Detailed information for compound 53525

Basic information

Technical information
  • TDR Targets ID: 53525
  • Name: (E)-2-benzyl-3-[2-butyl-3-[(2-chlorophenyl)me thyl]imidazol-4-yl]prop-2-enoic acid
  • MW: 408.921 | Formula: C24H25ClN2O2
  • H donors: 1 H acceptors: 3 LogP: 5.89 Rotable bonds: 9
    Rule of 5 violations (Lipinski): 1
  • SMILES: CCCCc1ncc(n1Cc1ccccc1Cl)/C=C(/C(=O)O)\Cc1ccccc1
  • InChi: 1S/C24H25ClN2O2/c1-2-3-13-23-26-16-21(27(23)17-19-11-7-8-12-22(19)25)15-20(24(28)29)14-18-9-5-4-6-10-18/h4-12,15-16H,2-3,13-14,17H2,1H3,(H,28,29)/b20-15+
  • InChiKey: MNKLESADFMVAAA-HMMYKYKNSA-N  


Substructure search Similarity search

Network

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Synonyms

  • (E)-2-benzyl-3-[2-butyl-3-[(2-chlorophenyl)methyl]-4-imidazolyl]-2-propenoic acid
  • (E)-3-[2-butyl-3-[(2-chlorophenyl)methyl]imidazol-4-yl]-2-(phenylmethyl)prop-2-enoic acid
  • (E)-2-benzyl-3-[2-butyl-3-(2-chlorobenzyl)imidazol-4-yl]acrylic acid
  • (E)-3-[2-butyl-3-[(2-chlorophenyl)methyl]-4-imidazolyl]-2-(phenylmethyl)prop-2-enoic acid
  • (E)-2-(benzyl)-3-[2-butyl-3-(2-chlorobenzyl)imidazol-4-yl]acrylic acid

