Detailed information for compound 254405

Basic information

Technical information
  • TDR Targets ID: 254405
  • Name: (2R)-N-(1-benzylpiperidin-4-yl)-2-[(1R)-3,3-d ifluorocyclopentyl]-2-hydroxy-2-phenylacetami de
  • MW: 428.515 | Formula: C25H30F2N2O2
  • H donors: 2 H acceptors: 2 LogP: 4.26 Rotable bonds: 7
    Rule of 5 violations (Lipinski): 1
  • SMILES: O=C([C@@]([C@@H]1CCC(C1)(F)F)(c1ccccc1)O)NC1CCN(CC1)Cc1ccccc1
  • InChi: 1S/C25H30F2N2O2/c26-24(27)14-11-21(17-24)25(31,20-9-5-2-6-10-20)23(30)28-22-12-15-29(16-13-22)18-19-7-3-1-4-8-19/h1-10,21-22,31H,11-18H2,(H,28,30)/t21-,25+/m1/s1
  • InChiKey: KTCCCXMNJFFEIS-BWKNWUBXSA-N  


Substructure search Similarity search

Network

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Synonyms

  • (2R)-N-(1-benzyl-4-piperidyl)-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenyl-acetamide
  • (2R)-N-(1-benzyl-4-piperidinyl)-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetamide
  • (2R)-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenyl-N-[1-(phenylmethyl)piperidin-4-yl]ethanamide
  • (2R)-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenyl-N-[1-(phenylmethyl)piperidin-4-yl]acetamide
  • (2R)-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenyl-N-[1-(phenylmethyl)-4-piperidyl]acetamide
  • (2R)-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenyl-N-[1-(phenylmethyl)-4-piperidinyl]acetamide
  • (2R)-N-[1-(benzyl)-4-piperidyl]-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenyl-acetamide

