TDR Targets

Basic information

Technical information

TDR Targets ID: 44207
Name: N-[2-(6-methoxy-2-phenylindol-1-yl)ethyl]prop anamide
MW: 322.401 | Formula: C20H22N2O2
H donors: 1 H acceptors: 1 LogP: 3.35 Rotable bonds: 7
Rule of 5 violations (Lipinski): 1
SMILES: CCC(=O)NCCn1c(cc2c1cc(OC)cc2)c1ccccc1
InChi: 1S/C20H22N2O2/c1-3-20(23)21-11-12-22-18(15-7-5-4-6-8-15)13-16-9-10-17(24-2)14-19(16)22/h4-10,13-14H,3,11-12H2,1-2H3,(H,21,23)
InChiKey: DMQVDZBLVXWQQW-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

N-[2-(6-methoxy-2-phenyl-indol-1-yl)ethyl]propanamide
N-[2-(6-methoxy-2-phenyl-1-indolyl)ethyl]propanamide
N-[2-(6-methoxy-2-phenyl-indol-1-yl)ethyl]propionamide

Targets

Known targets for this compound

Species	Target name	Source	Bibliographic reference
Homo sapiens	melatonin receptor 1A		References
Homo sapiens	melatonin receptor 1B	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	hypothetical protein	melatonin receptor 1B	362 aa	329 aa	18.8 %

