Detailed information for compound 331944

Basic information

Technical information
  • TDR Targets ID: 331944
  • Name: 2-[5-[4-[[N-[(2,4-difluorophenyl)methyl]-3-(m ethanesulfonamido)-2-methylanilino]methyl]phe noxy]-2-fluorophenoxy]acetic acid
  • MW: 600.605 | Formula: C30H27F3N2O6S
  • H donors: 2 H acceptors: 4 LogP: 5.76 Rotable bonds: 12
    Rule of 5 violations (Lipinski): 2
  • SMILES: OC(=O)COc1cc(ccc1F)Oc1ccc(cc1)CN(c1cccc(c1C)NS(=O)(=O)C)Cc1ccc(cc1F)F
  • InChi: 1S/C30H27F3N2O6S/c1-19-27(34-42(2,38)39)4-3-5-28(19)35(17-21-8-9-22(31)14-26(21)33)16-20-6-10-23(11-7-20)41-24-12-13-25(32)29(15-24)40-18-30(36)37/h3-15,34H,16-18H2,1-2H3,(H,36,37)
  • InChiKey: SEVGDNHYESBDRZ-UHFFFAOYSA-N  


Substructure search Similarity search

Network

Hover on a compound node to display the structore

Synonyms

  • 2-[5-[4-[[N-[(2,4-difluorophenyl)methyl]-3-(methanesulfonamido)-2-methyl-anilino]methyl]phenoxy]-2-fluoro-phenoxy]acetic acid
  • 2-[5-[4-[[(2,4-difluorophenyl)methyl-[2-methyl-3-(methylsulfonylamino)phenyl]amino]methyl]phenoxy]-2-fluoro-phenoxy]ethanoic acid
  • 2-[5-[4-[[N-(2,4-difluorobenzyl)-3-(methanesulfonamido)-2-methyl-anilino]methyl]phenoxy]-2-fluoro-phenoxy]acetic acid
  • 2-[5-[4-[[(2,4-difluorophenyl)methyl-(3-methanesulfonamido-2-methylphenyl)amino]methyl]phenoxy]-2-fluorophenoxy]acetic acid
  • 2-[5-[4-[[(2,4-difluorophenyl)methyl-(3-methanesulfonamido-2-methyl-phenyl)amino]methyl]phenoxy]-2-fluoro-phenoxy]acetic acid
  • 2-[5-[4-[[(2,4-difluorobenzyl)-(3-methanesulfonamido-2-methyl-phenyl)amino]methyl]phenoxy]-2-fluoro-phenoxy]acetic acid