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens cholinergic receptor, muscarinic 1 Starlite/ChEMBL References
Homo sapiens cholinergic receptor, muscarinic 2 Starlite/ChEMBL References
Homo sapiens cholinergic receptor, muscarinic 3 Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_133264 All targets in OG5_133264
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_133264 All targets in OG5_133264
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) oxidoreductase 0.076 1 1
Echinococcus granulosus aldo keto reductase family 1 member B4 0.076 1 1
Trichomonas vaginalis aldo/keto reductase, putative 0.076 1 1
Schistosoma mansoni pol-related 0.076 1 1
Trichomonas vaginalis aldo-keto reductase, putative 0.076 1 1
Echinococcus multilocularis snurportin 1 0.0309 0.38 0.3768
Echinococcus granulosus aldo keto reductase 0.076 1 1
Brugia malayi GTP-binding regulatory protein Gs alpha-S chain, putative 0.0046 0.0191 0.0141
Loa Loa (eye worm) nucleolar RNA-associated protein alpha 0.0309 0.38 0.3768
Entamoeba histolytica alcohol dehydrogenase, putative 0.022 0.2585 0.2547
Schistosoma mansoni patched 1 0.0041 0.0122 0.0071
Echinococcus granulosus voltage gated potassium channel subunit 0.022 0.2585 0.2547
Trichomonas vaginalis aldo-keto reductase, putative 0.022 0.2585 0.2547
Toxoplasma gondii oxidoreductase, aldo/keto reductase family protein 0.022 0.2585 0.2547
Loa Loa (eye worm) hypothetical protein 0.0095 0.0867 0.082
Echinococcus multilocularis aldo keto reductase family 1, member B4 0.076 1 1
Wolbachia endosymbiont of Brugia malayi fructose-1,6-bisphosphatase 0.0036 0.0051 0.5
Trichomonas vaginalis alcohol dehydrogenase, putative 0.022 0.2585 0.2547
Plasmodium vivax oxidoreductase, aldo/keto reductase domain containing protein 0.022 0.2585 0.5
Loa Loa (eye worm) hypothetical protein 0.0041 0.0122 0.0071
Schistosoma mansoni Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein) 0.0046 0.0191 0.0141
Echinococcus multilocularis aldo keto reductase 0.076 1 1
Brugia malayi MH2 domain containing protein 0.012 0.1206 0.116
Echinococcus multilocularis guanine nucleotide binding protein G(s) subunit 0.0046 0.0191 0.0141
Trichomonas vaginalis aldo-keto reductase, putative 0.076 1 1
Loa Loa (eye worm) hypothetical protein 0.051 0.6564 0.6546
Echinococcus multilocularis aldo keto reductase 0.076 1 1
Echinococcus granulosus aldo keto reductase family 1 member B4 0.076 1 1
Brugia malayi follicle stimulating hormone receptor 0.0232 0.2751 0.2714
Trichomonas vaginalis aldo-keto reductase, putative 0.076 1 1
Echinococcus granulosus aldo keto reductase family 1 member B4 0.076 1 1
Schistosoma mansoni hypothetical protein 0.0039 0.0102 0.0051
Echinococcus granulosus Niemann Pick C1 protein 0.0095 0.0867 0.082
Echinococcus granulosus Protein patched homolog 1 0.0041 0.0122 0.0071
Trypanosoma brucei aldo-keto reductase, putative 0.076 1 1
Echinococcus multilocularis aldo keto reductase family 1, member B4 0.076 1 1
Echinococcus multilocularis sterol regulatory element binding protein 0.0041 0.0122 0.0071
Trypanosoma brucei prostaglandin f synthase 0.076 1 1
Echinococcus granulosus guanine nucleotide binding protein Gs subunit 0.0046 0.0191 0.0141
Giardia lamblia Aldose reductase 0.076 1 0.5
Toxoplasma gondii aldo/keto reductase family oxidoreductase 0.022 0.2585 0.2547
Schistosoma mansoni Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein) 0.0046 0.0191 0.0141
Echinococcus granulosus aldo keto reductase family 1 member B4 0.076 1 1
Echinococcus multilocularis voltage gated potassium channel subunit 0.022 0.2585 0.2547
Loa Loa (eye worm) GTP-binding regulatory protein Gs alpha-S chain 0.0046 0.0191 0.0141
Loa Loa (eye worm) follicle stimulating hormone receptor 0.0232 0.2751 0.2714
Trichomonas vaginalis aldo/keto reductase, putative 0.076 1 1
Onchocerca volvulus 0.076 1 1
Loa Loa (eye worm) transcription factor SMAD2 0.012 0.1206 0.116
Leishmania major aldo/keto reductase, putative,aldo/keto reductase family-like protein 0.022 0.2585 0.2547
Leishmania major aldo-keto reductase-like protein 0.076 1 1
Echinococcus multilocularis Niemann Pick C1 protein 0.0136 0.1427 0.1383
Echinococcus multilocularis expressed conserved protein 0.0089 0.0788 0.074
Trypanosoma cruzi aldo/keto reductase, putative 0.022 0.2585 0.2547
Mycobacterium leprae Conserved hypothetical protein 0.054 0.6976 0.6976
Echinococcus multilocularis aldo keto reductase family 1, member B4 0.076 1 1
Trypanosoma cruzi aldo-keto reductase 0.076 1 1
Schistosoma mansoni aldo-keto reductase 0.076 1 1
Echinococcus multilocularis aldo keto reductase 0.076 1 1
Echinococcus multilocularis aldo keto reductase 0.076 1 1
Trichomonas vaginalis aldo-keto reductase, putative 0.022 0.2585 0.2547
Schistosoma mansoni potassium channel beta 0.022 0.2585 0.2547
Onchocerca volvulus 0.076 1 1
Mycobacterium leprae PROBABLE OXIDOREDUCTASE 0.076 1 1
Trichomonas vaginalis aldo-keto reductase, putative 0.076 1 1
Echinococcus granulosus expressed conserved protein 0.0089 0.0788 0.074
Trichomonas vaginalis dihydrodiol dehydrogenase, putative 0.076 1 1
Echinococcus multilocularis aldo keto reductase family 1, member B4 0.076 1 1
Brugia malayi Niemann-Pick C1 protein precursor 0.0095 0.0867 0.082
Brugia malayi CHE-14 protein 0.0041 0.0122 0.0071
Trichomonas vaginalis conserved hypothetical protein 0.022 0.2585 0.2547
Entamoeba histolytica aldose reductase, putative 0.076 1 1
Echinococcus multilocularis protein patched 0.0041 0.0122 0.0071
