Detailed information for compound 342309

Basic information

Technical information
  • TDR Targets ID: 342309
  • Name: 3-[[5-(1-adamantyloxymethyl)-2-cyclohexyl-1H- imidazole-4-carbonyl]amino]benzoic acid
  • MW: 477.595 | Formula: C28H35N3O4
  • H donors: 3 H acceptors: 4 LogP: 5.32 Rotable bonds: 8
    Rule of 5 violations (Lipinski): 1
  • SMILES: O=C(c1nc([nH]c1COC12CC3CC(C2)CC(C1)C3)C1CCCCC1)Nc1cccc(c1)C(=O)O
  • InChi: 1S/C28H35N3O4/c32-26(29-22-8-4-7-21(12-22)27(33)34)24-23(30-25(31-24)20-5-2-1-3-6-20)16-35-28-13-17-9-18(14-28)11-19(10-17)15-28/h4,7-8,12,17-20H,1-3,5-6,9-11,13-16H2,(H,29,32)(H,30,31)(H,33,34)
  • InChiKey: RKPUHYCGNGSOCF-UHFFFAOYSA-N  


Substructure search Similarity search

Network

Hover on a compound node to display the structore

Synonyms

  • 3-[[[5-(1-adamantyloxymethyl)-2-cyclohexyl-1H-imidazol-4-yl]-oxomethyl]amino]benzoic acid
  • 3-[[5-(1-adamantyloxymethyl)-2-cyclohexyl-1H-imidazol-4-yl]carbonylamino]benzoic acid
  • 3-[[5-(1-adamantyloxymethyl)-2-cyclohexyl1H-imidazole-4-carbonyl]amino]benzoic acid

