TDR Targets

Basic information

Technical information

TDR Targets ID: 181825
Name: methyl 3-[(4S)-8-chloro-6-(2-fluorophenyl)-4H -imidazo[1,2-a][1,4]benzodiazepin-4-yl]propan oate
MW: 397.83 | Formula: C21H17ClFN3O2
H donors: 0 H acceptors: 2 LogP: 3.73 Rotable bonds: 5
Rule of 5 violations (Lipinski): 1
SMILES: COC(=O)CC[C@@H]1N=C(c2c(n3c1ncc3)ccc(c2)Cl)c1ccccc1F
InChi: 1S/C21H17ClFN3O2/c1-28-19(27)9-7-17-21-24-10-11-26(21)18-8-6-13(22)12-15(18)20(25-17)14-4-2-3-5-16(14)23/h2-6,8,10-12,17H,7,9H2,1H3/t17-/m0/s1
InChiKey: SWYFQJGWUBNZHT-KRWDZBQOSA-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-[(4S)-8-chloro-6-(2-fluorophenyl)-4H-imidazo[1,2-a][1,4]benzodiazepin-4-yl]propanoic acid methyl ester
3-[(4S)-8-chloro-6-(2-fluorophenyl)-4H-imidazo[1,2-a][1,4]benzodiazepin-4-yl]propionic acid methyl ester

Targets

Known targets for this compound

Species	Target name	Source	Bibliographic reference
Rattus norvegicus	Peripheral-type benzodiazepine receptor	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_129542	All targets in OG5_129542
Loa Loa (eye worm)	hypothetical protein	Get druggable targets OG5_129542	All targets in OG5_129542
Onchocerca volvulus		Get druggable targets OG5_129542	All targets in OG5_129542
Onchocerca volvulus		Get druggable targets OG5_129542	All targets in OG5_129542
Echinococcus multilocularis	translocator protein	Get druggable targets OG5_129542	All targets in OG5_129542
Brugia malayi	TspO/MBR family protein	Get druggable targets OG5_129542	All targets in OG5_129542
Echinococcus granulosus	translocator protein	Get druggable targets OG5_129542	All targets in OG5_129542
Loa Loa (eye worm)	hypothetical protein	Get druggable targets OG5_129542	All targets in OG5_129542
Schistosoma mansoni	peripheral-type benzodiazepine receptor	Get druggable targets OG5_129542	All targets in OG5_129542
Onchocerca volvulus		Get druggable targets OG5_129542	All targets in OG5_129542
Mycobacterium ulcerans	tryptophan-rich sensory protein	Get druggable targets OG5_129542	All targets in OG5_129542
Onchocerca volvulus		Get druggable targets OG5_129542	All targets in OG5_129542
Loa Loa (eye worm)	hypothetical protein	Get druggable targets OG5_129542	All targets in OG5_129542

By sequence similarity to non orthologous known druggable targets

Species	Potential target	Known druggable target	Length	Alignment span	Identity
Onchocerca volvulus		Peripheral-type benzodiazepine receptor	169 aa	156 aa	25.6 %
Echinococcus granulosus	vacuolar h atpase	Peripheral-type benzodiazepine receptor	169 aa	137 aa	25.5 %