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Rattus norvegicus Type-1B angiotensin II receptor Starlite/ChEMBL References
Rattus norvegicus Angiotensin II type 2 (AT-2) 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
Species Potential target Known druggable target Length Alignment span Identity
Onchocerca volvulus Type-1B angiotensin II receptor   359 aa 309 aa 18.8 %
Echinococcus multilocularis neuropeptide receptor Angiotensin II type 2 (AT-2) receptor   363 aa 308 aa 21.4 %
Echinococcus granulosus allatostatin A receptor Angiotensin II type 2 (AT-2) receptor   363 aa 340 aa 24.1 %
Loa Loa (eye worm) hypothetical protein Type-1B angiotensin II receptor   359 aa 329 aa 24.0 %
Echinococcus granulosus tm gpcr rhodopsin Type-1B angiotensin II receptor   359 aa 300 aa 21.0 %
Loa Loa (eye worm) neuropeptide F receptor Angiotensin II type 2 (AT-2) receptor   363 aa 356 aa 23.3 %
Onchocerca volvulus Type-1B angiotensin II receptor   359 aa 355 aa 23.9 %
Schistosoma japonicum Rhodopsin, putative Angiotensin II type 2 (AT-2) receptor   363 aa 341 aa 22.0 %
Onchocerca volvulus E3 ubiquitin-protein ligase rpm-1 homolog Type-1B angiotensin II receptor   359 aa 354 aa 20.6 %
Schistosoma mansoni adenoreceptor Angiotensin II type 2 (AT-2) receptor   363 aa 328 aa 22.0 %
Echinococcus multilocularis allatostatin A receptor Angiotensin II type 2 (AT-2) receptor   363 aa 342 aa 24.6 %
Echinococcus multilocularis tm gpcr rhodopsin gpcr rhodopsin superfamily Type-1B angiotensin II receptor   359 aa 300 aa 21.0 %
Echinococcus granulosus thyrotropin releasing hormone receptor Angiotensin II type 2 (AT-2) receptor   363 aa 308 aa 22.1 %
Schistosoma japonicum ko:K04209 neuropeptide Y receptor, invertebrate, putative Angiotensin II type 2 (AT-2) receptor   363 aa 310 aa 23.5 %
Echinococcus multilocularis thyrotropin releasing hormone receptor Angiotensin II type 2 (AT-2) receptor   363 aa 308 aa 21.8 %
Brugia malayi ORL1-like opioid receptor Type-1B angiotensin II receptor   359 aa 314 aa 20.4 %
Schistosoma mansoni peptide (FMRFamide/somatostatin)-like receptor Type-1B angiotensin II receptor   359 aa 346 aa 18.2 %
Brugia malayi putative neuropeptide receptor NPR1 Type-1B angiotensin II receptor   359 aa 295 aa 27.1 %
Schistosoma mansoni peptide (allatostatin)-like receptor Angiotensin II type 2 (AT-2) receptor   363 aa 364 aa 20.9 %
Echinococcus multilocularis pyroglutamylated rfamide peptide receptor Angiotensin II type 2 (AT-2) receptor   363 aa 398 aa 18.1 %
Onchocerca volvulus Angiotensin II type 2 (AT-2) receptor   363 aa 311 aa 23.8 %
Echinococcus granulosus growth hormone secretagogue receptor type 1 Type-1B angiotensin II receptor   359 aa 343 aa 23.0 %
Schistosoma mansoni biogenic amine (octopamine/dopamine) receptor Type-1B angiotensin II receptor   359 aa 350 aa 23.1 %
Schistosoma japonicum ko:K04134 cholinergic receptor, invertebrate, putative Type-1B angiotensin II receptor   359 aa 325 aa 20.9 %
Onchocerca volvulus Type-1B angiotensin II receptor   359 aa 386 aa 24.4 %
Echinococcus granulosus pyroglutamylated rfamide peptide receptor Angiotensin II type 2 (AT-2) receptor   363 aa 398 aa 18.3 %
Loa Loa (eye worm) hypothetical protein Type-1B angiotensin II receptor   359 aa 308 aa 27.6 %
Echinococcus multilocularis G-protein coupled receptor, putative Type-1B angiotensin II receptor   359 aa 307 aa 22.1 %
Echinococcus granulosus neuropeptide receptor Angiotensin II type 2 (AT-2) receptor   363 aa 306 aa 22.2 %
Onchocerca volvulus Type-1B angiotensin II receptor   359 aa 314 aa 25.2 %
Schistosoma mansoni opsin-like receptor Type-1B angiotensin II receptor   359 aa 299 aa 25.8 %
Onchocerca volvulus Type-1B angiotensin II receptor   359 aa 350 aa 24.0 %
Brugia malayi GnHR receptor homolog Type-1B angiotensin II receptor   359 aa 357 aa 20.4 %
Onchocerca volvulus Angiotensin II type 2 (AT-2) receptor   363 aa 305 aa 21.6 %
Onchocerca volvulus Angiotensin II type 2 (AT-2) receptor   363 aa 306 aa 22.5 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Loa Loa (eye worm) Sodium:neurotransmitter symporter family protein 0.0143 0.0188 0.1049
Plasmodium vivax hypothetical protein, conserved 0.0143 0.0188 0.5
Loa Loa (eye worm) norepinephrine transporter 0.0845 0.1794 1
Echinococcus multilocularis insulin receptor 0.0367 0.0699 0.0699
Schistosoma mansoni sodium/chloride dependent transporter 0.0143 0.0188 0.0188
Trypanosoma brucei RNA helicase, putative 0.0083 0.0049 0.0049
Brugia malayi Protein kinase domain containing protein 0.0173 0.0255 0.1422
Leishmania major PIF1 helicase-like protein, putative,DNA repair and recombination protein, mitochondrial precursor, putative 0.4429 1 1
Loa Loa (eye worm) TK/INSR protein kinase 0.0367 0.0699 0.3898
Loa Loa (eye worm) hypothetical protein 0.0845 0.1794 1
Toxoplasma gondii Sodium:neurotransmitter symporter family protein 0.0143 0.0188 1
Echinococcus granulosus sodium:chloride dependent neurotransmitter 0.0143 0.0188 0.0188
Schistosoma mansoni sodium-dependent neurotransmitter transporter 0.0143 0.0188 0.0188
Trypanosoma brucei DNA repair and recombination helicase protein PIF7 0.4429 1 1
Loa Loa (eye worm) hypothetical protein 0.0143 0.0188 0.1049
Schistosoma mansoni sodium/chloride dependent transporter 0.0144 0.0189 0.0189
Schistosoma mansoni hypothetical protein 0.4429 1 1
Echinococcus granulosus uncharacterized sodium dependent transporter 0.0143 0.0188 0.0188
Onchocerca volvulus 0.0845 0.1794 1
Loa Loa (eye worm) hypothetical protein 0.0143 0.0188 0.1049
Toxoplasma gondii Sodium:neurotransmitter symporter family protein 0.0143 0.0188 1
Echinococcus granulosus uncharacterized sodium dependent transporter 0.0143 0.0188 0.0188
Echinococcus granulosus insulin growth factor 1 receptor beta 0.0367 0.0699 0.0699
