Detailed information for compound 27744

Basic information

Technical information
  • TDR Targets ID: 27744
  • Name: sodium (Z)-2-(1,3-benzodioxol-5-yl)-4-(4-meth oxyphenyl)-4-oxo-3-[(3,4,5-trimethoxyphenyl)m ethyl]but-2-enoate
  • MW: 528.482 | Formula: C28H25NaO9
  • H donors: 0 H acceptors: 3 LogP: 5.29 Rotable bonds: 10
    Rule of 5 violations (Lipinski): 2
  • SMILES: COc1ccc(cc1)C(=O)/C(=C(/c1ccc2c(c1)OCO2)\C(=O)[O-])/Cc1cc(OC)c(c(c1)OC)OC.[Na+]
  • InChi: 1S/C28H26O9.Na/c1-32-19-8-5-17(6-9-19)26(29)20(11-16-12-23(33-2)27(35-4)24(13-16)34-3)25(28(30)31)18-7-10-21-22(14-18)37-15-36-21;/h5-10,12-14H,11,15H2,1-4H3,(H,30,31);/q;+1/p-1/b25-20-;
  • InChiKey: ZLHQEGFYBMZQGM-RKVLWQGQSA-M  


Substructure search Similarity search

Network

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Synonyms

  • sodium (Z)-2-(1,3-benzodioxol-5-yl)-4-(4-methoxyphenyl)-4-oxo-3-[(3,4,5-trimethoxyphenyl)methyl]-2-butenoate
  • sodium (Z)-2-(1,3-benzodioxol-5-yl)-4-keto-4-(4-methoxyphenyl)-3-(3,4,5-trimethoxybenzyl)but-2-enoate
  • PD 156707

