TDR Targets

Basic information

Technical information

TDR Targets ID: 439416
Name: 6-chloro-2-[4-methoxy-3-(2-piperidin-1-yletho xy)phenyl]-4-methyl-3H-pyrrolo[3,4-b]indol-1- one
MW: 453.961 | Formula: C25H28ClN3O3
H donors: 0 H acceptors: 1 LogP: 4.08 Rotable bonds: 6
Rule of 5 violations (Lipinski): 1
SMILES: COc1ccc(cc1OCCN1CCCCC1)N1Cc2c(C1=O)c1c(n2C)cc(cc1)Cl
InChi: 1S/C25H28ClN3O3/c1-27-20-14-17(26)6-8-19(20)24-21(27)16-29(25(24)30)18-7-9-22(31-2)23(15-18)32-13-12-28-10-4-3-5-11-28/h6-9,14-15H,3-5,10-13,16H2,1-2H3
InChiKey: NJQUATWTCFAQNO-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

6-chloro-2-[4-methoxy-3-[2-(1-piperidyl)ethoxy]phenyl]-4-methyl-3H-pyrrolo[3,4-b]indol-1-one
6-chloro-2-[4-methoxy-3-(2-piperidinoethoxy)phenyl]-4-methyl-3H-pyrrolo[3,4-b]indol-1-one
6-chloro-2-[4-methoxy-3-(2-piperidin-1-ylethoxy)phenyl]-4-methyl-3H-pyrrolo[4,3-b]indol-1-one
6-chloro-2-[4-methoxy-3-[2-(1-piperidyl)ethoxy]phenyl]-4-methyl-3H-pyrrolo[4,3-b]indol-1-one
6-chloro-2-[4-methoxy-3-(2-piperidinoethoxy)phenyl]-4-methyl-3H-pyrrolo[4,3-b]indol-1-one

Targets

Known targets for this compound

Species	Target name	Source	Bibliographic reference
Homo sapiens	5-hydroxytryptamine (serotonin) receptor 2B, G protein-coupled	Starlite/ChEMBL	References
Homo sapiens	5-hydroxytryptamine (serotonin) receptor 2A, G protein-coupled	Starlite/ChEMBL	References
Homo sapiens	5-hydroxytryptamine (serotonin) receptor 2C, G protein-coupled	Starlite/ChEMBL	References

Predicted pathogen targets for this compound

By orthology

Species	Potential target	Known druggable target/s	Ortholog Group
Brugia malayi	Serotonin receptor	Get druggable targets OG5_135430	All targets in OG5_135430
Echinococcus granulosus	hypothetical protein	Get druggable targets OG5_144688	All targets in OG5_144688
Echinococcus multilocularis	conserved hypothetical protein	Get druggable targets OG5_144688	All targets in OG5_144688

