TDR Targets

Basic information

Technical information

TDR Targets ID: 59302
Name: 3-[2-[(3aR,9bR)-6-methoxy-1,3,3a,4,5,9b-hexah ydrobenzo[e]isoindol-2-yl]ethyl]-2,4-dioxo-1H -[1]benzothiolo[3,2-d]pyrimidine-7-carbonitri le
MW: 472.559 | Formula: C26H24N4O3S
H donors: 1 H acceptors: 3 LogP: 3.88 Rotable bonds: 4
Rule of 5 violations (Lipinski): 1
SMILES: N#Cc1ccc2c(c1)sc1c2[nH]c(=O)n(c1=O)CCN1C[C@H]2[C@@H](C1)c1cccc(c1CC2)OC
InChi: 1S/C26H24N4O3S/c1-33-21-4-2-3-17-18(21)8-6-16-13-29(14-20(16)17)9-10-30-25(31)24-23(28-26(30)32)19-7-5-15(12-27)11-22(19)34-24/h2-5,7,11,16,20H,6,8-10,13-14H2,1H3,(H,28,32)/t16-,20+/m0/s1
InChiKey: BEGSWXFCPNJFKG-OXJNMPFZSA-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-[2-[(3aR,9bR)-6-methoxy-1,3,3a,4,5,9b-hexahydrobenzo[e]isoindol-2-yl]ethyl]-2,4-dioxo-1H-benzothiopheno[3,2-d]pyrimidine-7-carbonitrile
3-[2-[(3aR,9bR)-6-methoxy-1,3,3a,4,5,9b-hexahydrobenzo[e]isoindol-2-yl]ethyl]-2,4-diketo-1H-benzothiopheno[3,2-d]pyrimidine-7-carbonitrile
3-[2-[(3aR,9bR)-6-methoxy-1,3,3a,4,5,9b-hexahydrobenzo[g]isoindol-2-yl]ethyl]-2,4-dioxo-1H-[1]benzothiolo[3,2-d]pyrimidine-7-carbonitrile
3-[2-[(3aR,9bR)-6-methoxy-1,3,3a,4,5,9b-hexahydrobenzo[g]isoindol-2-yl]ethyl]-2,4-dioxo-1H-benzothiopheno[3,2-d]pyrimidine-7-carbonitrile
3-[2-[(3aR,9bR)-6-methoxy-1,3,3a,4,5,9b-hexahydrobenzo[g]isoindol-2-yl]ethyl]-2,4-diketo-1H-benzothiopheno[3,2-d]pyrimidine-7-carbonitrile

Targets

Known targets for this compound

Species	Target name	Source	Bibliographic reference
Rattus norvegicus	Alpha-1d adrenergic receptor	Starlite/ChEMBL	References
Rattus norvegicus	Alpha-1a adrenergic receptor	Starlite/ChEMBL	References
Mesocricetus auratus	Alpha-1b adrenergic receptor	Starlite/ChEMBL	References

Predicted pathogen targets for this compound

By orthology

Species	Potential target	Known druggable target/s	Ortholog Group
Schistosoma mansoni	amine GPCR	Get druggable targets OG5_128924	All targets in OG5_128924
Schistosoma japonicum	ko:K04135 adrenergic receptor, alpha 1a, putative	Get druggable targets OG5_128924	All targets in OG5_128924
Schistosoma japonicum	Alpha-1D adrenergic receptor, putative	Get druggable targets OG5_128924	All targets in OG5_128924

By sequence similarity to non orthologous known druggable targets

Species	Potential target	Known druggable target	Length	Alignment span	Identity
Schistosoma japonicum	FMRFamide receptor, putative	Alpha-1a adrenergic receptor	466 aa	374 aa	19.5 %
Schistosoma japonicum	ko:K04135 adrenergic receptor, alpha 1a, putative	Alpha-1a adrenergic receptor	466 aa	443 aa	31.2 %
Echinococcus multilocularis	g protein coupled receptor	Alpha-1a adrenergic receptor	466 aa	414 aa	20.3 %
Echinococcus multilocularis	neuropeptide Y receptor	Alpha-1a adrenergic receptor	466 aa	419 aa	19.6 %
Echinococcus granulosus	rhodopsin orphan GPCR	Alpha-1a adrenergic receptor	466 aa	418 aa	20.3 %
Echinococcus multilocularis	g protein coupled receptor	Alpha-1a adrenergic receptor	466 aa	398 aa	21.4 %
Schistosoma japonicum	ko:K04136 adrenergic receptor, alpha 1b, putative	Alpha-1a adrenergic receptor	466 aa	386 aa	31.6 %
Echinococcus granulosus	g protein coupled receptor	Alpha-1a adrenergic receptor	466 aa	414 aa	20.5 %
Echinococcus granulosus	g protein coupled receptor	Alpha-1a adrenergic receptor	466 aa	399 aa	20.8 %
Echinococcus granulosus	biogenic amine 5HT receptor	Alpha-1a adrenergic receptor	466 aa	418 aa	30.4 %

