TDR Targets

Basic information

Technical information

TDR Targets ID: 220083
Name: 3-(3-fluorophenyl)-5-propan-2-ylimidazo[1,5-a ]quinoxalin-4-one
MW: 321.348 | Formula: C19H16FN3O
H donors: 0 H acceptors: 2 LogP: 3.66 Rotable bonds: 2
Rule of 5 violations (Lipinski): 1
SMILES: Fc1cccc(c1)c1ncn2c1c(=O)n(c1c2cccc1)C(C)C
InChi: 1S/C19H16FN3O/c1-12(2)23-16-9-4-3-8-15(16)22-11-21-17(18(22)19(23)24)13-6-5-7-14(20)10-13/h3-12H,1-2H3
InChiKey: SZFZZAJPKCGSIY-UHFFFAOYSA-N

Network

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Target Layer

Model Organisms

Species	Viewmode
Arabidopsis thaliana
Caenorhabditis elegans
Dictyostelium discoideum
Drosophila melanogaster
Escherichia coli
Homo sapiens
Mus musculus
Oryza sativa
Saccharomyces cerevisiae
Schmidtea mediterranea
Other organisms

TDR Pathogens:

Species	Viewmode
Brugia malayi
Chlamydia trachomatis
Echinococcus granulosus
Entamoeba histolytica
Echinococcus multilocularis
Giardia lamblia
Leishmania major
Loa Loa (eye worm)
Mycobacterium leprae
Mycobacterium tuberculosis
Mycobacterium ulcerans
Onchocerca volvulus
Plasmodium falciparum
Plasmodium vivax
Schistosoma mansoni
Trypanosoma brucei
Trypanosoma cruzi
Toxoplasma gondii
Treponema pallidum
Trichomonas vaginalis
Wolbachia endosymbiont of Brugia malayi

Other Pathogens:

Species	Viewmode
Babesia bovis
Candida albicans
Cryptosporidium hominis
Cryptosporidium parvum
Leishmania braziliensis
Leishmania donovani
Leishmania infantum
Leishmania mexicana
Neospora caninum
Plasmodium berghei
Plasmodium knowlesi
Plasmodium yoelii
Schistosoma japonicum
Trypanosoma brucei gambiense
Trypanosoma congolense
Theileria parva

Compound Layer

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Clustering layers

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Synonyms

3-(3-fluorophenyl)-5-isopropyl-imidazo[1,5-a]quinoxalin-4-one
3-(3-fluorophenyl)-5-isopropyl-4-imidazo[1,5-a]quinoxalinone
3-(3-fluorophenyl)-5-propan-2-yl-imidazo[1,5-a]quinoxalin-4-one
3-(3-fluorophenyl)-5-propan-2-ylimidazo[5,1-c]quinoxalin-4-one
3-(3-fluorophenyl)-5-isopropyl-imidazo[5,1-c]quinoxalin-4-one
3-(3-fluorophenyl)-5-isopropyl-4-imidazo[5,1-c]quinoxalinone
3-(3-fluorophenyl)-5-propan-2-yl-imidazo[5,1-c]quinoxalin-4-one

