TDR Targets

Basic information

Technical information

TDR Targets ID: 78279
Name: ethyl 6-oxo-5-prop-2-enyl-4H-imidazo[1,5-a][1 ,4]benzodiazepine-3-carboxylate
MW: 311.335 | Formula: C17H17N3O3
H donors: 0 H acceptors: 3 LogP: 1.94 Rotable bonds: 5
Rule of 5 violations (Lipinski): 1
SMILES: C=CCN1Cc2c(ncn2c2c(C1=O)cccc2)C(=O)OCC
InChi: 1S/C17H17N3O3/c1-3-9-19-10-14-15(17(22)23-4-2)18-11-20(14)13-8-6-5-7-12(13)16(19)21/h3,5-8,11H,1,4,9-10H2,2H3
InChiKey: FSICLUCUDPWJEQ-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

ethyl 5-allyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate
5-allyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid ethyl ester
5-allyl-6-keto-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid ethyl ester

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
Brugia malayi	Cation transporter family protein	GABA-A receptor; anion channel	467 aa	453 aa	28.5 %
Echinococcus granulosus	glycine receptor subunit beta	GABA-A receptor; anion channel	467 aa	439 aa	29.6 %
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 %
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 %
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 %
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	468 aa	28.6 %
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 %
Loa Loa (eye worm)	hypothetical protein	GABA-A receptor; anion channel	467 aa	494 aa	25.5 %
Onchocerca volvulus	Eukaryotic initiation factor 4A-III homolog	GABA-A receptor; anion channel	467 aa	453 aa	26.9 %
Onchocerca volvulus	Gamma-aminobutyric acid receptor subunit beta homolog	GABA-A receptor; anion channel	467 aa	433 aa	34.6 %
Onchocerca volvulus	Large subunit GTPase 1 homolog	GABA-A receptor; anion channel	467 aa	496 aa	26.0 %
Onchocerca volvulus		GABA-A receptor; anion channel	467 aa	435 aa	29.7 %
Onchocerca volvulus		GABA-A receptor; anion channel	467 aa	446 aa	28.0 %
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
Loa Loa (eye worm)	hypothetical protein	0.0023	0.0111	0.0111
Trypanosoma brucei	mitogen activated protein kinase 4, putative	0.005	0.367	0.5
Loa Loa (eye worm)	hypothetical protein	0.0041	0.255	0.255
Loa Loa (eye worm)	LGC-31 protein	0.0023	0.0111	0.0111
Loa Loa (eye worm)	pigment dispersing factor receptor c	0.0049	0.3529	0.3529
Echinococcus multilocularis	mitogen activated protein kinase 3	0.005	0.367	0.5026
Loa Loa (eye worm)	ACC-1 protein	0.0023	0.0111	0.0111
Loa Loa (eye worm)	hypothetical protein	0.0023	0.0111	0.0111
Loa Loa (eye worm)	hypothetical protein	0.0023	0.0111	0.0111
Entamoeba histolytica	hypothetical protein	0.0035	0.1749	0.5
Onchocerca volvulus		0.0041	0.255	1
Loa Loa (eye worm)	hypothetical protein	0.0023	0.0111	0.0111
Loa Loa (eye worm)	hypothetical protein	0.0023	0.0111	0.0111
Trypanosoma cruzi	mitogen activated protein kinase 4, putative	0.005	0.367	0.5
Schistosoma mansoni	hypothetical protein	0.0033	0.1505	0.1969
Loa Loa (eye worm)	hypothetical protein	0.0023	0.0111	0.0111
Brugia malayi	hypothetical protein	0.0041	0.255	0.2467
Loa Loa (eye worm)	hypothetical protein	0.0049	0.3529	0.3529
Brugia malayi	GTP-binding regulatory protein Gs alpha-S chain, putative	0.0045	0.3002	0.2923
Loa Loa (eye worm)	hypothetical protein	0.0023	0.0111	0.0111
Trichomonas vaginalis	CMGC family protein kinase	0.005	0.367	0.5
Onchocerca volvulus		0.0041	0.255	1
Loa Loa (eye worm)	hypothetical protein	0.0041	0.255	0.255
Giardia lamblia	Kinase, CMGC MAPK	0.005	0.367	0.5
Brugia malayi	hypothetical protein	0.0041	0.255	0.2467
Loa Loa (eye worm)	nicotinic acetylcholine receptor non-alpha subunit	0.0023	0.0111	0.0111
Loa Loa (eye worm)	immunoglobulin I-set domain-containing protein	0.0098	1	1
Loa Loa (eye worm)	hypothetical protein	0.0023	0.0111	0.0111
Loa Loa (eye worm)	hypothetical protein	0.0023	0.0111	0.0111
Echinococcus granulosus	mitogen activated protein kinase 3	0.005	0.367	0.5026
Onchocerca volvulus		0.0041	0.255	1
Schistosoma mansoni	Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein)	0.0045	0.3002	0.4082
Loa Loa (eye worm)	hypothetical protein	0.0033	0.1505	0.1505
Loa Loa (eye worm)	ACC-1 protein	0.0023	0.0111	0.0111
Entamoeba histolytica	hypothetical protein	0.0035	0.1749	0.5
Loa Loa (eye worm)	GTP-binding regulatory protein Gs alpha-S chain	0.0045	0.3002	0.3002
Schistosoma mansoni	c4b-binding protein beta chain	0.0041	0.255	0.3445
Loa Loa (eye worm)	hypothetical protein	0.0041	0.255	0.255
Brugia malayi	pregnancy-associated plasma protein-A	0.0041	0.255	0.2467
Brugia malayi	hypothetical protein	0.0041	0.255	0.2467
Loa Loa (eye worm)	hypothetical protein	0.0023	0.0111	0.0111
Entamoeba histolytica	hypothetical protein	0.0035	0.1749	0.5
Echinococcus multilocularis	mitogen activated protein kinase	0.005	0.367	0.5026
Echinococcus multilocularis	guanine nucleotide binding protein G(s) subunit	0.0045	0.3002	0.4082
Loa Loa (eye worm)	immunoglobulin I-set domain-containing protein	0.0098	1	1
Echinococcus granulosus	nephrin	0.0076	0.7193	1
Loa Loa (eye worm)	hypothetical protein	0.0023	0.0111	0.0111
Schistosoma mansoni	Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein)	0.0045	0.3002	0.4082
