Detailed information for compound 165728

Basic information

Technical information
  • TDR Targets ID: 165728
  • Name: 4-[2-[[(E)-3-[1-[bis(4-chlorophenyl)methyl]in dol-5-yl]but-2-enoyl]amino]phenoxy]butanoic a cid
  • MW: 613.53 | Formula: C35H30Cl2N2O4
  • H donors: 2 H acceptors: 3 LogP: 8.26 Rotable bonds: 12
    Rule of 5 violations (Lipinski): 2
  • SMILES: OC(=O)CCCOc1ccccc1NC(=O)/C=C(/c1ccc2c(c1)ccn2C(c1ccc(cc1)Cl)c1ccc(cc1)Cl)\C
  • InChi: 1S/C35H30Cl2N2O4/c1-23(21-33(40)38-30-5-2-3-6-32(30)43-20-4-7-34(41)42)26-12-17-31-27(22-26)18-19-39(31)35(24-8-13-28(36)14-9-24)25-10-15-29(37)16-11-25/h2-3,5-6,8-19,21-22,35H,4,7,20H2,1H3,(H,38,40)(H,41,42)/b23-21+
  • InChiKey: GGJPNETVTCVAOB-XTQSDGFTSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 4-[2-[[(E)-3-[1-[bis(4-chlorophenyl)methyl]-5-indolyl]-1-oxobut-2-enyl]amino]phenoxy]butanoic acid
  • 4-[2-[[(E)-3-[1-[bis(4-chlorophenyl)methyl]indol-5-yl]but-2-enoyl]amino]phenoxy]butyric acid

