Detailed information for compound 213394

Basic information

Technical information
  • TDR Targets ID: 213394
  • Name: (2R)-3-(4-acetamidophenyl)sulfanyl-2-hydroxy- 2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl ]propanamide
  • MW: 457.424 | Formula: C19H18F3N3O5S
  • H donors: 3 H acceptors: 5 LogP: 2.77 Rotable bonds: 10
    Rule of 5 violations (Lipinski): 1
  • SMILES: CC(=O)Nc1ccc(cc1)SC[C@@](C(=O)Nc1ccc(c(c1)C(F)(F)F)[N+](=O)[O-])(O)C
  • InChi: 1S/C19H18F3N3O5S/c1-11(26)23-12-3-6-14(7-4-12)31-10-18(2,28)17(27)24-13-5-8-16(25(29)30)15(9-13)19(20,21)22/h3-9,28H,10H2,1-2H3,(H,23,26)(H,24,27)/t18-/m0/s1
  • InChiKey: NDPHFBYLOVVWLR-SFHVURJKSA-N  


Substructure search Similarity search

Network

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Synonyms

  • (2R)-3-[(4-acetamidophenyl)thio]-2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
  • N-[4-[[(2R)-2-hydroxy-3-keto-2-methyl-3-[4-nitro-3-(trifluoromethyl)anilino]propyl]thio]phenyl]acetamide
  • N-[4-[[(2R)-2-hydroxy-3-keto-2-methyl-3-[[4-nitro-3-(trifluoromethyl)phenyl]amino]propyl]thio]phenyl]acetamide