Loa Loa (eye worm)	nicotinic acetylcholine receptor alpha subunit	0.0023	0.0111	0.0111
Schistosoma mansoni	serine/threonine protein kinase	0.005	0.367	0.5026
Loa Loa (eye worm)	hypothetical protein	0.0023	0.0111	0.0111
Loa Loa (eye worm)	hypothetical protein	0.0023	0.0111	0.0111
Echinococcus multilocularis	irregular chiasm roughest protein immunoglobulin set domain containing protein	0.0076	0.7193	1
Echinococcus multilocularis	Basic leucine zipper (bZIP) transcription	0.0035	0.1749	0.2313
Echinococcus granulosus	c4b binding protein beta chain	0.0041	0.255	0.3445
Echinococcus multilocularis	c4b binding protein beta chain	0.0041	0.255	0.3445
Loa Loa (eye worm)	hypothetical protein	0.0041	0.255	0.255
Trypanosoma brucei	protein kinase, putative	0.005	0.367	0.5
Brugia malayi	hypothetical protein	0.0041	0.255	0.2467
Leishmania major	mitogen activated protein kinase, putative,map kinase, putative	0.005	0.367	0.5
Loa Loa (eye worm)	acetylcholine receptor alpha subunit	0.0023	0.0111	0.0111
Loa Loa (eye worm)	hypothetical protein	0.0023	0.0111	0.0111
Leishmania major	mitogen activated protein kinase 4, putative;with=GeneDB:LmxM19.1440	0.005	0.367	0.5
Echinococcus granulosus	Immunoglobulin	0.0076	0.7193	1
Loa Loa (eye worm)	hypothetical protein	0.0046	0.3158	0.3158
Trichomonas vaginalis	CMGC family protein kinase	0.005	0.367	0.5
Trichomonas vaginalis	CMGC family protein kinase	0.005	0.367	0.5
Echinococcus granulosus	nephrin	0.0076	0.7193	1
Loa Loa (eye worm)	hypothetical protein	0.0023	0.0111	0.0111
Echinococcus granulosus	guanine nucleotide binding protein Gs subunit	0.0045	0.3002	0.4082
Trichomonas vaginalis	CMGC family protein kinase	0.005	0.367	0.5
Loa Loa (eye worm)	hypothetical protein	0.0023	0.0111	0.0111
Brugia malayi	hypothetical protein	0.0041	0.255	0.2467
Onchocerca volvulus		0.0041	0.255	1
Brugia malayi	hypothetical protein	0.0041	0.255	0.2467
Onchocerca volvulus		0.0041	0.255	1
Onchocerca volvulus		0.0041	0.255	1
Brugia malayi	GCC2 and GCC3 family protein	0.0054	0.4305	0.4241
Echinococcus granulosus	irregular chiasm roughest protein	0.0076	0.7193	1
Loa Loa (eye worm)	hypothetical protein	0.0023	0.0111	0.0111
Brugia malayi	Corticotropin releasing factor receptor 2 precursor, putative	0.0049	0.3529	0.3456
Loa Loa (eye worm)	glutamate-gated chloride channel alpha3A subunit	0.0023	0.0111	0.0111
Loa Loa (eye worm)	hypothetical protein	0.0041	0.255	0.255
Trypanosoma cruzi	mitogen-activated protein kinase 11, putative	0.005	0.367	0.5
Brugia malayi	hypothetical protein	0.0098	1	1
Echinococcus multilocularis	conserved hypothetical protein	0.0076	0.7193	1
Plasmodium vivax	apical sushi protein, putative	0.0041	0.255	0.5
Loa Loa (eye worm)	hypothetical protein	0.0041	0.255	0.255
Onchocerca volvulus		0.0041	0.255	1
Onchocerca volvulus		0.0041	0.255	1
Loa Loa (eye worm)	excitatory GABA receptor EXP-1A	0.0023	0.0111	0.0111
Brugia malayi	hypothetical protein	0.0035	0.1749	0.1657
Plasmodium falciparum	apical sushi protein	0.0041	0.255	0.5
Onchocerca volvulus		0.0041	0.255	1
Brugia malayi	Calcitonin receptor-like protein seb-1	0.0049	0.3529	0.3456
Echinococcus multilocularis	Immunoglobulin	0.0076	0.7193	1
Trypanosoma cruzi	mitogen-activated protein kinase 11, putative	0.005	0.367	0.5
Brugia malayi	Sushi domain	0.0041	0.255	0.2467
Schistosoma mansoni	hypothetical protein	0.0076	0.7193	1
Loa Loa (eye worm)	ligand-Gated ion Channel family member	0.0023	0.0111	0.0111
Brugia malayi	MAP kinase sur-1	0.005	0.367	0.3599
Loa Loa (eye worm)	hypothetical protein	0.0041	0.255	0.255
Echinococcus granulosus	mitogen activated protein kinase	0.005	0.367	0.5026
Trypanosoma cruzi	mitogen activated protein kinase 2, putative	0.005	0.367	0.5
Loa Loa (eye worm)	pregnancy-associated plasma protein-E	0.0041	0.255	0.255
Schistosoma mansoni	Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein)	0.0045	0.3002	0.4082
Echinococcus granulosus	guanine nucleotide binding protein Gs subunit	0.0045	0.3002	0.4082
Echinococcus granulosus	C type lectin domian containing protein	0.0041	0.255	0.3445
Schistosoma mansoni	hypothetical protein	0.0035	0.1749	0.2313
Echinococcus multilocularis	nephrin	0.0076	0.7193	1
Echinococcus granulosus	Basic leucine zipper bZIP transcription	0.0035	0.1749	0.2313
Brugia malayi	Immunoglobulin I-set domain containing protein	0.0098	1	1
Onchocerca volvulus		0.0041	0.255	1
Schistosoma mansoni	hypothetical protein	0.0076	0.7193	1
Loa Loa (eye worm)	hypothetical protein	0.0023	0.0111	0.0111
Loa Loa (eye worm)	hypothetical protein	0.0054	0.4305	0.4305
Loa Loa (eye worm)	hypothetical protein	0.0023	0.0111	0.0111
Entamoeba histolytica	hypothetical protein	0.0035	0.1749	0.5
Echinococcus multilocularis	C type lectin domian containing protein	0.0041	0.255	0.3445
Brugia malayi	latrophilin 2 splice variant baaae	0.0033	0.1505	0.141
Echinococcus multilocularis	guanine nucleotide binding protein G(s) subunit	0.0045	0.3002	0.4082
Brugia malayi	hypothetical protein	0.0041	0.255	0.2467
Loa Loa (eye worm)	CMGC/MAPK/ERK1 protein kinase	0.005	0.367	0.367
Schistosoma mansoni	transcription factor LCR-F1	0.0035	0.1749	0.2313
Toxoplasma gondii	CMGC kinase, MAPK family (ERK) MAPK-1	0.005	0.367	1