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens nuclear receptor subfamily 3, group C, member 1 (glucocorticoid receptor) Starlite/ChEMBL References
Homo sapiens progesterone receptor Starlite/ChEMBL References
Rattus norvegicus Glucocorticoid 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
Echinococcus multilocularis guanine nucleotide binding protein G(s) subunit 0.0046 0.005 0.0874
Toxoplasma gondii shikimate dehydrogenase substrate binding domain-containing protein 0.0332 0.0817 0.0782
Loa Loa (eye worm) hypothetical protein 0.0134 0.0286 0.48
Echinococcus granulosus geminin 0.017 0.0383 0.2815
Mycobacterium tuberculosis 3-phosphoshikimate 1-carboxyvinyltransferase AroA (5-enolpyruvylshikimate-3-phosphate synthase) (EPSP synthase) (EPSPS) 0.0129 0.0273 0.0483
Schistosoma mansoni hypothetical protein 0.0253 0.0606 1
Echinococcus multilocularis cdgsh iron sulfur domain containing protein 0.0239 0.0567 1
Trypanosoma cruzi UDP-galactopyranose mutase 0.0042 0.0039 0.5
Loa Loa (eye worm) hypothetical protein 0.0042 0.0039 0.0653
Treponema pallidum UDP-N-acetylglucosamine 1-carboxyvinyltransferase 0.0203 0.0471 0.5
Schistosoma mansoni hypothetical protein 0.017 0.0383 0.6319
Echinococcus granulosus lysine specific histone demethylase 1A 0.0042 0.0039 0.0286
Echinococcus multilocularis geminin 0.017 0.0383 0.675
Leishmania major UDP-galactopyranose mutase 0.0042 0.0039 0.5
Schistosoma mansoni amine oxidase 0.0042 0.0039 0.0642
Toxoplasma gondii chorismate synthase, putative 0.3758 1 1
Mycobacterium leprae 3-dehydroquinate synthase AroB 0.0129 0.0273 0.0483
Mycobacterium ulcerans flavin-containing monoamine oxidase AofH 0.0596 0.1523 0.149
Loa Loa (eye worm) hypothetical protein 0.0067 0.0106 0.1778
Mycobacterium ulcerans UDP-N-acetylglucosamine 1-carboxyvinyltransferase 0.0203 0.0471 0.0433
Onchocerca volvulus 0.0042 0.0039 0.1955
Trypanosoma cruzi UDP-galactopyranose mutase 0.0042 0.0039 0.5
Plasmodium vivax chorismate synthase 0.3758 1 1
Mycobacterium tuberculosis Probable chorismate synthase AroF (5-enolpyruvylshikimate-3-phosphate phospholyase) 0.1853 0.4894 1
Plasmodium falciparum chorismate synthase 0.3758 1 1
Schistosoma mansoni Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein) 0.0046 0.005 0.0819
Onchocerca volvulus 0.0102 0.0199 1
Brugia malayi amine oxidase, flavin-containing family protein 0.0042 0.0039 0.0501
Echinococcus granulosus cdgsh iron sulfur domain containing protein 0.0239 0.0567 0.4171
Echinococcus multilocularis guanine nucleotide binding protein G(s) subunit 0.0046 0.005 0.0874
Brugia malayi Uncharacterized hematopoietic stem/progenitor cells protein MDS029 0.0102 0.0199 0.2565
Mycobacterium tuberculosis Probable flavin-containing monoamine oxidase AofH (amine oxidase) (MAO) 0.0554 0.1411 0.2826
Brugia malayi Amyloid A4 extracellular domain containing protein 0.0317 0.0775 1
Schistosoma mansoni amine oxidase 0.0042 0.0039 0.0642
