Page last updated: 2024-11-10

2-phenylmelatonin

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Cross-References

ID SourceID
PubMed CID4018512
CHEMBL ID15060
CHEBI ID107661
SCHEMBL ID3508630
MeSH IDM0263865

Synonyms (34)

Synonym
melatonin,2-phenyl
n-[2-(5-methoxy-2-phenyl-1h-indol-3-yl)-ethyl]-acetamide
bdbm50034110
HMS3266J05 ,
BRD-K41869275-001-01-0
NCGC00024727-01
tocris-0680
PDSP1_001795
PDSP2_001779
PDSP1_001796
NCGC00024727-02
PDSP2_001778
CHEBI:107661
n-[2-(5-methoxy-2-phenyl-1h-indol-3-yl)ethyl]acetamide
2-phenylmelatonin
CHEMBL15060 ,
151889-03-1
AM20030035
SCHEMBL3508630
n-[2-(5-methoxy-2-phenylindol-3-yl)ethyl]acetamide
AKOS024458605
DTXSID80398573
Q27185983
SR-01000597657-1
sr-01000597657
J-008860
jey ,
HMS3675O18
ucm 608
ucm608;ucm-608
HMS3411O18
MS-24473
HY-101074
CS-0020785
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
phenylindole
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (32)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, HADH2 proteinHomo sapiens (human)Potency31.62280.025120.237639.8107AID886; AID893
Chain B, HADH2 proteinHomo sapiens (human)Potency31.62280.025120.237639.8107AID886; AID893
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency31.62280.177814.390939.8107AID2147
Chain A, CruzipainTrypanosoma cruziPotency25.11890.002014.677939.8107AID1476
USP1 protein, partialHomo sapiens (human)Potency44.66840.031637.5844354.8130AID504865
TDP1 proteinHomo sapiens (human)Potency18.47820.000811.382244.6684AID686978; AID686979
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency28.37090.011212.4002100.0000AID1030
cytochrome P450 2D6 isoform 1Homo sapiens (human)Potency25.11890.00207.533739.8107AID891
cytochrome P450 2C19 precursorHomo sapiens (human)Potency7.94330.00255.840031.6228AID899
cytochrome P450 2C9 precursorHomo sapiens (human)Potency15.84890.00636.904339.8107AID883
15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1Homo sapiens (human)Potency35.48130.001815.663839.8107AID894
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency12.58930.031610.279239.8107AID884; AID885
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Histamine H2 receptorCavia porcellus (domestic guinea pig)Potency15.84890.00638.235039.8107AID883
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Inositol monophosphatase 1Rattus norvegicus (Norway rat)Potency31.62281.000010.475628.1838AID1457
GABA theta subunitRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Melatonin receptor type 1AHomo sapiens (human)IC50 (µMol)0.00010.00000.06401.0200AID107558; AID107559
Melatonin receptor type 1AHomo sapiens (human)Ki0.00000.00000.27359.1000AID107564; AID107565; AID107567
Melatonin receptor type 1BHomo sapiens (human)IC50 (µMol)0.00010.00000.34894.0000AID107558; AID107559
Melatonin receptor type 1BHomo sapiens (human)Ki0.00000.00000.16289.1000AID107564; AID107565; AID107567
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Melatonin receptor type 1AHomo sapiens (human)EC50 (µMol)16.50000.00000.01530.2570AID1858339