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens cholecystokinin A receptor Starlite/ChEMBL References
Canis lupus familiaris Cholecystokinin B receptor Starlite/ChEMBL References
Homo sapiens cholecystokinin B receptor Starlite/ChEMBL References
Mus musculus cholecystokinin B receptor Starlite/ChEMBL References
Rattus norvegicus Cholecystokinin B receptor Starlite/ChEMBL References
Cavia porcellus Cholecystokinin A receptor Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Brugia malayi hypothetical protein Get druggable targets OG5_132882 All targets in OG5_132882
Brugia malayi sulfakinin receptor protein Get druggable targets OG5_132882 All targets in OG5_132882
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_132882 All targets in OG5_132882
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Echinococcus multilocularis orexin receptor type 2 Cholecystokinin A receptor   430 aa 381 aa 23.6 %
Schistosoma japonicum ko:K04136 adrenergic receptor, alpha 1b, putative Cholecystokinin A receptor   430 aa 375 aa 26.4 %
Loa Loa (eye worm) hypothetical protein Cholecystokinin B receptor   452 aa 389 aa 31.4 %
Onchocerca volvulus Cholecystokinin A receptor   430 aa 410 aa 25.4 %
Schistosoma mansoni biogenic amine (5HT) receptor Cholecystokinin A receptor   430 aa 373 aa 28.4 %
Schistosoma japonicum ko:K04209 neuropeptide Y receptor, invertebrate, putative Cholecystokinin A receptor   430 aa 356 aa 27.5 %
Echinococcus granulosus rhodopsin orphan GPCR cholecystokinin A receptor 428 aa 373 aa 19.6 %
Onchocerca volvulus Phospholipase d-related homolog Cholecystokinin A receptor   430 aa 359 aa 20.9 %
Echinococcus granulosus biogenic amine 5HT receptor Cholecystokinin A receptor   430 aa 428 aa 23.6 %
Echinococcus multilocularis g protein coupled receptor Cholecystokinin A receptor   430 aa 414 aa 23.4 %
Echinococcus granulosus g protein coupled receptor Cholecystokinin A receptor   430 aa 415 aa 23.1 %
Echinococcus multilocularis g protein coupled receptor Cholecystokinin A receptor   430 aa 405 aa 24.2 %
Onchocerca volvulus Cholecystokinin A receptor   430 aa 397 aa 29.0 %
Echinococcus granulosus rhodopsin orphan GPCR Cholecystokinin A receptor   430 aa 363 aa 19.6 %
Schistosoma japonicum FMRFamide receptor, putative Cholecystokinin A receptor   430 aa 364 aa 22.8 %
Echinococcus multilocularis dro:myosuppressin receptor Cholecystokinin A receptor   430 aa 369 aa 23.0 %
Echinococcus multilocularis rhodopsin orphan GPCR Cholecystokinin A receptor   430 aa 363 aa 19.3 %
Schistosoma mansoni rhodopsin-like orphan GPCR Cholecystokinin A receptor   430 aa 378 aa 23.8 %
Schistosoma mansoni peptide (FMRFamide/somatostatin)-like receptor Cholecystokinin A receptor   430 aa 384 aa 21.4 %
Schistosoma japonicum ko:K04207 neuropeptide Y receptor Y5, putative Cholecystokinin A receptor   430 aa 402 aa 26.1 %
Schistosoma japonicum IPR000276,Rhodopsin-like GPCR superfamily,domain-containing Cholecystokinin A receptor   430 aa 382 aa 25.1 %
Schistosoma japonicum ko:K04135 adrenergic receptor, alpha 1a, putative Cholecystokinin A receptor   430 aa 373 aa 27.3 %
Schistosoma mansoni peptide (FMRFamide/neurokinin-3)-like receptor Cholecystokinin A receptor   430 aa 381 aa 21.5 %
Echinococcus granulosus orexin receptor type 2 Cholecystokinin A receptor   430 aa 383 aa 23.2 %
Echinococcus granulosus g protein coupled receptor Cholecystokinin A receptor   430 aa 398 aa 23.9 %
Schistosoma japonicum IPR000276,Rhodopsin-like GPCR superfamily,domain-containing Cholecystokinin A receptor   430 aa 383 aa 22.7 %