Echinococcus multilocularis lysine specific histone demethylase 1A 0.0042 0.0039 0.0685
Wolbachia endosymbiont of Brugia malayi UDP-N-acetylglucosamine 1-carboxyvinyltransferase 0.0203 0.0471 0.5
Mycobacterium leprae probable 3-phosphoshikimate 1-carboxyvinyl transferase AroA (5-ENOLPYRUVYLSHIKIMATE-3-PHOSPHATE SYNTHASE) (EPSP SYNTHASE) (EPSPS 0.0332 0.0817 0.1604
Schistosoma mansoni Lysine-specific histone demethylase 1 0.0042 0.0039 0.0642
Echinococcus multilocularis protoporphyrinogen oxidase 0.0042 0.0039 0.0685
Schistosoma mansoni Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein) 0.0046 0.005 0.0819
Mycobacterium leprae Chorismate synthase AroF (5-enolpyruvylshikimate-3-phosphate phospholyase). 0.1853 0.4894 1
Brugia malayi GTP-binding regulatory protein Gs alpha-S chain, putative 0.0046 0.005 0.064
Loa Loa (eye worm) GTP-binding regulatory protein Gs alpha-S chain 0.0046 0.005 0.0833
Loa Loa (eye worm) hypothetical protein 0.0042 0.0039 0.0653
Schistosoma mansoni hypothetical protein 0.017 0.0383 0.6319
Chlamydia trachomatis phosphoshikimate 1-carboxyl vinyltransferase 0.0332 0.0817 0.0782
Chlamydia trachomatis dehyroquinate synthase 0.0129 0.0273 0.0235
Echinococcus multilocularis 0.0042 0.0039 0.0685
Schistosoma mansoni Protoporphyrinogen oxidase chloroplast/mitochondrial precursor 0.0042 0.0039 0.0642
Schistosoma mansoni 3-dehydroquinate synthase 0.0129 0.0273 0.451
Loa Loa (eye worm) hypothetical protein 0.0102 0.0199 0.334
Chlamydia trachomatis UDP-N-acetylglucosamine 1-carboxyvinyltransferase 0.0203 0.0471 0.0433
Mycobacterium ulcerans 3-dehydroquinate synthase 0.0129 0.0273 0.0235
Loa Loa (eye worm) hypothetical protein 0.025 0.0595 1
Mycobacterium ulcerans chorismate synthase 0.3758 1 1
Brugia malayi hypothetical protein 0.0042 0.0039 0.0501
Mycobacterium ulcerans flavin-containing monoamine oxidase AofH 0.0596 0.1523 0.149
Schistosoma mansoni Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein) 0.0046 0.005 0.0819
Echinococcus granulosus macrophage colony stimulating factor 1 receptor 0.0535 0.136 1
Schistosoma mansoni CDGSH-type Zn finger-containing protein-like protein 0.0253 0.0606 1
Echinococcus granulosus guanine nucleotide binding protein Gs subunit 0.0046 0.005 0.0365
Loa Loa (eye worm) hypothetical protein 0.0042 0.0039 0.0653
Loa Loa (eye worm) hypothetical protein 0.0042 0.0039 0.0653
Mycobacterium ulcerans 3-phosphoshikimate 1-carboxyvinyltransferase 0.0332 0.0817 0.0782
Loa Loa (eye worm) hypothetical protein 0.0042 0.0039 0.0653
Schistosoma mansoni alzheimer's disease beta-amyloid related 0.0115 0.0236 0.3894
Mycobacterium tuberculosis 3-dehydroquinate synthase AroB 0.0129 0.0273 0.0483
Brugia malayi SWIRM domain containing protein 0.0042 0.0039 0.0501
Echinococcus granulosus lysine specific histone demethylase 1A 0.0042 0.0039 0.0286
Echinococcus granulosus guanine nucleotide binding protein Gs subunit 0.0046 0.005 0.0365
Loa Loa (eye worm) hypothetical protein 0.0042 0.0039 0.0653

