to 2% or 10 minutes, whichever occurs first. ChEMBL. No reference
IC50 (binding) = 60 nM BindingDB_Patents: Binding Assay. The competition assay was performed in a 96-well plate (polystyrene*) which binds <2.0% of the total input [3H]-17beta-estradiol and each data point was gathered in triplicate. 100 uG/100 uL of the receptor preparation was aliquoted per well. A saturating dose of 2.5 nM [3H]17beta-estradiol+competitor (or buffer) in a 50 uL volume was added in the preliminary competition when 100x and 500x competitor were evaluated, only 0.8 nM [3H]17beta-estradiol was used. The plate was incubated at room temperature for 2.5 h. At the end of this incubation period 150 uL of ice-cold dextran coated charcoal (5% activated charcoal coated with 0.05% 69K dextran) was added to each well and the plate was immediately centrifuged at 99 g for 5 minutes at 4 C. 200 uL of the supernatant solution was then removed for scintillation counting. Samples were counted to 2% or 10 minutes, whichever occurs first. ChEMBL. No reference
IC50 (functional) = 0.4 uM Cytotoxicity against human MCF7 cells assessed as cell viability after 5 days by CellTiter-Glo assay ChEMBL. 25879485

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Homo sapiens ChEMBL23 25879485

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

2 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.