Loa Loa (eye worm) abnormal chemotaxis protein 14 0.0041 0.0122 0.0071
Trichomonas vaginalis aldo-keto reductase, putative 0.076 1 1
Onchocerca volvulus 0.076 1 1
Echinococcus granulosus aldo keto reductase family 1 member B4 0.076 1 1
Entamoeba histolytica alcohol dehydrogenase, putative 0.022 0.2585 0.2547
Schistosoma mansoni hypothetical protein 0.0309 0.38 0.3768
Mycobacterium tuberculosis Probable oxidoreductase 0.076 1 1
Echinococcus multilocularis Niemann Pick C1 protein 0.0095 0.0867 0.082
Echinococcus granulosus aldo keto reductase family 1 member B4 0.076 1 1
Schistosoma mansoni aldo-keto reductase 0.076 1 1
Brugia malayi glutamate-cysteine ligase modifier subunit 0.022 0.2585 0.2547
Echinococcus multilocularis aldo keto reductase family 1, member B4 0.076 1 1
Trichomonas vaginalis aldo-keto reductase, putative 0.076 1 1
Echinococcus multilocularis aldo keto reductase family 1, member B4 0.076 1 1
Trichomonas vaginalis aldo-keto reductase, putative 0.076 1 1
Trichomonas vaginalis aldo-keto reductase, putative 0.076 1 1
Plasmodium falciparum aldehyde reductase, putative 0.022 0.2585 0.5
Toxoplasma gondii aldose reductase, putative 0.076 1 1
Loa Loa (eye worm) MH2 domain-containing protein 0.012 0.1206 0.116
Schistosoma mansoni hypothetical protein 0.0039 0.0102 0.0051
Trichomonas vaginalis dihydrodiol dehydrogenase, putative 0.076 1 1
Echinococcus granulosus hypothetical protein 0.076 1 1
Trichomonas vaginalis aldo-keto reductase, putative 0.076 1 1
Plasmodium vivax aldehyde reductase, putative 0.022 0.2585 0.5
Onchocerca volvulus 0.076 1 1
Leishmania major aldehyde reductase, putative,oxidoreductase, putative 0.076 1 1
Loa Loa (eye worm) oxidoreductase 0.076 1 1
Echinococcus multilocularis guanine nucleotide binding protein G(s) subunit 0.0046 0.0191 0.0141
Leishmania major prostaglandin f2-alpha synthase/D-arabinose dehydrogenase 0.076 1 1
Trypanosoma brucei aldo/keto reductase, putative 0.022 0.2585 0.2547
Echinococcus multilocularis aldo keto reductase family 1, member B4 0.076 1 1
Echinococcus granulosus Niemann Pick C1 protein 0.0136 0.1427 0.1383
Echinococcus granulosus aldo keto reductase family 1 member B4 0.076 1 1
Loa Loa (eye worm) oxidoreductase 0.076 1 1
Trichomonas vaginalis aldo-keto reductase, putative 0.076 1 1
Trichomonas vaginalis aldo-keto reductase, putative 0.076 1 1
Trichomonas vaginalis dihydrodiol dehydrogenase, putative 0.076 1 1
Schistosoma mansoni niemann-pick C1 (NPC1) 0.0097 0.0887 0.084
Entamoeba histolytica Niemann-Pick C1 protein, putative 0.0095 0.0867 0.082
Onchocerca volvulus 0.076 1 1
Echinococcus multilocularis aldo keto reductase family 1, member B4 0.076 1 1
Entamoeba histolytica aldose reductase, putative 0.076 1 1
Echinococcus granulosus snurportin 1 0.0309 0.38 0.3768
Giardia lamblia Aldose reductase 0.076 1 0.5
Loa Loa (eye worm) oxidoreductase 0.076 1 1
Brugia malayi oxidoreductase, aldo/keto reductase family protein 0.076 1 1
Mycobacterium tuberculosis Conserved protein 0.022 0.2585 0.2585
Plasmodium falciparum aldo-keto reductase, putative 0.022 0.2585 0.5
Mycobacterium leprae Possible oxidoreductase 0.022 0.2585 0.2585
Echinococcus granulosus aldo keto reductase family 1 member B4 0.076 1 1
Loa Loa (eye worm) hypothetical protein 0.051 0.6564 0.6546
Loa Loa (eye worm) hypothetical protein 0.005 0.0248 0.0198
Echinococcus granulosus aldo keto reductase family 1, member B4 0.022 0.2585 0.2547
Schistosoma mansoni Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein) 0.0046 0.0191 0.0141
Trichomonas vaginalis aldo-keto reductase, putative 0.076 1 1
Echinococcus multilocularis aldehyde reductase 0.054 0.6976 0.6961
Echinococcus multilocularis aldo keto reductase family 1, member B4 0.076 1 1
Toxoplasma gondii aldo-keto reductase 0.022 0.2585 0.2547
Mycobacterium ulcerans oxidoreductase 0.076 1 1
Echinococcus multilocularis aldo keto reductase family 1, member B4 0.076 1 1
Echinococcus granulosus aldo keto reductase family 1 member B4 0.076 1 1
Schistosoma mansoni hypothetical protein 0.0039 0.0102 0.0051
Loa Loa (eye worm) hypothetical protein 0.076 1 1
Trichomonas vaginalis aldo/keto reductase, putative 0.076 1 1
Mycobacterium ulcerans hypothetical protein 0.022 0.2585 0.2547
Trypanosoma cruzi aldo/keto reductase, putative 0.076 1 1
Onchocerca volvulus 0.076 1 1
Loa Loa (eye worm) glutamate-cysteine ligase modifier subunit 0.022 0.2585 0.2547
Trichomonas vaginalis conserved hypothetical protein 0.0041 0.0122 0.0071
Echinococcus granulosus guanine nucleotide binding protein Gs subunit 0.0046 0.0191 0.0141
Echinococcus granulosus aldo keto reductase 0.076 1 1
Entamoeba histolytica aldose reductase, putative 0.076 1 1
Schistosoma mansoni hypothetical protein 0.0039 0.0102 0.0051
Echinococcus granulosus sterol regulatory element binding protein 0.0041 0.0122 0.0071
Brugia malayi RNA, U transporter 1 0.0082 0.0691 0.0643
Brugia malayi oxidoreductase, aldo/keto reductase family protein 0.076 1 1
Echinococcus granulosus aldehyde reductase 0.054 0.6976 0.6961
Brugia malayi oxidoreductase, aldo/keto reductase family protein 0.076 1 1
Trichomonas vaginalis aldo-keto reductase, putative 0.022 0.2585 0.2547
Loa Loa (eye worm) oxidoreductase 0.076 1 1
Echinococcus multilocularis aldo keto reductase family 1, member B4 0.076 1 1
Brugia malayi NADH-dependent xylose reductase 0.022 0.2585 0.2547
Leishmania major prostaglandin f synthase, putative 0.076 1 1
Echinococcus multilocularis protein dispatched 1 0.0047 0.0201 0.015
Echinococcus granulosus aldo keto reductase 0.076 1 1