Ranking Plot

Putative Targets List

Species	Potential target	Raw	Global	Species
Loa Loa (eye worm)	hypothetical protein	0.0186	0.7846	0.7846
Trichomonas vaginalis	alpha-glucosidase, putative	0.0035	0.0459	0.5
Trypanosoma cruzi	hypothetical protein, conserved	0.0035	0.0459	0.5
Trichomonas vaginalis	neutral alpha-glucosidase ab precursor, putative	0.0035	0.0459	0.5
Onchocerca volvulus	Dual oxidase homolog	0.0186	0.7846	1
Loa Loa (eye worm)	hypothetical protein	0.0034	0.0412	0.0412
Schistosoma mansoni	hypothetical protein	0.0034	0.0412	0.0497
Loa Loa (eye worm)	hypothetical protein	0.0186	0.7846	0.7846
Onchocerca volvulus		0.0034	0.0412	0.0497
Echinococcus multilocularis	slit 2 protein	0.0034	0.0412	0.0497
Schistosoma mansoni	hypothetical protein	0.0034	0.0412	0.0497
Loa Loa (eye worm)	hypothetical protein	0.0186	0.7846	0.7846
Echinococcus multilocularis	neurogenic locus notch protein 4	0.0034	0.0412	0.0497
Brugia malayi	Glycosyl hydrolases family 31 protein	0.0157	0.6464	0.6456
Onchocerca volvulus	Huntingtin homolog	0.0118	0.455	0.5786
Loa Loa (eye worm)	notch protein	0.0034	0.0412	0.0412
Onchocerca volvulus	Chorion peroxidase homolog	0.0186	0.7846	1
Onchocerca volvulus	Peroxidase homolog	0.0186	0.7846	1
Loa Loa (eye worm)	hypothetical protein	0.0034	0.0412	0.0412
Loa Loa (eye worm)	hypothetical protein	0.0034	0.0412	0.0412
Loa Loa (eye worm)	hypothetical protein	0.0034	0.0412	0.0412
Schistosoma mansoni	notch	0.0034	0.0412	0.0497
Loa Loa (eye worm)	animal heme peroxidase	0.0186	0.7846	0.7846
Echinococcus granulosus	slit 2 protein	0.0034	0.0412	0.0497
Brugia malayi	EGF-like domain containing protein	0.0034	0.0412	0.0389
Echinococcus granulosus	peroxidasin	0.0186	0.7846	1
Echinococcus granulosus	delta-like protein 1	0.0034	0.0412	0.0497
Loa Loa (eye worm)	hypothetical protein	0.0034	0.0412	0.0412
Trichomonas vaginalis	alpha-glucosidase, putative	0.0035	0.0459	0.5
Schistosoma mansoni	alpha-glucosidase	0.0135	0.539	0.6859
Schistosoma mansoni	notch	0.0034	0.0412	0.0497
Loa Loa (eye worm)	hypothetical protein	0.0034	0.0412	0.0412
Brugia malayi	EGF-like domain containing protein	0.0034	0.0412	0.0389
Onchocerca volvulus	Huntingtin homolog	0.0118	0.455	0.5786
Schistosoma mansoni	peroxidasin	0.0186	0.7846	1
Entamoeba histolytica	glycosyl hydrolase, family 31 protein	0.0035	0.0459	0.5
Loa Loa (eye worm)	hypothetical protein	0.0186	0.7846	0.7846
Loa Loa (eye worm)	hypothetical protein	0.0186	0.7846	0.7846
Schistosoma mansoni	alpha glucosidase	0.0035	0.0459	0.0556
Loa Loa (eye worm)	intermediate filament protein	0.0026	0.0023	0.0023
Entamoeba histolytica	glycosyl hydrolase, family 31 protein	0.0035	0.0459	0.5
Brugia malayi	hypothetical protein	0.0118	0.455	0.4537
Brugia malayi	Muscle positioning protein 4	0.0034	0.0412	0.0389
Loa Loa (eye worm)	hypothetical protein	0.0034	0.0412	0.0412
Brugia malayi	Transmembrane cell adhesion receptor mua-3 precursor, putative	0.0034	0.0412	0.0389
Onchocerca volvulus		0.0186	0.7846	1
Loa Loa (eye worm)	hypothetical protein	0.0034	0.0412	0.0412
Brugia malayi	Cadherin domain containing protein	0.0034	0.0412	0.0389
Brugia malayi	Peroxidasin	0.0186	0.7846	0.7841
Echinococcus granulosus	neurogenic locus notch protein	0.0034	0.0412	0.0497
Schistosoma mansoni	hypothetical protein	0.0034	0.0412	0.0497
Loa Loa (eye worm)	intermediate filament tail domain-containing protein	0.0026	0.0023	0.0023
Brugia malayi	EGF-like domain containing protein	0.0034	0.0412	0.0389
Trichomonas vaginalis	alpha-glucosidase, putative	0.0035	0.0459	0.5
Echinococcus multilocularis	fibropellin Ia	0.0034	0.0412	0.0497
Loa Loa (eye worm)	hypothetical protein	0.0034	0.0412	0.0412
Onchocerca volvulus		0.0034	0.0412	0.0497
Brugia malayi	EGF-like domain containing protein	0.0034	0.0412	0.0389
