Compounds > acetyl-histidyl-phenylalanyl-arginyl-tryptophanamide
Page last updated: 2024-11-12

acetyl-histidyl-phenylalanyl-arginyl-tryptophanamide

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Cross-References

ID SourceID
PubMed CID10484741
CHEMBL ID50056
MeSH IDM0430160

Synonyms (9)

Synonym
2-{2-[2-acetylamino-3-(1h-imidazol-4-yl)-propionylamino]-3-phenyl-propionylamino}-5-guanidino-pentanoic acid [1-carbamoyl-2-(1h-indol-3-yl)-ethyl]-amideac-his-dphe-darg-trp-nh2
2-{2-[2-acetylamino-3-(3h-imidazol-4-yl)-propionylamino]-3-phenyl-propionylamino}-5-guanidino-pentanoic acid [1-carbamoyl-2-(1h-indol-3-yl)-ethyl]-amide(ac-his-phe-arg-trp-nh2)
ac-his-phe-arg-trp-nh2
(s)-2-{(s)-2-[(s)-2-acetylamino-3-(3h-imidazol-4-yl)-propionylamino]-3-phenyl-propionylamino}-5-guanidino-pentanoic acid [(s)-1-carbamoyl-2-(1h-indol-3-yl)-ethyl]-amide
2-{2-[2-acetylamino-3-(3h-imidazol-4-yl)-propionylamino]-3-phenyl-propionylamino}-5-guanidino-pentanoic acid [1-carbamoyl-2-(1h-indol-3-yl)-ethyl]-amide
bdbm50034910
ac-his-d-phe-arg-d-trp-nh2
CHEMBL50056 ,
ac-his-phe-arg-trp-nh(2)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (7)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Melanocortin receptor 4Homo sapiens (human)Ki0.26300.00000.30864.8860AID109137; AID268362
Melanocortin receptor 3Homo sapiens (human)Ki1.81750.00010.24522.8650AID108798; AID268361
Melanocyte-stimulating hormone receptorHomo sapiens (human)Ki0.03600.00000.00650.0370AID108622; AID268360
[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)
Melanocortin receptor 4Homo sapiens (human)EC50 (µMol)0.05930.00000.09112.6000AID268365; AID82381
Melanocortin receptor 3Mus musculus (house mouse)EC50 (µMol)2.80000.00010.28575.4000AID109617; AID1229381; AID1547511; AID221832
Melanocortin receptor 5Mus musculus (house mouse)EC50 (µMol)0.12400.00000.03211.4900AID107046; AID1229385; AID1547516; AID221835
Melanocortin receptor 3Homo sapiens (human)EC50 (µMol)0.20900.00010.01270.2480AID268364; AID82380
Melanocortin receptor 4Mus musculus (house mouse)EC50 (µMol)1.35550.00000.12472.4700AID107035; AID1229383; AID1547514; AID221834
Melanocyte-stimulating hormone receptorHomo sapiens (human)EC50 (µMol)0.01350.00000.00800.2280AID268363; AID82379
Melanocyte-stimulating hormone receptorMus musculus (house mouse)EC50 (µMol)5.18500.00000.30047.6900AID109602; AID1229379; AID1547509; AID221830
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (33)

Processvia Protein(s)Taxonomy
diet induced thermogenesisMelanocortin receptor 4Homo sapiens (human)
energy reserve metabolic processMelanocortin receptor 4Homo sapiens (human)
adenylate cyclase-modulating G protein-coupled receptor signaling pathwayMelanocortin receptor 4Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayMelanocortin receptor 4Homo sapiens (human)
feeding behaviorMelanocortin receptor 4Homo sapiens (human)
insulin secretionMelanocortin receptor 4Homo sapiens (human)
response to insulinMelanocortin receptor 4Homo sapiens (human)
positive regulation of bone resorptionMelanocortin receptor 4Homo sapiens (human)
regulation of eating behaviorMelanocortin receptor 4Homo sapiens (human)
response to melanocyte-stimulating hormoneMelanocortin receptor 4Homo sapiens (human)
negative regulation of feeding behaviorMelanocortin receptor 4Homo sapiens (human)
regulation of grooming behaviorMelanocortin receptor 4Homo sapiens (human)
regulation of metabolic processMelanocortin receptor 4Homo sapiens (human)
regulation of heart rateMelanocortin receptor 3Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerMelanocortin receptor 3Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayMelanocortin receptor 3Homo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayMelanocortin receptor 3Homo sapiens (human)
regulation of blood pressureMelanocortin receptor 3Homo sapiens (human)
circadian regulation of gene expressionMelanocortin receptor 3Homo sapiens (human)
