Detailed information for compound 22282

Basic information

Technical information
  • TDR Targets ID: 22282
  • Name: 5-[3-[4-[(3-fluorophenyl)methyl]piperidin-1-y l]prop-1-ynyl]-1,3-dihydrobenzimidazol-2-one
  • MW: 363.428 | Formula: C22H22FN3O
  • H donors: 2 H acceptors: 2 LogP: 4.5 Rotable bonds: 3
    Rule of 5 violations (Lipinski): 1
  • SMILES: Fc1cccc(c1)CC1CCN(CC1)CC#Cc1ccc2c(c1)nc([nH]2)O
  • InChi: 1S/C22H22FN3O/c23-19-5-1-3-18(14-19)13-17-8-11-26(12-9-17)10-2-4-16-6-7-20-21(15-16)25-22(27)24-20/h1,3,5-7,14-15,17H,8-13H2,(H2,24,25,27)
  • InChiKey: MIIJMODVRMTWJP-UHFFFAOYSA-N  


Substructure search Similarity search

Network

Hover on a compound node to display the structore

Synonyms

  • 5-[3-[4-[(3-fluorophenyl)methyl]-1-piperidyl]prop-1-ynyl]-1,3-dihydrobenzimidazol-2-one
  • 5-[3-[4-[(3-fluorophenyl)methyl]-1-piperidinyl]prop-1-ynyl]-1,3-dihydrobenzimidazol-2-one
  • 5-[3-[4-(3-fluorobenzyl)piperidino]prop-1-ynyl]-1,3-dihydrobenzimidazol-2-one
  • 5-[3-[4-(3-fluorobenzyl)-1-piperidyl]prop-1-ynyl]-1,3-dihydrobenzimidazol-2-one