Schistosoma mansoni	notch	0.0034	0.0412	0.0497
Echinococcus granulosus	protein jagged 1	0.0034	0.0412	0.0497
Onchocerca volvulus		0.0034	0.0412	0.0497
Echinococcus granulosus	protein jagged 2	0.0034	0.0412	0.0497
Echinococcus granulosus	neurogenic locus protein delta	0.0034	0.0412	0.0497
Loa Loa (eye worm)	hypothetical protein	0.0118	0.455	0.455
Brugia malayi	Animal haem peroxidase family protein	0.0186	0.7846	0.7841
Loa Loa (eye worm)	hypothetical protein	0.0034	0.0412	0.0412
Schistosoma mansoni	slit	0.0034	0.0412	0.0497
Loa Loa (eye worm)	hypothetical protein	0.0034	0.0412	0.0412
Loa Loa (eye worm)	hypothetical protein	0.0186	0.7846	0.7846
Loa Loa (eye worm)	hypothetical protein	0.0034	0.0412	0.0412
Brugia malayi	EGF-like domain containing protein	0.0034	0.0412	0.0389
Loa Loa (eye worm)	glycosyl hydrolase family 31 protein	0.0157	0.6464	0.6464
Loa Loa (eye worm)	animal heme peroxidase	0.0186	0.7846	0.7846
Echinococcus multilocularis	peroxidasin	0.0186	0.7846	1
Trichomonas vaginalis	neutral alpha-glucosidase ab precursor, putative	0.0035	0.0459	0.5
Echinococcus multilocularis	lysosomal alpha glucosidase	0.0157	0.6464	0.8233
Echinococcus multilocularis	neurogenic locus protein delta	0.0034	0.0412	0.0497
Loa Loa (eye worm)	glycosyl hydrolase family 31 protein	0.0035	0.0459	0.0459
Echinococcus multilocularis	lysosomal alpha glucosidase	0.0157	0.6464	0.8233
Brugia malayi	EGF-like domain containing protein	0.0034	0.0412	0.0389
Brugia malayi	Calcium binding EGF domain containing protein	0.0034	0.0412	0.0389
Brugia malayi	GCC2 and GCC3 family protein	0.0034	0.0412	0.0389
Schistosoma mansoni	cell polarity protein	0.0034	0.0412	0.0497
Loa Loa (eye worm)	hypothetical protein	0.0026	0.0023	0.0023
Loa Loa (eye worm)	hypothetical protein	0.0186	0.7846	0.7846
Leishmania major	alpha glucosidase II subunit, putative	0.0035	0.0459	0.5
Schistosoma mansoni	hypothetical protein	0.0034	0.0412	0.0497
Trypanosoma brucei	glucosidase, putative	0.0035	0.0459	0.5
Loa Loa (eye worm)	hypothetical protein	0.0034	0.0412	0.0412
Toxoplasma gondii	glycosyl hydrolase, family 31 protein	0.0035	0.0459	1
Onchocerca volvulus		0.0034	0.0412	0.0497
Brugia malayi	EGF-like domain containing protein	0.0034	0.0412	0.0389
Schistosoma mansoni	notch	0.0034	0.0412	0.0497
Loa Loa (eye worm)	hypothetical protein	0.0186	0.7846	0.7846
Schistosoma mansoni	Pro-neuregulin-4 membrane-bound isoform (Pro-NRG4) [Contains: Neuregulin-4 (NRG-4)]	0.0034	0.0412	0.0497
Onchocerca volvulus	Peroxidasin homolog	0.0186	0.7846	1
Loa Loa (eye worm)	hypothetical protein	0.0034	0.0412	0.0412
Loa Loa (eye worm)	hypothetical protein	0.0034	0.0412	0.0412
Echinococcus granulosus	fibropellin Ia	0.0034	0.0412	0.0497
Schistosoma mansoni	laminin gamma-3 chain	0.0034	0.0412	0.0497
Onchocerca volvulus	Peroxidase homolog	0.0186	0.7846	1
Brugia malayi	Delta serrate ligand family protein	0.0034	0.0412	0.0389
Trichomonas vaginalis	alpha-glucosidase, putative	0.0035	0.0459	0.5
Echinococcus multilocularis	protein jagged 1	0.0034	0.0412	0.0497
Trichomonas vaginalis	alpha-glucosidase, putative	0.0035	0.0459	0.5
Schistosoma mansoni	notch	0.0034	0.0412	0.0497
Echinococcus multilocularis	protein jagged 2	0.0034	0.0412	0.0497
Brugia malayi	notch-like transmembrane receptor	0.0034	0.0412	0.0389
Onchocerca volvulus		0.0186	0.7846	1
Echinococcus granulosus	lysosomal alpha glucosidase	0.0157	0.6464	0.8233
Giardia lamblia	High cysteine protein	0.0034	0.0412	0.5
Loa Loa (eye worm)	hypothetical protein	0.0034	0.0412	0.0412
Loa Loa (eye worm)	blistered cuticle protein 3	0.0186	0.7846	0.7846
Loa Loa (eye worm)	hypothetical protein	0.0186	0.7846	0.7846
Loa Loa (eye worm)	hypothetical protein	0.0186	0.7846	0.7846
