TDR Targets

Basic information

Technical information

TDR Targets ID: 152751
Name: 1-(5-chloro-6-fluoroindol-1-yl)propan-2-amine
MW: 226.678 | Formula: C11H12ClFN2
H donors: 1 H acceptors: 0 LogP: 2.15 Rotable bonds: 2
Rule of 5 violations (Lipinski): 1
SMILES: CC(Cn1ccc2c1cc(F)c(c2)Cl)N
InChi: 1S/C11H12ClFN2/c1-7(14)6-15-3-2-8-4-9(12)10(13)5-11(8)15/h2-5,7H,6,14H2,1H3
InChiKey: CDRZAFWCPFTACB-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

1-(5-chloro-6-fluoro-indol-1-yl)propan-2-amine
1-(5-chloro-6-fluoro-1-indolyl)-2-propanamine
[2-(5-chloro-6-fluoro-indol-1-yl)-1-methyl-ethyl]amine
1-(5-chloro-6-fluoro-1-indolyl)propan-2-amine

Targets

Known targets for this compound

Species	Target name	Source	Bibliographic reference
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
Rattus norvegicus	Serotonin 2c (5-HT2c) receptor	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

By sequence similarity to non orthologous known druggable targets

Species	Potential target	Known druggable target	Length	Alignment span	Identity
Loa Loa (eye worm)	hypothetical protein	Serotonin 2c (5-HT2c) receptor	460 aa	417 aa	21.3 %
Echinococcus multilocularis	neuropeptides capa receptor	Serotonin 2c (5-HT2c) receptor	460 aa	408 aa	20.8 %
Echinococcus multilocularis	g protein coupled receptor	Serotonin 2c (5-HT2c) receptor	460 aa	409 aa	21.5 %
Schistosoma japonicum	ko:K04135 adrenergic receptor, alpha 1a, putative	Serotonin 2c (5-HT2c) receptor	460 aa	405 aa	31.1 %
Schistosoma japonicum	ko:K04136 adrenergic receptor, alpha 1b, putative	Serotonin 2c (5-HT2c) receptor	460 aa	427 aa	28.3 %
Echinococcus granulosus	g protein coupled receptor	Serotonin 2c (5-HT2c) receptor	460 aa	412 aa	19.7 %
Echinococcus multilocularis	g protein coupled receptor	Serotonin 2c (5-HT2c) receptor	460 aa	412 aa	19.9 %
Echinococcus granulosus	g protein coupled receptor	Serotonin 2c (5-HT2c) receptor	460 aa	409 aa	21.8 %