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Rattus norvegicus Dopamine D2 receptor Starlite/ChEMBL References
Rattus norvegicus Glutamate NMDA receptor; Grin1/Grin2b Starlite/ChEMBL References
Homo sapiens glutamate receptor, ionotropic, N-methyl D-aspartate 1 Starlite/ChEMBL References
Rattus norvegicus Adrenergic receptor alpha-1 Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Schistosoma mansoni glutamate receptor NMDA Get druggable targets OG5_133478 All targets in OG5_133478
Echinococcus multilocularis glutamate receptor NMDA Get druggable targets OG5_133478 All targets in OG5_133478
Echinococcus multilocularis nmda type glutamate receptor Get druggable targets OG5_133478 All targets in OG5_133478
Echinococcus granulosus nmda type glutamate receptor Get druggable targets OG5_133478 All targets in OG5_133478
Schistosoma japonicum Glutamate [NMDA] receptor subunit zeta-1 precursor, putative Get druggable targets OG5_133478 All targets in OG5_133478
Echinococcus granulosus glutamate receptor NMDA Get druggable targets OG5_133478 All targets in OG5_133478
Echinococcus granulosus nmda type glutamate receptor Get druggable targets OG5_133478 All targets in OG5_133478
Schistosoma japonicum Glutamate [NMDA] receptor subunit zeta-1 precursor, putative Get druggable targets OG5_133478 All targets in OG5_133478
Schistosoma japonicum Glutamate [NMDA] receptor subunit zeta-1 precursor, putative Get druggable targets OG5_133478 All targets in OG5_133478
Schistosoma japonicum expressed protein Get druggable targets OG5_133478 All targets in OG5_133478
Echinococcus multilocularis nmda type glutamate receptor Get druggable targets OG5_133478 All targets in OG5_133478
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Onchocerca volvulus Glycoprotein hormone beta 5 homolog Dopamine D2 receptor   444 aa 476 aa 24.2 %
Schistosoma japonicum ko:K04145 dopamine receptor D2, putative Dopamine D2 receptor   444 aa 432 aa 30.8 %
Drosophila melanogaster Glutamate receptor IA Glutamate NMDA receptor; Grin1/Grin2b   938 aa 979 aa 23.7 %
Onchocerca volvulus Dopamine D2 receptor   444 aa 418 aa 23.0 %
Onchocerca volvulus RB1-inducible coiled-coil protein 1 homolog Dopamine D2 receptor   444 aa 474 aa 23.4 %
Echinococcus granulosus biogenic amine 5HT receptor Dopamine D2 receptor   444 aa 429 aa 31.7 %
Echinococcus multilocularis serotonin receptor Dopamine D2 receptor   444 aa 428 aa 31.3 %
Schistosoma mansoni biogenic amine receptor Dopamine D2 receptor   444 aa 452 aa 30.1 %
Schistosoma japonicum Octopamine receptor, putative Dopamine D2 receptor   444 aa 456 aa 29.4 %
Schistosoma japonicum ko:K04207 neuropeptide Y receptor Y5, putative Dopamine D2 receptor   444 aa 386 aa 19.7 %
Echinococcus multilocularis glutamate (NMDA) receptor subunit Glutamate NMDA receptor; Grin1/Grin2b   938 aa 822 aa 23.2 %
Schistosoma mansoni muscarinic acetylcholine (GAR) receptor Dopamine D2 receptor   444 aa 487 aa 23.8 %
Schistosoma mansoni biogenic amine (dopamine) receptor Dopamine D2 receptor   444 aa 494 aa 26.3 %
Schistosoma mansoni glutamate receptor NMDA Glutamate NMDA receptor; Grin1/Grin2b   938 aa 933 aa 39.1 %
Drosophila melanogaster NMDA receptor 2 Glutamate NMDA receptor; Grin1/Grin2b   938 aa 878 aa 27.4 %
Echinococcus granulosus g protein coupled receptor Dopamine D2 receptor   444 aa 457 aa 21.0 %
Schistosoma japonicum ko:K04136 adrenergic receptor, alpha 1b, putative Dopamine D2 receptor   444 aa 440 aa 30.0 %
Schistosoma mansoni amine GPCR Dopamine D2 receptor   444 aa 424 aa 32.1 %
Echinococcus multilocularis g protein coupled receptor Dopamine D2 receptor   444 aa 465 aa 21.5 %
Loa Loa (eye worm) hypothetical protein Dopamine D2 receptor   444 aa 433 aa 21.2 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Echinococcus granulosus nmda type glutamate receptor 0.0136 0.9864 1
Echinococcus granulosus guanine nucleotide binding protein Gs subunit 0.0045 0.1488 0.1508
Brugia malayi Glutamate receptor 1 precursor 0.0033 0.0379 0.255
Schistosoma mansoni glutamate receptor kainate 0.0033 0.0379 0.0379
Schistosoma mansoni glutamate receptor NMDA 0.0033 0.0379 0.0379
Loa Loa (eye worm) glutamate receptor 1 0.0033 0.0379 0.255
Echinococcus multilocularis glutamate receptor 2 0.0033 0.0379 0.0385
Trypanosoma cruzi DNA repair and recombination helicase protein PIF6, putative 0.006 0.2805 0.5
Echinococcus multilocularis Glutamate receptor, ionotropic kainate 3 0.0041 0.1091 0.1106
Echinococcus multilocularis Glutamate receptor, ionotropic kainate 2 0.0042 0.1227 0.1243
Schistosoma mansoni ATP-binding cassette transporter 0.0033 0.0379 0.0379
Giardia lamblia Rrm3p helicase 0.006 0.2805 0.5
Schistosoma mansoni glutamate receptor AMPA 0.0033 0.0379 0.0379
Schistosoma mansoni glutamate receptor kainate 0.0033 0.0379 0.0379
Echinococcus granulosus Glutamate receptor ionotropic kainate 2 0.0042 0.1227 0.1243
Echinococcus granulosus Glutamate receptor ionotropic kainate 2 0.0042 0.1227 0.1243
Leishmania major PIF1 helicase-like protein, putative,DNA repair and recombination protein, mitochondrial precursor, putative 0.006 0.2805 0.5
Echinococcus multilocularis glutamate receptor, ionotrophic, AMPA 3 0.0042 0.1227 0.1243
Echinococcus granulosus glutamate receptor NMDA 0.0095 0.6094 0.6178
Echinococcus granulosus glutamate receptor 2 0.0042 0.1227 0.1243
Schistosoma mansoni glutamate receptor AMPA 0.0033 0.0379 0.0379
Trypanosoma cruzi DNA repair and recombination helicase protein PIF7, putative 0.006 0.2805 0.5
Echinococcus multilocularis Glutamate receptor, ionotropic kainate 2 0.0042 0.1227 0.1243
Echinococcus multilocularis glutamate receptor NMDA 0.0095 0.6094 0.6178
Leishmania major PIF1 helicase-like protein, putative,DNA repair and recombination protein, mitochondrial precursor, putative 0.006 0.2805 0.5
Onchocerca volvulus 0.0029 0 0.5
Brugia malayi GTP-binding regulatory protein Gs alpha-S chain, putative 0.0045 0.1488 1
Echinococcus granulosus ATP dependent DNA helicase PIF1 0.006 0.2805 0.2844
Schistosoma mansoni Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein) 0.0045 0.1488 0.1488
Loa Loa (eye worm) GTP-binding regulatory protein Gs alpha-S chain 0.0045 0.1488 1
Onchocerca volvulus Steroid hormone receptor family member cnr14 homolog 0.0029 0 0.5
Echinococcus multilocularis ATP dependent DNA helicase PIF1 0.006 0.2805 0.2844
Echinococcus multilocularis glutamate receptor 2 0.0042 0.1227 0.1243
Echinococcus granulosus guanine nucleotide binding protein Gs subunit 0.0045 0.1488 0.1508
Schistosoma mansoni glutamate receptor kainate 0.0033 0.0379 0.0379
Trypanosoma brucei DNA repair and recombination helicase protein PIF7 0.006 0.2805 0.5
Onchocerca volvulus Protein ultraspiracle homolog 0.0029 0 0.5
Echinococcus multilocularis nmda type glutamate receptor 0.0136 0.9864 1
Echinococcus multilocularis glutamate (NMDA) receptor subunit 0.0033 0.0379 0.0385
Echinococcus granulosus glutamate receptor ionotrophic AMPA 3 0.0042 0.1227 0.1243
Trichomonas vaginalis conserved hypothetical protein 0.006 0.2805 0.5
Schistosoma mansoni Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein) 0.0045 0.1488 0.1488
Trypanosoma cruzi DNA repair and recombination helicase protein PIF7, putative 0.006 0.2805 0.5
Echinococcus multilocularis guanine nucleotide binding protein G(s) subunit 0.0045 0.1488 0.1508
Echinococcus granulosus Glutamate receptor ionotropic kainate 2 0.0042 0.1227 0.1243
Schistosoma mansoni Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein) 0.0045 0.1488 0.1488
Entamoeba histolytica hypothetical protein, conserved 0.006 0.2805 0.5
Loa Loa (eye worm) glutamate receptor 2 0.0033 0.0379 0.255
Trypanosoma brucei DNA repair and recombination helicase protein PIF6 0.006 0.2805 0.5
Brugia malayi Glutamate receptor 2 precursor 0.0033 0.0379 0.255
Echinococcus multilocularis nmda type glutamate receptor 0.0104 0.6941 0.7037
Echinococcus multilocularis Glutamate receptor, ionotropic kainate 2 0.0042 0.1227 0.1243
Entamoeba histolytica DNA repair and recombination protein, putative 0.006 0.2805 0.5
Schistosoma mansoni hypothetical protein 0.006 0.2805 0.2805
Echinococcus granulosus glutamate NMDA receptor subunit 0.0033 0.0379 0.0385
Echinococcus multilocularis guanine nucleotide binding protein G(s) subunit 0.0045 0.1488 0.1508
Echinococcus granulosus nmda type glutamate receptor 0.0104 0.6941 0.7037
Onchocerca volvulus Bile acid receptor homolog 0.0029 0 0.5