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Rattus norvegicus Androgen Receptor 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
No druggable targets predicted by sequence similarity
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Entamoeba histolytica cyclin family protein 0.0234 0.0821 0.4486
Echinococcus granulosus cyclin B3 1 0.0234 0.0821 0.0818
Echinococcus multilocularis high affinity choline transporter 1 0.0337 0.1297 0.1294
Mycobacterium tuberculosis Possible amidase (aminohydrolase) 0.0269 0.0981 0.9105
Leishmania major CYC2-like cyclin, putative,cyclin 6, putative 0.0452 0.1825 1
Schistosoma mansoni cyclin B 0.0452 0.1825 0.1822
Echinococcus granulosus cyclins 0.0234 0.0821 0.0818
Trichomonas vaginalis CMGC family protein kinase 0.038 0.1491 0.8167
Echinococcus granulosus cyclin B 0.0452 0.1825 0.1822
Brugia malayi putative amidase 0.0269 0.0981 0.0978
Brugia malayi Cyclin, N-terminal domain containing protein 0.0452 0.1825 0.1822
Trypanosoma brucei cdc2-related kinase 3 0.038 0.1491 0.8167
Echinococcus multilocularis cyclin dependent kinase 1 0.038 0.1491 0.1488
Mycobacterium tuberculosis Probable amidase AmiA2 (aminohydrolase) 0.0269 0.0981 0.9105
Plasmodium falciparum glutamyl-tRNA(Gln) amidotransferase subunit A 0.0269 0.0981 0.6568
Loa Loa (eye worm) CMGC/CDK/CDK5 protein kinase 0.038 0.1491 0.1488
Echinococcus granulosus cyclin dependent kinase 5 0.038 0.1491 0.1488
Echinococcus multilocularis Glutamate receptor, ionotropic kainate 2 0.0072 0.0074 0.0071
Brugia malayi GH02984p 0.0337 0.1297 0.1294
Trypanosoma brucei fatty-acid amide hydrolase, putative 0.0269 0.0981 0.5364
Echinococcus multilocularis cyclins 0.0234 0.0821 0.0818
Echinococcus multilocularis cyclin dependent kinase 0.038 0.1491 0.1488
Echinococcus granulosus glutamate receptor ionotrophic AMPA 3 0.0072 0.0074 0.0071
Schistosoma mansoni tar DNA-binding protein 0.0061 0.0027 0.0023
Plasmodium vivax glutamyl-tRNA(Gln) amidotransferase subunit A, putative 0.0269 0.0981 0.6568
Echinococcus granulosus Glutamate receptor ionotropic kainate 2 0.0072 0.0074 0.0071
Loa Loa (eye worm) hypothetical protein 0.0452 0.1825 0.1822
Echinococcus multilocularis cyclin dependent kinase 1 0.038 0.1491 0.1488
Echinococcus multilocularis cyclins 0.0234 0.0821 0.0818
Echinococcus multilocularis cyclin b3 0.0234 0.0821 0.0818
Trichomonas vaginalis cyclin B3, putative 0.0234 0.0821 0.4486
Schistosoma mansoni fatty-acid amide hydrolase 0.0269 0.0981 0.0978
Trichomonas vaginalis CMGC family protein kinase 0.038 0.1491 0.8167
Loa Loa (eye worm) CMGC/CDK/CDC2 protein kinase 0.038 0.1491 0.1488
Echinococcus granulosus tar DNA binding protein 0.0061 0.0027 0.0023
Loa Loa (eye worm) CMGC/CDK/CDC2 protein kinase 0.038 0.1491 0.1488
Mycobacterium ulcerans amidase 0.0269 0.0981 0.8184
Echinococcus multilocularis cyclin dependent kinase 5 0.038 0.1491 0.1488
Onchocerca volvulus 0.0452 0.1825 1
Loa Loa (eye worm) amidase 0.0269 0.0981 0.0978
Trichomonas vaginalis cyclin B, putative 0.0452 0.1825 1
Trypanosoma cruzi cyclin, putative 0.0452 0.1825 1
Schistosoma mansoni serine/threonine protein kinase 0.038 0.1491 0.1488
Echinococcus granulosus fatty acid amide hydrolase 1 0.2227 1 1
Giardia lamblia G2/mitotic-specific cyclin B 0.0452 0.1825 1
Echinococcus multilocularis fatty acid amide hydrolase 1 0.2227 1 1
Trichomonas vaginalis cyclins, putative 0.0275 0.1008 0.5514