By sequence similarity to non orthologous known druggable targets

No druggable targets predicted by sequence similarity

Ranking Plot

Putative Targets List

Species	Potential target	Raw	Global	Species
Mycobacterium tuberculosis	Possible electron transfer protein FdxB	0.0226	0.1259	0.5
Brugia malayi	nuclear receptor NHR-88	0.0195	0.0938	0.122
Echinococcus multilocularis	nuclear receptor 2DBD gamma	0.0195	0.0938	0.1256
Brugia malayi	Nuclear hormone receptor family member nhr-49	0.0195	0.0938	0.122
Echinococcus multilocularis	Nuclear hormone receptor family member nhr 41	0.0195	0.0938	0.1256
Echinococcus multilocularis	ecdysone induced protein 78C	0.0195	0.0938	0.1256
Schistosoma mansoni	fatty acid desaturase	0.0226	0.1259	1
Schistosoma mansoni	RAR-like nuclear receptor	0.0195	0.0938	0.7453
Echinococcus granulosus	Fatty acid desaturase type 1	0.0226	0.1259	0.1666
Schistosoma mansoni	nuclear hormone receptor nor-1/nor-2	0.0195	0.0938	0.7453
Loa Loa (eye worm)	acyl-CoA desaturase	0.0855	0.769	1
Echinococcus granulosus	nuclear receptor 2DBD gamma	0.0195	0.0938	0.1241
Echinococcus multilocularis	nuclear receptor 2DBD gamma	0.0195	0.0938	0.1256
Mycobacterium ulcerans	hypothetical protein	0.0226	0.1259	0.5
Brugia malayi	acyl-CoA desaturase	0.0855	0.769	1
Schistosoma mansoni	nuclear receptor 2DBD-gamma	0.0195	0.0938	0.7453
Brugia malayi	photoreceptor-specific nuclear receptor	0.0195	0.0938	0.122
Mycobacterium ulcerans	hypothetical protein	0.0226	0.1259	0.5
Echinococcus granulosus	Nuclear hormone receptor family member nhr 41	0.0195	0.0938	0.1241
Echinococcus granulosus	FTZ F1 nuclear receptor protein	0.0195	0.0938	0.1241
Brugia malayi	Nuclear hormone receptor family member nhr-14	0.0195	0.0938	0.122
Mycobacterium ulcerans	transmembrane alkane 1-monooxygenase AlkB	0.0226	0.1259	0.5
Loa Loa (eye worm)	hypothetical protein	0.0195	0.0938	0.122
Brugia malayi	Nuclear hormone receptor family member nhr-3	0.0195	0.0938	0.122
Loa Loa (eye worm)	nuclear hormone receptor family member nhr-1	0.0195	0.0938	0.122
Brugia malayi	Nuclear hormone receptor family member nhr-40	0.0195	0.0938	0.122
Echinococcus multilocularis	FTZ F1 alpha	0.0195	0.0938	0.1256
Mycobacterium tuberculosis	Probable conserved membrane protein	0.0226	0.1259	0.5
Schistosoma mansoni	retinoid-x-receptor (RXR)	0.0195	0.0938	0.7453
Trypanosoma brucei	fatty acid desaturase, putative	0.1081	1	1
Loa Loa (eye worm)	hypothetical protein	0.0226	0.1259	0.1637
Echinococcus granulosus	FTZ F1 alpha	0.0195	0.0938	0.1241
Echinococcus multilocularis	Peptidase M, neutral zinc metallopeptidases, zinc binding site	0.0226	0.1259	0.1685
Brugia malayi	Nuclear hormone receptor family member nhr-41	0.0195	0.0938	0.122
Loa Loa (eye worm)	steroid hormone receptor	0.0195	0.0938	0.122
Loa Loa (eye worm)	nuclear Hormone Receptor family member	0.0195	0.0938	0.122
Brugia malayi	Fatty acid desaturase family protein	0.0226	0.1259	0.1637
Echinococcus granulosus	ecdysone induced protein 78C	0.0195	0.0938	0.1241
Loa Loa (eye worm)	nuclear hormone receptor family member nhr-40	0.0195	0.0938	0.122
Trypanosoma cruzi	fatty acid desaturase, putative	0.1081	1	1
Echinococcus granulosus	hepatocyte nuclear factor 4 alpha	0.0195	0.0938	0.1241
Schistosoma mansoni	thyroid hormone receptor	0.0195	0.0938	0.7453
Loa Loa (eye worm)	hypothetical protein	0.0195	0.0938	0.122
Onchocerca volvulus		0.0226	0.1259	0.0354
Echinococcus multilocularis	hepatocyte nuclear factor 4 alpha	0.0195	0.0938	0.1256
Schistosoma mansoni	Tr4/Tr2 (homologue)	0.0195	0.0938	0.7453
Trypanosoma cruzi	fatty acid desaturase, putative	0.0855	0.769	0.7358
Toxoplasma gondii	sphingolipid delta 4 desaturase/c-4 hydroxylase protein des2 family protein	0.0226	0.1259	0.5
Brugia malayi	Delta5 fatty acid desaturase	0.0226	0.1259	0.1637
Mycobacterium ulcerans	linoleoyl-CoA desaturase, DesA3	0.0226	0.1259	0.5
Echinococcus multilocularis	thyroid hormone receptor alpha	0.0195	0.0938	0.1256
Plasmodium falciparum	stearoyl-CoA desaturase	0.0855	0.769	0.5