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens endothelin receptor type B Starlite/ChEMBL References
Sus scrofa Endothelin receptor ET-B Starlite/ChEMBL References
Rattus norvegicus Endothelin receptor ET-A 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
Onchocerca volvulus Endothelin receptor ET-B   443 aa 371 aa 20.5 %
Echinococcus multilocularis pyroglutamylated rfamide peptide receptor Endothelin receptor ET-A   426 aa 412 aa 21.1 %
Schistosoma japonicum ko:K04135 adrenergic receptor, alpha 1a, putative Endothelin receptor ET-B   443 aa 392 aa 23.5 %
Echinococcus granulosus pyroglutamylated rfamide peptide receptor Endothelin receptor ET-A   426 aa 412 aa 20.1 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Loa Loa (eye worm) inositol-1 0.0037 0.1043 0.1043
Echinococcus granulosus nuclear receptor 2DBD gamma 0.0025 0.0522 0.0758
Brugia malayi RhoGAP domain containing protein 0.0063 0.2212 0.2212
Echinococcus multilocularis ATP dependent Clp protease proteolytic subunit 0.0078 0.2861 0.4158
Loa Loa (eye worm) hypothetical protein 0.0025 0.0522 0.0522
Onchocerca volvulus 0.0025 0.0522 1
Echinococcus multilocularis hepatocyte nuclear factor 4 alpha 0.0025 0.0522 0.0758
Plasmodium falciparum ATP-dependent Clp protease proteolytic subunit 0.0078 0.2861 1
Brugia malayi RhoGAP domain containing protein 0.0073 0.2655 0.2655
Schistosoma mansoni retinoic acid receptor RXR 0.0025 0.0522 0.0758
Echinococcus multilocularis Polycystic kidney disease protein 0.002 0.0284 0.0413
Schistosoma mansoni nuclear hormone receptor 0.0025 0.0522 0.0758
Echinococcus multilocularis FTZ F1 nuclear receptor protein 0.0025 0.0522 0.0758
Brugia malayi Nuclear hormone receptor family member nhr-41 0.0025 0.0522 0.0522
Loa Loa (eye worm) hypothetical protein 0.0025 0.0522 0.0522
Brugia malayi Nuclear hormone receptor family member nhr-31 0.0025 0.0522 0.0522
Schistosoma mansoni thyroid hormone receptor 0.0025 0.0522 0.0758
Brugia malayi hypothetical protein 0.0071 0.2551 0.2551
Trypanosoma cruzi myo-inositol-1(or 4)-monophosphatase 1, putative 0.0037 0.1043 0.5
Schistosoma mansoni lipoxygenase 0.0117 0.4611 0.6702
Onchocerca volvulus Protein ultraspiracle homolog 0.0025 0.0522 1
Echinococcus granulosus hepatocyte nuclear factor 4 alpha 0.0025 0.0522 0.0758
Schistosoma mansoni hypothetical protein 0.0168 0.688 1
Loa Loa (eye worm) hypothetical protein 0.0025 0.0522 0.0522
Schistosoma mansoni polycystin 1-related 0.002 0.0284 0.0413
Schistosoma mansoni hypothetical protein 0.002 0.0284 0.0413
Plasmodium vivax ATP-dependent Clp protease proteolytic subunit, putative 0.0078 0.2861 1
Mycobacterium tuberculosis Probable ATP-dependent CLP protease proteolytic subunit 2 ClpP2 (endopeptidase CLP 2) 0.0051 0.1674 1
Entamoeba histolytica hypothetical protein 0.0071 0.2551 1
Echinococcus multilocularis thyroid hormone receptor alpha 0.0025 0.0522 0.0758
Entamoeba histolytica hypothetical protein 0.0071 0.2551 1
Brugia malayi Ligand-binding domain of nuclear hormone receptor family protein 0.0025 0.0522 0.0522
Brugia malayi Nuclear hormone receptor family member nhr-19 0.0025 0.0522 0.0522
Trypanosoma cruzi myo-inositol-1(or 4)-monophosphatase 1, putative 0.0037 0.1043 0.5
Loa Loa (eye worm) hypothetical protein 0.0025 0.0522 0.0522
Loa Loa (eye worm) nuclear hormone receptor family member nhr-1 0.0025 0.0522 0.0522
Loa Loa (eye worm) hypothetical protein 0.0073 0.2655 0.2655
Echinococcus granulosus nuclear receptor 2DBD gamma 0.0025 0.0522 0.0758
Brugia malayi Nuclear hormone receptor family member nhr-49 0.0025 0.0522 0.0522
Loa Loa (eye worm) hypothetical protein 0.0025 0.0522 0.0522
Toxoplasma gondii ATP-dependent Clp endopeptidase, proteolytic subunit ClpP domain-containing protein 0.0078 0.2861 1
Schistosoma mansoni inositol monophosphatase 0.0037 0.1043 0.1516
Plasmodium vivax ATP-dependent Clp protease proteolytic subunit, putative 0.0027 0.0603 0.1235
Echinococcus multilocularis FTZ F1 alpha 0.0025 0.0522 0.0758
Echinococcus granulosus RUN 0.002 0.0284 0.0413
Brugia malayi Steroid receptor seven-up type 2 0.0025 0.0522 0.0522