Echinococcus multilocularis neuropeptides capa receptor Cholecystokinin A receptor   430 aa 414 aa 19.8 %
Echinococcus multilocularis serotonin receptor Cholecystokinin A receptor   430 aa 427 aa 23.7 %
Onchocerca volvulus Mitochondrial inner membrane protein homolog Cholecystokinin A receptor   430 aa 363 aa 24.5 %
Schistosoma japonicum ko:K04145 dopamine receptor D2, putative Cholecystokinin A receptor   430 aa 395 aa 24.8 %
Echinococcus granulosus dro:myosuppressin receptor Cholecystokinin A receptor   430 aa 369 aa 23.0 %
Onchocerca volvulus Cholecystokinin A receptor   430 aa 377 aa 22.3 %
Onchocerca volvulus Forkhead box protein biniou homolog Cholecystokinin A receptor   430 aa 353 aa 22.1 %
Schistosoma mansoni amine GPCR Cholecystokinin A receptor   430 aa 409 aa 24.7 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Schistosoma mansoni polycystin 1-related 0.0111 0.0335 0.0815
Onchocerca volvulus 0.0903 0.3808 0.3431
Loa Loa (eye worm) matrixin family protein 0.1539 0.66 1
Loa Loa (eye worm) hypothetical protein 0.0637 0.2642 0.3998
Brugia malayi Eukaryotic-type carbonic anhydrase family protein 0.0431 0.1739 0.263
Echinococcus multilocularis tyrosine protein kinase Fyn 0.0039 0.0021 0.0021
Echinococcus granulosus carbonic anhydrase II 0.0917 0.3872 0.3872
Brugia malayi Matrix metalloprotease, N-terminal domain containing protein 0.0775 0.325 0.4921
Echinococcus granulosus proto oncogene tyrosine protein kinase LCK 0.0039 0.0021 0.0021
Brugia malayi Matrixin family protein 0.0637 0.2642 0.3998
Brugia malayi Eukaryotic-type carbonic anhydrase family protein 0.0431 0.1739 0.263
Echinococcus multilocularis tyrosine protein kinase Fyn 0.0039 0.0021 0.0021
Mycobacterium ulcerans hydrolase 0.0775 0.325 0.5
Echinococcus multilocularis proto oncogene tyrosine protein kinase LCK 0.0039 0.0021 0.0021
Toxoplasma gondii hypothetical protein 0.0431 0.1739 0.5
Echinococcus multilocularis carbonic anhydrase II 0.0917 0.3872 0.3872
Loa Loa (eye worm) matrixin family protein 0.1412 0.6042 0.9154
Echinococcus multilocularis tyrosine protein kinase Src42A 0.0039 0.0021 0.0021
Loa Loa (eye worm) SRC-1 0.0039 0.0021 0.0025
Brugia malayi Matrixin family protein 0.0637 0.2642 0.3998
Loa Loa (eye worm) hypothetical protein 0.0637 0.2642 0.3998
Loa Loa (eye worm) hypothetical protein 0.0528 0.2166 0.3277
Echinococcus multilocularis tyrosine protein kinase Src64B 0.0039 0.0021 0.0021
Schistosoma mansoni hypothetical protein 0.0903 0.3808 0.9835
Echinococcus granulosus tyrosine kinase|tyrosine protein kinase Fyn 0.0035 0.0005 0.0005
Schistosoma mansoni matrix metallopeptidase-9 (M10 family) 0.0526 0.2156 0.5545
Echinococcus multilocularis tyrosine protein kinase lyn tyrosine protein kinase blk 0.0039 0.0021 0.0021
Echinococcus multilocularis tyrosine protein kinase Fyn 0.0039 0.0021 0.0021
Echinococcus granulosus carbonic anhydrase 0.0431 0.1739 0.1739
Loa Loa (eye worm) carbonic anhydrase 3 0.0917 0.3872 0.5863
Schistosoma mansoni matrix metallopeptidase-7 (M10 family) 0.0637 0.2642 0.6805
Echinococcus granulosus tyrosine protein kinase Fyn 0.0039 0.0021 0.0021
Schistosoma mansoni carbonic anhydrase-related 0.0431 0.1739 0.4462
Brugia malayi Carbonic anhydrase like protein 2 precursor 0.0431 0.1739 0.263
Echinococcus granulosus carbonic anhydrase 0.0431 0.1739 0.1739
Echinococcus granulosus tyrosine protein kinase Blk 0.0035 0.0005 0.0005
Echinococcus multilocularis carbonic anhydrase 0.0431 0.1739 0.1739
Schistosoma mansoni carbonic anhydrase II (carbonate dehydratase II) 0.0917 0.3872 1