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Rattus norvegicus Steroid 5-alpha-reductase 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
Trichomonas vaginalis conserved hypothetical protein Steroid 5-alpha-reductase   254 aa 239 aa 21.8 %
Toxoplasma gondii 3-oxo-5-alpha-steroid 4-dehydrogenase Steroid 5-alpha-reductase   254 aa 255 aa 36.1 %
Loa Loa (eye worm) hypothetical protein Steroid 5-alpha-reductase   254 aa 218 aa 45.9 %
Leishmania major 3-oxo-5-alpha-steroid 4-dehydrogenase-like protein Steroid 5-alpha-reductase   254 aa 334 aa 25.1 %
Trypanosoma cruzi 3-oxo-5-alpha-steroid 4-dehydrogenase, putative Steroid 5-alpha-reductase   254 aa 284 aa 32.7 %
Trichomonas vaginalis 3-oxo-5-alpha-steroid 4-dehydrogenase, putative Steroid 5-alpha-reductase   254 aa 226 aa 36.7 %
Trichomonas vaginalis 3-oxo-5-alpha-steroid 4-dehydrogenase, putative Steroid 5-alpha-reductase   254 aa 249 aa 34.9 %
Trichomonas vaginalis 3-oxo-5-alpha-steroid 4-dehydrogenase, putative Steroid 5-alpha-reductase   254 aa 211 aa 29.9 %
Trypanosoma cruzi 3-oxo-5-alpha-steroid 4-dehydrogenase, putative Steroid 5-alpha-reductase   254 aa 284 aa 33.1 %
Leishmania mexicana 3-oxo-5-alpha-steroid 4-dehydrogenase-like protein Steroid 5-alpha-reductase   254 aa 435 aa 22.3 %
Trypanosoma brucei gambiense 3-oxo-5-alpha-steroid 4-dehydrogenase-like, putative Steroid 5-alpha-reductase   254 aa 283 aa 29.7 %
Trichomonas vaginalis conserved hypothetical protein Steroid 5-alpha-reductase   254 aa 238 aa 25.6 %
Trypanosoma brucei 3-oxo-5-alpha-steroid 4-dehydrogenase-like, putative Steroid 5-alpha-reductase   254 aa 283 aa 29.7 %
Leishmania braziliensis 3-oxo-5-alpha-steroid 4-dehydrogenase-like protein Steroid 5-alpha-reductase   254 aa 329 aa 23.1 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Trichomonas vaginalis synaptic glycoprotein sc2, putative 0.0053 0.2087 1
Loa Loa (eye worm) carboxylesterase 0.0138 0.7062 1
Loa Loa (eye worm) carboxylesterase 0.0023 0.034 0.0482
Echinococcus multilocularis BC026374 protein (S09 family) 0.0023 0.034 0.034
Toxoplasma gondii 3-oxo-5-alpha-steroid 4-dehydrogenase 0.0053 0.2087 1
Brugia malayi Isocitrate dehydrogenase 0.0018 0.0002 0.0002
Loa Loa (eye worm) abnormal epIthelia family member 0.0024 0.0408 0.0578
Loa Loa (eye worm) hypothetical protein 0.0038 0.1191 0.1687
Echinococcus multilocularis neurogenic locus notch protein 0.0024 0.0408 0.0408
Schistosoma mansoni acetylcholinesterase 0.0023 0.034 0.034
Echinococcus multilocularis synaptic glycoprotein sc2 0.0053 0.2087 0.2087
Loa Loa (eye worm) hypothetical protein 0.0024 0.0408 0.0578
Echinococcus multilocularis pikachurin 0.0024 0.0408 0.0408
Loa Loa (eye worm) hypothetical protein 0.0023 0.034 0.0482
Echinococcus granulosus neurogenic locus notch protein 0.0024 0.0408 0.0408
Brugia malayi Carboxylesterase family protein 0.0023 0.034 0.0482
Brugia malayi laminin alpha chain 0.0024 0.0408 0.0578
Trichomonas vaginalis 3-oxo-5-alpha-steroid 4-dehydrogenase, putative 0.0053 0.2087 1
Trichomonas vaginalis 3-oxo-5-alpha-steroid 4-dehydrogenase, putative 0.0053 0.2087 1
Schistosoma mansoni family S9 non-peptidase homologue (S09 family) 0.0023 0.034 0.034
Echinococcus granulosus BC026374 protein S09 family 0.0023 0.034 0.034
Echinococcus multilocularis isocitrate dehydrogenase 2 (NADP+) 0.0018 0.0002 0.0002
Echinococcus multilocularis para nitrobenzyl esterase 0.0023 0.034 0.034
Echinococcus multilocularis 3 oxo 5 alpha steroid 4 dehydrogenase, C terminal 0.0053 0.2087 0.2087
Brugia malayi Carboxylesterase family protein 0.0138 0.7062 1
Schistosoma mansoni synaptic glycoprotein sc2 related 0.0053 0.2087 0.2087
Loa Loa (eye worm) acetylcholinesterase 1 0.0138 0.7062 1
