Page last updated: 2024-12-07

glycylglutamine

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

Description

glycylglutamine: inhibitory neuropeptide derived from beta-endorphin; RN given refers to (L)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
GlycinegenusA non-essential amino acid. It is found primarily in gelatin and silk fibroin and used therapeutically as a nutrient. It is also a fast inhibitory neurotransmitter.[MeSH]FabaceaeThe large family of plants characterized by pods. Some are edible and some cause LATHYRISM or FAVISM and other forms of poisoning. Other species yield useful materials like gums from ACACIA and various LECTINS like PHYTOHEMAGGLUTININS from PHASEOLUS. Many of them harbor NITROGEN FIXATION bacteria on their roots. Many but not all species of beans belong to this family.[MeSH]

Cross-References

ID SourceID
PubMed CID123913
CHEMBL ID330038
CHEBI ID73898
SCHEMBL ID150160
MeSH IDM0118891

Synonyms (36)

Synonym
13115-71-4
chebi:73898 ,
CHEMBL330038 ,
5-amino-2-[(2-aminoacetyl)amino]-5-oxopentanoic acid
l-glutamine, n2-glycyl-
glycylglutamine
(2s)-5-amino-2-[(2-aminoacetyl)amino]-5-oxopentanoic acid
glycyl-l-glutamine
inchi=1/c7h13n3o4/c8-3-6(12)10-4(7(13)14)1-2-5(9)11/h4h,1-3,8h2,(h2,9,11)(h,10,12)(h,13,14)/t4-/m0/s1
pnmuaggsdzxthx-bypyzucnsa-
h-gly-gln-oh
G0251
AKOS010405991
bdbm50407463
gly-l-gln
glycyl-glutamine
gq
ec 700-144-0
(2s)-5-amino-2-((aminoacetyl)amino)-5-oxopentanoic acid
h7125z98ht ,
unii-h7125z98ht
l-glutamine, glycyl-
(s)-5-amino-2-(2-aminoacetamido)-5-oxopentanoic acid
AKOS015855062
SCHEMBL150160
glycyl-l-glutamine [usp-rs]
glycylglutamine [who-dd]
glycyl glutamine
DTXSID20156917
mfcd00077124
Q27144223
CS-0066415
HY-117541
DS-13405
D94472
(s)-5-amino-2-(2-aminoacetamido)-5-oxopentanoicacid

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Complications and adverse events due to the infused amino acid solutions were not observed."( [Safety and tolerance of a new dipeptide-containing amino acid solution DP-Gln 20 versus a conventional amino acid solution Vamin 18EF in patients after elective colon surgery].
Dietl, KH; Goeters, C; Kuhmann, M; Lange, V; Lawin, P; Mertes, N, 1994
)
0.29
" Thus, the administration of even high doses of GLY-GLN is feasible and safe in patients with polytrauma and is not associated with any relevant renal substrate loss."( Safety and efficacy of increasing dosages of glycyl-glutamine for total parenteral nutrition in polytrauma patients.
Fridrich, P; Germann, P; Götzinger, P; Karner, J; Mauritz, W; Mittlböck, M; Roth, E; Weingartmann, G, 1996
)
0.29

Bioavailability

ExcerptReferenceRelevance
" A therapeutic application of the present results is that if bioavailability of orally administered peptidomimetic drugs is limited, patients may be tried on a high-protein diet to enhance their absorption."( Mechanism of dipeptide stimulation of its own transport in a human intestinal cell line.
Adibi, SA; Bawani, SZ; Thamotharan, M; Zhou, X,
)
0.13