Ranking Plot

Putative Targets List

Species	Potential target	Raw	Global	Species
Schistosoma mansoni	amine GPCR	0.0411	0.3884	0.3733
Echinococcus granulosus	eukaryotic initiation factor 4A III	0.0321	0.2786	0.121
Loa Loa (eye worm)	gamma-secretase subunit aph-1	0.024	0.1793	0.1592
Loa Loa (eye worm)	hypothetical protein	0.0911	1	1
Schistosoma mansoni	DEAD box ATP-dependent RNA helicase	0.0321	0.2786	0.2609
Loa Loa (eye worm)	hypothetical protein	0.0321	0.2786	0.2609
Leishmania major	eukaryotic initiation factor 4a, putative	0.0321	0.2786	0.5
Onchocerca volvulus		0.0316	0.2721	0.2543
Mycobacterium tuberculosis	Probable cold-shock DeaD-box protein A homolog DeaD (ATP-dependent RNA helicase dead homolog)	0.0321	0.2786	0.5
Onchocerca volvulus	Eukaryotic initiation factor 4A homolog	0.0321	0.2786	0.2609
Schistosoma mansoni	DEAD box ATP-dependent RNA helicase	0.0321	0.2786	0.2609
Schistosoma mansoni	hypothetical protein	0.0316	0.2721	0.2543
Trypanosoma cruzi	Eukaryotic initiation factor 4A-1	0.0321	0.2786	1
Schistosoma mansoni	caspase-7 (C14 family)	0.0316	0.2721	0.2543
Loa Loa (eye worm)	hypothetical protein	0.0911	1	1
Echinococcus multilocularis	eukaryotic initiation factor 4A	0.0321	0.2786	0.121
Schistosoma mansoni	hypothetical protein	0.0911	1	1
Onchocerca volvulus	Deterin homolog	0.0911	1	1
Brugia malayi	hypothetical protein	0.0316	0.2721	0.2543
Schistosoma mansoni	gamma-secretase subunit aph-1	0.024	0.1793	0.1592
Entamoeba histolytica	DEAD/DEAH box helicase, putative	0.0321	0.2786	0.5
Brugia malayi	Inhibitor of Apoptosis domain containing protein	0.0911	1	1
Schistosoma mansoni	inhibitor of apoptosis protein	0.0911	1	1
Echinococcus granulosus	eukaryotic initiation factor 4A	0.0321	0.2786	0.121
Onchocerca volvulus		0.0911	1	1
Toxoplasma gondii	eukaryotic initiation factor-4A, putative	0.0321	0.2786	0.5
Echinococcus granulosus	caspase 2	0.0316	0.2721	0.1131
Plasmodium falciparum	eukaryotic initiation factor 4A	0.0321	0.2786	0.5
Echinococcus multilocularis	inhibitor of apoptosis protein	0.0911	1	1
Schistosoma mansoni	inhibitor of apoptosis (iap) domain family member	0.0911	1	1
Echinococcus multilocularis	apoptotic protease activating factor 1	0.0316	0.2721	0.1131
Onchocerca volvulus	Cell death protein 3 homolog	0.0316	0.2721	0.2543
Leishmania major	eukaryotic initiation factor 4a, putative	0.0321	0.2786	0.5
Trichomonas vaginalis	DEAD box ATP-dependent RNA helicase, putative	0.0321	0.2786	0.5
Trypanosoma brucei	Eukaryotic initiation factor 4A-1	0.0321	0.2786	1
Echinococcus granulosus	inhibitor of apoptosis protein	0.0911	1	1
Echinococcus granulosus	apoptotic protease activating factor 1	0.0316	0.2721	0.1131
Echinococcus multilocularis	caspase 2	0.0316	0.2721	0.1131
Loa Loa (eye worm)	hypothetical protein	0.0316	0.2721	0.2543
Brugia malayi	Cell death protein 3 precursor	0.0316	0.2721	0.2543
Echinococcus multilocularis	eukaryotic initiation factor 4A III	0.0321	0.2786	0.121
Echinococcus granulosus	baculoviral IAP repeat containing protein	0.0911	1	1
Plasmodium vivax	RNA helicase-1, putative	0.0321	0.2786	0.5
Trypanosoma cruzi	Eukaryotic initiation factor 4A-1	0.0321	0.2786	1
Treponema pallidum	ATP-dependent RNA helicase	0.0321	0.2786	0.5
Brugia malayi	eukaryotic initiation factor 4A	0.0321	0.2786	0.2609
Loa Loa (eye worm)	hypothetical protein	0.0316	0.2721	0.2543
Trichomonas vaginalis	DEAD box ATP-dependent RNA helicase, putative	0.0321	0.2786	0.5
Giardia lamblia	Translation initiation factor eIF-4A, putative	0.0321	0.2786	0.5
Echinococcus multilocularis	baculoviral IAP repeat containing protein	0.0911	1	1
Brugia malayi	gamma-secretase subunit aph-1	0.024	0.1793	0.1592
Trichomonas vaginalis	DEAD box ATP-dependent RNA helicase, putative	0.0321	0.2786	0.5

Activities

Activity type	Activity value	Assay description	Source	Reference
Ki (binding)	= 0.4 nM	In vitro binding affinity using [3H]-prazosin as radioligand against alpha-1A adrenergic receptor	ChEMBL.	10780916
Ki (binding)	= 0.4 nM	In vitro binding affinity using [3H]-prazosin as radioligand against alpha-1A adrenergic receptor	ChEMBL.	10780916
Ki (binding)	= 0.74 nM	In vitro binding affinity using [3H]-prazosin as radioligand against alpha-1D adrenergic receptor expressed in LTK cell	ChEMBL.	10780916
Ki (binding)	= 0.74 nM	In vitro binding affinity using [3H]-prazosin as radioligand against alpha-1D adrenergic receptor expressed in LTK cell	ChEMBL.	10780916
Ki (binding)	= 6.2 nM	In vitro binding affinity using [3H]-prazosin as radioligand against alpha-1B adrenergic receptor expressed in LTK cell	ChEMBL.	10780916
Ki (binding)	= 6.2 nM	In vitro binding affinity using [3H]-prazosin as radioligand against alpha-1B adrenergic receptor expressed in LTK cell	ChEMBL.	10780916
Selectivity ratio (binding)	= 15.5	Ratio between Ki(alpha1b)/Ki(alpha1A)	ChEMBL.	10780916

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: CHEMBL40780
PubChem: 10839391

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 59302