Giardia lamblia Cyclin A 0.0234 0.0821 0.4486
Echinococcus granulosus high affinity choline transporter 1 0.0337 0.1297 0.1294
Schistosoma mansoni tar DNA-binding protein 0.0061 0.0027 0.0023
Echinococcus granulosus cyclins 0.0234 0.0821 0.0818
Brugia malayi RNA recognition motif domain containing protein 0.0061 0.0027 0.0023
Trichomonas vaginalis cyclins, putative 0.0452 0.1825 1
Echinococcus granulosus Glutamate receptor ionotropic kainate 2 0.0072 0.0074 0.0071
Loa Loa (eye worm) hypothetical protein 0.0218 0.0748 0.0745
Trypanosoma cruzi amidase, putative 0.0269 0.0981 0.5364
Trichomonas vaginalis cyclins, putative 0.0452 0.1825 1
Mycobacterium tuberculosis Probable amidase AmiD (acylamidase) (acylase) 0.0269 0.0981 0.9105
Trypanosoma cruzi CYC2-like cyclin, putative 0.0452 0.1825 1
Echinococcus granulosus cyclins 0.0234 0.0821 0.0818
Trichomonas vaginalis conserved hypothetical protein 0.0234 0.0821 0.4486
Giardia lamblia Kinase, CMGC CDK 0.038 0.1491 0.8167
Trichomonas vaginalis cyclin A, putative 0.0452 0.1825 1
Mycobacterium ulcerans amidase 0.0269 0.0981 0.8184
Echinococcus multilocularis fatty acid amide hydrolase 1 0.2227 1 1
Echinococcus multilocularis cyclins 0.0234 0.0821 0.0818
Loa Loa (eye worm) hypothetical protein 0.2227 1 1
Echinococcus granulosus cyclin b3 0.0234 0.0821 0.0818
Entamoeba histolytica cyclin, putative 0.0234 0.0821 0.4486
Brugia malayi Cyclin, N-terminal domain containing protein 0.0452 0.1825 0.1822
Echinococcus multilocularis Glutamate receptor, ionotropic kainate 3 0.009 0.0156 0.0152
Mycobacterium tuberculosis Possible penicillin-binding protein 0.0223 0.0772 0.7163
Brugia malayi Amidase family protein 0.0269 0.0981 0.0978
Trichomonas vaginalis cyclins, putative 0.0234 0.0821 0.4486
Echinococcus granulosus cyclins 0.0234 0.0821 0.0818
Trypanosoma cruzi cdc2-related kinase 3 0.038 0.1491 0.8167
Leishmania major cell division related protein kinase 2,cdc2-related kinase 0.038 0.1491 0.8167
Chlamydia trachomatis glutamyl-tRNA(Gln) amidotransferase subunit A 0.0269 0.0981 1
Echinococcus granulosus Glutamate receptor ionotropic kainate 2 0.0072 0.0074 0.0071
Echinococcus multilocularis cyclin B 0.0452 0.1825 0.1822
Brugia malayi RNA binding protein 0.0061 0.0027 0.0023
Trichomonas vaginalis cyclins, putative 0.0452 0.1825 1
Echinococcus granulosus glutamate receptor 2 0.0072 0.0074 0.0071
Echinococcus multilocularis glutamyl tRNA(Gln) amidotransferase subunit A 0.0269 0.0981 0.0978
Mycobacterium ulcerans aspartyl/glutamyl-tRNA amidotransferase subunit A 0.0269 0.0981 0.8184
Brugia malayi Protein kinase domain containing protein 0.038 0.1491 0.1488
Schistosoma mansoni d-amino acid oxidase 0.0316 0.1198 0.1195
Trichomonas vaginalis cyclin B, putative 0.0452 0.1825 1
Mycobacterium leprae PROBABLE D-AMINO ACID OXIDASE AAO 0.0316 0.1198 1
Loa Loa (eye worm) cyclin domain-containing protein 0.0723 0.3071 0.3069
Mycobacterium ulcerans peptide amidase, GatA 0.0269 0.0981 0.8184
Echinococcus multilocularis glutamate receptor, ionotrophic, AMPA 3 0.0072 0.0074 0.0071
Echinococcus multilocularis glutamate receptor 2 0.0072 0.0074 0.0071
Echinococcus multilocularis cyclins 0.0234 0.0821 0.0818
Entamoeba histolytica cell division protein kinase 2, putative 0.038 0.1491 0.8167
Echinococcus multilocularis tar DNA binding protein 0.0061 0.0027 0.0023