Melatonin receptor type 1BHomo sapiens (human)EC50 (µMol)7.00000.00010.34027.0000AID1858343
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (18)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerMelatonin receptor type 1AHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwayMelatonin receptor type 1AHomo sapiens (human)
mating behaviorMelatonin receptor type 1AHomo sapiens (human)
circadian rhythmMelatonin receptor type 1AHomo sapiens (human)
G protein-coupled receptor signaling pathwayMelatonin receptor type 1AHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerMelatonin receptor type 1BHomo sapiens (human)
chemical synaptic transmissionMelatonin receptor type 1BHomo sapiens (human)
negative regulation of cGMP-mediated signalingMelatonin receptor type 1BHomo sapiens (human)
glucose homeostasisMelatonin receptor type 1BHomo sapiens (human)
camera-type eye developmentMelatonin receptor type 1BHomo sapiens (human)
negative regulation of neuron apoptotic processMelatonin receptor type 1BHomo sapiens (human)
negative regulation of vasoconstrictionMelatonin receptor type 1BHomo sapiens (human)
positive regulation of circadian sleep/wake cycle, non-REM sleepMelatonin receptor type 1BHomo sapiens (human)
negative regulation of insulin secretionMelatonin receptor type 1BHomo sapiens (human)
regulation of insulin secretionMelatonin receptor type 1BHomo sapiens (human)
negative regulation of cytosolic calcium ion concentrationMelatonin receptor type 1BHomo sapiens (human)
negative regulation of transmission of nerve impulseMelatonin receptor type 1BHomo sapiens (human)
positive regulation of transmission of nerve impulseMelatonin receptor type 1BHomo sapiens (human)
regulation of neuronal action potentialMelatonin receptor type 1BHomo sapiens (human)
G protein-coupled receptor signaling pathwayMelatonin receptor type 1BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
protein bindingMelatonin receptor type 1AHomo sapiens (human)
melatonin receptor activityMelatonin receptor type 1AHomo sapiens (human)
hormone bindingMelatonin receptor type 1AHomo sapiens (human)
organic cyclic compound bindingMelatonin receptor type 1AHomo sapiens (human)
G protein-coupled receptor activityMelatonin receptor type 1AHomo sapiens (human)
protein bindingMelatonin receptor type 1BHomo sapiens (human)
melatonin receptor activityMelatonin receptor type 1BHomo sapiens (human)
G protein-coupled receptor activityMelatonin receptor type 1BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
plasma membraneMelatonin receptor type 1AHomo sapiens (human)
receptor complexMelatonin receptor type 1AHomo sapiens (human)
plasma membraneMelatonin receptor type 1AHomo sapiens (human)
plasma membraneMelatonin receptor type 1BHomo sapiens (human)
synapseMelatonin receptor type 1BHomo sapiens (human)
plasma membraneMelatonin receptor type 1BHomo sapiens (human)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (31)