homoiothermyMelanocortin receptor 3Homo sapiens (human)
locomotor rhythmMelanocortin receptor 3Homo sapiens (human)
sodium ion homeostasisMelanocortin receptor 3Homo sapiens (human)
regulation of feeding behaviorMelanocortin receptor 3Homo sapiens (human)
regulation of metabolic processMelanocortin receptor 3Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerMelanocyte-stimulating hormone receptorHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayMelanocyte-stimulating hormone receptorHomo sapiens (human)
UV protectionMelanocyte-stimulating hormone receptorHomo sapiens (human)
positive regulation of protein kinase A signalingMelanocyte-stimulating hormone receptorHomo sapiens (human)
sensory perception of painMelanocyte-stimulating hormone receptorHomo sapiens (human)
negative regulation of tumor necrosis factor productionMelanocyte-stimulating hormone receptorHomo sapiens (human)
intracellular signal transductionMelanocyte-stimulating hormone receptorHomo sapiens (human)
melanin biosynthetic processMelanocyte-stimulating hormone receptorHomo sapiens (human)
pigmentationMelanocyte-stimulating hormone receptorHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIMelanocyte-stimulating hormone receptorHomo sapiens (human)
UV-damage excision repairMelanocyte-stimulating hormone receptorHomo sapiens (human)
positive regulation of protein kinase C signalingMelanocyte-stimulating hormone receptorHomo sapiens (human)
positive regulation of feeding behaviorMelanocyte-stimulating hormone receptorHomo sapiens (human)
regulation of metabolic processMelanocyte-stimulating hormone receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
melanocortin receptor activityMelanocortin receptor 4Homo sapiens (human)
melanocyte-stimulating hormone receptor activityMelanocortin receptor 4Homo sapiens (human)
protein bindingMelanocortin receptor 4Homo sapiens (human)
peptide hormone bindingMelanocortin receptor 4Homo sapiens (human)
ubiquitin protein ligase bindingMelanocortin receptor 4Homo sapiens (human)
neuropeptide bindingMelanocortin receptor 4Homo sapiens (human)
melanocortin receptor activityMelanocortin receptor 3Homo sapiens (human)
melanocyte-stimulating hormone receptor activityMelanocortin receptor 3Homo sapiens (human)
protein bindingMelanocortin receptor 3Homo sapiens (human)
neuropeptide bindingMelanocortin receptor 3Homo sapiens (human)
peptide hormone bindingMelanocortin receptor 3Homo sapiens (human)
melanocortin receptor activityMelanocyte-stimulating hormone receptorHomo sapiens (human)
melanocyte-stimulating hormone receptor activityMelanocyte-stimulating hormone receptorHomo sapiens (human)
protein bindingMelanocyte-stimulating hormone receptorHomo sapiens (human)
G protein-coupled peptide receptor activityMelanocyte-stimulating hormone receptorHomo sapiens (human)
ubiquitin protein ligase bindingMelanocyte-stimulating hormone receptorHomo sapiens (human)
hormone bindingMelanocyte-stimulating hormone receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
plasma membraneMelanocortin receptor 4Homo sapiens (human)
membraneMelanocortin receptor 4Homo sapiens (human)
plasma membraneMelanocortin receptor 4Homo sapiens (human)
cytoplasmMelanocortin receptor 4Homo sapiens (human)
plasma membraneMelanocortin receptor 3Homo sapiens (human)
cytoplasmMelanocortin receptor 3Homo sapiens (human)
plasma membraneMelanocortin receptor 3Homo sapiens (human)
plasma membraneMelanocyte-stimulating hormone receptorHomo sapiens (human)
plasma membraneMelanocyte-stimulating hormone receptorHomo sapiens (human)
cytoplasmMelanocyte-stimulating hormone receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (36)

Assay IDTitleYearJournalArticle
AID101999Activity expressed as EC50 was measured in lizard.1995Journal of medicinal chemistry, May-12, Volume: 38, Issue:10
Design, synthesis, biology, and conformations of bicyclic alpha-melanotropin analogues.