Targets

Known targets for this compound

Species	Target name	Source	Bibliographic reference
Rattus norvegicus	GABA-A receptor; anion channel	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
Echinococcus granulosus	glycine receptor subunit beta	GABA-A receptor; anion channel	467 aa	439 aa	29.6 %
Brugia malayi	Cation transporter family protein	GABA-A receptor; anion channel	467 aa	453 aa	28.5 %
Echinococcus multilocularis	glycine receptor subunit alpha 1	GABA-A receptor; anion channel	467 aa	430 aa	32.3 %
Loa Loa (eye worm)	hypothetical protein	GABA-A receptor; anion channel	467 aa	461 aa	27.8 %
Loa Loa (eye worm)	hypothetical protein	GABA-A receptor; anion channel	467 aa	441 aa	33.8 %
Onchocerca volvulus	Acetylcholine receptor subunit alpha-type homolog	GABA-A receptor; anion channel	467 aa	418 aa	19.6 %
Schistosoma mansoni	Cys-loop ligand gated ion channel subunit	GABA-A receptor; anion channel	467 aa	479 aa	29.2 %
Brugia malayi	Neurotransmitter-gated ion-channel ligand binding domain containing protein	GABA-A receptor; anion channel	467 aa	375 aa	21.9 %
Brugia malayi	Neurotransmitter-gated ion-channel ligand binding domain containing protein	GABA-A receptor; anion channel	467 aa	454 aa	29.5 %
Onchocerca volvulus		GABA-A receptor; anion channel	467 aa	434 aa	26.7 %
Loa Loa (eye worm)	nicotinic acetylcholine receptor alpha subunit	GABA-A receptor; anion channel	467 aa	379 aa	19.3 %
Echinococcus multilocularis	glycine receptor subunit beta	GABA-A receptor; anion channel	467 aa	478 aa	28.7 %
Onchocerca volvulus		GABA-A receptor; anion channel	467 aa	447 aa	25.7 %
Onchocerca volvulus		GABA-A receptor; anion channel	467 aa	435 aa	29.7 %
Loa Loa (eye worm)	hypothetical protein	GABA-A receptor; anion channel	467 aa	494 aa	25.5 %
Echinococcus granulosus	glycine receptor subunit alpha 1	GABA-A receptor; anion channel	467 aa	430 aa	32.3 %
Loa Loa (eye worm)	hypothetical protein	GABA-A receptor; anion channel	467 aa	446 aa	29.1 %
Onchocerca volvulus	Gamma-aminobutyric acid receptor subunit beta homolog	GABA-A receptor; anion channel	467 aa	433 aa	34.6 %
Onchocerca volvulus	Eukaryotic initiation factor 4A-III homolog	GABA-A receptor; anion channel	467 aa	453 aa	26.9 %
Onchocerca volvulus		GABA-A receptor; anion channel	467 aa	468 aa	28.6 %
Onchocerca volvulus		GABA-A receptor; anion channel	467 aa	446 aa	28.0 %
Onchocerca volvulus	Large subunit GTPase 1 homolog	GABA-A receptor; anion channel	467 aa	496 aa	26.0 %
Brugia malayi	nicotinic acetylcholine receptor alpha subunit, putative	GABA-A receptor; anion channel	467 aa	384 aa	19.5 %
Onchocerca volvulus		GABA-A receptor; anion channel	467 aa	454 aa	30.4 %