Assay IDTitleYearJournalArticle
AID107563Inhibition of 2-[125I]iodomelatonin binding to melatonin receptor in quail brain1993Journal of medicinal chemistry, Dec-10, Volume: 36, Issue:25
2-Substituted 5-methoxy-N-acyltryptamines: synthesis, binding affinity for the melatonin receptor, and evaluation of the biological activity.
AID108040Relative Intrinsic activity evaluated on [35S]GTP-gamma-S, binding in NIH3T3 cells stably transfected with human Melatonin receptor type 1B2003Journal of medicinal chemistry, Apr-10, Volume: 46, Issue:8
Three-dimensional quantitative structure-activity relationship studies on selected MT1 and MT2 melatonin receptor ligands: requirements for subtype selectivity and intrinsic activity modulation.
AID107400Negative logarithm of relative affinity (pRA) towards melatonin receptor (relative to N-acetyl-5-methoxytryptamine (aMT))1998Journal of medicinal chemistry, Sep-24, Volume: 41, Issue:20
Melatonin receptor ligands: synthesis of new melatonin derivatives and comprehensive comparative molecular field analysis (CoMFA) study.
AID107876Relative Intrinsic activity evaluated on [35S]GTP-gamma-S, binding in NIH3T3 cells stably transfected with human Melatonin receptor type 1A2003Journal of medicinal chemistry, Apr-10, Volume: 46, Issue:8
Three-dimensional quantitative structure-activity relationship studies on selected MT1 and MT2 melatonin receptor ligands: requirements for subtype selectivity and intrinsic activity modulation.
AID227176Activity considered from GTP-gamma-S and cAMP index values;A-PA= agonist-partial agonist1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
Conformationally restrained melatonin analogues: synthesis, binding affinity for the melatonin receptor, evaluation of the biological activity, and molecular modeling study.
AID107536Binding affinity in chicken brain membranes by using [2-125I]melatonin in a competition radioligand binding assay1995Journal of medicinal chemistry, Mar-31, Volume: 38, Issue:7
Mapping the melatonin receptor. 3. Design and synthesis of melatonin agonists and antagonists derived from 2-phenyltryptamines.
AID107381Pigment aggregation response in Xenopus laevis Melanophores at 10e-8 M of concentration; Agonist response1995Journal of medicinal chemistry, Mar-31, Volume: 38, Issue:7
Mapping the melatonin receptor. 3. Design and synthesis of melatonin agonists and antagonists derived from 2-phenyltryptamines.
AID227388GTPgammaS index is the ratio of the IC50 of compound with GTP and without GTP to the IC50 of melatonin with GTP and without GTP1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
Conformationally restrained melatonin analogues: synthesis, binding affinity for the melatonin receptor, evaluation of the biological activity, and molecular modeling study.
AID1527849Displacement of 2-[1251]-iodomelatonin from whole quail brain membrane melatonin receptor2020European journal of medicinal chemistry, Jan-01, Volume: 185Indole-based melatonin analogues: Synthetic approaches and biological activity.
AID107567Inhibition of 2-[125I]iodomelatonin binding to melatonin receptor in quail brain as 1/Ka1993Journal of medicinal chemistry, Dec-10, Volume: 36, Issue:25
2-Substituted 5-methoxy-N-acyltryptamines: synthesis, binding affinity for the melatonin receptor, and evaluation of the biological activity.
AID230718Relative binding to melatonin receptor compared to melatonin, ratio of IC501997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
Conformationally restrained melatonin analogues: synthesis, binding affinity for the melatonin receptor, evaluation of the biological activity, and molecular modeling study.
AID227181Activity considered from GTP-gamma-S index and cAMP index; AN = Antagonist1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
1-(2-Alkanamidoethyl)-6-methoxyindole derivatives: a new class of potent indole melatonin analogues.
AID108056Relative Binding Affinity (pRA1) to cloned human Melatonin receptor type 1B, stably expressed in NIH3T3 rat fibroblast cells, determined using 2-[125I]iodomelatonin2003Journal of medicinal chemistry, Apr-10, Volume: 46, Issue:8
Three-dimensional quantitative structure-activity relationship studies on selected MT1 and MT2 melatonin receptor ligands: requirements for subtype selectivity and intrinsic activity modulation.
AID1858345Agonist activity at human MT1 Q181A mutant receptor transfected in HEK293T cells co-transfected with tet-inducible luciferase reporter plasmid, pCDNA3.1(+)-CMV-betaArrestin2-tev plasmid and TANGO plasmid assessed as shift in concentration response curve i2022RSC medicinal chemistry, Oct-19, Volume: 13, Issue:10
Synthesis and biological evaluation of paeoveitol D derivatives as new melatonin receptor agonists with antidepressant activities.
AID107559Inhibitory activity against melatonin receptor in the quail optica tecta using 2-[125] iodomelatonin as radiolabeled ligand1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
Conformationally restrained melatonin analogues: synthesis, binding affinity for the melatonin receptor, evaluation of the biological activity, and molecular modeling study.
AID230719Ratio of the IC50 of compound to the IC50 of melatonin1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
1-(2-Alkanamidoethyl)-6-methoxyindole derivatives: a new class of potent indole melatonin analogues.