Brugia malayi	Animal haem peroxidase family protein	0.0186	0.7846	0.7841
Onchocerca volvulus	Peroxidasin homolog	0.0186	0.7846	1
Loa Loa (eye worm)	hypothetical protein	0.0034	0.0412	0.0412
Echinococcus granulosus	protein jagged 1	0.0034	0.0412	0.0497
Loa Loa (eye worm)	hypothetical protein	0.0034	0.0412	0.0412
Brugia malayi	Calcium binding EGF domain containing protein	0.0034	0.0412	0.0389
Echinococcus multilocularis	protein jagged 1	0.0034	0.0412	0.0497
Echinococcus multilocularis	notch	0.0034	0.0412	0.0497
Onchocerca volvulus		0.0091	0.321	0.4073
Loa Loa (eye worm)	hypothetical protein	0.0118	0.455	0.455
Echinococcus granulosus	notch	0.0034	0.0412	0.0497
Loa Loa (eye worm)	hypothetical protein	0.0186	0.7846	0.7846
Trypanosoma cruzi	hypothetical protein, conserved	0.0035	0.0459	0.5
Brugia malayi	Cadherin domain containing protein	0.0034	0.0412	0.0389
Loa Loa (eye worm)	Notch2	0.0034	0.0412	0.0412
Loa Loa (eye worm)	animal heme peroxidase	0.0186	0.7846	0.7846
Loa Loa (eye worm)	hypothetical protein	0.0186	0.7846	0.7846
Brugia malayi	Blistered cuticle protein 3	0.0186	0.7846	0.7841
Brugia malayi	Glycosyl hydrolases family 31 protein	0.0035	0.0459	0.0436
Onchocerca volvulus		0.0034	0.0412	0.0497
Loa Loa (eye worm)	hypothetical protein	0.0034	0.0412	0.0412
Onchocerca volvulus		0.0186	0.7846	1
Loa Loa (eye worm)	hypothetical protein	0.0186	0.7846	0.7846
Loa Loa (eye worm)	hypothetical protein	0.0034	0.0412	0.0412
Loa Loa (eye worm)	animal heme peroxidase	0.0186	0.7846	0.7846
Loa Loa (eye worm)	hypothetical protein	0.0186	0.7846	0.7846
Echinococcus multilocularis	neurogenic locus protein delta	0.0034	0.0412	0.0497
Echinococcus granulosus	neural cadherin	0.0034	0.0412	0.0497
Loa Loa (eye worm)	follicle stimulating hormone receptor	0.0229	1	1
Echinococcus multilocularis	neural cadherin	0.0034	0.0412	0.0497
Echinococcus granulosus	neurogenic locus notch protein	0.0034	0.0412	0.0497
Onchocerca volvulus	Slit protein homolog	0.0034	0.0412	0.0497
Echinococcus granulosus	neurogenic locus notch protein 4	0.0034	0.0412	0.0497
Brugia malayi	Calcium binding EGF domain containing protein	0.0034	0.0412	0.0389
Schistosoma mansoni	alpha-glucosidase	0.0135	0.539	0.6859
Schistosoma mansoni	peroxidasin	0.0186	0.7846	1
Brugia malayi	Animal haem peroxidase family protein	0.0186	0.7846	0.7841
Schistosoma mansoni	hypothetical protein	0.0034	0.0412	0.0497
Loa Loa (eye worm)	hypothetical protein	0.0034	0.0412	0.0412
Brugia malayi	hypothetical protein	0.0186	0.7846	0.7841
Onchocerca volvulus	Neurogenic locus notch protein homolog	0.0034	0.0412	0.0497
Onchocerca volvulus	Putative cubilin	0.0034	0.0412	0.0497
Echinococcus multilocularis	neutral alpha glucosidase AB	0.0035	0.0459	0.0556
Trichomonas vaginalis	sucrase-isomaltase, putative	0.0035	0.0459	0.5
Trichomonas vaginalis	maltase-glucoamylase, putative	0.0035	0.0459	0.5
Schistosoma mansoni	hypothetical protein	0.0034	0.0412	0.0497
Schistosoma mansoni	hypothetical protein	0.0034	0.0412	0.0497
Echinococcus granulosus	protein jagged 2	0.0034	0.0412	0.0497
Schistosoma mansoni	notch	0.0034	0.0412	0.0497
Schistosoma mansoni	septate junction protein	0.0034	0.0412	0.0497
Echinococcus multilocularis	neurogenic locus notch protein	0.0034	0.0412	0.0497
Echinococcus multilocularis	neurogenic locus notch protein	0.0034	0.0412	0.0497
Brugia malayi	Animal haem peroxidase family protein	0.0186	0.7846	0.7841
Echinococcus multilocularis	fat cadherin tumor suppressor	0.0034	0.0412	0.0497
Brugia malayi	Animal haem peroxidase family protein	0.0186	0.7846	0.7841
Onchocerca volvulus	Neurogenic locus notch homolog	0.0034	0.0412	0.0497
Loa Loa (eye worm)	hypothetical protein	0.0034	0.0412	0.0412
Echinococcus granulosus	neutral alpha glucosidase AB	0.0035	0.0459	0.0556