Onchocerca volvulus		0.1081	1	1
Loa Loa (eye worm)	nuclear hormone receptor family member nhr-41	0.0195	0.0938	0.122
Leishmania major	fatty-acid desaturase, putative	0.1081	1	1
Brugia malayi	Steroid receptor seven-up type 2	0.0195	0.0938	0.122
Schistosoma mansoni	retinoic acid receptor RXR	0.0195	0.0938	0.7453
Brugia malayi	nuclear hormone receptor	0.0195	0.0938	0.122
Echinococcus granulosus	nuclear receptor 2DBD gamma	0.0195	0.0938	0.1241
Echinococcus granulosus	hypothetical protein	0.0842	0.7558	1
Echinococcus granulosus	retinoic acid receptor rxr beta a	0.0195	0.0938	0.1241
Loa Loa (eye worm)	hypothetical protein	0.0195	0.0938	0.122
Echinococcus multilocularis	Peptidase M, neutral zinc metallopeptidases, zinc binding site	0.0226	0.1259	0.1685
Brugia malayi	Nuclear hormone receptor family member nhr-25	0.0195	0.0938	0.122
Brugia malayi	Fatty acid desaturase family protein	0.0226	0.1259	0.1637
Brugia malayi	Nuclear hormone receptor family member nhr-19	0.0195	0.0938	0.122
Brugia malayi	Serotonin receptor	0.0564	0.4718	0.6135
Schistosoma mansoni	coup transcription factor	0.0195	0.0938	0.7453
Loa Loa (eye worm)	fatty acid desaturase	0.0226	0.1259	0.1637
Schistosoma mansoni	FTZ-F1 nuclear receptor-like protein	0.0195	0.0938	0.7453
Brugia malayi	Nuclear hormone receptor family member nhr-25	0.0195	0.0938	0.122
Loa Loa (eye worm)	nuclear hormone receptor family member nhr-14	0.0195	0.0938	0.122
Schistosoma mansoni	photoreceptor-specific nuclear receptor related	0.0195	0.0938	0.7453
Loa Loa (eye worm)	hypothetical protein	0.0195	0.0938	0.122
Brugia malayi	Nuclear hormone receptor family member nhr-19	0.0195	0.0938	0.122
Mycobacterium ulcerans	linoleoyl-CoA desaturase, DesA3_2	0.0226	0.1259	0.5
Brugia malayi	Nuclear hormone receptor family member nhr-31	0.0195	0.0938	0.122
Echinococcus multilocularis	COUP TF:Svp nuclear hormone receptor	0.0195	0.0938	0.1256
Mycobacterium tuberculosis	Probable transmembrane alkane 1-monooxygenase AlkB (alkane 1-hydroxylase) (lauric acid omega-hydroxylase) (omega-hydroxylase) (f	0.0226	0.1259	0.5
Onchocerca volvulus		0.1081	1	1
Echinococcus granulosus	Sphingolipid delta4 desaturase DES1	0.0226	0.1259	0.1666
Echinococcus multilocularis	FTZ F1 nuclear receptor protein	0.0195	0.0938	0.1256
Brugia malayi	steroid hormone receptor	0.0195	0.0938	0.122
Schistosoma mansoni	steroid hormone receptor ad4bp	0.0195	0.0938	0.7453
Echinococcus multilocularis	Fatty acid desaturase, type 1	0.0226	0.1259	0.1685
Brugia malayi	Ligand-binding domain of nuclear hormone receptor family protein	0.0195	0.0938	0.122
Loa Loa (eye worm)	nuclear hormone receptor family member nhr-49	0.0195	0.0938	0.122
Mycobacterium ulcerans	linoleoyl-CoA desaturase, DesA3	0.0226	0.1259	0.5
Loa Loa (eye worm)	FAT-3 protein	0.0226	0.1259	0.1637
Brugia malayi	Ligand-binding domain of nuclear hormone receptor family protein	0.0195	0.0938	0.122
Brugia malayi	Nuclear hormone receptor-like 1	0.0195	0.0938	0.122
Trypanosoma cruzi	fatty acid desaturase, putative	0.0855	0.769	0.7358
Loa Loa (eye worm)	fatty acid desaturase	0.0226	0.1259	0.1637
Loa Loa (eye worm)	hypothetical protein	0.0195	0.0938	0.122
Schistosoma mansoni	thyroid hormone receptor	0.0195	0.0938	0.7453
Loa Loa (eye worm)	hypothetical protein	0.0195	0.0938	0.122
Mycobacterium ulcerans	electron transfer protein FdxB	0.0226	0.1259	0.5
Brugia malayi	Nuclear hormone receptor family member nhr-1	0.0195	0.0938	0.122
Echinococcus multilocularis	conserved hypothetical protein	0.0833	0.747	1
Brugia malayi	ecdysteroid receptor	0.0195	0.0938	0.122
Loa Loa (eye worm)	hypothetical protein	0.0195	0.0938	0.122
Loa Loa (eye worm)	hypothetical protein	0.0195	0.0938	0.122
Echinococcus granulosus	COUP TF:Svp nuclear hormone receptor	0.0195	0.0938	0.1241
Loa Loa (eye worm)	nuclear hormone receptor family member nhr-31	0.0195	0.0938	0.122
Plasmodium vivax	stearoyl-CoA desaturase (acyl-CoA desaturase, faty acid desaturase), putative	0.0855	0.769	0.5
Schistosoma mansoni	nuclear hormone receptor	0.0195	0.0938	0.7453