Activities

Activity type Activity value Assay description Source Reference
Activity (functional) = 1.9 uM Activity against dexamethasone-induced GR-mediated TAT activity in rat hepatocytes ChEMBL. 16078847
Activity (functional) = 1.9 uM Activity against dexamethasone-induced GR-mediated TAT activity in rat hepatocytes ChEMBL. 16078847
Agonistic activity (functional) % Agonistic activity against VP-16 GR transcriptional activation assay in human Huh-7 cells; No effect up to 10-100 uM ChEMBL. 16078847
Agonistic activity (functional) 0 % Agonistic activity against VP-16 GR transcriptional activation assay in human Huh-7 cells; No effect up to 10-100 uM ChEMBL. 16078847
AUC (ADMET) = 3.85 ug hr-1 ml-1 Area under the concentration-time curve in SD rats after 5 mg/kg oral dose ChEMBL. 16078847
clogP = 6.17 Calculated partition coefficient (clogP) ChEMBL. 16078847
EC50 (functional) nM Antagonistic activity against VP-16 transcriptional activation domain protein; No effect up to 10-100 uM ChEMBL. 16078847
EC50 (functional) 0 nM Antagonistic activity against VP-16 transcriptional activation domain protein; No effect up to 10-100 uM ChEMBL. 16078847
F (ADMET) = 40 % Oral bioavailability of the compound in SD rats after 5 mg/kg oral dose ChEMBL. 16078847
IC50 (binding) nM Inhibition of human mineralocorticoid receptor; Not determined ChEMBL. 16078847
IC50 (binding) 0 nM Inhibition of human androgen receptor; Not determined ChEMBL. 16078847
IC50 (binding) 0 nM Inhibition of human mineralocorticoid receptor; Not determined ChEMBL. 16078847
IC50 (binding) = 0.2 nM Inhibition of [3H]-dexamethasone binding to rat glucocorticoid receptor ChEMBL. 16078847
IC50 (binding) = 0.2 nM Inhibition of [3H]-dexamethasone binding to rat glucocorticoid receptor ChEMBL. 16078847
IC50 (binding) = 4.8 nM Inhibition of [3H]-dexamethasone binding to human glucocorticoid receptor ChEMBL. 16078847
IC50 (binding) = 4.8 nM Inhibition of [3H]-dexamethasone binding to human glucocorticoid receptor ChEMBL. 16078847
IC50 (binding) = 180 nM Inhibition of human progesterone receptor ChEMBL. 16078847
IC50 (binding) = 180 nM Inhibition of human progesterone receptor ChEMBL. 16078847
IC50 (functional) = 440 nM Antagonistic activity against 5 nM dexamethasone induced glucocorticoid receptor mediated alkaline phosphatase activity ChEMBL. 16078847
IC50 (functional) = 440 nM Antagonistic activity against 5 nM dexamethasone induced glucocorticoid receptor mediated alkaline phosphatase activity ChEMBL. 16078847
Level (ADMET) = 7.7 % HbA1c levels in ob/ob mice after 30 days of oral dose at 300 mpk b.i.d. ChEMBL. 16078847
Level (ADMET) = 8.9 % HbA1c levels in ob/ob mice after 30 days of oral dose at 30 mpk b.i.d. ChEMBL. 16078847
Level (ADMET) = 0.99 mequiv/L Free fatty acid (FFA) levels in ob/ob mice after 14 days of oral dose at 30 mpk b.i.d. ChEMBL. 16078847
Level (ADMET) = 0.99 mequiv/L Free fatty acid (FFA) levels in ob/ob mice after 30 days of oral dose at 30 mpk b.i.d. ChEMBL. 16078847
Level (ADMET) = 1.01 mequiv/L Free fatty acid (FFA) levels in ob/ob mice after 14 days of oral dose at 100 mpk b.i.d. ChEMBL. 16078847
Level (ADMET) = 1.27 mequiv/L Free fatty acid (FFA) levels in ob/ob mice after 30 days of oral dose at 100 mpk b.i.d. ChEMBL. 16078847
Level (ADMET) = 134 mg dl-1 Cholesterol levels in ob/ob mice after 14 days of oral dose at 100 mpk b.i.d. ChEMBL. 16078847
Level (ADMET) = 163 mg dl-1 Triglyceride levels in ob/ob mice after 30 days of oral dose at 100 mpk b.i.d. ChEMBL. 16078847
Level (ADMET) = 214 mg dl-1 Triglyceride levels in ob/ob mice after 30 days of oral dose at 30 mpk b.i.d. ChEMBL. 16078847
Level (ADMET) = 225 mg dl-1 Cholesterol levels in ob/ob mice after 14 days of oral dose at 30 mpk b.i.d. ChEMBL. 16078847
Level (ADMET) = 233 mg dl-1 Glucose levels in ob/ob mice after 14 days of oral dose at 100 mpk b.i.d. ChEMBL. 16078847
Level (ADMET) = 239 mg dl-1 Cholesterol levels in ob/ob mice after 30 days of oral dose at 100 mpk b.i.d. ChEMBL. 16078847
Level (ADMET) = 266 mg dl-1 Cholesterol levels of the compound levels in ob/ob mice after 30 days of oral dose at 30 mpk b.i.d. ChEMBL. 16078847