AID108622Binding affinity towards human Melanocortin 1 receptor (hMC1R)2003Bioorganic & medicinal chemistry letters, Aug-18, Volume: 13, Issue:16
Sub-nanomolar hMC1R agonists by end-capping of the melanocortin tetrapeptide His-D-Phe-Arg-Trp-NH(2).
AID268365Agonist activity at human MC4R transfected in HEK293 cells2006Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15
Design, synthesis, and evaluation of proline and pyrrolidine based melanocortin receptor agonists. A conformationally restricted dipeptide mimic approach.
AID71797Activity expressed as EC50 was measured in frog.1995Journal of medicinal chemistry, May-12, Volume: 38, Issue:10
Design, synthesis, biology, and conformations of bicyclic alpha-melanotropin analogues.
AID268360Displacement of europium labeled NDP-alpha-MSH from human MC1R expressed in HEK293 cells2006Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15
Design, synthesis, and evaluation of proline and pyrrolidine based melanocortin receptor agonists. A conformationally restricted dipeptide mimic approach.
AID268364Agonist activity at human MC3R transfected in HEK293 cells2006Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15
Design, synthesis, and evaluation of proline and pyrrolidine based melanocortin receptor agonists. A conformationally restricted dipeptide mimic approach.
AID1229383Agonist activity at mouse MC4 receptor expressed in HEK-293 cells assessed as cAMP response measured after 2 hrs incubation by cAMP Alphascreen assay2015ACS medicinal chemistry letters, May-14, Volume: 6, Issue:5
Synthesis and Pharmacology of α/β(3)-Peptides Based on the Melanocortin Agonist Ac-His-dPhe-Arg-Trp-NH2 Sequence.
AID1547511Agonist activity at mouse melanocortin receptor 3 expressed in HEK293 cells assessed as stimulation of cAMP accumulation incubated for 2 hrs by cAMP Alpha-screen assay2020ACS medicinal chemistry letters, Mar-12, Volume: 11, Issue:3
Single Nucleotide Polymorphisms in the Melanocortin His-Phe-Arg-Trp Sequences Decrease Tetrapeptide Potency and Efficacy.
AID221835Functional activity at the mouse melanocortin 5 receptor2001Journal of medicinal chemistry, Jun-21, Volume: 44, Issue:13
Characterization of melanocortin NDP-MSH agonist peptide fragments at the mouse central and peripheral melanocortin receptors.
AID268368Agonist activity at human MC4R transfected in HEK293 cells relative to NDP-MSH2006Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15
Design, synthesis, and evaluation of proline and pyrrolidine based melanocortin receptor agonists. A conformationally restricted dipeptide mimic approach.
AID108798Binding affinity towards human Melanocortin 3 receptor (hMC3R)2003Bioorganic & medicinal chemistry letters, Aug-18, Volume: 13, Issue:16
Sub-nanomolar hMC1R agonists by end-capping of the melanocortin tetrapeptide His-D-Phe-Arg-Trp-NH(2).
AID1229385Agonist activity at mouse MC5 receptor expressed in HEK-293 cells assessed as cAMP response measured after 2 hrs incubation by cAMP Alphascreen assay2015ACS medicinal chemistry letters, May-14, Volume: 6, Issue:5
Synthesis and Pharmacology of α/β(3)-Peptides Based on the Melanocortin Agonist Ac-His-dPhe-Arg-Trp-NH2 Sequence.
AID268367Agonist activity at human MC3R transfected in HEK293 cells relative to NDP-MSH2006Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15
Design, synthesis, and evaluation of proline and pyrrolidine based melanocortin receptor agonists. A conformationally restricted dipeptide mimic approach.
AID268361Displacement of europium labeled NDP-alpha-MSH from human MC3R expressed in HEK293 cells2006Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15
Design, synthesis, and evaluation of proline and pyrrolidine based melanocortin receptor agonists. A conformationally restricted dipeptide mimic approach.