Echinococcus multilocularis 0.0095 0.0078 0.0078
Brugia malayi Sodium:neurotransmitter symporter family protein 0.0845 0.1794 1
Brugia malayi Sodium:neurotransmitter symporter family protein 0.0143 0.0188 0.1049
Echinococcus granulosus sodium and chloride dependent glycine 0.0143 0.0188 0.0188
Schistosoma mansoni norepinephrine/norepinephrine transporter 0.0845 0.1794 0.1794
Echinococcus granulosus insulin receptor 0.0367 0.0699 0.0699
Schistosoma mansoni tyrosine kinase 0.0233 0.0392 0.0392
Schistosoma mansoni sodium/chloride dependent neurotransmitter transporter 0.0143 0.0188 0.0188
Schistosoma mansoni sodium-dependent neurotransmitter transporter 0.0143 0.0188 0.0188
Schistosoma mansoni tyrosine kinase 0.0367 0.0699 0.0699
Schistosoma mansoni sodium/chloride dependent transporter 0.0845 0.1794 0.1794
Echinococcus multilocularis sodium:chloride dependent neurotransmitter 0.0143 0.0188 0.0188
Schistosoma mansoni hypothetical protein 0.0083 0.0049 0.0049
Echinococcus granulosus melanoma receptor tyrosine protein kinase 0.0236 0.04 0.04
Schistosoma mansoni sodium-dependent neurotransmitter transporter 0.0143 0.0188 0.0188
Schistosoma mansoni tyrosine kinase 0.0233 0.0392 0.0392
Trypanosoma cruzi DNA repair and recombination helicase protein PIF7, putative 0.4429 1 1
Brugia malayi Protein kinase domain containing protein 0.0367 0.0699 0.3898
Loa Loa (eye worm) hypothetical protein 0.0845 0.1794 1
Schistosoma mansoni tyrosine kinase 0.0233 0.0392 0.0392
Schistosoma mansoni family A2 unassigned peptidase (A02 family) 0.0229 0.0385 0.0385
Brugia malayi Sodium:neurotransmitter symporter family protein 0.0143 0.0188 0.1049
Plasmodium falciparum amino acid transporter, putative 0.0143 0.0188 0.5
Schistosoma mansoni norepinephrine/norepinephrine transporter 0.0143 0.0188 0.0188
Loa Loa (eye worm) hypothetical protein 0.0169 0.0247 0.1377
Toxoplasma gondii Sodium:neurotransmitter symporter family protein 0.0143 0.0188 1
Brugia malayi Sodium:neurotransmitter symporter family protein 0.0143 0.0188 0.1049
Echinococcus multilocularis ATP dependent DNA helicase PIF1 0.4429 1 1
Schistosoma mansoni sodium-dependent amino acid transporter 0.0143 0.0188 0.0188
Giardia lamblia Rrm3p helicase 0.4429 1 1
Loa Loa (eye worm) serotonin transporter b 0.0845 0.1794 1
Loa Loa (eye worm) Sodium:neurotransmitter symporter family protein 0.0143 0.0188 0.1049
Leishmania major PIF1 helicase-like protein, putative,DNA repair and recombination protein, mitochondrial precursor, putative 0.4429 1 1
Trichomonas vaginalis conserved hypothetical protein 0.4429 1 1
Echinococcus multilocularis sodium and chloride dependent glycine 0.0143 0.0188 0.0188
Chlamydia trachomatis Ssodium-dependent amino acid transporter 0.0143 0.0188 0.5
Schistosoma mansoni tyrosine kinase 0.0236 0.04 0.04
Echinococcus multilocularis uncharacterized sodium dependent transporter 0.0143 0.0188 0.0188
Schistosoma mansoni intracisternal A-particle retropepsin (A02 family) 0.1262 0.2748 0.2748
Loa Loa (eye worm) TK/EGFR protein kinase 0.0318 0.0587 0.3274
Treponema pallidum sodium- and chloride- dependent transporter 0.0845 0.1794 0.5
Echinococcus multilocularis sodium and chloride dependent glycine 0.0143 0.0188 0.0188
Loa Loa (eye worm) hypothetical protein 0.0845 0.1794 1
Loa Loa (eye worm) hypothetical protein 0.0143 0.0188 0.1049
Loa Loa (eye worm) hypothetical protein 0.0143 0.0188 0.1049
Brugia malayi hypothetical protein 0.0143 0.0188 0.1049
Schistosoma mansoni tyrosine kinase 0.0236 0.04 0.04
Echinococcus multilocularis epidermal growth factor receptor 0.0318 0.0587 0.0587
Schistosoma mansoni sodium/chloride dependent neurotransmitter transporter 0.0143 0.0188 0.0188
Brugia malayi Sodium:neurotransmitter symporter family protein 1, putative 0.0143 0.0188 0.1049
Echinococcus multilocularis sodium dependent neurotransmitter transporter 0.0143 0.0188 0.0188
Entamoeba histolytica DNA repair and recombination protein, putative 0.4429 1 0.5
Loa Loa (eye worm) hypothetical protein 0.0143 0.0188 0.1049
Toxoplasma gondii hypothetical protein 0.0143 0.0188 1
Plasmodium vivax amine transporter, putative 0.0143 0.0188 0.5
Loa Loa (eye worm) solute carrier family 6 member 4 0.0845 0.1794 1
Schistosoma mansoni sodium/chloride dependent neurotransmitter transporter 0.0143 0.0188 0.0188
Schistosoma mansoni tyrosine kinase 0.0367 0.0699 0.0699
Entamoeba histolytica hypothetical protein, conserved 0.4429 1 0.5
Loa Loa (eye worm) hypothetical protein 0.0143 0.0188 0.1049
Trypanosoma brucei DNA repair and recombination helicase protein PIF6 0.4429 1 1
Echinococcus granulosus sodium and chloride dependent glycine 0.0143 0.0188 0.0188
Toxoplasma gondii hypothetical protein 0.0143 0.0188 1
Echinococcus granulosus sodium dependent neurotransmitter transporter 0.0143 0.0188 0.0188
Loa Loa (eye worm) hypothetical protein 0.0143 0.0188 0.1049
Trypanosoma cruzi DNA repair and recombination helicase protein PIF6, putative 0.4429 1 1
Echinococcus granulosus serotonin transporter 0.0845 0.1794 0.1794
Echinococcus multilocularis insulin growth factor 1 receptor beta 0.0367 0.0699 0.0699
Trypanosoma cruzi DNA repair and recombination helicase protein PIF7, putative 0.4429 1 1
Schistosoma mansoni tyrosine kinase 0.0318 0.0587 0.0587
Echinococcus granulosus epidermal growth factor receptor 0.0318 0.0587 0.0587
Echinococcus multilocularis epidermal growth factor receptor 0.0236 0.04 0.04
Plasmodium falciparum transporter, putative 0.0143 0.0188 0.5
Brugia malayi Furin-like cysteine rich region family protein 0.0318 0.0587 0.3274
Schistosoma mansoni norepinephrine/norepinephrine transporter 0.0143 0.0188 0.0188
Echinococcus granulosus epidermal growth factor receptor 0.0236 0.04 0.04
Echinococcus multilocularis serotonin transporter 0.0845 0.1794 0.1794