Level (ADMET) = 314 mg dl-1 Glucose levels in ob/ob mice after 14 days of oral dose at 30 mpk b.i.d. ChEMBL. 16078847
Level (ADMET) = 44.2 mg g-1 Glycogen levels in ob/ob mice after 14 days of oral dose at 100 mpk b.i.d. ChEMBL. 16078847
Level (ADMET) = 54.6 mg g-1 Glycogen levels in ob/ob mice after 14 days of oral dose at 30 mpk b.i.d. ChEMBL. 16078847
Level (ADMET) = 25 ng ml-1 Insulin levels in ob/ob mice after 14 days of oral dose at 30 mpk b.i.d. ChEMBL. 16078847
Level (ADMET) = 32.8 ng ml-1 Insulin levels in ob/ob mice after 14 days of oral dose at 100 mpk b.i.d. ChEMBL. 16078847
Level (ADMET) = 1.7 nmol ofpHB/min/mgof protein Liver TAT levels in ob/ob mice after 14 days of oral dose at 30 mpk b.i.d. ChEMBL. 16078847
Level (ADMET) = 2.4 nmol ofpHB/min/mgof protein Liver TAT levels in ob/ob mice after 14 days of oral dose at 100 mpk b.i.d. ChEMBL. 16078847
Level (ADMET) = 20 ug g-1 Compound level in liver in ob/ob mice after 13 days of 30 mpk oral dose of compound ChEMBL. 16078847
Level (ADMET) = 40 ug g-1 Compound level in liver in SD rats after 7 hr of 5 mg/kg i.v. dose ChEMBL. 16078847
Level (ADMET) = 74 ug g-1 Compound level in liver in SD rats after 1 hr of 5 mg/kg i.v. dose ChEMBL. 16078847
Level (ADMET) = 157 ug g-1 Compound level in liver in ob/ob mice after 13 days of 100 mpk oral dose of compound ChEMBL. 16078847
Level (ADMET) = 0.65 ug ml-1 Compound level in plasma in SD rats after 7 hr of 5 mg/kg i.v. dose ChEMBL. 16078847
Level (ADMET) = 0.82 ug ml-1 Compound level in plasma in ob/ob mice after 13 days of 100 mpk oral dose of compound ChEMBL. 16078847
Level (ADMET) = 1.6 ug ml-1 Compound level in plasma in SD rats after 1 hr of 5 mg/kg i.v. dose ChEMBL. 16078847
Level (ADMET) = 6 ug ml-1 Compound level in plasma in ob/ob mice after 13 days of 100 mpk oral dose of compound ChEMBL. 16078847
Level (ADMET) = 303 units/mL Aspartate aminotransferase /alanine aminotransferase levels in ob/ob mice after 30 days of oral dose at 100 mpk b.i.d. ChEMBL. 16078847
Level (ADMET) = 395 units/mL Aspartate aminotransferase /alanine aminotransferase levels in ob/ob mice after 30 days of oral dose at 30 mpk b.i.d. ChEMBL. 16078847
Protien binding (ADMET) = 99.7 % Plasma protien binding of tritium labled compound in mouse plasma was determined ChEMBL. 16078847
Protien binding (ADMET) = 99.9 % Plasma protien binding of tritium labled compound in human plasma was determined ChEMBL. 16078847
Protien binding (ADMET) = 99.9 % Plasma protien binding of tritium labled compound in rat plasma was determined ChEMBL. 16078847
T1/2 (ADMET) = 2.3 hr Half life period of the comopund in human liver microsomes was determined ChEMBL. 16078847
T1/2 (ADMET) = 4.1 hr Half life period of the comopund in rat liver microsomes was determined ChEMBL. 16078847
T1/2 (ADMET) = 6.5 hr Half life period of the comopund in rat hepatocytes was determined ChEMBL. 16078847
T1/2 (ADMET) = 9.1 hr Half life period of the comopund in human hepatocytes was determined ChEMBL. 16078847
Weight (functional) = 40 g Initial weight of the ob/ob mice before oral treatment at 100 mpk b.i.d. for 14 days ChEMBL. 16078847
WEIGHT (functional) = 40 g Initial weight of the ob/ob mice before oral treatment at 100 mpk b.i.d. for 14 days ChEMBL. 16078847
Weight (functional) = 41.5 g Initial weight of the ob/ob mice before oral treatment at 30 mpk b.i.d. for 14 days ChEMBL. 16078847
WEIGHT (functional) = 41.5 g Initial weight of the ob/ob mice before oral treatment at 30 mpk b.i.d. for 14 days ChEMBL. 16078847
Weight (functional) = 46.9 g Final weight of the ob/ob mice after 14 days of oral treatment at 100 mpk b.i.d. ChEMBL. 16078847
WEIGHT (functional) = 46.9 g Final weight of the ob/ob mice after 14 days of oral treatment at 100 mpk b.i.d. ChEMBL. 16078847
Weight (functional) = 49.2 g Final weight of the ob/ob mice after 14 days of oral treatment at 30 mpk b.i.d. ChEMBL. 16078847
WEIGHT (functional) = 49.2 g Final weight of the ob/ob mice after 14 days of oral treatment at 30 mpk b.i.d. ChEMBL. 16078847

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.

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