Trypanosoma brucei carbonic anhydrase-like protein 0.0917 0.3872 0.5
Loa Loa (eye worm) eukaryotic-type carbonic anhydrase 0.0431 0.1739 0.263
Loa Loa (eye worm) matrix metalloproteinase 0.0637 0.2642 0.3998
Schistosoma mansoni carbonic anhydrase 0.0431 0.1739 0.4462
Schistosoma mansoni carbonic anhydrase-related 0.0431 0.1739 0.4462
Echinococcus granulosus tyrosine kinase 0.0035 0.0005 0.0005
Brugia malayi Putative carbonic anhydrase 5 precursor 0.0917 0.3872 0.5863
Loa Loa (eye worm) hypothetical protein 0.0431 0.1739 0.263
Echinococcus multilocularis tyrosine protein kinase Fyn 0.0035 0.0005 0.0005
Echinococcus multilocularis tyrosine protein kinase Blk 0.0035 0.0005 0.0005
Wolbachia endosymbiont of Brugia malayi extracellular metallopeptidase 0.1258 0.5368 0.5
Mycobacterium leprae PROBABLE HYDROLASE 0.0775 0.325 0.5
Brugia malayi Matrixin family protein 0.0637 0.2642 0.3998
Echinococcus granulosus tyrosine protein kinase Fyn 0.0039 0.0021 0.0021
Onchocerca volvulus Matrix metalloproteinase homolog 0.1412 0.6042 1
Echinococcus granulosus 3'partial|tyrosine protein kinase Fgr 0.0039 0.0021 0.0021
Brugia malayi sulfakinin receptor protein 0.0528 0.2166 0.3277
Schistosoma mansoni hypothetical protein 0.0431 0.1739 0.4462
Plasmodium falciparum carbonic anhydrase 0.0431 0.1739 0.5
Mycobacterium tuberculosis Probable peptidoglycan hydrolase 0.0775 0.325 0.5
Brugia malayi Matrixin family protein 0.1539 0.66 1
Onchocerca volvulus Matrilysin homolog 0.1412 0.6042 1
Echinococcus granulosus tyrosine protein kinase Src64B 0.0039 0.0021 0.0021
Echinococcus granulosus tyrosine protein kinase Fyn 0.0039 0.0021 0.0021
Loa Loa (eye worm) eukaryotic-type carbonic anhydrase 0.0917 0.3872 0.5863
Schistosoma mansoni carbonic anhydrase II (carbonate dehydratase II) 0.0917 0.3872 1
Brugia malayi Matrixin family protein 0.0637 0.2642 0.3998
Schistosoma mansoni carbonic anhydrase-related 0.0431 0.1739 0.4462
Brugia malayi SRC-1 0.0039 0.0021 0.0025
Echinococcus multilocularis carbonic anhydrase 0.0431 0.1739 0.1739
Echinococcus multilocularis tyrosine protein kinase Fgr 0.0039 0.0021 0.0021
Echinococcus multilocularis matrix metallopeptidase 7 (M10 family) 0.2315 1 1
Echinococcus granulosus tyrosine protein kinase Lyn 0.0039 0.0021 0.0021
Echinococcus granulosus tyrosine protein kinase Src42A 0.0039 0.0021 0.0021
Loa Loa (eye worm) hypothetical protein 0.0431 0.1739 0.263
Loa Loa (eye worm) hypothetical protein 0.0637 0.2642 0.3998
Brugia malayi hypothetical protein 0.0528 0.2166 0.3277
Brugia malayi Eukaryotic-type carbonic anhydrase family protein 0.0431 0.1739 0.263
Brugia malayi Eukaryotic-type carbonic anhydrase family protein 0.0917 0.3872 0.5863
Echinococcus multilocularis tyrosine protein kinase Srms 0.0035 0.0005 0.0005
Trypanosoma cruzi carbonic anhydrase-like protein, putative 0.0917 0.3872 0.5
Loa Loa (eye worm) hypothetical protein 0.0775 0.325 0.4921
Echinococcus multilocularis tyrosine protein kinase lyn lyn a protein tyrosine kinase lymphocyte specific protein tyrosine kinase 0.0039 0.0021 0.0021
Loa Loa (eye worm) hypothetical protein 0.0431 0.1739 0.263
Brugia malayi Hemopexin family protein 0.0903 0.3808 0.5767
Trypanosoma cruzi carbonic anhydrase-like protein, putative 0.0917 0.3872 0.5
Leishmania major carbonic anhydrase-like protein 0.0917 0.3872 0.5
Brugia malayi Carbonic anhydrase like protein 2 precursor 0.0431 0.1739 0.263
Echinococcus granulosus carbonic anhydrase 0.0431 0.1739 0.1739
Echinococcus multilocularis carbonic anhydrase 0.0431 0.1739 0.1739

