Detailed information for compound 220222

Basic information

Technical information
  • TDR Targets ID: 220222
  • Name: 2-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl ]-3,4-dihydropyrazino[1,2-a]indol-1-one
  • MW: 432.558 | Formula: C26H32N4O2
  • H donors: 0 H acceptors: 1 LogP: 3.82 Rotable bonds: 7
    Rule of 5 violations (Lipinski): 1
  • SMILES: COc1ccccc1N1CCN(CC1)CCCCN1CCn2c(C1=O)cc1c2cccc1
  • InChi: 1S/C26H32N4O2/c1-32-25-11-5-4-10-23(25)28-16-14-27(15-17-28)12-6-7-13-29-18-19-30-22-9-3-2-8-21(22)20-24(30)26(29)31/h2-5,8-11,20H,6-7,12-19H2,1H3
  • InChiKey: BUVJSGDYMDZIDN-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 2-[4-[4-(2-methoxyphenyl)-1-piperazinyl]butyl]-3,4-dihydropyrazino[1,2-a]indol-1-one
  • 2-[4-[4-(2-methoxyphenyl)piperazino]butyl]-3,4-dihydropyrazino[1,2-a]indol-1-one
  • 2-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]-3,4-dihydropyrazino[4,3-a]indol-1-one
  • 2-[4-[4-(2-methoxyphenyl)-1-piperazinyl]butyl]-3,4-dihydropyrazino[4,3-a]indol-1-one

