Detailed information for compound 31665

Basic information

Technical information
  • TDR Targets ID: 31665
  • Name: 4-[3-[4-[(1S)-1-[4-(2-methylpropyl)phenyl]eth oxy]benzoyl]indol-1-yl]butanoic acid
  • MW: 483.598 | Formula: C31H33NO4
  • H donors: 1 H acceptors: 3 LogP: 6.59 Rotable bonds: 11
    Rule of 5 violations (Lipinski): 1
  • SMILES: OC(=O)CCCn1cc(c2c1cccc2)C(=O)c1ccc(cc1)O[C@H](c1ccc(cc1)CC(C)C)C
  • InChi: 1S/C31H33NO4/c1-21(2)19-23-10-12-24(13-11-23)22(3)36-26-16-14-25(15-17-26)31(35)28-20-32(18-6-9-30(33)34)29-8-5-4-7-27(28)29/h4-5,7-8,10-17,20-22H,6,9,18-19H2,1-3H3,(H,33,34)/t22-/m0/s1
  • InChiKey: SMSOYFGWXDACGL-QFIPXVFZSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 4-[3-[4-[(1S)-1-(4-isobutylphenyl)ethoxy]benzoyl]indol-1-yl]butanoic acid
  • 4-[3-[[4-[(1S)-1-(4-isobutylphenyl)ethoxy]phenyl]-oxomethyl]-1-indolyl]butanoic acid
  • 4-[3-[4-[(1S)-1-[4-(2-methylpropyl)phenyl]ethoxy]phenyl]carbonylindol-1-yl]butanoic acid
  • 4-[3-[4-[(1S)-1-(4-isobutylphenyl)ethoxy]benzoyl]indol-1-yl]butyric acid

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens steroid-5-alpha-reductase, alpha polypeptide 2 (3-oxo-5 alpha-steroid delta 4-dehydrogenase alpha 2) Starlite/ChEMBL References
Rattus norvegicus Steroid 5-alpha-reductase Starlite/ChEMBL References
Homo sapiens steroid-5-alpha-reductase, alpha polypeptide 1 (3-oxo-5 alpha-steroid delta 4-dehydrogenase alpha 1) Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Leishmania major 3-oxo-5-alpha-steroid 4-dehydrogenase-like protein Get druggable targets OG5_128852 All targets in OG5_128852
Trichomonas vaginalis 3-oxo-5-alpha-steroid 4-dehydrogenase, putative Get druggable targets OG5_128852 All targets in OG5_128852
Entamoeba histolytica steroid 5-alpha reductase, putative Get druggable targets OG5_128852 All targets in OG5_128852
Trichomonas vaginalis 3-oxo-5-alpha-steroid 4-dehydrogenase, putative Get druggable targets OG5_128852 All targets in OG5_128852
Brugia malayi 3-oxo-5-alpha-steroid 4-dehydrogenase 1 Get druggable targets OG5_128852 All targets in OG5_128852
Leishmania braziliensis 3-oxo-5-alpha-steroid 4-dehydrogenase-like protein Get druggable targets OG5_128852 All targets in OG5_128852
Leishmania infantum 3-oxo-5-alpha-steroid 4-dehydrogenase-like protein Get druggable targets OG5_128852 All targets in OG5_128852
Trypanosoma brucei 3-oxo-5-alpha-steroid 4-dehydrogenase-like, putative Get druggable targets OG5_128852 All targets in OG5_128852
Mycobacterium ulcerans hypothetical protein Get druggable targets OG5_128852 All targets in OG5_128852
Trypanosoma cruzi 3-oxo-5-alpha-steroid 4-dehydrogenase, putative Get druggable targets OG5_128852 All targets in OG5_128852
Toxoplasma gondii 3-oxo-5-alpha-steroid 4-dehydrogenase Get druggable targets OG5_128852 All targets in OG5_128852
Trichomonas vaginalis 3-oxo-5-alpha-steroid 4-dehydrogenase, putative Get druggable targets OG5_128852 All targets in OG5_128852
Trypanosoma cruzi 3-oxo-5-alpha-steroid 4-dehydrogenase, putative Get druggable targets OG5_128852 All targets in OG5_128852
Leishmania mexicana 3-oxo-5-alpha-steroid 4-dehydrogenase-like protein Get druggable targets OG5_128852 All targets in OG5_128852
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_128852 All targets in OG5_128852