Schistosoma mansoni laminin gamma-3 chain 0.0024 0.0408 0.0408
Brugia malayi isocitrate dehydrogenase 0.0018 0.0002 0.0002
Plasmodium vivax 3-oxo-5-alpha-steroid 4-dehydrogenase, putative 0.0053 0.2087 1
Trichomonas vaginalis synaptic glycoprotein sc2, putative 0.0053 0.2087 1
Loa Loa (eye worm) hypothetical protein 0.0023 0.034 0.0482
Loa Loa (eye worm) hypothetical protein 0.0023 0.034 0.0482
Loa Loa (eye worm) hypothetical protein 0.0053 0.2087 0.2956
Schistosoma mansoni BC026374 protein (S09 family) 0.0023 0.034 0.034
Echinococcus granulosus family S9 non peptidase ue S09 family 0.0023 0.034 0.034
Loa Loa (eye worm) hypothetical protein 0.0023 0.034 0.0482
Schistosoma mansoni hypothetical protein 0.0188 1 1
Echinococcus multilocularis isocitrate dehydrogenase 0.0018 0.0002 0.0002
Echinococcus multilocularis NADP dependent isocitrate dehydrogenase 0.0018 0.0002 0.0002
Plasmodium falciparum polyprenol reductase, putative 0.0053 0.2087 1
Trichomonas vaginalis 3-oxo-5-alpha-steroid 4-dehydrogenase, putative 0.0053 0.2087 1
Brugia malayi 3-oxo-5-alpha-steroid 4-dehydrogenase 1 0.0053 0.2087 0.2956
Loa Loa (eye worm) pigment dispersing factor receptor c 0.0055 0.2218 0.314
Loa Loa (eye worm) hypothetical protein 0.0053 0.2087 0.2956
Brugia malayi hypothetical protein 0.0023 0.034 0.0482
Onchocerca volvulus 0.0053 0.2087 1
Brugia malayi Carboxylesterase family protein 0.0023 0.034 0.0482
Loa Loa (eye worm) isocitrate dehydrogenase 0.0018 0.0002 0.0002
Echinococcus multilocularis NADP dependent isocitrate dehydrogenase 0.0018 0.0002 0.0002
Loa Loa (eye worm) carboxylesterase 0.0023 0.034 0.0482
Loa Loa (eye worm) hypothetical protein 0.0055 0.2218 0.314
Echinococcus granulosus pikachurin 0.0024 0.0408 0.0408
Schistosoma mansoni gliotactin 0.0023 0.034 0.034
Schistosoma mansoni family S9 non-peptidase homologue (S09 family) 0.0023 0.034 0.034
Brugia malayi latrophilin 2 splice variant baaae 0.0038 0.1191 0.1687
Brugia malayi Carboxylesterase family protein 0.0023 0.034 0.0482
Echinococcus multilocularis family S9 non peptidase ue (S09 family) 0.0023 0.034 0.034
Loa Loa (eye worm) hypothetical protein 0.0024 0.0408 0.0578
Brugia malayi Carboxylesterase family protein 0.0023 0.034 0.0482
Brugia malayi Synaptic glycoprotein SC2 0.0053 0.2087 0.2956
Echinococcus multilocularis acetylcholinesterase 0.0138 0.7062 0.7062
Loa Loa (eye worm) hypothetical protein 0.0023 0.034 0.0482
Brugia malayi Corticotropin releasing factor receptor 2 precursor, putative 0.0055 0.2218 0.314
Schistosoma mansoni cell polarity protein 0.0024 0.0408 0.0408
Mycobacterium ulcerans hypothetical protein 0.0053 0.2087 1
Mycobacterium tuberculosis POSSIBLE PARA-NITROBENZYL ESTERASE (FRAGMENT) 0.0023 0.034 1
Trypanosoma cruzi 3-oxo-5-alpha-steroid 4-dehydrogenase, putative 0.0053 0.2087 1
Entamoeba histolytica 3-oxo-5-alpha-steroid 4-dehydrogenase domain-containing protein 0.0053 0.2087 0.5
Schistosoma mansoni synaptic glycoprotein sc2 related 0.0053 0.2087 0.2087
Loa Loa (eye worm) hypothetical protein 0.0138 0.7062 1
Echinococcus granulosus synaptic glycoprotein sc2 0.0053 0.2087 0.2087
Echinococcus granulosus slit 2 protein 0.0024 0.0408 0.0408
Schistosoma mansoni family S9 non-peptidase homologue (S09 family) 0.0138 0.7062 0.7062
Schistosoma mansoni neuroligin 3 (S09 family) 0.0023 0.034 0.034
Entamoeba histolytica trans-2,3-enoyl-CoA reductase, putative 0.0053 0.2087 0.5
Echinococcus multilocularis geminin 0.0188 1 1
Trypanosoma brucei 3-oxo-5-alpha-steroid 4-dehydrogenase-like, putative 0.0053 0.2087 1
Echinococcus multilocularis carboxylesterase 5A 0.0138 0.7062 0.7062
Trypanosoma cruzi 3-oxo-5-alpha-steroid 4-dehydrogenase, putative 0.0053 0.2087 1