Echinococcus multilocularis nmda type glutamate receptor 0.0094 0.0174 0.0171
Schistosoma mansoni tar DNA-binding protein 0.0061 0.0027 0.0023
Echinococcus multilocularis cyclins 0.0234 0.0821 0.0818
Loa Loa (eye worm) hypothetical protein 0.0337 0.1297 0.1294
Echinococcus granulosus glutamyl tRNAGln amidotransferase subunit A 0.0269 0.0981 0.0978
Mycobacterium ulcerans D-amino acid oxidase Aao 0.0316 0.1198 1
Echinococcus multilocularis G2:mitotic specific cyclin B3 0.0723 0.3071 0.3069
Echinococcus multilocularis cyclins 0.0234 0.0821 0.0818
Mycobacterium ulcerans amidase 0.0269 0.0981 0.8184
Trichomonas vaginalis cyclin B, putative 0.0234 0.0821 0.4486
Loa Loa (eye worm) RNA recognition domain-containing protein domain-containing protein 0.0061 0.0027 0.0023
Brugia malayi TAR-binding protein 0.0061 0.0027 0.0023
Mycobacterium ulcerans amidase 0.0269 0.0981 0.8184
Trypanosoma cruzi cdc2-related kinase 3 0.038 0.1491 0.8167
Schistosoma mansoni glutamate receptor NMDA 0.0148 0.0425 0.0422
Toxoplasma gondii cell-cycle-associated protein kinase CDK, putative 0.038 0.1491 1
Plasmodium falciparum cyclin 0.0234 0.0821 0.5492
Loa Loa (eye worm) hypothetical protein 0.0452 0.1825 0.1822
Echinococcus granulosus nmda type glutamate receptor 0.0094 0.0174 0.0171
Trichomonas vaginalis cyclin B, putative 0.0452 0.1825 1
Treponema pallidum aspartyl/glutamyl-tRNA amidotransferase subunit A 0.0269 0.0981 1
Entamoeba histolytica cell division protein kinase 2, putative 0.038 0.1491 0.8167
Echinococcus granulosus glutamate receptor NMDA 0.0076 0.0094 0.0091
Schistosoma mansoni serine/threonine protein kinase 0.038 0.1491 0.1488
Echinococcus granulosus fatty acid amide hydrolase 1 0.0269 0.0981 0.0978
Trichomonas vaginalis cyclins, putative 0.0452 0.1825 1
Echinococcus multilocularis cyclin B3 1 0.0234 0.0821 0.0818
Loa Loa (eye worm) amidase 0.0269 0.0981 0.0978
Schistosoma mansoni cyclin B3 0.0723 0.3071 0.3069
Leishmania major hypothetical protein, conserved 0.0269 0.0981 0.5364
Trypanosoma cruzi cdc2-related kinase 1 0.038 0.1491 0.8167
Plasmodium falciparum protein kinase 5 0.038 0.1491 1
Schistosoma mansoni tar DNA-binding protein 0.0061 0.0027 0.0023
Wolbachia endosymbiont of Brugia malayi aspartyl/glutamyl-tRNA amidotransferase subunit A 0.0269 0.0981 0.5
Echinococcus granulosus cyclin dependent kinase 0.038 0.1491 0.1488
Brugia malayi Amidase family protein 0.0269 0.0981 0.0978
Mycobacterium tuberculosis Probable D-amino acid oxidase Aao 0.029 0.1077 1
Echinococcus granulosus nmda type glutamate receptor 0.0166 0.0507 0.0503
Schistosoma mansoni cyclins 0.0234 0.0821 0.0818
Echinococcus granulosus G2:mitotic specific cyclin B3 0.0723 0.3071 0.3069
Trypanosoma cruzi cyclin 6, putative 0.0452 0.1825 1
Trypanosoma brucei mitotic cyclin 6 0.0452 0.1825 1
Loa Loa (eye worm) RNA binding protein 0.0061 0.0027 0.0023
Schistosoma mansoni amidase 0.2227 1 1
Echinococcus multilocularis nmda type glutamate receptor 0.0166 0.0507 0.0503
Trypanosoma cruzi cdc2-related kinase 1 0.038 0.1491 0.8167
Echinococcus granulosus cyclins 0.0234 0.0821 0.0818
Leishmania major cyclin 0.0452 0.1825 1
Entamoeba histolytica cyclin, putative 0.0452 0.1825 1
Trichomonas vaginalis cyclin D, putative 0.0234 0.0821 0.4486
Plasmodium vivax protein kinase Crk2 0.038 0.1491 1
Echinococcus multilocularis cyclins 0.0234 0.0821 0.0818
Echinococcus multilocularis fatty acid amide hydrolase 1 0.0269 0.0981 0.0978