Ranking Plot

Putative Targets List

Species	Potential target	Raw	Global	Species
Onchocerca volvulus		0.0322	0.1919	1
Loa Loa (eye worm)	hypothetical protein	0.0195	0.0692	0.0692
Brugia malayi	TspO/MBR family protein	0.0322	0.1919	0.1919
Mycobacterium ulcerans	tryptophan-rich sensory protein	0.0322	0.1919	1
Loa Loa (eye worm)	carboxylesterase	0.1156	1	1
Loa Loa (eye worm)	hypothetical protein	0.0195	0.0692	0.0692
Brugia malayi	Carboxylesterase family protein	0.1156	1	1
Onchocerca volvulus		0.0322	0.1919	1
Trichomonas vaginalis	spcc417.12 protein, putative	0.0195	0.0692	0.5
Schistosoma mansoni	family S9 non-peptidase homologue (S09 family)	0.1156	1	1
Schistosoma mansoni	neuroligin 3 (S09 family)	0.0195	0.0692	0.0692
Echinococcus granulosus	acetylcholinesterase	0.1156	1	1
Schistosoma mansoni	family S9 non-peptidase homologue (S09 family)	0.0195	0.0692	0.0692
Echinococcus granulosus	neuroligin	0.0195	0.0692	0.0692
Schistosoma mansoni	BC026374 protein (S09 family)	0.0195	0.0692	0.0692
Trypanosoma cruzi	trypanothione reductase, putative	0.0124	0	0.5
Loa Loa (eye worm)	hypothetical protein	0.0322	0.1919	0.1919
Echinococcus granulosus	translocator protein	0.0322	0.1919	0.1919
Loa Loa (eye worm)	hypothetical protein	0.0195	0.0692	0.0692
Echinococcus granulosus	carboxylesterase 5A	0.1156	1	1
Mycobacterium tuberculosis	Carboxylesterase LipT	0.0195	0.0692	1
Loa Loa (eye worm)	hypothetical protein	0.0322	0.1919	0.1919
Echinococcus multilocularis	acetylcholinesterase	0.1156	1	1
Schistosoma mansoni	family S9 non-peptidase homologue (S09 family)	0.0195	0.0692	0.0692
Brugia malayi	Carboxylesterase family protein	0.0195	0.0692	0.0692
Onchocerca volvulus		0.0322	0.1919	1
Onchocerca volvulus		0.0322	0.1919	1
Trichomonas vaginalis	carboxylesterase domain containing protein, putative	0.0195	0.0692	0.5
Brugia malayi	Carboxylesterase family protein	0.0195	0.0692	0.0692
Trypanosoma brucei	trypanothione reductase	0.0124	0	0.5
Schistosoma mansoni	acetylcholinesterase	0.0195	0.0692	0.0692
Echinococcus granulosus	BC026374 protein S09 family	0.0195	0.0692	0.0692
Echinococcus multilocularis	translocator protein	0.0322	0.1919	0.1919
Echinococcus multilocularis	para nitrobenzyl esterase	0.0195	0.0692	0.0692
Schistosoma mansoni	memapsin-2 (A01 family)	0.0424	0.2906	0.2906
Loa Loa (eye worm)	hypothetical protein	0.0322	0.1919	0.1919
Echinococcus multilocularis	BC026374 protein (S09 family)	0.0195	0.0692	0.0692
Echinococcus granulosus	para nitrobenzyl esterase	0.0195	0.0692	0.0692
Loa Loa (eye worm)	hypothetical protein	0.0195	0.0692	0.0692
Plasmodium falciparum	glutathione reductase	0.0124	0	0.5
Plasmodium falciparum	thioredoxin reductase	0.0124	0	0.5
Loa Loa (eye worm)	hypothetical protein	0.1156	1	1
Loa Loa (eye worm)	hypothetical protein	0.1156	1	1
Leishmania major	trypanothione reductase	0.0124	0	0.5
Echinococcus granulosus	family S9 non peptidase ue S09 family	0.0195	0.0692	0.0692
Loa Loa (eye worm)	hypothetical protein	0.0195	0.0692	0.0692
Plasmodium vivax	thioredoxin reductase, putative	0.0124	0	0.5
Loa Loa (eye worm)	hypothetical protein	0.0195	0.0692	0.0692
Echinococcus multilocularis	acetylcholinesterase	0.1156	1	1
Echinococcus granulosus	acetylcholinesterase	0.1156	1	1
Brugia malayi	hypothetical protein	0.0195	0.0692	0.0692
Loa Loa (eye worm)	hypothetical protein	0.0195	0.0692	0.0692
Loa Loa (eye worm)	acetylcholinesterase 1	0.1156	1	1
Loa Loa (eye worm)	carboxylesterase	0.0195	0.0692	0.0692
Brugia malayi	Carboxylesterase family protein	0.0195	0.0692	0.0692
Plasmodium vivax	glutathione reductase, putative	0.0124	0	0.5
Brugia malayi	hypothetical protein	0.013	0.0059	0.0059
Mycobacterium tuberculosis	POSSIBLE PARA-NITROBENZYL ESTERASE (FRAGMENT)	0.0195	0.0692	1
Echinococcus multilocularis	family S9 non peptidase ue (S09 family)	0.0195	0.0692	0.0692
Schistosoma mansoni	peripheral-type benzodiazepine receptor	0.0322	0.1919	0.1919
Toxoplasma gondii	thioredoxin reductase	0.0124	0	0.5
Schistosoma mansoni	gliotactin	0.0195	0.0692	0.0692
Schistosoma mansoni	family S9 non-peptidase homologue (S09 family)	0.0195	0.0692	0.0692
Mycobacterium tuberculosis	POSSIBLE PARA-NITROBENZYL ESTERASE (FRAGMENT)	0.0195	0.0692	1
Echinococcus multilocularis	carboxylesterase 5A	0.1156	1	1
Brugia malayi	Carboxylesterase family protein	0.0195	0.0692	0.0692
Loa Loa (eye worm)	hypothetical protein	0.0322	0.1919	0.1919
Loa Loa (eye worm)	carboxylesterase	0.0195	0.0692	0.0692
Echinococcus multilocularis	neuroligin	0.0195	0.0692	0.0692

Activities

Activity type	Activity value	Assay description	Source	Reference
Ki (binding)	= 7 nM	Binding affinity of the compound was determined against rat benzodiazepine (BZD) receptor	ChEMBL.	12372538
Ki (binding)	= 7 nM	Binding affinity of the compound was determined against rat benzodiazepine (BZD) receptor	ChEMBL.	12372538
Recovery time (functional)	= 17 mg kg-1	Compound was tested for its initial (rat) loss-of-righting reflex LORR recovery time at a dose of 25 mg/kg	ChEMBL.	12372538
Recovery time (functional)	= 23 mg kg-1	Compound was tested for its total (rat) loss-of-righting reflex LORR recovery time at a dose of 25 mg/kg	ChEMBL.	12372538
Selectivity (binding)	= 64	Selectivity of the compound was determined by the ratio of binding affinity of acid to the binding affinity of its ester	ChEMBL.	12372538
Solubility	0 mg ml-1	Aqueous solubility of the compound at pH 3 was determined; ND means not determined	ChEMBL.	12372538

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: CHEMBL111633
PubChem: 9800970

Bibliographic References

1 literature reference was collected for this gene.

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Detailed information for compound 181825