AID1858344Agonist activity at human MT1 N162A mutant receptor transfected in HEK293T cells co-transfected with tet-inducible luciferase reporter plasmid, pCDNA3.1(+)-CMV-betaArrestin2-tev plasmid and TANGO plasmid assessed as shift in concentration response curve i2022RSC medicinal chemistry, Oct-19, Volume: 13, Issue:10
Synthesis and biological evaluation of paeoveitol D derivatives as new melatonin receptor agonists with antidepressant activities.
AID227390Inhibition of forskolin stimulated cAMP accumulation and represented as cAMP index which is the ratio of percent inhibition to percent inhibition of melatonin1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
Conformationally restrained melatonin analogues: synthesis, binding affinity for the melatonin receptor, evaluation of the biological activity, and molecular modeling study.
AID107558Inhibitory activity against melatonin receptor in the quail optica tecta using 2-[125] iodomelatonin as labelled ligand1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
1-(2-Alkanamidoethyl)-6-methoxyindole derivatives: a new class of potent indole melatonin analogues.
AID107549Compound was tested in vivo for its activity against melatonin receptor in Syrian hamster gonadal regression model; Antagonist1993Journal of medicinal chemistry, Dec-10, Volume: 36, Issue:25
2-Substituted 5-methoxy-N-acyltryptamines: synthesis, binding affinity for the melatonin receptor, and evaluation of the biological activity.
AID1858339Agonist activity at human MT1 receptor transfected in HEK293T cells co-transfected with tet-inducible luciferase reporter plasmid, pCDNA3.1(+)-CMV-betaArrestin2-tev plasmid and TANGO plasmid assessed as tango arrestin recruitment incubated for 24 hrs by T2022RSC medicinal chemistry, Oct-19, Volume: 13, Issue:10
Synthesis and biological evaluation of paeoveitol D derivatives as new melatonin receptor agonists with antidepressant activities.
AID1858340Agonist activity at human MT1 receptor transfected in HEK293T cells co-transfected with tet-inducible luciferase reporter plasmid, pCDNA3.1(+)-CMV-betaArrestin2-tev plasmid and TANGO plasmid assessed as relative luminescence unit incubated for 24 hrs by T2022RSC medicinal chemistry, Oct-19, Volume: 13, Issue:10
Synthesis and biological evaluation of paeoveitol D derivatives as new melatonin receptor agonists with antidepressant activities.
AID108023Relative Binding Affinity (pRA1) to cloned human Melatonin receptor type 1A, stably expressed in NIH3T3 rat fibroblast cells, determined using 2-[125I]iodomelatonin2003Journal of medicinal chemistry, Apr-10, Volume: 46, Issue:8
Three-dimensional quantitative structure-activity relationship studies on selected MT1 and MT2 melatonin receptor ligands: requirements for subtype selectivity and intrinsic activity modulation.
AID227389GTPgammaS index is the ratio of the IC50 of compound with GTP and without GTP to the IC50 of melatonin with GTP and without GTP1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
1-(2-Alkanamidoethyl)-6-methoxyindole derivatives: a new class of potent indole melatonin analogues.
AID107565Binding affinity against melatonin receptor in the quail optica tecta using 2-[125] iodomelatonin as labelled ligand1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
Conformationally restrained melatonin analogues: synthesis, binding affinity for the melatonin receptor, evaluation of the biological activity, and molecular modeling study.
AID107569Compound was tested in vivo for its activity against melatonin receptor in rabbit parietal cortex model; Mixed activity1993Journal of medicinal chemistry, Dec-10, Volume: 36, Issue:25
2-Substituted 5-methoxy-N-acyltryptamines: synthesis, binding affinity for the melatonin receptor, and evaluation of the biological activity.
AID107564Binding affinity against melatonin receptor in the quail optica tecta using 2-[125] iodomelatonin (100 pM) as labelled ligand1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
1-(2-Alkanamidoethyl)-6-methoxyindole derivatives: a new class of potent indole melatonin analogues.
AID227391Inhibition of forskolin stimulated cAMP accumulation and represented as cAMP index which is the ratio of percent inhibition to percent inhibition of melatonin1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
1-(2-Alkanamidoethyl)-6-methoxyindole derivatives: a new class of potent indole melatonin analogues.
AID1858343Agonist activity at human MT2 receptor transfected in HEK293T cells co-transfected with tet-inducible luciferase reporter plasmid, pCDNA3.1(+)-CMV-betaArrestin2-tev plasmid and TANGO plasmid assessed as relative luminescence unit incubated for 24 hrs by T2022RSC medicinal chemistry, Oct-19, Volume: 13, Issue:10
Synthesis and biological evaluation of paeoveitol D derivatives as new melatonin receptor agonists with antidepressant activities.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's6 (37.50)18.2507
2000's5 (31.25)29.6817
2010's1 (6.25)24.3611
2020's4 (25.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.70

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.70 (24.57)
Research Supply Index2.89 (2.92)
Research Growth Index4.59 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.70)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (5.88%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other16 (94.12%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]