Detailed information for compound 595445

Basic information

Technical information
  • TDR Targets ID: 595445
  • Name: ethyl 4-chloro-6-(dimethylaminomethyl)-5-hydr oxy-2-(phenylsulfanylmethyl)-1-benzofuran-3-c arboxylate
  • MW: 419.922 | Formula: C21H22ClNO4S
  • H donors: 1 H acceptors: 2 LogP: 4.69 Rotable bonds: 8
    Rule of 5 violations (Lipinski): 1
  • SMILES: CCOC(=O)c1c(CSc2ccccc2)oc2c1c(Cl)c(c(c2)CN(C)C)O
  • InChi: 1S/C21H22ClNO4S/c1-4-26-21(25)18-16(12-28-14-8-6-5-7-9-14)27-15-10-13(11-23(2)3)20(24)19(22)17(15)18/h5-10,24H,4,11-12H2,1-3H3
  • InChiKey: CUPOPGWAZZSJLG-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • ethyl 4-chloro-6-(dimethylaminomethyl)-5-hydroxy-2-(phenylsulfanylmethyl)benzofuran-3-carboxylate
  • 4-chloro-6-(dimethylaminomethyl)-5-hydroxy-2-[(phenylthio)methyl]-3-benzofurancarboxylic acid ethyl ester
  • 4-chloro-6-(dimethylaminomethyl)-5-hydroxy-2-[(phenylthio)methyl]benzofuran-3-carboxylic acid ethyl ester
  • STK083464
  • BAS 02098835
  • ChemDiv1_010274
  • Oprea1_556479
  • Oprea1_290295

Targets

Known targets for this compound

No curated genes were found associated with this compound

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
Loa Loa (eye worm) hypothetical protein 0.0064 0.0644 0.2383
Schistosoma mansoni hypothetical protein 0.0138 0.1749 0.1749
Echinococcus granulosus diuretic hormone 44 receptor GPRdih2 0.0064 0.0644 0.0644
Schistosoma mansoni hypothetical protein 0.0064 0.0644 0.0644
Echinococcus granulosus cadherin EGF LAG seven pass G type receptor 0.0064 0.0644 0.0644
Schistosoma mansoni microtubule-associated protein tau 0.0692 1 1
Schistosoma mansoni hypothetical protein 0.0064 0.0644 0.0644
Loa Loa (eye worm) hypothetical protein 0.0025 0.0067 0.0248
Echinococcus granulosus Mitotic checkpoint protein PRCC C terminal 0.0258 0.3539 0.3539
Schistosoma mansoni hypothetical protein 0.0064 0.0644 0.0644
Trypanosoma cruzi PAB1-binding protein , putative 0.0025 0.0067 0.5
Echinococcus granulosus GPCR family 2 0.0064 0.0644 0.0644
Loa Loa (eye worm) hypothetical protein 0.0138 0.1749 0.6474
Plasmodium vivax ataxin-2 like protein, putative 0.0025 0.0067 0.5
Brugia malayi Calcitonin receptor-like protein seb-1 0.0202 0.2702 1
Echinococcus multilocularis cadherin EGF LAG seven pass G type receptor 0.0064 0.0644 0.0644
Brugia malayi calcium-independent alpha-latrotoxin receptor 2, putative 0.0064 0.0644 0.2383
Leishmania major hypothetical protein, conserved 0.0025 0.0067 0.5
Loa Loa (eye worm) transcription factor SMAD2 0.012 0.1475 0.5457
Onchocerca volvulus Bile acid receptor homolog 0.0021 0 0.5
Schistosoma mansoni thyroid hormone receptor 0.0279 0.3848 0.3848
Toxoplasma gondii LsmAD domain-containing protein 0.0025 0.0067 0.5
Loa Loa (eye worm) latrophilin receptor protein 2 0.0064 0.0644 0.2383
Brugia malayi Latrophilin receptor protein 2 0.0064 0.0644 0.2383
Onchocerca volvulus Steroid hormone receptor family member cnr14 homolog 0.0021 0 0.5
Plasmodium falciparum ataxin-2 like protein, putative 0.0025 0.0067 0.5
Loa Loa (eye worm) hypothetical protein 0.0202 0.2702 1
Brugia malayi MH2 domain containing protein 0.012 0.1475 0.5457
Onchocerca volvulus Protein ultraspiracle homolog 0.0021 0 0.5
Echinococcus multilocularis diuretic hormone 44 receptor GPRdih2 0.0064 0.0644 0.0644
Brugia malayi Corticotropin releasing factor receptor 2 precursor, putative 0.0202 0.2702 1
Onchocerca volvulus 0.0021 0 0.5
Trypanosoma cruzi PAB1-binding protein , putative 0.0025 0.0067 0.5
Plasmodium falciparum ataxin-2 like protein, putative 0.0025 0.0067 0.5
Trypanosoma brucei PAB1-binding protein , putative 0.0025 0.0067 0.5
Brugia malayi latrophilin 2 splice variant baaae 0.0138 0.1749 0.6474
Loa Loa (eye worm) pigment dispersing factor receptor c 0.0202 0.2702 1
Brugia malayi hypothetical protein 0.0025 0.0067 0.0248
Schistosoma mansoni thyroid hormone receptor 0.0279 0.3848 0.3848
Echinococcus multilocularis GPCR, family 2 0.0064 0.0644 0.0644
Schistosoma mansoni hypothetical protein 0.0064 0.0644 0.0644
Schistosoma mansoni hypothetical protein 0.0258 0.3539 0.3539
Loa Loa (eye worm) MH2 domain-containing protein 0.012 0.1475 0.5457
Echinococcus multilocularis thyroid hormone receptor alpha 0.0279 0.3848 0.3848
Echinococcus multilocularis microtubule associated protein 2 0.0692 1 1
Echinococcus multilocularis Mitotic checkpoint protein PRCC, C terminal 0.0258 0.3539 0.3539