Leishmania donovani 3-oxo-5-alpha-steroid 4-dehydrogenase-like protein Get druggable targets OG5_128852 All targets in OG5_128852
Trypanosoma brucei gambiense 3-oxo-5-alpha-steroid 4-dehydrogenase-like, putative Get druggable targets OG5_128852 All targets in OG5_128852
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Leishmania braziliensis 3-oxo-5-alpha-steroid 4-dehydrogenase-like protein Steroid 5-alpha-reductase   254 aa 329 aa 23.1 %
Trypanosoma cruzi 3-oxo-5-alpha-steroid 4-dehydrogenase, putative Steroid 5-alpha-reductase   254 aa 284 aa 33.1 %
Trypanosoma cruzi 3-oxo-5-alpha-steroid 4-dehydrogenase, putative Steroid 5-alpha-reductase   254 aa 284 aa 32.7 %
Toxoplasma gondii 3-oxo-5-alpha-steroid 4-dehydrogenase Steroid 5-alpha-reductase   254 aa 255 aa 36.1 %
Trichomonas vaginalis conserved hypothetical protein Steroid 5-alpha-reductase   254 aa 238 aa 25.6 %
Trichomonas vaginalis 3-oxo-5-alpha-steroid 4-dehydrogenase, putative Steroid 5-alpha-reductase   254 aa 211 aa 29.9 %
Leishmania major 3-oxo-5-alpha-steroid 4-dehydrogenase-like protein Steroid 5-alpha-reductase   254 aa 334 aa 25.1 %
Plasmodium falciparum 3-oxo-5-alpha-steroid 4-dehydrogenase, putative steroid-5-alpha-reductase, alpha polypeptide 1 (3-oxo-5 alpha-steroid delta 4-dehydrogenase alpha 1) 259 aa 254 aa 25.6 %
Trichomonas vaginalis 3-oxo-5-alpha-steroid 4-dehydrogenase, putative Steroid 5-alpha-reductase   254 aa 226 aa 36.7 %
Loa Loa (eye worm) hypothetical protein Steroid 5-alpha-reductase   254 aa 218 aa 45.9 %
Brugia malayi Synaptic glycoprotein SC2 steroid-5-alpha-reductase, alpha polypeptide 2 (3-oxo-5 alpha-steroid delta 4-dehydrogenase alpha 2) 254 aa 208 aa 28.9 %
Trichomonas vaginalis 3-oxo-5-alpha-steroid 4-dehydrogenase, putative Steroid 5-alpha-reductase   254 aa 249 aa 34.9 %
Trypanosoma brucei 3-oxo-5-alpha-steroid 4-dehydrogenase-like, putative Steroid 5-alpha-reductase   254 aa 283 aa 29.7 %
Leishmania mexicana 3-oxo-5-alpha-steroid 4-dehydrogenase-like protein Steroid 5-alpha-reductase   254 aa 435 aa 22.3 %
Trichomonas vaginalis conserved hypothetical protein Steroid 5-alpha-reductase   254 aa 239 aa 21.8 %
Trypanosoma brucei gambiense 3-oxo-5-alpha-steroid 4-dehydrogenase-like, putative Steroid 5-alpha-reductase   254 aa 283 aa 29.7 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Loa Loa (eye worm) hypothetical protein 0.043 0.3533 0.9253
Plasmodium falciparum NADPH--cytochrome P450 reductase, putative 0.0175 0.0746 0.1955
Giardia lamblia Nitric oxide synthase, inducible 0.0405 0.3253 1
Trypanosoma cruzi cytochrome P450 reductase, putative 0.0457 0.3818 1
Echinococcus multilocularis NADPH dependent diflavin oxidoreductase 1 0.0457 0.3818 1
Echinococcus granulosus methionine synthase reductase 0.0282 0.1915 0.5016
Plasmodium vivax hypothetical protein, conserved 0.0175 0.0746 0.1955
Toxoplasma gondii flavodoxin domain-containing protein 0.0227 0.1312 0.1312
Brugia malayi 3-oxo-5-alpha-steroid 4-dehydrogenase 1 0.043 0.3533 0.9253
Schistosoma mansoni 5-methyl tetrahydrofolate-homocysteine methyltransferase reductase 0.0282 0.1915 0.5016
Trypanosoma cruzi cytochrome P450 reductase, putative 0.0457 0.3818 1
Schistosoma mansoni cytochrome P450 reductase 0.0457 0.3818 1
Trichomonas vaginalis 3-oxo-5-alpha-steroid 4-dehydrogenase, putative 0.043 0.3533 0.9253