Ranking Plot

Putative Targets List

Species	Potential target	Raw	Global	Species
Echinococcus multilocularis	purine nucleoside phosphorylase	0.0418	0.5095	0.5095
Mycobacterium tuberculosis	Probable ATP-dependent CLP protease proteolytic subunit 2 ClpP2 (endopeptidase CLP 2)	0.0056	0.0094	0.0143
Loa Loa (eye worm)	pigment dispersing factor receptor c	0.0056	0.0088	0.0172
Brugia malayi	TAR-binding protein	0.0071	0.0297	0.0449
Trichomonas vaginalis	purine nucleoside phosphorylase, putative	0.0109	0.0825	0.1095
Brugia malayi	Corticotropin releasing factor receptor 2 precursor, putative	0.0056	0.0088	0.0133
Schistosoma mansoni	methylthioadenosine phosphorylase	0.0109	0.0825	0.0825
Trichomonas vaginalis	purine nucleoside phosphorylase, putative	0.0109	0.0825	0.1095
Toxoplasma gondii	phosphorylase family protein	0.0109	0.0825	0.2738
Brugia malayi	MTAP	0.0109	0.0825	0.1249
Trypanosoma cruzi	dihydrofolate reductase-thymidylate synthase	0.0171	0.1678	1
Echinococcus granulosus	purine nucleoside phosphorylase	0.0527	0.6604	0.6604
Echinococcus multilocularis	purine nucleoside phosphorylase	0.0527	0.6604	0.6604
Brugia malayi	hypothetical protein	0.0058	0.0114	0.0173
Echinococcus granulosus	thymidylate synthase	0.0121	0.0994	0.0994
Plasmodium falciparum	bifunctional dihydrofolate reductase-thymidylate synthase	0.0171	0.1678	1
Echinococcus granulosus	purine nucleoside phosphorylase	0.0527	0.6604	0.6604
Loa Loa (eye worm)	hypothetical protein	0.0086	0.0503	0.0988
Mycobacterium tuberculosis	Conserved hypothetical protein	0.0109	0.0825	0.1249
Trypanosoma cruzi	nucleoside phosphorylase, putative	0.0109	0.0825	0.4546
Echinococcus multilocularis	purine nucleoside phosphorylase	0.0527	0.6604	0.6604
Loa Loa (eye worm)	hypothetical protein	0.0056	0.0088	0.0172
Entamoeba histolytica	hypothetical protein	0.0109	0.0825	0.5
Mycobacterium ulcerans	ATP-dependent Clp protease proteolytic subunit	0.0086	0.0503	0.0762
Trichomonas vaginalis	purine nucleoside phosphorylase, putative	0.0109	0.0825	0.1095
Schistosoma mansoni	purine nucleoside phosphorylase	0.0527	0.6604	0.6604
Loa Loa (eye worm)	MH2 domain-containing protein	0.0134	0.1164	0.2285
Plasmodium falciparum	purine nucleoside phosphorylase	0.0109	0.0825	0.2738
Echinococcus granulosus	purine nucleoside phosphorylase	0.0527	0.6604	0.6604
Mycobacterium leprae	probable uridine phosphorylase	0.0109	0.0825	0.1249
Loa Loa (eye worm)	uridine phosphorylase	0.0109	0.0825	0.1619
Trypanosoma cruzi	nucleoside phosphorylase, putative	0.0109	0.0825	0.4546
Schistosoma mansoni	purine nucleoside phosphorylase	0.0527	0.6604	0.6604
Brugia malayi	Probable ClpP-like protease	0.0086	0.0503	0.0762
Mycobacterium ulcerans	5'-methylthioadenosine phosphorylase	0.0109	0.0825	0.1249
Loa Loa (eye worm)	hypothetical protein	0.0418	0.5095	1
Echinococcus granulosus	purine nucleoside phosphorylase	0.0527	0.6604	0.6604
Mycobacterium ulcerans	purine nucleoside phosphorylase	0.0527	0.6604	1
Onchocerca volvulus	Purine nucleoside phosphorylase homolog	0.0527	0.6604	1
Echinococcus granulosus	tumor protein p63	0.0378	0.4547	0.4547
Entamoeba histolytica	purine nucleoside phosphorylase, putative	0.0109	0.0825	0.5
Treponema pallidum	purine nucleoside phosphorylase (deoD)	0.0109	0.0825	1
Schistosoma mansoni	tar DNA-binding protein	0.0071	0.0297	0.0297
Echinococcus multilocularis	purine nucleoside phosphorylase	0.0527	0.6604	0.6604
Loa Loa (eye worm)	RNA recognition domain-containing protein domain-containing protein	0.0071	0.0297	0.0582
Echinococcus multilocularis	ATP dependent Clp protease proteolytic subunit	0.0086	0.0503	0.0503
Mycobacterium tuberculosis	Probable ATP-dependent CLP protease proteolytic subunit 1 ClpP1 (endopeptidase CLP)	0.0056	0.0094	0.0143
Echinococcus multilocularis	tumor protein p63	0.0378	0.4547	0.4547
Loa Loa (eye worm)	transcription factor SMAD2	0.0134	0.1164	0.2285
Echinococcus multilocularis	purine nucleoside phosphorylase	0.0527	0.6604	0.6604
Toxoplasma gondii	bifunctional dihydrofolate reductase-thymidylate synthase	0.0171	0.1678	1
Schistosoma mansoni	tar DNA-binding protein	0.0071	0.0297	0.0297
Echinococcus granulosus	tar DNA binding protein	0.0071	0.0297	0.0297
Schistosoma mansoni	microtubule-associated protein tau	0.0772	1	1
Schistosoma mansoni	tar DNA-binding protein	0.0071	0.0297	0.0297
Onchocerca volvulus		0.0121	0.0994	0.1398
Chlamydia trachomatis	ATP-dependent Clp protease proteolytic subunit	0.0086	0.0503	0.6102
Loa Loa (eye worm)	TAR-binding protein	0.0071	0.0297	0.0582
Mycobacterium leprae	PROBABLE ATP-DEPENDENT CLP PROTEASE PROTEOLYTIC SUBUNIT 1 CLPP1 (ENDOPEPTIDASE CLP)	0.0056	0.0094	0.0143
Plasmodium vivax	bifunctional dihydrofolate reductase-thymidylate synthase, putative	0.0171	0.1678	1
Brugia malayi	RNA recognition motif domain containing protein	0.0071	0.0297	0.0449
Mycobacterium leprae	PROBABLE ATP-DEPENDENT CLP PROTEASE PROTEOLYTIC SUBUNIT 2 CLPP2 (ENDOPEPTIDASE CLP 2)	0.0086	0.0503	0.0762
Echinococcus multilocularis	purine nucleoside phosphorylase	0.0418	0.5095	0.5095
Mycobacterium tuberculosis	Hypothetical protein	0.0109	0.0825	0.1249
Echinococcus granulosus	uridine phosphorylase 1	0.0109	0.0825	0.0825
Brugia malayi	uridine phosphorylase family protein	0.0109	0.0825	0.1249
Trichomonas vaginalis	purine nucleoside phosphorylase, putative	0.0109	0.0825	0.1095
Echinococcus multilocularis	methylthioadenosine phosphorylase	0.0109	0.0825	0.0825