AID1229379Agonist activity at mouse MC1 receptor expressed in HEK-293 cells assessed as cAMP response measured after 2 hrs incubation by cAMP Alphascreen assay2015ACS medicinal chemistry letters, May-14, Volume: 6, Issue:5
Synthesis and Pharmacology of α/β(3)-Peptides Based on the Melanocortin Agonist Ac-His-dPhe-Arg-Trp-NH2 Sequence.
AID107046Agonist activity towards mouse Melanocortin-5 receptor (mMC5R)2002Journal of medicinal chemistry, Jul-04, Volume: 45, Issue:14
Structure-activity relationships of the melanocortin tetrapeptide Ac-His-DPhe-Arg-Trp-NH(2) at the mouse melanocortin receptors: part 2 modifications at the Phe position.
AID221832Functional activity at the mouse melanocortin 3 receptor2001Journal of medicinal chemistry, Jun-21, Volume: 44, Issue:13
Characterization of melanocortin NDP-MSH agonist peptide fragments at the mouse central and peripheral melanocortin receptors.
AID102006Potency of compound was measured in lizard where (-) indicates peptide is not prolonged acting.1995Journal of medicinal chemistry, May-12, Volume: 38, Issue:10
Design, synthesis, biology, and conformations of bicyclic alpha-melanotropin analogues.
AID71817Potency measured in frog where (-) indicates peptide is not long acting.1995Journal of medicinal chemistry, May-12, Volume: 38, Issue:10
Design, synthesis, biology, and conformations of bicyclic alpha-melanotropin analogues.
AID268366Agonist activity at human MC1R transfected in HEK293 cells relative to NDP-MSH2006Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15
Design, synthesis, and evaluation of proline and pyrrolidine based melanocortin receptor agonists. A conformationally restricted dipeptide mimic approach.
AID109137Binding affinity towards human melanocortin 4 receptor (hMC4R)2003Bioorganic & medicinal chemistry letters, Aug-18, Volume: 13, Issue:16
Sub-nanomolar hMC1R agonists by end-capping of the melanocortin tetrapeptide His-D-Phe-Arg-Trp-NH(2).
AID268362Displacement of europium labeled NDP-alpha-MSH from human MC4R expressed in HEK293 cells2006Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15
Design, synthesis, and evaluation of proline and pyrrolidine based melanocortin receptor agonists. A conformationally restricted dipeptide mimic approach.
AID109602Agonist activity to the mouse Melanocortin-1 receptor (mMC1R)2002Journal of medicinal chemistry, Jul-04, Volume: 45, Issue:14
Structure-activity relationships of the melanocortin tetrapeptide Ac-His-DPhe-Arg-Trp-NH(2) at the mouse melanocortin receptors: part 2 modifications at the Phe position.
AID82381In vitro agonist potency was evaluated in HEK293 cells transfected with human melanocortin receptor (hMC4R)2003Bioorganic & medicinal chemistry letters, Aug-18, Volume: 13, Issue:16
Sub-nanomolar hMC1R agonists by end-capping of the melanocortin tetrapeptide His-D-Phe-Arg-Trp-NH(2).
AID109617Agonist activity to the mouse Melanocortin-3 receptor (mMC3R)2002Journal of medicinal chemistry, Jul-04, Volume: 45, Issue:14
Structure-activity relationships of the melanocortin tetrapeptide Ac-His-DPhe-Arg-Trp-NH(2) at the mouse melanocortin receptors: part 2 modifications at the Phe position.
AID1547514Agonist activity at mouse melanocortin receptor 4 expressed in HEK293 cells assessed as stimulation of cAMP accumulation incubated for 2 hrs by cAMP Alpha-screen assay2020ACS medicinal chemistry letters, Mar-12, Volume: 11, Issue:3
Single Nucleotide Polymorphisms in the Melanocortin His-Phe-Arg-Trp Sequences Decrease Tetrapeptide Potency and Efficacy.
AID1547509Agonist activity at mouse melanocortin receptor 1 expressed in HEK293 cells assessed as stimulation of cAMP accumulation incubated for 2 hrs by cAMP AlphaScreen assay2020ACS medicinal chemistry letters, Mar-12, Volume: 11, Issue:3
Single Nucleotide Polymorphisms in the Melanocortin His-Phe-Arg-Trp Sequences Decrease Tetrapeptide Potency and Efficacy.