Trypanosoma brucei 3-oxo-5-alpha-steroid 4-dehydrogenase-like, putative 0.043 0.3533 0.9253
Leishmania major cytochrome P450 reductase, putative 0.0405 0.3253 0.8159
Entamoeba histolytica type A flavoprotein, putative 0.0175 0.0746 0.2113
Loa Loa (eye worm) FAD binding domain-containing protein 0.0457 0.3818 1
Trichomonas vaginalis NADPH cytochrome P450, putative 0.0175 0.0746 0.1955
Brugia malayi flavodoxin family protein 0.0175 0.0746 0.1955
Entamoeba histolytica type A flavoprotein, putative 0.0175 0.0746 0.2113
Chlamydia trachomatis sulfite reductase 0.0282 0.1915 0.5
Entamoeba histolytica steroid 5-alpha reductase, putative 0.043 0.3533 1
Trypanosoma cruzi p450 reductase, putative 0.0457 0.3818 1
Trypanosoma brucei NADPH-dependent diflavin oxidoreductase 1 0.0457 0.3818 1
Brugia malayi flavodoxin family protein 0.0457 0.3818 1
Trichomonas vaginalis NADPH cytochrome P450, putative 0.0175 0.0746 0.1955
Trypanosoma cruzi 3-oxo-5-alpha-steroid 4-dehydrogenase, putative 0.043 0.3533 0.9253
Toxoplasma gondii 3-oxo-5-alpha-steroid 4-dehydrogenase 0.043 0.3533 0.3533
Trichomonas vaginalis NADPH cytochrome P450, putative 0.0175 0.0746 0.1955
Plasmodium vivax flavodoxin domain containing protein 0.0405 0.3253 0.8519
Echinococcus granulosus NADPH dependent diflavin oxidoreductase 1 0.0457 0.3818 1
Trypanosoma cruzi Flavodoxin/Radical SAM superfamily/Wyosine base formation, putative 0.0175 0.0746 0.1955
Echinococcus multilocularis NADPH cytochrome P450 reductase 0.0457 0.3818 1
Trypanosoma brucei NADPH--cytochrome P450 reductase, putative 0.0457 0.3818 1
Entamoeba histolytica type A flavoprotein, putative 0.0175 0.0746 0.2113
Loa Loa (eye worm) hypothetical protein 0.0457 0.3818 1
Leishmania major 3-oxo-5-alpha-steroid 4-dehydrogenase-like protein 0.043 0.3533 0.9071
Trypanosoma brucei NADPH--cytochrome P450 reductase, putative 0.0457 0.3818 1
Loa Loa (eye worm) FAD binding domain-containing protein 0.0282 0.1915 0.5016
Echinococcus granulosus NADPH cytochrome P450 reductase 0.0457 0.3818 1
Toxoplasma gondii flavodoxin domain-containing protein 0.0227 0.1312 0.1312
Plasmodium falciparum nitric oxide synthase, putative 0.0457 0.3818 1
Schistosoma mansoni NADPH flavin oxidoreductase 0.023 0.135 0.3535
Brugia malayi FAD binding domain containing protein 0.0282 0.1915 0.5016
Mycobacterium ulcerans formate dehydrogenase H FdhF 0.0457 0.3818 1
Brugia malayi FAD binding domain containing protein 0.0457 0.3818 1
Trichomonas vaginalis 3-oxo-5-alpha-steroid 4-dehydrogenase, putative 0.043 0.3533 0.9253
Plasmodium vivax NADPH-cytochrome p450 reductase, putative 0.0457 0.3818 1
Leishmania major NADPH-cytochrome p450 reductase-like protein 0.0457 0.3818 1
Treponema pallidum flavodoxin 0.0175 0.0746 0.5
Schistosoma mansoni diflavin oxidoreductase 0.0227 0.1312 0.3436
Loa Loa (eye worm) flavodoxin family protein 0.0175 0.0746 0.1955
Trypanosoma cruzi Flavodoxin/Radical SAM superfamily/Wyosine base formation, putative 0.0175 0.0746 0.1955
Giardia lamblia Hypothetical protein 0.0405 0.3253 1
Trypanosoma cruzi 3-oxo-5-alpha-steroid 4-dehydrogenase, putative 0.043 0.3533 0.9253
Trichomonas vaginalis sulfite reductase, putative 0.0457 0.3818 1
Trichomonas vaginalis 3-oxo-5-alpha-steroid 4-dehydrogenase, putative 0.043 0.3533 0.9253
Echinococcus multilocularis methionine synthase reductase 0.0282 0.1915 0.5016