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 2600 nM In vitro inhibition of [125I]-AII specific binding towards Angiotensin II receptor in rat mesenteric membranes. ChEMBL. 2016730
IC50 (binding) = 2600 nM In vitro inhibition of [125I]-AII specific binding towards Angiotensin II receptor in rat mesenteric membranes. ChEMBL. 2016730
IC50 (binding) = 2.6 uM Inhibition of [125I]-Angiotensin II receptor specific binding to rat mesenteric arteries ChEMBL. 1433195
IC50 (binding) = 2.6 uM Inhibition of [125I]-Angiotensin II receptor specific binding to rat mesenteric arteries ChEMBL. 1433195
IC50 (binding) = 38 uM Inhibition of [125I]-angiotensin II specific binding to rat mesenteric arteries ChEMBL. 1433195
ID50 (functional) = 14 mg kg-1 In vivo inhibition of the pressor response to AII in conscious normotensive rats upon intravenous administration ChEMBL. 2016730
ID50 (functional) = 14 mg kg-1 Compound was evaluated in vivo, for the dose that produced 50% inhibition of the pressor response to AII in conscious normotensive rats after iv administration ChEMBL. 1433195
KB (functional) = 64 nM In vitro inhibition of AII-induced vasoconstriction of rabbit aorta. ChEMBL. 2016730
Kb (functional) = 64 nM In vitro inhibition of AII-induced vasoconstriction of rabbit aorta. ChEMBL. 2016730
Kb (binding) = 0.064 uM Compound was evaluated for the inhibition of AII-induced vasoconstriction of the rabbit aorta ChEMBL. 1433195
Kb (binding) = 0.064 uM Compound was evaluated for the inhibition of AII-induced vasoconstriction of the rabbit aorta ChEMBL. 1433195
Kb (functional) = 8.7 uM Compound was evaluated for the inhibition of AII-induced vasoconstriction of the rabbit aorta ChEMBL. 1433195

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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