Activities

Activity type	Activity value	Assay description	Source	Reference
Activity (functional)		Agonist activity at human 5HT2C receptor expressed in HEK293 cells by measuring intracellular calcium mobilization upto 10 uM	ChEMBL.	17079142
Activity (functional)		Agonist activity at human 5HT2A receptor expressed in HEK293 cells by measuring intracellular calcium mobilization upto 10 uM	ChEMBL.	17079142
Activity (functional)		Agonist activity at human 5HT2B receptor expressed in HEK293 cells by measuring intracellular calcium mobilization upto 10 uM	ChEMBL.	17079142
Activity (functional)	0	Agonist activity at human 5HT2A receptor expressed in HEK293 cells by measuring intracellular calcium mobilization upto 10 uM	ChEMBL.	17079142
Activity (functional)	0	Agonist activity at human 5HT2B receptor expressed in HEK293 cells by measuring intracellular calcium mobilization upto 10 uM	ChEMBL.	17079142
Activity (functional)	0	Agonist activity at human 5HT2C receptor expressed in HEK293 cells by measuring intracellular calcium mobilization upto 10 uM	ChEMBL.	17079142
Ki (binding)	= -8.3	Displacement of [3H]mesulergine from human 5HT2C receptor expressed in HEK293 cells	ChEMBL.	17079142
Ki (binding)	= -6.8	Displacement of [3H]5HT from human 5HT2B receptor expressed in HEK293 cells	ChEMBL.	17079142
Ki (binding)	= -6.5	Displacement of [3H]ketanserin from human 5HT2A receptor expressed in HEK293 cells	ChEMBL.	17079142
Log Ki (binding)	= 6.5	Displacement of [3H]ketanserin from human 5HT2A receptor expressed in HEK293 cells	ChEMBL.	17079142
Log Ki (binding)	= 6.8	Displacement of [3H]5HT from human 5HT2B receptor expressed in HEK293 cells	ChEMBL.	17079142
Log Ki (binding)	= 8.3	Displacement of [3H]mesulergine from human 5HT2C receptor expressed in HEK293 cells	ChEMBL.	17079142

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: CHEMBL397259
PubChem: 10413268

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 439416