Toxoplasma gondii 3-oxo-5-alpha-steroid 4-dehydrogenase 0.0053 0.2087 1
Mycobacterium tuberculosis Carboxylesterase LipT 0.0023 0.034 1
Loa Loa (eye worm) hypothetical protein 0.0138 0.7062 1
Plasmodium vivax polyprenol reductase, putative 0.0053 0.2087 1
Echinococcus multilocularis neuroligin 0.0023 0.034 0.034
Brugia malayi Thrombospondin N-terminal -like domain containing protein 0.0024 0.0408 0.0578
Echinococcus granulosus para nitrobenzyl esterase 0.0023 0.034 0.034
Trichomonas vaginalis conserved hypothetical protein 0.0053 0.2087 1
Echinococcus granulosus NADP dependent isocitrate dehydrogenase 0.0018 0.0002 0.0002
Echinococcus granulosus neuroligin 0.0023 0.034 0.034
Entamoeba histolytica steroid 5-alpha reductase, putative 0.0053 0.2087 0.5
Brugia malayi Carboxylesterase family protein 0.0138 0.7062 1
Echinococcus multilocularis acetylcholinesterase 0.0138 0.7062 0.7062
Plasmodium falciparum 3-oxo-5-alpha-steroid 4-dehydrogenase, putative 0.0053 0.2087 1
Mycobacterium tuberculosis POSSIBLE PARA-NITROBENZYL ESTERASE (FRAGMENT) 0.0023 0.034 1
Echinococcus multilocularis slit 2 protein 0.0024 0.0408 0.0408
Schistosoma mansoni family S9 non-peptidase homologue (S09 family) 0.0023 0.034 0.034
Leishmania major 3-oxo-5-alpha-steroid 4-dehydrogenase-like protein 0.0053 0.2087 1
Trichomonas vaginalis 3-oxo-5-alpha-steroid 4-dehydrogenase, putative 0.0053 0.2087 1
Echinococcus granulosus acetylcholinesterase 0.0138 0.7062 0.7062
Schistosoma mansoni hypothetical protein 0.0188 1 1
Loa Loa (eye worm) hypothetical protein 0.0024 0.0408 0.0578
Schistosoma mansoni chondroitin sulfate proteoglycan-related 0.0024 0.0408 0.0408
Brugia malayi laminin-like protein K08C7.3 precursor 0.0024 0.0408 0.0578
Loa Loa (eye worm) hypothetical protein 0.0023 0.034 0.0482
Echinococcus granulosus acetylcholinesterase 0.0138 0.7062 0.7062
Trichomonas vaginalis conserved hypothetical protein 0.0053 0.2087 1
Loa Loa (eye worm) hypothetical protein 0.0053 0.2087 0.2956
Brugia malayi Calcitonin receptor-like protein seb-1 0.0055 0.2218 0.314
Echinococcus granulosus carboxylesterase 5A 0.0138 0.7062 0.7062
Trichomonas vaginalis synaptic glycoprotein sc2, putative 0.0053 0.2087 1
Entamoeba histolytica hypothetical protein 0.0053 0.2087 0.5
Brugia malayi EGF-like domain containing protein 0.0024 0.0408 0.0578
Echinococcus granulosus 3 oxo 5 alpha steroid 4 dehydrogenase C terminal 0.0053 0.2087 0.2087
Loa Loa (eye worm) hypothetical protein 0.0023 0.034 0.0482
Schistosoma mansoni hypothetical protein 0.0038 0.1191 0.1191
Schistosoma mansoni slit 0.0024 0.0408 0.0408
Trypanosoma brucei 3-oxo-5-alpha-steroid 4-dehydrogenase, putative 0.0053 0.2087 1
Toxoplasma gondii 3-oxo-5-alpha-steroid 4-dehydrogenase 0.0053 0.2087 1
Echinococcus multilocularis NADP dependent isocitrate dehydrogenase 0.0018 0.0002 0.0002
Trypanosoma cruzi 3-oxo-5-alpha-steroid 4-dehydrogenase, putative 0.0053 0.2087 1
Schistosoma mansoni NADP-specific isocitrate dehydrogenase 0.0018 0.0002 0.0002
Giardia lamblia Synaptic glycoprotein SC2 0.0053 0.2087 0.5

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 25 nM Inhibitory actitivity against Steroid 5-alpha-reductase in prostates from male rats ChEMBL. 7636849
IC50 (binding) = 25 nM Inhibitory actitivity against Steroid 5-alpha-reductase in prostates from male rats ChEMBL. 7636849

Phenotypes

Whole-cell/tissue/organism interactions

We have no records of whole-cell/tissue assays done with this compound What does this mean?

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

1 literature reference was collected for this gene.

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