Schistosoma mansoni	cellular tumor antigen P53	0.0055	0.0082	0.0082
Echinococcus multilocularis	peptidase Clp (S14 family)	0.0056	0.0094	0.0094
Echinococcus granulosus	peptidase Clp S14 family	0.0056	0.0094	0.0094
Echinococcus multilocularis	tar DNA binding protein	0.0071	0.0297	0.0297
Chlamydia trachomatis	ATP-dependent Clp protease proteolytic subunit	0.0086	0.0503	0.6102
Loa Loa (eye worm)	thymidylate synthase	0.0121	0.0994	0.195
Brugia malayi	RNA binding protein	0.0071	0.0297	0.0449
Loa Loa (eye worm)	S-methyl-5'-thioadenosine phosphorylase MTAP	0.0109	0.0825	0.1619
Echinococcus granulosus	inosine guanosine and xanthosine phosphorylase	0.0418	0.5095	0.5095
Trichomonas vaginalis	purine nucleoside phosphorylase I, putative	0.0527	0.6604	1
Mycobacterium ulcerans	bifunctional Mta/Sah nucleosidase Mtn	0.0109	0.0825	0.1249
Echinococcus granulosus	purine nucleoside phosphorylase	0.0527	0.6604	0.6604
Leishmania major	dihydrofolate reductase-thymidylate synthase	0.0171	0.1678	1
Trichomonas vaginalis	purine nucleoside phosphorylase, putative	0.0109	0.0825	0.1095
Trypanosoma cruzi	methylthioadenosine phosphorylase, putative	0.0109	0.0825	0.4546
Echinococcus granulosus	purine nucleoside phosphorylase	0.0527	0.6604	0.6604
Loa Loa (eye worm)	hypothetical protein	0.0055	0.0082	0.016
Echinococcus multilocularis	purine nucleoside phosphorylase	0.0527	0.6604	0.6604
Toxoplasma gondii	phosphorylase family protein	0.0109	0.0825	0.2738
Loa Loa (eye worm)	RNA binding protein	0.0071	0.0297	0.0582
Mycobacterium ulcerans	ATP-dependent Clp protease proteolytic subunit	0.0086	0.0503	0.0762
Schistosoma mansoni	bifunctional dihydrofolate reductase-thymidylate synthase	0.0121	0.0994	0.0994
Schistosoma mansoni	methylthioadenosine phosphorylase	0.0109	0.0825	0.0825
Echinococcus multilocularis	microtubule associated protein 2	0.0772	1	1
Trichomonas vaginalis	purine nucleoside phosphorylase, putative	0.0109	0.0825	0.1095
Echinococcus multilocularis	purine nucleoside phosphorylase	0.0527	0.6604	0.6604
Echinococcus granulosus	purine nucleoside phosphorylase	0.0527	0.6604	0.6604
Trichomonas vaginalis	conserved hypothetical protein	0.0109	0.0825	0.1095
Schistosoma mansoni	uridine phosphorylase	0.0109	0.0825	0.0825
Echinococcus granulosus	methylthioadenosine phosphorylase	0.0109	0.0825	0.0825
Mycobacterium tuberculosis	Probable purine nucleoside phosphorylase DeoD (inosine phosphorylase) (PNP)	0.0527	0.6604	1
Brugia malayi	purine nucleoside phosphorylase I, inosine and guanosine-specific family protein	0.0527	0.6604	1
Treponema pallidum	uridine phosphorylase (udp)	0.0109	0.0825	1
Mycobacterium tuberculosis	Probable thymidylate synthase ThyA (ts) (TSASE)	0.0121	0.0994	0.1505
Mycobacterium tuberculosis	Probable bifunctional MTA/SAH nucleosidase Mtn: 5'-methylthioadenosine nucleosidase (methylthioadenosine methylthioribohydrolase	0.0109	0.0825	0.1249
Treponema pallidum	pfs protein (pfs)	0.0109	0.0825	1
Plasmodium vivax	purine nucleoside phosphorylase, putative	0.0109	0.0825	0.2738
Schistosoma mansoni	tar DNA-binding protein	0.0071	0.0297	0.0297
Trichomonas vaginalis	purine nucleoside phosphorylase, putative	0.0109	0.0825	0.1095
Echinococcus granulosus	ATP dependent Clp protease proteolytic subunit	0.0086	0.0503	0.0503
Schistosoma mansoni	tar DNA-binding protein	0.0071	0.0297	0.0297
Wolbachia endosymbiont of Brugia malayi	ATP-dependent Clp protease proteolytic subunit	0.0086	0.0503	0.5
Chlamydia trachomatis	AMP nucleosidase	0.0109	0.0825	1
Trichomonas vaginalis	conserved hypothetical protein	0.0109	0.0825	0.1095
Schistosoma mansoni	peptidase Clp (S14 family)	0.0086	0.0503	0.0503
Schistosoma mansoni	methylthioadenosine phosphorylase	0.0109	0.0825	0.0825
Entamoeba histolytica	MTA/SAH nucleosidase, putative	0.0109	0.0825	0.5
Trypanosoma brucei	dihydrofolate reductase-thymidylate synthase	0.0171	0.1678	1
Brugia malayi	MH2 domain containing protein	0.0134	0.1164	0.1763
Brugia malayi	Calcitonin receptor-like protein seb-1	0.0056	0.0088	0.0133
Entamoeba histolytica	purine nucleoside phosphorylase, putative	0.0109	0.0825	0.5
Echinococcus granulosus	purine nucleoside phosphorylase	0.0527	0.6604	0.6604
Giardia lamblia	Purine nucleoside phosphorylase lateral transfer candidate	0.0527	0.6604	1
Echinococcus multilocularis	thymidylate synthase	0.0121	0.0994	0.0994
Schistosoma mansoni	uridine phosphorylase	0.0109	0.0825	0.0825
Entamoeba histolytica	purine nucleoside phosphorylase, putative	0.0109	0.0825	0.5
Mycobacterium ulcerans	thymidylate synthase	0.0121	0.0994	0.1505
Trypanosoma cruzi	nucleoside phosphorylase, putative	0.0109	0.0825	0.4546
Entamoeba histolytica	purine nucleoside phosphorylase, putative	0.0109	0.0825	0.5
Trypanosoma cruzi	methylthioadenosine phosphorylase, putative	0.0109	0.0825	0.4546
Toxoplasma gondii	Purine nucleoside phosphorylase	0.0109	0.0825	0.2738
Echinococcus multilocularis	uridine phosphorylase 1	0.0109	0.0825	0.0825
Brugia malayi	thymidylate synthase	0.0121	0.0994	0.1505
Mycobacterium leprae	PROBABLE THYMIDYLATE SYNTHASE THYA (TS) (TSASE)	0.0121	0.0994	0.1505
Entamoeba histolytica	purine nucleoside phosphorylase, putative	0.0109	0.0825	0.5
Mycobacterium leprae	Probable purine nucleoside phosphorylase DeoD (INOSINE PHOSPHORYLASE) (PNP)	0.0527	0.6604	1
Mycobacterium tuberculosis	Hypothetical protein	0.0058	0.0114	0.0173
Giardia lamblia	Deoxynucleoside kinase	0.0409	0.4975	0.7181