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Rattus norvegicus Dopamine D3 receptor Starlite/ChEMBL References
Rattus norvegicus Alpha-1a adrenergic receptor Starlite/ChEMBL References
Rattus norvegicus Dopamine D1 receptor Starlite/ChEMBL References
Rattus norvegicus Dopamine D2 receptor Starlite/ChEMBL References
Rattus norvegicus Serotonin 1a (5-HT1a) receptor Starlite/ChEMBL References
Rattus norvegicus Alpha-2a adrenergic receptor Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Schistosoma japonicum 5-hydroxytryptamine receptor 1, putative Get druggable targets OG5_132667 All targets in OG5_132667
Schistosoma japonicum Octopamine receptor, putative Get druggable targets OG5_133249 All targets in OG5_133249
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_133249 All targets in OG5_133249
Schistosoma japonicum ko:K04153 5-hydroxytryptamine (serotonin) receptor 1A, putative Get druggable targets OG5_133249 All targets in OG5_133249
Echinococcus multilocularis serotonin receptor Get druggable targets OG5_133249 All targets in OG5_133249
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_133249 All targets in OG5_133249
Schistosoma mansoni biogenic amine (5HT) receptor Get druggable targets OG5_133249 All targets in OG5_133249
Schistosoma japonicum expressed protein Get druggable targets OG5_133249 All targets in OG5_133249
Schistosoma japonicum 5-hydroxytryptamine receptor, putative Get druggable targets OG5_132667 All targets in OG5_132667
Echinococcus granulosus biogenic amine 5HT receptor Get druggable targets OG5_133249 All targets in OG5_133249
Echinococcus multilocularis serotonin receptor Get druggable targets OG5_133249 All targets in OG5_133249
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Echinococcus multilocularis alpha 1A adrenergic receptor Dopamine D3 receptor   446 aa 473 aa 21.6 %
Schistosoma japonicum ko:K04145 dopamine receptor D2, putative Dopamine D1 receptor   446 aa 373 aa 25.5 %
Echinococcus granulosus rhodopsin orphan GPCR Alpha-1a adrenergic receptor   466 aa 418 aa 20.3 %
Schistosoma mansoni muscarinic acetylcholine (GAR) receptor Dopamine D2 receptor   444 aa 487 aa 23.8 %
Echinococcus multilocularis fmrfamide receptor Alpha-2a adrenergic receptor   450 aa 366 aa 19.9 %
Schistosoma japonicum ko:K04135 adrenergic receptor, alpha 1a, putative Dopamine D1 receptor   446 aa 407 aa 33.7 %
Echinococcus multilocularis g protein coupled receptor Serotonin 1a (5-HT1a) receptor   422 aa 432 aa 23.6 %
Echinococcus granulosus g protein coupled receptor Serotonin 1a (5-HT1a) receptor   422 aa 432 aa 24.3 %
Schistosoma mansoni biogenic amine (5HT) receptor Dopamine D1 receptor   446 aa 394 aa 29.9 %
Echinococcus multilocularis neuropeptides capa receptor Serotonin 1a (5-HT1a) receptor   422 aa 430 aa 20.0 %
Onchocerca volvulus Glycoprotein hormone beta 5 homolog Serotonin 1a (5-HT1a) receptor   422 aa 477 aa 24.3 %
Echinococcus multilocularis biogenic amine (5HT) receptor Dopamine D3 receptor   446 aa 499 aa 30.9 %
Schistosoma japonicum Octopamine receptor 1, putative Serotonin 1a (5-HT1a) receptor   422 aa 424 aa 24.3 %
Echinococcus granulosus orexin receptor type 2 Serotonin 1a (5-HT1a) receptor   422 aa 369 aa 22.0 %
Echinococcus multilocularis orexin receptor type 2 Serotonin 1a (5-HT1a) receptor   422 aa 369 aa 22.2 %
Schistosoma mansoni biogenic amine (dopamine) receptor Dopamine D2 receptor   444 aa 494 aa 26.3 %
Schistosoma mansoni amine GPCR Serotonin 1a (5-HT1a) receptor   422 aa 440 aa 31.6 %
Onchocerca volvulus Mitochondrial inner membrane protein homolog Serotonin 1a (5-HT1a) receptor   422 aa 383 aa 30.5 %
Schistosoma japonicum ko:K04136 adrenergic receptor, alpha 1b, putative Dopamine D1 receptor   446 aa 366 aa 35.2 %
Echinococcus granulosus biogenic amine 5HT receptor Alpha-1a adrenergic receptor   466 aa 418 aa 30.4 %
Schistosoma mansoni biogenic amine receptor Dopamine D3 receptor   446 aa 455 aa 28.6 %
Echinococcus multilocularis g protein coupled receptor Serotonin 1a (5-HT1a) receptor   422 aa 433 aa 22.4 %
Schistosoma japonicum IPR000276,Rhodopsin-like GPCR superfamily,domain-containing Serotonin 1a (5-HT1a) receptor   422 aa 392 aa 20.7 %
Loa Loa (eye worm) TYRA-2 protein Serotonin 1a (5-HT1a) receptor   422 aa 491 aa 27.3 %
Schistosoma japonicum ko:K04145 dopamine receptor D2, putative Dopamine D3 receptor   446 aa 463 aa 29.8 %
Onchocerca volvulus Dopamine D3 receptor   446 aa 462 aa 26.0 %
Schistosoma japonicum Octopamine receptor, putative Dopamine D3 receptor   446 aa 501 aa 28.5 %
Onchocerca volvulus RB1-inducible coiled-coil protein 1 homolog Dopamine D3 receptor   446 aa 478 aa 22.8 %
Schistosoma mansoni ancient conserved domain protein 2 (cyclin m2) Dopamine D3 receptor   446 aa 463 aa 25.5 %
Schistosoma japonicum IPR000276,Rhodopsin-like GPCR superfamily,domain-containing Serotonin 1a (5-HT1a) receptor   422 aa 417 aa 21.1 %
Schistosoma japonicum FMRFamide receptor, putative Alpha-1a adrenergic receptor   466 aa 374 aa 19.5 %
Onchocerca volvulus Serotonin 1a (5-HT1a) receptor   422 aa 426 aa 29.6 %
Schistosoma japonicum ko:K04207 neuropeptide Y receptor Y5, putative Serotonin 1a (5-HT1a) receptor   422 aa 339 aa 23.0 %
Loa Loa (eye worm) hypothetical protein Dopamine D1 receptor   446 aa 370 aa 24.9 %
Echinococcus multilocularis serotonin receptor Alpha-2a adrenergic receptor   450 aa 426 aa 31.9 %
Onchocerca volvulus Dopamine D1 receptor   446 aa 357 aa 21.0 %
Echinococcus granulosus g protein coupled receptor Serotonin 1a (5-HT1a) receptor   422 aa 432 aa 23.4 %
Onchocerca volvulus Serotonin 1a (5-HT1a) receptor   422 aa 436 aa 23.9 %
Onchocerca volvulus Serotonin 1a (5-HT1a) receptor   422 aa 407 aa 23.3 %
Echinococcus multilocularis neuropeptide Y receptor Alpha-1a adrenergic receptor   466 aa 419 aa 19.6 %
Schistosoma mansoni peptide (FMRFamide/neurokinin-3)-like receptor Serotonin 1a (5-HT1a) receptor   422 aa 350 aa 20.6 %
Onchocerca volvulus Serotonin 1a (5-HT1a) receptor   422 aa 390 aa 33.6 %
Echinococcus granulosus alpha 1A adrenergic receptor Serotonin 1a (5-HT1a) receptor   422 aa 452 aa 21.0 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Leishmania major phenylalanine-4-hydroxylase,phenylalanine-4-hydroxylase, putative 0.034 0.4907 0.5
Wolbachia endosymbiont of Brugia malayi phosphoribosylamine--glycine ligase 0.0305 0.4309 1
Toxoplasma gondii aromatic amino acid hydrolase AAH2 0.0375 0.5513 1
Mycobacterium ulcerans phosphoribosylamine--glycine ligase 0.0305 0.4309 1
Echinococcus multilocularis serotonin receptor 0.018 0.2163 0.1245
Brugia malayi Biopterin-dependent aromatic amino acid hydroxylase family protein 0.0115 0.1048 0.5
Schistosoma mansoni biogenic amine (5HT) receptor 0.018 0.2163 1
Loa Loa (eye worm) hypothetical protein 0.018 0.2163 1
Mycobacterium tuberculosis Probable phosphoribosylformylglycinamidine CYCLO-ligase PurM (AIRS) (phosphoribosyl-aminoimidazole synthetase) (air synthase) 0.0067 0.0235 0.5
Mycobacterium leprae PROBABLE PHOSPHORIBOSYLAMINE--GLYCINE LIGASE PURD (GARS) (GLYCINAMIDE RIBONUCLEOTIDE SYNTHETASE) (PHOSPHORIBOSYLGLYCINAMIDE SYNT 0.0305 0.4309 1
Toxoplasma gondii aromatic amino acid hydrolase AAH1 0.034 0.4907 0.8383
Onchocerca volvulus 0.0067 0.0235 1
Echinococcus granulosus biogenic amine 5HT receptor 0.018 0.2163 0.1245
Loa Loa (eye worm) hypothetical protein 0.018 0.2163 1
Echinococcus multilocularis serotonin receptor 0.018 0.2163 0.1245
Echinococcus multilocularis folate receptor beta 0.0636 1 1
Toxoplasma gondii phenylalanine-4-hydroxylase 0.0375 0.5513 1