Entamoeba histolytica hypothetical protein 0.0071 0.2551 1
Brugia malayi Doublecortin family protein 0.002 0.0284 0.0284
Echinococcus multilocularis lipoxygenase domain containing protein 0.002 0.0284 0.0413
Echinococcus multilocularis Nuclear hormone receptor family member nhr 41 0.0025 0.0522 0.0758
Echinococcus multilocularis Basic leucine zipper (bZIP) transcription 0.0071 0.2551 0.3708
Loa Loa (eye worm) hypothetical protein 0.0025 0.0522 0.0522
Echinococcus multilocularis Rac GTPase activating protein 1 0.0073 0.2655 0.386
Brugia malayi hypothetical protein 0.002 0.0284 0.0284
Echinococcus multilocularis geminin 0.0168 0.688 1
Echinococcus granulosus Basic leucine zipper bZIP transcription 0.0071 0.2551 0.3708
Echinococcus granulosus peptidase Clp S14 family 0.0051 0.1674 0.2433
Schistosoma mansoni RAR-like nuclear receptor 0.0025 0.0522 0.0758
Brugia malayi Nuclear hormone receptor-like 1 0.0025 0.0522 0.0522
Loa Loa (eye worm) hypothetical protein 0.0063 0.2212 0.2212
Schistosoma mansoni nuclear hormone receptor nor-1/nor-2 0.0025 0.0522 0.0758
Echinococcus multilocularis lipoxygenase domain containing protein 0.002 0.0284 0.0413
Echinococcus granulosus inositol monophosphatase 1 0.0037 0.1043 0.1516
Brugia malayi hypothetical protein 0.002 0.0284 0.0284
Schistosoma mansoni hypothetical protein 0.0168 0.688 1
Mycobacterium ulcerans ATP-dependent Clp protease proteolytic subunit 0.0078 0.2861 1
Wolbachia endosymbiont of Brugia malayi ATP-dependent Clp protease proteolytic subunit 0.0078 0.2861 1
Loa Loa (eye worm) doublecortin family protein 0.002 0.0284 0.0284
Echinococcus granulosus Polycystic kidney disease protein 0.002 0.0284 0.0413
Schistosoma mansoni transcription factor LCR-F1 0.0071 0.2551 0.3708
Echinococcus multilocularis RUN 0.002 0.0284 0.0413
Loa Loa (eye worm) nuclear hormone receptor family member nhr-14 0.0025 0.0522 0.0522
Echinococcus granulosus Nuclear hormone receptor family member nhr 41 0.0025 0.0522 0.0758
Echinococcus granulosus lipoxygenase domain containing protein 0.002 0.0284 0.0413
Loa Loa (eye worm) hypothetical protein 0.0025 0.0522 0.0522
Echinococcus multilocularis ecdysone induced protein 78C 0.0025 0.0522 0.0758
Loa Loa (eye worm) nuclear hormone receptor family member nhr-40 0.0025 0.0522 0.0522
Echinococcus granulosus Rac GTPase activating protein 1 0.0073 0.2655 0.386
Brugia malayi Probable ClpP-like protease 0.0078 0.2861 0.2861
Trichomonas vaginalis myo inositol monophosphatase, putative 0.0037 0.1043 0.5
Schistosoma mansoni loxhd1 0.002 0.0284 0.0413
Schistosoma mansoni rab6-interacting 0.002 0.0284 0.0413
Brugia malayi Nuclear hormone receptor family member nhr-25 0.0025 0.0522 0.0522
Plasmodium falciparum ATP-dependent Clp protease proteolytic subunit 0.0027 0.0603 0.1235
Echinococcus granulosus COUP TF:Svp nuclear hormone receptor 0.0025 0.0522 0.0758
Schistosoma mansoni thyroid hormone receptor 0.0025 0.0522 0.0758
Leishmania major myo-inositol-1(or 4)-monophosphatase 1, putative 0.0037 0.1043 0.5
Schistosoma mansoni nuclear receptor 2DBD-gamma 0.0025 0.0522 0.0758
Brugia malayi Ligand-binding domain of nuclear hormone receptor family protein 0.0025 0.0522 0.0522
Loa Loa (eye worm) steroid hormone receptor 0.0025 0.0522 0.0522
Schistosoma mansoni steroid hormone receptor ad4bp 0.0025 0.0522 0.0758
Schistosoma mansoni inositol monophosphatase 0.0037 0.1043 0.1516
Brugia malayi Nuclear hormone receptor family member nhr-14 0.0025 0.0522 0.0522
Echinococcus granulosus arachidonate 5 lipoxygenase 0.0117 0.4611 0.6702
Mycobacterium leprae PROBABLE ATP-DEPENDENT CLP PROTEASE PROTEOLYTIC SUBUNIT 1 CLPP1 (ENDOPEPTIDASE CLP) 0.0051 0.1674 0.4744
Brugia malayi Nuclear hormone receptor family member nhr-40 0.0025 0.0522 0.0522
Echinococcus granulosus geminin 0.0168 0.688 1
Loa Loa (eye worm) follicle stimulating hormone receptor 0.0239 1 1
Toxoplasma gondii inositol(myo)-1(or 4)-monophosphatase 2, putative 0.0037 0.1043 0.1949
Loa Loa (eye worm) hypothetical protein 0.002 0.0284 0.0284
Loa Loa (eye worm) nuclear hormone receptor family member nhr-31 0.0025 0.0522 0.0522