AID268363Agonist activity at human MC1R transfected in HEK293 cells2006Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15
Design, synthesis, and evaluation of proline and pyrrolidine based melanocortin receptor agonists. A conformationally restricted dipeptide mimic approach.
AID82380In vitro agonist potency was evaluated in HEK293 cells transfected with human melanocortin receptor (hMC3R)2003Bioorganic & medicinal chemistry letters, Aug-18, Volume: 13, Issue:16
Sub-nanomolar hMC1R agonists by end-capping of the melanocortin tetrapeptide His-D-Phe-Arg-Trp-NH(2).
AID221830Functional activity at the mouse melanocortin 1 receptor2001Journal of medicinal chemistry, Jun-21, Volume: 44, Issue:13
Characterization of melanocortin NDP-MSH agonist peptide fragments at the mouse central and peripheral melanocortin receptors.
AID107035Agonist activity to the mouse Melanocortin-4 receptor (mMC4R)2002Journal of medicinal chemistry, Jul-04, Volume: 45, Issue:14
Structure-activity relationships of the melanocortin tetrapeptide Ac-His-DPhe-Arg-Trp-NH(2) at the mouse melanocortin receptors: part 2 modifications at the Phe position.
AID1547516Agonist activity at mouse melanocortin receptor 5 expressed in HEK293 cells assessed as stimulation of cAMP accumulation incubated for 2 hrs by cAMP Alpha-screen assay2020ACS medicinal chemistry letters, Mar-12, Volume: 11, Issue:3
Single Nucleotide Polymorphisms in the Melanocortin His-Phe-Arg-Trp Sequences Decrease Tetrapeptide Potency and Efficacy.
AID1229381Agonist activity at mouse MC3 receptor expressed in HEK-293 cells assessed as cAMP response measured after 2 hrs incubation by cAMP Alphascreen assay2015ACS medicinal chemistry letters, May-14, Volume: 6, Issue:5
Synthesis and Pharmacology of α/β(3)-Peptides Based on the Melanocortin Agonist Ac-His-dPhe-Arg-Trp-NH2 Sequence.
AID82379In vitro agonist potency was evaluated in HEK293 cells transfected with human melanocortin receptor (hMC1R)2003Bioorganic & medicinal chemistry letters, Aug-18, Volume: 13, Issue:16
Sub-nanomolar hMC1R agonists by end-capping of the melanocortin tetrapeptide His-D-Phe-Arg-Trp-NH(2).
AID71932In vitro potency relative to alpha-melanotropin (alpha-MSH), in the frog (Rana pipiens) skin bioassay1987Journal of medicinal chemistry, Nov, Volume: 30, Issue:11
alpha-Melanotropin: the minimal active sequence in the frog skin bioassay.
AID221834Functional activity at the mouse melanocortin 4 receptor2001Journal of medicinal chemistry, Jun-21, Volume: 44, Issue:13
Characterization of melanocortin NDP-MSH agonist peptide fragments at the mouse central and peripheral melanocortin receptors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (12.50)18.7374
1990's1 (12.50)18.2507
2000's4 (50.00)29.6817
2010's1 (12.50)24.3611
2020's1 (12.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.63

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 Index12.63 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.83 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.63)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
mannitol
[no description available]		2.0310mannitolallergen;
antiglaucoma drug;
compatible osmolytes;
Escherichia coli metabolite;
food anticaking agent;
food bulking agent;
food humectant;
food stabiliser;
food thickening agent;
hapten;
metabolite;
osmotic diuretic;
sweetening agent
melanotan-ii
melanotan-II: synthetic cyclic heptapeptide, an analog of alpha-melanotropin (4,10); capable of stimulating melanin synthesis & promoting rapid tanning of skin; currently in trials for use in the prevention of sunlight-induced skin cancer		2.420organic molecular entity
phenylalanylarginine
phenylalanylarginine: RN given refers to all (L)-isomer. Phe-Arg : A dipeptide composed of L-phenylalanine and L-arginine joined by a peptide linkage.		1.9710dipeptidemetabolite
ac-his-dphe-arg-trp-nh2
[no description available]		3.1350
alpha-msh
[no description available]		3.2760peptide hormoneanti-inflammatory agent
msh, 4-nle-7-phe-alpha-
[no description available]		2.9540polypeptidedermatologic drug
ConditionIndicatedRelationship StrengthStudiesTrials