Activities

Activity type	Activity value	Assay description	Source	Reference
Cl - current change (functional)	= 0.11	In vitro efficacy calculated by chlorine current assay on alpha1-beta2-gamma2 (GABA-A) receptor subtype	ChEMBL.	8809170
Cl - current change (functional)	= 0.11	In vitro efficacy calculated by chlorine current assay on alpha1-beta2-gamma2 (GABA-A) receptor subtype	ChEMBL.	8809170
ED50 (functional)	> 50 mg kg-1	Ability to antagonize metrazole-induced seizures (clonic and tonic) in mice after intraperitoneal injection	ChEMBL.	8809170
ED50 (functional)	> 50 mg kg-1	Ability to antagonize metrazole-induced seizures (clonic and tonic) in mice after intraperitoneal injection	ChEMBL.	8809170
Ki (binding)	= 480 nM	Binding affinity against benzodiazepine receptor (BzR) in rat cortical membranes determined by competition experiments with radiolabeled [3H]-flunitrazepam (Fnz)	ChEMBL.	8809170
Ki (binding)	= 480 nM	Binding affinity against benzodiazepine receptor (BzR) in rat cortical membranes determined by competition experiments with radiolabeled [3H]-flunitrazepam (Fnz)	ChEMBL.	8809170
TBPS shift (binding)	= 0.31	In vitro efficacy by [35S]-t-butyl-bicyclophosphorothionate (TBPS) binding to the picrotoxin convulsant site on the GABA-A receptor chloride complex.	ChEMBL.	8809170
TBPS shift (binding)	= 0.31	In vitro efficacy by [35S]-t-butyl-bicyclophosphorothionate (TBPS) binding to the picrotoxin convulsant site on the GABA-A receptor chloride complex.	ChEMBL.	8809170

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

ChEMBL: CHEMBL126798
PubChem: 10829588

Bibliographic References

1 literature reference was collected for this gene.

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

Detailed information for compound 220083