Chlamydia trachomatis ATP-dependent Clp protease proteolytic subunit 0.0078 0.2861 0.5
Schistosoma mansoni rac gtpase activating protein 0.0073 0.2655 0.386
Chlamydia trachomatis ATP-dependent Clp protease proteolytic subunit 0.0078 0.2861 0.5
Brugia malayi nuclear receptor NHR-88 0.0025 0.0522 0.0522
Giardia lamblia Rho GAP, putative 0.0063 0.2212 0.5
Brugia malayi steroid hormone receptor 0.0025 0.0522 0.0522
Echinococcus multilocularis peptidase Clp (S14 family) 0.0051 0.1674 0.2433
Echinococcus multilocularis nuclear receptor 2DBD gamma 0.0025 0.0522 0.0758
Echinococcus multilocularis COUP TF:Svp nuclear hormone receptor 0.0025 0.0522 0.0758
Mycobacterium leprae PROBABLE ATP-DEPENDENT CLP PROTEASE PROTEOLYTIC SUBUNIT 2 CLPP2 (ENDOPEPTIDASE CLP 2) 0.0078 0.2861 1
Echinococcus granulosus lipoxygenase domain containing protein 0.002 0.0284 0.0413
Echinococcus multilocularis nuclear receptor 2DBD gamma 0.0025 0.0522 0.0758
Loa Loa (eye worm) hypothetical protein 0.0078 0.2861 0.2861
Entamoeba histolytica hypothetical protein 0.0071 0.2551 1
Loa Loa (eye worm) hypothetical protein 0.0025 0.0522 0.0522
Brugia malayi Inositol-1 0.0037 0.1043 0.1043
Echinococcus granulosus retinoic acid receptor rxr beta a 0.0025 0.0522 0.0758
Schistosoma mansoni rab6-interacting 0.002 0.0284 0.0413
Trypanosoma brucei inositol-1(or 4)-monophosphatase 1, putative 0.0037 0.1043 0.5
Schistosoma mansoni coup transcription factor 0.0025 0.0522 0.0758
Brugia malayi Nuclear hormone receptor family member nhr-19 0.0025 0.0522 0.0522
Brugia malayi Nuclear hormone receptor family member nhr-25 0.0025 0.0522 0.0522
Echinococcus multilocularis inositol monophosphatase 1 0.0037 0.1043 0.1516
Schistosoma mansoni peptidase Clp (S14 family) 0.0078 0.2861 0.4158
Brugia malayi Nuclear hormone receptor family member nhr-1 0.0025 0.0522 0.0522
Schistosoma mansoni hypothetical protein 0.0071 0.2551 0.3708
Mycobacterium leprae possible inositol monophosphatase SubH (IMPase) (inositol-1-phosphatase) (I-1-Pase ). 0.0033 0.0872 0.1194
Treponema pallidum ATP-dependent Clp protease proteolytic subunit 0.0078 0.2861 1
Echinococcus multilocularis arachidonate 5 lipoxygenase 0.0117 0.4611 0.6702
Brugia malayi ecdysteroid receptor 0.0025 0.0522 0.0522
Brugia malayi photoreceptor-specific nuclear receptor 0.0025 0.0522 0.0522
Mycobacterium ulcerans ATP-dependent Clp protease proteolytic subunit 0.0078 0.2861 1
Brugia malayi nuclear hormone receptor 0.0025 0.0522 0.0522
Mycobacterium tuberculosis Probable ATP-dependent CLP protease proteolytic subunit 1 ClpP1 (endopeptidase CLP) 0.0051 0.1674 1
Loa Loa (eye worm) hypothetical protein 0.002 0.0284 0.0284
Trichomonas vaginalis inositol monophosphatase, putative 0.0037 0.1043 0.5
Loa Loa (eye worm) nuclear hormone receptor family member nhr-41 0.0025 0.0522 0.0522
Schistosoma mansoni Tr4/Tr2 (homologue) 0.0025 0.0522 0.0758
Schistosoma mansoni retinoid-x-receptor (RXR) 0.0025 0.0522 0.0758
Brugia malayi Nuclear hormone receptor family member nhr-3 0.0025 0.0522 0.0522
Onchocerca volvulus Bile acid receptor homolog 0.0025 0.0522 1
Schistosoma mansoni FTZ-F1 nuclear receptor-like protein 0.0025 0.0522 0.0758
Loa Loa (eye worm) nuclear Hormone Receptor family member 0.0025 0.0522 0.0522
Loa Loa (eye worm) nuclear hormone receptor family member nhr-49 0.0025 0.0522 0.0522
Echinococcus granulosus FTZ F1 nuclear receptor protein 0.0025 0.0522 0.0758
Schistosoma mansoni lipoxygenase 0.0082 0.3048 0.443
Echinococcus granulosus ecdysone induced protein 78C 0.0025 0.0522 0.0758
Trichomonas vaginalis myo inositol monophosphatase, putative 0.0037 0.1043 0.5
Schistosoma mansoni photoreceptor-specific nuclear receptor related 0.0025 0.0522 0.0758
Echinococcus granulosus ATP dependent Clp protease proteolytic subunit 0.0078 0.2861 0.4158
Toxoplasma gondii ATP-dependent Clp endopeptidase, proteolytic subunit ClpP domain-containing protein 0.0078 0.2861 1
Echinococcus granulosus FTZ F1 alpha 0.0025 0.0522 0.0758
Onchocerca volvulus Steroid hormone receptor family member cnr14 homolog 0.0025 0.0522 1