Ranking Plot

Putative Targets List

Species	Potential target	Raw	Global	Species
Loa Loa (eye worm)	hypothetical protein	0.045	0.2782	0.5382
Loa Loa (eye worm)	hypothetical protein	0.045	0.2782	0.5382
Echinococcus granulosus	peroxidasin	0.045	0.2782	0.4593
Loa Loa (eye worm)	animal heme peroxidase	0.045	0.2782	0.5382
Loa Loa (eye worm)	hypothetical protein	0.045	0.2782	0.5382
Brugia malayi	Peptidase family M1 containing protein	0.0727	0.577	0.5664
Trypanosoma cruzi	metallo-peptidase, clan MA(E), family M1, putative	0.0214	0.0244	0.5
Trypanosoma brucei	Aminopeptidase M1, putative	0.0214	0.0244	0.5
Leishmania major	aminopeptidase-like protein,metallo-peptidase, Clan MA(E), Family M1	0.0214	0.0244	0.5
Schistosoma mansoni	lipoxygenase	0.0274	0.0887	0.3189
Loa Loa (eye worm)	peptidase family M1 containing protein	0.0588	0.4275	0.8549
Trypanosoma brucei	Aminopeptidase M1, putative	0.0214	0.0244	0.5
Onchocerca volvulus	Chorion peroxidase homolog	0.045	0.2782	0.4593
Onchocerca volvulus	Peroxidasin homolog	0.045	0.2782	0.4593
Echinococcus multilocularis	peroxidasin	0.045	0.2782	0.4593
Loa Loa (eye worm)	hypothetical protein	0.045	0.2782	0.5382
Onchocerca volvulus		0.045	0.2782	0.4593
Loa Loa (eye worm)	hypothetical protein	0.0513	0.3465	0.683
Trypanosoma brucei	metallo-peptidase, Clan MA(E) Family M1	0.0214	0.0244	0.5
Brugia malayi	Animal haem peroxidase family protein	0.045	0.2782	0.2601
Trichomonas vaginalis	Clan MA, family M1, aminopeptidase N-like metallopeptidase	0.0214	0.0244	0.5
Loa Loa (eye worm)	hypothetical protein	0.045	0.2782	0.5382
Echinococcus multilocularis	aminopeptidase N	0.0727	0.577	1
Schistosoma mansoni	peroxidasin	0.045	0.2782	1
Onchocerca volvulus		0.045	0.2782	0.4593
Loa Loa (eye worm)	blistered cuticle protein 3	0.045	0.2782	0.5382
Loa Loa (eye worm)	hypothetical protein	0.045	0.2782	0.5382
Trichomonas vaginalis	Clan MA, family M1, aminopeptidase N-like metallopeptidase	0.0214	0.0244	0.5
Schistosoma mansoni	cytosol alanyl aminopeptidase (M01 family)	0.0214	0.0244	0.0877
Trypanosoma cruzi	aminopeptidase, putative	0.0214	0.0244	0.5
Loa Loa (eye worm)	hypothetical protein	0.045	0.2782	0.5382
Loa Loa (eye worm)	hypothetical protein	0.045	0.2782	0.5382
Loa Loa (eye worm)	hypothetical protein	0.0652	0.4959	1
Brugia malayi	Blistered cuticle protein 3	0.045	0.2782	0.2601
Onchocerca volvulus	Peroxidasin homolog	0.045	0.2782	0.4593
Loa Loa (eye worm)	animal heme peroxidase	0.045	0.2782	0.5382
Schistosoma mansoni	peroxidasin	0.045	0.2782	1
Loa Loa (eye worm)	hypothetical protein	0.045	0.2782	0.5382
Onchocerca volvulus	Peroxidase homolog	0.045	0.2782	0.4593
Onchocerca volvulus		0.045	0.2782	0.4593
Mycobacterium ulcerans	aminopeptidase N PepN	0.0214	0.0244	0.5
Schistosoma mansoni	aminopeptidase PILS (M01 family)	0.0214	0.0244	0.0877
Loa Loa (eye worm)	hypothetical protein	0.045	0.2782	0.5382
Loa Loa (eye worm)	hypothetical protein	0.045	0.2782	0.5382
Echinococcus multilocularis	arachidonate 5 lipoxygenase	0.0274	0.0887	0.1164
Brugia malayi	hypothetical protein	0.045	0.2782	0.2601
Loa Loa (eye worm)	hypothetical protein	0.045	0.2782	0.5382
Loa Loa (eye worm)	animal heme peroxidase	0.045	0.2782	0.5382
Onchocerca volvulus		0.0727	0.577	1
Loa Loa (eye worm)	animal heme peroxidase	0.045	0.2782	0.5382
Brugia malayi	Peroxidasin	0.045	0.2782	0.2601
Onchocerca volvulus	Dual oxidase homolog	0.045	0.2782	0.4593
Echinococcus granulosus	aminopeptidase N	0.0727	0.577	1
Trypanosoma cruzi	Aminopeptidase M1, putative	0.0214	0.0244	0.5
Brugia malayi	Animal haem peroxidase family protein	0.045	0.2782	0.2601
Loa Loa (eye worm)	hypothetical protein	0.045	0.2782	0.5382
Leishmania major	aminopeptidase, putative,metallo-peptidase, Clan MA(E), Family M1	0.0214	0.0244	0.5
Echinococcus granulosus	arachidonate 5 lipoxygenase	0.0274	0.0887	0.1164
Brugia malayi	Animal haem peroxidase family protein	0.045	0.2782	0.2601
Brugia malayi	Animal haem peroxidase family protein	0.045	0.2782	0.2601
Entamoeba histolytica	aminopeptidase, putative	0.0214	0.0244	0.5
Loa Loa (eye worm)	hypothetical protein	0.045	0.2782	0.5382
Brugia malayi	Animal haem peroxidase family protein	0.045	0.2782	0.2601
Onchocerca volvulus	Peroxidase homolog	0.045	0.2782	0.4593

Activities

Activity type	Activity value	Assay description	Source	Reference
EC50 (functional)	= -6.4	Efficacy (pEC50) was evaluated for 5-HT2C receptor-mediated stimulation of IP3 formation in vitro in choroid plexus of the rat	ChEMBL.	9276022
ED50 (functional)	= 1 mg kg-1	Induction of penile erection in rats after subcutaneous administration, indicative of 5-HT 2c receptor activation	ChEMBL.	9276022
ED50 (functional)	= 1 mg kg-1	Induction of penile erection in rats after subcutaneous administration, indicative of 5-HT 2c receptor activation	ChEMBL.	9276022
ED50 (functional)	= 15 mg kg-1	Induction of penile erection in rats following p.o. administration, indicative of 5-HT 2c receptor activation	ChEMBL.	9276022
ED50 (functional)	= 15 mg kg-1	Induction of penile erection in rats following p.o. administration, indicative of 5-HT 2c receptor activation	ChEMBL.	9276022
Efficacy (functional)	= 1	Intrinsic 5-HT 2c receptor activity as induced IP3 turn-over in vitro in rat choroid plexus	ChEMBL.	9276022
Ki (binding)	= -8.7	Binding affinity against human 5-hydroxytryptamine 2C receptor using displacement of [3H]-DOB	ChEMBL.	9276022
Ki (binding)	= -7.4	Binding affinity against human 5-hydroxytryptamine 2A receptor using displacement of [3H]-5-HT	ChEMBL.	9276022
Log EC50 (functional)	= 6.4	Efficacy (pEC50) was evaluated for 5-HT2C receptor-mediated stimulation of IP3 formation in vitro in choroid plexus of the rat	ChEMBL.	9276022
Log Ki (binding)	= 7.4	Binding affinity against human 5-hydroxytryptamine 2A receptor using displacement of [3H]-5-HT	ChEMBL.	9276022
Log Ki (binding)	= 8.7	Binding affinity against human 5-hydroxytryptamine 2C receptor using displacement of [3H]-DOB	ChEMBL.	9276022
Max suppression (functional)	= -88 %	Compound was tested in schedule induced polydipsia in rats expressed as %maximum suppression at minimum effective dose of 3 mg/kg intraperitoneally	ChEMBL.	9276022
Selectivity ratio (binding)	= 20	Selectivity ratio was measured as pKi ratio of 5-HT2C to that of 5-HT2A receptor	ChEMBL.	9276022

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: CHEMBL313856
PubChem: 18986247

Bibliographic References

1 literature reference was collected for this gene.

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Detailed information for compound 152751