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = -7.71 Concentration required to inhibit the binding of [125I]-BH-CCK-8S radioligand to canine gastric mucosa CCK2 receptor ChEMBL. 16250639
Inhibition (binding) = 63 % Percent inhibition (i.d., 3.0 mg/Kg) against dog CCK2 receptor ChEMBL. 16250639
Inhibition (binding) = 63 % Percent inhibition (i.d., 3.0 mg/Kg) against dog CCK2 receptor ChEMBL. 16250639
Inhibition (functional) = 66 % Inhibition of pentagastrin-stimulated gastric acid secretion in conscious gastric fistula dog at 1 mg/kg, iv ChEMBL. 17536796
Inhibition (functional) = 66 % Inhibition of pentagastrin-stimulated gastric acid secretion in conscious gastric fistula dog at 1 mg/kg, iv ChEMBL. 17536796
Inhibition (binding) = 76 % Percent inhibition (i.v., 1.0 mg/Kg) against dog CCK2 receptor ChEMBL. 16250639
Inhibition (binding) = 76 % Percent inhibition (i.v., 1.0 mg/Kg) against dog CCK2 receptor ChEMBL. 16250639
Inhibition (functional) = 97 % Inhibition of pentagastrin-stimulated gastric acid secretion in conscious gastric fistula dog at 0.05 mg/kg, iv ChEMBL. 17536796
Inhibition (functional) = 97 % Inhibition of pentagastrin-stimulated gastric acid secretion in conscious gastric fistula dog at 0.05 mg/kg, iv ChEMBL. 17536796
Kd (functional) = 9.06 Antagonist activity against CCK2 receptor estimated from single shifts of pentagastrin concentration-effect curves in the isolated rat stomach ChEMBL. 16250639
Kd (functional) = 9.06 Antagonist activity at CCK2 receptor in perfused rat stomach assessed as inhibition of pentagastrin-stimulated gastric acid secretion ChEMBL. 17536796
Ki (functional) = -7.94 Displacement of [125I]BH-CCK8-8S from CCK2 receptor in canine gastric mucosa ChEMBL. 17536796
Ki (binding) = -7.87 Concentration required to inhibit the binding of 20 pM [125I]-BH-CCK-8S radioligand to mouse cortical membrane CCK2 receptor ChEMBL. 16250639
Ki (binding) = -7.71 Displacement of [3H]BH-CCK-8S from human recombinant CCK2 receptor expressed in NIH3T3 cells ChEMBL. 17536796
Ki (binding) = -6.3 Displacement of [125I]BH-CCK-8S from CC1 receptor expressed in guinea pig pancreatic cells ChEMBL. 18201065
Ki (binding) = -6.25 Concentration required to inhibit the binding of 20 pM [125I]-BH-CCK-8S radioligand to guinea pig pancreas CCK1 receptor ChEMBL. 16250639
Ki (binding) < -5 Displacement of [3H]L-364,718 from human recombinant CCK1 receptor expressed in PC3 cells ChEMBL. 17536796
Log IC50 (binding) = 7.71 Concentration required to inhibit the binding of [125I]-BH-CCK-8S radioligand to canine gastric mucosa CCK2 receptor ChEMBL. 16250639
Log Ki (binding) < 5 Displacement of [3H]L-364,718 from human recombinant CCK1 receptor expressed in PC3 cells ChEMBL. 17536796
Log Ki (binding) = 6.25 Concentration required to inhibit the binding of 20 pM [125I]-BH-CCK-8S radioligand to guinea pig pancreas CCK1 receptor ChEMBL. 16250639
Log Ki (binding) = 6.3 Displacement of [125I]BH-CCK-8S from CC1 receptor expressed in guinea pig pancreatic cells ChEMBL. 18201065
Log Ki (binding) = 7.71 Displacement of [3H]BH-CCK-8S from human recombinant CCK2 receptor expressed in NIH3T3 cells ChEMBL. 17536796
Log Ki (binding) = 7.87 Concentration required to inhibit the binding of 20 pM [125I]-BH-CCK-8S radioligand to mouse cortical membrane CCK2 receptor ChEMBL. 16250639
Log Ki (functional) = 7.94 Displacement of [125I]BH-CCK8-8S from CCK2 receptor in canine gastric mucosa ChEMBL. 17536796
logD = 2.73 Lipophilicity was measured in octanol/buffer (pH 7.4) in dog ChEMBL. 16250639
pA2 (functional) = 9.06 Antagonist activity against CCK2 receptor estimated from single shifts of pentagastrin concentration-effect curves in the isolated rat stomach ChEMBL. 16250639
pA2 (functional) = 9.06 Antagonist activity at CCK2 receptor in perfused rat stomach assessed as inhibition of pentagastrin-stimulated gastric acid secretion ChEMBL. 17536796
pKb (functional) = 9.1 Antagonist activity at CCK2 receptor in stomach-lumen perfused immature rat ChEMBL. 18201065
pKb (functional) = 9.1 Antagonist activity at CCK2 receptor in stomach-lumen perfused immature rat ChEMBL. 18201065

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

3 literature references were collected for this gene.

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