Activities

Activity type Activity value Assay description Source Reference
Ki (binding) = 0.87 nM Binding affinity for rat striatum Dopamine receptor D3 (sf9 cells) by [3H]-7-OH-DPAT displacement. ChEMBL. 12930145
Ki (binding) = 0.92 nM Binding affinity for rat striatum Dopamine receptor D3 (sf9 cells) by [3H]-7-OH-DPAT displacement. ChEMBL. 12930145
Ki (binding) = 4.9 nM Binding affinity for rat hippocampus 5-hydroxytryptamine 1A receptor by inhibition of [3H]-8-OH-DPAT binding ChEMBL. 12930145
Ki (binding) = 33 nM Binding affinity for rat cortex alpha-1 adrenergic receptor by inhibition of [3H]-prazosin binding ChEMBL. 12930145
Ki (binding) = 45 nM Binding affinity for rat striatum Dopamine receptor D2 by [3H]-spiperone displacement. ChEMBL. 12930145
Ki (binding) = 60 nM Binding affinity for rat cortex alpha-1 adrenergic receptor by inhibition of [3H]-prazosin binding ChEMBL. 12930145
Ki (binding) = 61 nM Binding affinity for rat striatum Dopamine receptor D2 by [3H]-spiperone displacement. ChEMBL. 12930145
Ki (binding) = 83 nM Binding affinity for rat cortex Alpha-2 adrenergic receptor was determined using [3H]-RX 81002 binding ChEMBL. 12930145
Ki (binding) = 84 nM Binding affinity for rat hippocampus 5-hydroxytryptamine 1A receptor by inhibition of [3H]-8-OH-DPAT binding ChEMBL. 12930145
Ki (binding) = 89 nM Binding affinity for rat cortex Alpha-2 adrenergic receptor was determined using [3H]-RX 81002 binding ChEMBL. 12930145
Ki (binding) = 1567 nM Binding affinity for rat striatum dopamine Dopamine receptor D1 by [3H]-SCH- -2339 displacement. ChEMBL. 12930145
Ki (binding) = 3000 nM Binding affinity for rat striatum dopamine Dopamine receptor D1 by [3H]-SCH- -2339 displacement. ChEMBL. 12930145

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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