Activities

Activity type	Activity value	Assay description	Source	Reference
Activity (functional)	0	Activity considered from GTP-gamma-S index and cAMP index; A = Agonist	ChEMBL.	9207941
Activity (functional)	0	Activity considered from GTP-gamma-S index; A = Agonist	ChEMBL.	9207941
GTP-gammaS Index (functional)	= 1.42	Ratio of the compound to that of aMT.	ChEMBL.	9207941
IC50 (binding)	= 0.052 nM	Inhibitory activity against melatonin receptor in the quail optica tecta using 2-[125] iodomelatonin as labelled ligand	ChEMBL.	9207941
IC50 (binding)	= 0.052 nM	Inhibitory activity against melatonin receptor in the quail optica tecta using 2-[125] iodomelatonin as labelled ligand	ChEMBL.	9207941
IC50 (functional)	= 0.189 nM	Agonist activity of the compound against melatonin receptor was tested in the absence of iodomelatonin	ChEMBL.	9207941
IC50 (functional)	= 0.189 nM	Agonist activity of the compound against melatonin receptor was tested in the absence of iodomelatonin	ChEMBL.	9207941
IC50 (functional)	= 1.18 nM	Agonist activity of the compound was tested against melatonin receptor in the presence of iodomelatonin	ChEMBL.	9207941
IC50 (functional)	= 1.18 nM	Agonist activity of the compound was tested against melatonin receptor in the presence of iodomelatonin	ChEMBL.	9207941
Index (functional)	= 1.15	Inhibition of forskolin stimulated cAMP accumulation and represented as cAMP index which is the ratio of percent inhibition of the compound to percent inhibition of melatonin	ChEMBL.	9207941
Index (functional)	= 1.45	GTPgammaS index is the ratio of the IC50 of compound with GTP and without GTP to the IC50 of melatonin with GTP and without GTP	ChEMBL.	9207941
Index (functional)	= 1.15	Inhibition of forskolin stimulated cAMP accumulation and represented as cAMP index which is the ratio of percent inhibition of the compound to percent inhibition of melatonin	ChEMBL.	9207941
Index (functional)	= 1.45	GTPgammaS index is the ratio of the IC50 of compound with GTP and without GTP to the IC50 of melatonin with GTP and without GTP	ChEMBL.	9207941
Intrinsic activity (functional)	= 0.92	Relative Intrinsic activity evaluated on [35S]-GTP-gammaS, binding in NIH3T3 cells stably transfected with human Melatonin receptor type 1A	ChEMBL.	12672242
Intrinsic activity (functional)	= 1.17	Relative Intrinsic activity evaluated on [35S]-GTP-gammaS, binding in NIH3T3 cells stably transfected with human Melatonin receptor type 1B	ChEMBL.	12672242
Intrinsic activity (functional)	= 0.92	Relative Intrinsic activity evaluated on [35S]-GTP-gammaS, binding in NIH3T3 cells stably transfected with human Melatonin receptor type 1A	ChEMBL.	12672242
Intrinsic activity (functional)	= 1.17	Relative Intrinsic activity evaluated on [35S]-GTP-gammaS, binding in NIH3T3 cells stably transfected with human Melatonin receptor type 1B	ChEMBL.	12672242
Ki (binding)	= 0.014 nM	Binding affinity against melatonin receptor in the quail optica tecta using 2-[125] iodomelatonin (100 pM) as labelled ligand	ChEMBL.	9207941
Ki (binding)	= 0.014 nM	Binding affinity against melatonin receptor in the quail optica tecta using 2-[125] iodomelatonin (100 pM) as labelled ligand	ChEMBL.	9207941
pRA (binding)	= 1.7	Negative logarithm of relative affinity (pRA) towards melatonin receptor (relative to N-actyl-5-methoxytryptamine (aMT))	ChEMBL.	9748358
pRA (binding)	= 1.7	Negative logarithm of relative affinity (pRA) towards melatonin receptor (relative to N-actyl-5-methoxytryptamine (aMT))	ChEMBL.	9748358
pRA1 (binding)	= 0.34	Relative Binding Affinity (pRA1) to cloned human Melatonin receptor type 1A, stably expressed in NIH3T3 rat fibroblast cells, determined using 2-[125I]-iodomelatonin	ChEMBL.	12672242
pRA1 (binding)	= 0.34	Relative Binding Affinity (pRA1) to cloned human Melatonin receptor type 1A, stably expressed in NIH3T3 rat fibroblast cells, determined using 2-[125I]-iodomelatonin	ChEMBL.	12672242
pRA2 (binding)	= 0.93	Relative Binding Affinity (pRA1) to cloned human Melatonin receptor type 1B, stably expressed in NIH3T3 rat fibroblast cells, determined using 2-[125I]-iodomelatonin	ChEMBL.	12672242
pRA2 (binding)	= 0.93	Relative Binding Affinity (pRA1) to cloned human Melatonin receptor type 1B, stably expressed in NIH3T3 rat fibroblast cells, determined using 2-[125I]-iodomelatonin	ChEMBL.	12672242
Ratio (binding)	= 0.024	Ratio of the IC50 of compound to the IC50 of melatonin	ChEMBL.	9207941
Ratio (binding)	= 0.024	Ratio of the IC50 of compound to the IC50 of melatonin	ChEMBL.	9207941
Ratio (functional)	= 6.24	Ratio calculated as IC50 in the presence of GTP-gamma-S.	ChEMBL.	9207941

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: CHEMBL433237
PubChem: 10448812

Bibliographic References

3 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 44207