Activities

Activity type Activity value Assay description Source Reference
Ki (binding) = 2.4 nM Inhibition of [3H]-NMS binding to human muscarinic acetylcholine receptor M1 expressed in CHO cells ChEMBL. 11150173
Ki (binding) = 2.4 nM Inhibition of [3H]-NMS binding to human muscarinic acetylcholine receptor M1 expressed in CHO cells ChEMBL. 11150173
Ki (binding) = 3.8 nM Inhibition of [3H]-NMS binding to human muscarinic acetylcholine receptor M3 expressed in CHO cells ChEMBL. 11150173
Ki (binding) = 3.8 nM Inhibition of [3H]-NMS binding to human muscarinic acetylcholine receptor M3 expressed in CHO cells ChEMBL. 11150173
Ki (binding) = 260 nM Inhibition of [3H]-NMS binding to human muscarinic acetylcholine receptor M2 expressed in CHO cells ChEMBL. 11150173
Ki (binding) = 260 nM Inhibition of [3H]-NMS binding to human muscarinic acetylcholine receptor M2 expressed in CHO cells ChEMBL. 11150173
Metabolic stability (functional) = 45 % In vitro metabolic stability in dog hepatic microsomes (1 mg protein/mL), expressed as the percent remaining after 30 min of incubation at 37uM. ChEMBL. 11150173
Metabolic stability (functional) = 47 % In vitro metabolic stability in human hepatic microsomes (1 mg protein/mL), expressed as the percent remaining after 30 min of incubation at 37uM. ChEMBL. 11150173
Selectivity (binding) = 69 Selectivity ratio between m2 muscarinic and m3 muscarinic receptors ChEMBL. 11150173

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.

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