Activities

Activity type Activity value Assay description Source Reference
CC50 (functional) = 61.57 uM Huh7 cytotoxicity for Pf inhibitors Novartis-GNF Malaria Box. No reference
CC50 = 61.57 uM NOVARTIS: Cytotoxicity against human hepatocellular carcinoma cell line (Huh7) ChEMBL. 18579783
EC50 (functional) = 0.2095 uM W2 Pf proliferation inhibition Novartis-GNF Malaria Box. No reference
EC50 (functional) = 0.2095 uM NOVARTIS: Inhibition of Plasmodium falciparum W2 (drug-resistant) proliferation in erythrocyte-based infection assay ChEMBL. 18579783
EC50 (functional) = 0.321 uM PF proliferation inhibition 3D7 Novartis-GNF Malaria Box. No reference
EC50 (functional) = 0.321 uM NOVARTIS: Inhibition of Plasmodium falciparum 3D7 (drug-susceptible) proliferation in erythrocyte-based infection assay ChEMBL. 18579783
IC50 (functional) = 7.2 uM NOVARTIS: Antimalarial liver stage activity measured as reduction in Plasmodium yoelii schizont area in HepG2-A16-CD81 cells by immuno-fluorescence, and median schizont size at 10uM compound concentration ChEMBL. 22096101
IFI promiscuity index = 0.04615 IFI promiscuity index Novartis-GNF Malaria Box. No reference
Inhibition (functional) = -0.41 % ST_JUDE_LEISH: Cytotoxicity at 2uM final concentration against transgenic Leishmania Mexicana promastigotes LmGT2 that are glucose transport deficient and complemented with the L. Mexicana glucose transporter 2. Activity is measured by by DNA content using SYBR green in vitro ChEMBL. No reference
Inhibition (functional) = 0 % GSK_TCMDC: Inhibition of Plasmodium falciparum 3D7 LDH activity, using an LDH reporter assay. Test compounds present at 2uM ChEMBL. 20485427
Inhibition (functional) = 0.44 % ST_JUDE_LEISH: Cytotoxicity at 2uM final concentration against transgenic Leishmania Mexicana promastigotes LmPfHT that are glucose transport deficient and complemented with the Plasmodium falciparum hexose transporter. Activity is measured by by DNA content using SYBR green in vitro ChEMBL. No reference
Inhibition (functional) = 1.18 % ST_JUDE_LEISH: Cytotoxicity at 2uM final concentration against transgenic Leishmania Mexicana promastigotes LmGLUT1 that are glucose transport deficient and complemented with the human glucose transporter GLUT1. Activity is measured by DNA content using SYBR green in vitro ChEMBL. No reference
Inhibition (functional) = 12 % GSK_TCMDC: Percent inhibition of human HepG2 cell line. Test compounds present at 10uM. ChEMBL. 20485427
Inhibition (functional) = 70 % GSK_TCMDC: Inhibition of Plasmodium falciparum Dd2 in whole red blood cells, using parasite LDH activity as an index of growth. Test compounds present at 2uM ChEMBL. 20485427
Inhibition (functional) = 99 % GSK_TCMDC: Inhibition of Plasmodium falciparum 3D7 in whole red blood cells, using parasite LDH activity as an index of growth. Test compounds present at 2uM ChEMBL. 20485427
Inhibition frequency index (IFI) (functional) = 1.55 Inhibition Frequency Index (IFI) GSK. 20485427
Percent growth inhibition (functional) = -4 % Percent inhibition of P. falciparum lactate dehydrogenase activity (at 2 uM) GSK. 20485427
Percent growth inhibition (functional) = 12 % Percent inhibition of HepG2 growth (at 10 uM) GSK. 20485427
Percent growth inhibition (functional) = 70 % Percent inhibition of P. falciparum Dd2 growth (at 2 uM) GSK. 20485427
Percent growth inhibition (functional) = 99 % Percent inhibition of P. falciparum 3D7 growth (at 2 uM) GSK. 20485427
Schizont size (functional) = 188.08 um NOVARTIS: Antimalarial liver stage activity measured as reduction in Plasmodium yoelii schizont area in HepG2-A16-CD81 cells by immuno-fluorescence, and median schizont size at 10uM compound concentration ChEMBL. 22096101
XC50 (functional) = 6.18 XC50 determination of P. falciparum 3D7 growth GSK. 20485427
XC50 (functional) = 0.65703 uM GSK_TCMDC: Inhibition of Plasmodium falciparum 3D7 in whole erythrocytes, using parasite LDH activity as an index of growth. ChEMBL. 20485427

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Plasmodium falciparum ChEMBL23 18579783
Plasmodium yoelii ChEMBL23 22096101

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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