Activities

Activity type	Activity value	Assay description	Source	Reference
IC50 (binding)	= 157 nM	Displacement of [3H]-flunitrazepam from diazepam-sensitive GABA-A benzodiazepine receptor of rat cortical membrane	ChEMBL.	8386247
IC50 (binding)	= 157 nM	Displacement of [3H]-flunitrazepam from diazepam-sensitive GABA-A benzodiazepine receptor of rat cortical membrane	ChEMBL.	8386247
Ki (binding)	= 39.2 nM	Binding affinity for diazepam sensitive (DS) isoform of the benzodiazepine (Bz) binding site on GABAA receptors	ChEMBL.	8390574
Ki (binding)	= 39.2 nM	Binding affinity for diazepam sensitive (DS) isoform of the benzodiazepine (Bz) binding site on GABAA receptors	ChEMBL.	8390574
Ki (binding)	= 1132 nM	Binding affinity for diazepam insensitive (DI) isoform of the benzodiazepine (Bz) binding site on GABAA receptors	ChEMBL.	8390574
Ki (binding)	= 1132 nM	Binding affinity for diazepam insensitive (DI) isoform of the benzodiazepine (Bz) binding site on GABAA receptors	ChEMBL.	8390574
Ratio (binding)	= 29	Ratio of binding affinity against DI Bz receptor to that of DS Bz receptor	ChEMBL.	8390574

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

PubChem: 10244940

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.

Detailed information for compound 78279