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 0.0061 uM Concentration required for 50% Inhibition of responses at cloned NR1A/2AB NMDA expressed in Xenopus oocytes ChEMBL. 10978188
IC50 (binding) = 0.0061 uM Concentration required for 50% Inhibition of responses at cloned NR1A/2AB NMDA expressed in Xenopus oocytes ChEMBL. 10978188
IC50 (binding) = 0.014 uM Binding affinity against NR1A/2B receptor in rat brains by [3H]-ifenprodil displacement. ChEMBL. 14980668
IC50 (binding) = 0.014 uM Binding affinity against NR1A/2B receptor in rat brains by [3H]-ifenprodil displacement. ChEMBL. 14980668
IC50 (binding) = 0.7 uM Displacement of [3H]-prazosin at alpha-1 adrenergic receptor in rat brain cortices (n=1) ChEMBL. 10978188
IC50 (binding) = 0.7 uM Displacement of [3H]-prazosin at alpha-1 adrenergic receptor in rat brain cortices (n=1) ChEMBL. 10978188
IC50 (binding) = 3.9 uM Displacement of [3H]-raclopride at Dopamine receptor D2 in brain striata (n=1) ChEMBL. 10978188
IC50 (binding) = 3.9 uM Displacement of [3H]-raclopride at Dopamine receptor D2 in brain striata (n=1) ChEMBL. 10978188
IC50 (binding) > 100 uM Concentration required for 50% Inhibition of responses at cloned NR1A/2A NMDA expressed in Xenopus oocytes ChEMBL. 10978188
IC50 (binding) > 100 uM Concentration required for 50% Inhibition of responses at cloned NR1A/2C NMDA expressed in Xenopus oocytes ChEMBL. 10978188
IC50 (binding) > 100 uM Concentration required for 50% Inhibition of responses at cloned NR1A/2A NMDA expressed in Xenopus oocytes ChEMBL. 10978188
IC50 (binding) > 100 uM Concentration required for 50% Inhibition of responses at cloned NR1A/2C NMDA expressed in Xenopus oocytes ChEMBL. 10978188
MED (functional) 0 mg kg-1 In vivo minimum effective dose for anti-Parkinsonian activity in 6-OHDA rat model upon p.o. administration; Not active. ChEMBL. 14980668
MED (functional) 0 mg kg-1 In vivo minimum effective dose inhibition of neuropathic pain (formalin test) upon p.o. administration; Not active. ChEMBL. 14980668
MED (functional) > 30 mg kg-1 Lowest oral dose that shows significant potentiation of total contraversive rotations over 3 h caused by L-DOPA (10mg/kg, sc) in 6-hydroxydopamine-lesioned rats (n=8)administered perorally ChEMBL. 10978188

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.

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