Schistosoma mansoni tar DNA-binding protein 0.0061 0.0027 0.0023
Brugia malayi Cyclin, N-terminal domain containing protein 0.0723 0.3071 0.3069
Loa Loa (eye worm) TAR-binding protein 0.0061 0.0027 0.0023
Brugia malayi cell division control protein 2 homolog 0.038 0.1491 0.1488
Echinococcus multilocularis glutamate receptor NMDA 0.0076 0.0094 0.0091
Echinococcus multilocularis Glutamate receptor, ionotropic kainate 2 0.0072 0.0074 0.0071
Trichomonas vaginalis cyclin D, putative 0.0234 0.0821 0.4486
Echinococcus multilocularis atpase aaa+ type core atpase aaa type core 0.0787 0.3367 0.3365
Mycobacterium tuberculosis Probable amidase AmiC (aminohydrolase) 0.0269 0.0981 0.9105
Echinococcus granulosus fatty acid amide hydrolase 1 0.2227 1 1
Echinococcus multilocularis Glutamate receptor, ionotropic kainate 2 0.0072 0.0074 0.0071
Echinococcus granulosus 5'partial|cyclin dependent kinase 1 0.038 0.1491 0.1488
Echinococcus granulosus cyclin dependent kinase 1 0.038 0.1491 0.1488
Loa Loa (eye worm) hypothetical protein 0.0375 0.1471 0.1468
Loa Loa (eye worm) hypothetical protein 0.0316 0.1198 0.1195
Entamoeba histolytica cyclin family protein 0.0234 0.0821 0.4486
Giardia lamblia Kinase, CMGC CDK 0.038 0.1491 0.8167
Trypanosoma cruzi cyclin, putative 0.0452 0.1825 1
Leishmania major cell division protein kinase 2,cdc2-related kinase 0.038 0.1491 0.8167
Mycobacterium ulcerans amidase 0.0269 0.0981 0.8184
Trypanosoma brucei cdc2-related kinase 1 0.038 0.1491 0.8167
Giardia lamblia Hypothetical protein 0.0234 0.0821 0.4486
Schistosoma mansoni glutamyl-tRNA(Gln) amidotransferase subunit A 0.0269 0.0981 0.0978
Schistosoma mansoni high-affinity choline transporter 0.0337 0.1297 0.1294
Trypanosoma cruzi amidase, putative 0.0269 0.0981 0.5364
Schistosoma mansoni fatty-acid amide hydrolase 0.2227 1 1
Trichomonas vaginalis CMGC family protein kinase 0.038 0.1491 0.8167
Mycobacterium tuberculosis Probable amidase AmiB2 (aminohydrolase) 0.0269 0.0981 0.9105
Toxoplasma gondii hypothetical protein 0.0177 0.0561 0.3745
Trichomonas vaginalis cyclin B, putative 0.0452 0.1825 1

Activities

Activity type Activity value Assay description Source Reference
Efficacy (binding) = 50 % Transactivation of intact rat androgen receptor in ventral prostate cytosol at 10 nM relative to dihydrotestosterone PATENT. No reference
Ki (binding) = -8.54 Inhibition of [3H]-mibolerone binding to cytosolic androgen receptor of rat ventral prostrate ChEMBL. 15715462
Ki (binding) = 4.9 nM Displacement of [3H]mibolerone from androgen receptor in intact rat ventral prostate cytosol by competitive binding assay PATENT. No reference
Log Ki (binding) = 8.54 Inhibition of [3H]-mibolerone binding to cytosolic androgen receptor of rat ventral prostrate ChEMBL. 15715462
Relative binding affinity (binding) = 1.03 Binding affinity against cytosolic androgen receptor from ventral prostate of rats using [3H]-MIB competitive binding assay (relative to dihydro testosterone) ChEMBL. 15239655
Relative binding affinity (binding) = 1.03 Binding affinity against cytosolic androgen receptor from ventral prostate of rats using [3H]-MIB competitive binding assay (relative to dihydro testosterone) ChEMBL. 15239655

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

2 literature references were collected for this gene.

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