Leishmania major p450 reductase, putative 0.0457 0.3818 1
Onchocerca volvulus 0.0106 0 0.5
Trypanosoma cruzi NADPH--cytochrome P450 reductase, putative 0.0175 0.0746 0.1955
Entamoeba histolytica type A flavoprotein, putative 0.0175 0.0746 0.2113
Trichomonas vaginalis NADPH cytochrome P450, putative 0.0175 0.0746 0.1955
Trypanosoma cruzi NADPH-dependent FMN/FAD containing oxidoreductase, putative 0.0457 0.3818 1
Plasmodium falciparum S-adenosyl-L-methionine-dependent tRNA 4-demethylwyosine synthase, putative 0.0175 0.0746 0.1955
Entamoeba histolytica type A flavoprotein, putative 0.0175 0.0746 0.2113
Toxoplasma gondii PAN domain-containing protein 0.1024 1 1
Trypanosoma brucei NADPH-cytochrome p450 reductase, putative 0.0457 0.3818 1
Trichomonas vaginalis NADPH fad oxidoreductase, putative 0.0405 0.3253 0.8519
Trypanosoma brucei S-adenosyl-L-methionine-dependent tRNA 4-demethylwyosine synthase, putative 0.0175 0.0746 0.1955

Activities

Activity type Activity value Assay description Source Reference
Clearance (ADMET) = 2.4 ml min-1 kg-1 Plasma clearance of the compound in dog ChEMBL. No reference
Clearance (ADMET) = 11 ml min-1 kg-1 Plasma clearance of the compound in rat. ChEMBL. No reference
F (ADMET) = 56 % Oral bioavailability in rat ChEMBL. No reference
F (ADMET) = 86 % Oral bioavailability in dog ChEMBL. No reference
IC50 (binding) = 1 nM Inhibition of rat 5alpha reductase isozyme. ChEMBL. 9135028
IC50 (binding) = 1 nM Inhibition of rat 5alpha reductase isozyme. ChEMBL. 9135028
IC50 (binding) = 4 nM Inhibition of human 5alpha reductase 2 isozyme. ChEMBL. 9135028
IC50 (binding) = 4 nM Inhibition of human 5alpha reductase 2 isozyme. ChEMBL. 9135028
IC50 (binding) = 40 nM Inhibitory concentration was tested on human 5-alpha reductase 1 isozyme ChEMBL. 9135028
IC50 (binding) = 40 nM Inhibitory concentration was tested on human 5-alpha reductase 1 isozyme ChEMBL. 9135028
Potency (binding) = 1 nM Compound was tested in vitro for its inhibitory activity against rat 5Alpha-R expressed as potency ChEMBL. No reference
Potency (binding) = 1 nM Compound was tested in vitro for its inhibitory activity against rat 5Alpha-R expressed as potency ChEMBL. No reference
Potency (binding) = 4 nM Compound was tested in vitro for its inhibitory activity against human 5Alpha-R2 expressed as potency. ChEMBL. No reference
Potency (binding) = 4 nM Compound was tested in vitro for its inhibitory activity against human 5Alpha-R2 expressed as potency. ChEMBL. No reference
Potency (binding) = 40 nM Compound was tested in vitro for its inhibitory activity against human 5Alpha-R1 expressed as potency. ChEMBL. No reference
Potency (binding) = 40 nM Compound was tested in vitro for its inhibitory activity against human 5Alpha-R1 expressed as potency. ChEMBL. No reference
T1/2 (ADMET) = 1.9 hr Half-life of the compound in dog plasma ChEMBL. No reference
T1/2 (ADMET) = 3.7 hr Half-life of the compound in rat plasma ChEMBL. No reference
T1/2 (ADMET) = 10 hr Half-life of the compound in dog plasma ChEMBL. No reference
Vd (ADMET) = 0.9 l kg-1 Volume of distribution of the compound in dog ChEMBL. No reference
Vd (ADMET) = 3.6 l kg-1 Volume of distribution of the compound in rat. ChEMBL. No reference

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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