Activities

Activity type Activity value Assay description Source Reference
Aqueous solubility > 125 ng ml-1 Aqueous solubility of the compound was determined in pH 7.4 phosphate buffer ChEMBL. 10377221
F (ADMET) = 41 % Bioavailability in rat ChEMBL. 9703472
IC50 (functional) = 0.31 nM Antagonistic activity against human Endothelin A receptor expressed in LtK ChEMBL. 7731010
IC50 (functional) = 0.31 nM Antagonistic activity against human Endothelin A receptor expressed in LtK ChEMBL. 7731010
IC50 (binding) = 1.3 nM In vitro ability to inhibit specific [125I]-ET-1 binding to rat aorta membranes Endothelin A receptor ChEMBL. 9873432
IC50 (binding) = 1.3 nM In vitro ability to inhibit specific [125I]-ET-1 binding to rat aorta membranes Endothelin A receptor ChEMBL. 9873432
IC50 (binding) = 340 nM In vitro ability to inhibit specific [125I]-ET-1 binding to porcine kidney (inner medulla) membranes Endothelin B receptor ChEMBL. 9873432
IC50 (binding) = 340 nM In vitro ability to inhibit specific [125I]-ET-1 binding to porcine kidney (inner medulla) membranes Endothelin B receptor ChEMBL. 9873432
IC50 (functional) = 417 nM Tested for antagonistic activity against Endothelin B receptor in the humans (CHO expressed). ChEMBL. 7731010
IC50 (functional) = 417 nM Tested for antagonistic activity against Endothelin B receptor in the humans (CHO expressed). ChEMBL. 7731010
Kd (functional) = 7.6 pA2 value of the compound towards endothelin receptor A was determined as functional ETA antagonism ChEMBL. 9871621
Ki (binding) = 0.17 nM Tested for binding affinity for human Endothelin A receptor by measuring its ability to displace [125I]-ET-1 from chinese hamster ovary cells(CHO) ChEMBL. 9703472
Ki (binding) = 0.17 nM Tested for binding affinity for human Endothelin A receptor by measuring its ability to displace [125I]-ET-1 from chinese hamster ovary cells(CHO) ChEMBL. 9703472
Ki (binding) = 139 nM Tested for binding affinity for human Endothelin B receptor by measuring its ability to displace [125I]-ET-3 from chinese hamster ovary cells(CHO) ChEMBL. 9703472
Ki (binding) = 139 nM Tested for binding affinity for human Endothelin B receptor by measuring its ability to displace [125I]-ET-3 from chinese hamster ovary cells(CHO) ChEMBL. 9703472
pA2 (functional) < 5.5 Compound was evaluated for the functional assay performed by obtaining ET-1 concentration-response curves [pA2(ETB)] in isolated rabbit jugularis vein ChEMBL. 9873432
pA2 (functional) = 7.6 pA2 value of the compound towards endothelin receptor A was determined as functional ETA antagonism ChEMBL. 9871621
pA2 (functional) = 7.6 Compound was evaluated for the functional assay performed by obtaining ET-1 concentration-response curves [pA2(ETA)] in isolated rat aortic rings ChEMBL. 9873432
T1/2 (ADMET) = 1 hr Pharmacokinetic profile-half life of the compound was evaluated in rats upon intravenous administration ChEMBL. 9703472

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.
 
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External resources for this compound

Bibliographic References

5 literature references were collected for this gene.

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