Dosage Studied

ExcerptRelevanceReference
" We conclude that the duration and dosage of glutamine administration (equivalent to 26 gm glutamine per day in a patient weighing 70 kg) used in this study are not sufficient to restore glutamine deficiency of the skeletal muscle in the depleted state."( Glutamine-containing dipeptides as infusion substrates in the septic state.
Fürst, P; Karner, J; Ollenschläger, G; Roth, E; Simmel, A, 1989
)
0.28
" No pathological accumulation of free glycine or of the dipeptide was seen with any of the three dosage steps of GLY-GLN."( Safety and efficacy of increasing dosages of glycyl-glutamine for total parenteral nutrition in polytrauma patients.
Fridrich, P; Germann, P; Götzinger, P; Karner, J; Mauritz, W; Mittlböck, M; Roth, E; Weingartmann, G, 1996
)
0.29
" the dose-response curve is bell-shaped."( The C-terminal tetrapeptide of beta-endorphin (MPF) enhances lymphocyte proliferative responses.
Ensor, DM; Miles, JB; Morley, JS; Owen, DL, 1998
)
0.3
"4-dihydroxyphenyl)methylene glycine hydrazide (GlyH-101) and glibenclamide and their dose-response effect was investigated."( Electrophysiological characterization of electrolyte and nutrient transport across the small intestine in horses.
Breves, G; Burmester, M; Cehak, A; Feige, K; Geburek, F, 2009
)
0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
protective agentSynthetic or natural substance which is given to prevent a disease or disorder or are used in the process of treating a disease or injury due to a poisonous agent.
[role 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]

Drug Classes (2)

ClassDescription
dipeptide zwitterionAny peptide zwitterion comprising two amino acid residues. Major structure at pH 7.3.
dipeptideAny molecule that contains two amino-acid residues connected by peptide linkages.
[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 (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Angiotensin-converting enzyme Homo sapiens (human)IC50 (µMol)7,079.46000.00010.533610.0000AID38876
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (56)

Processvia Protein(s)Taxonomy
response to hypoxiaAngiotensin-converting enzyme Homo sapiens (human)
kidney developmentAngiotensin-converting enzyme Homo sapiens (human)
blood vessel remodelingAngiotensin-converting enzyme Homo sapiens (human)
angiotensin maturationAngiotensin-converting enzyme Homo sapiens (human)
regulation of renal output by angiotensinAngiotensin-converting enzyme Homo sapiens (human)
neutrophil mediated immunityAngiotensin-converting enzyme Homo sapiens (human)
antigen processing and presentation of peptide antigen via MHC class IAngiotensin-converting enzyme Homo sapiens (human)
regulation of systemic arterial blood pressure by renin-angiotensinAngiotensin-converting enzyme Homo sapiens (human)
proteolysisAngiotensin-converting enzyme Homo sapiens (human)
spermatogenesisAngiotensin-converting enzyme Homo sapiens (human)
female pregnancyAngiotensin-converting enzyme Homo sapiens (human)
regulation of blood pressureAngiotensin-converting enzyme Homo sapiens (human)
male gonad developmentAngiotensin-converting enzyme Homo sapiens (human)
response to xenobiotic stimulusAngiotensin-converting enzyme Homo sapiens (human)
embryo development ending in birth or egg hatchingAngiotensin-converting enzyme Homo sapiens (human)
post-transcriptional regulation of gene expressionAngiotensin-converting enzyme Homo sapiens (human)
negative regulation of gene expressionAngiotensin-converting enzyme Homo sapiens (human)
substance P catabolic processAngiotensin-converting enzyme Homo sapiens (human)
bradykinin catabolic processAngiotensin-converting enzyme Homo sapiens (human)
regulation of smooth muscle cell migrationAngiotensin-converting enzyme Homo sapiens (human)
regulation of vasoconstrictionAngiotensin-converting enzyme Homo sapiens (human)
animal organ regenerationAngiotensin-converting enzyme Homo sapiens (human)
response to nutrient levelsAngiotensin-converting enzyme Homo sapiens (human)
response to lipopolysaccharideAngiotensin-converting enzyme Homo sapiens (human)
mononuclear cell proliferationAngiotensin-converting enzyme Homo sapiens (human)
response to laminar fluid shear stressAngiotensin-converting enzyme Homo sapiens (human)
angiotensin-activated signaling pathwayAngiotensin-converting enzyme Homo sapiens (human)
vasoconstrictionAngiotensin-converting enzyme Homo sapiens (human)
hormone metabolic processAngiotensin-converting enzyme Homo sapiens (human)
hormone catabolic processAngiotensin-converting enzyme Homo sapiens (human)
eating behaviorAngiotensin-converting enzyme Homo sapiens (human)
positive regulation of apoptotic processAngiotensin-converting enzyme Homo sapiens (human)
peptide catabolic processAngiotensin-converting enzyme Homo sapiens (human)
positive regulation of vasoconstrictionAngiotensin-converting enzyme Homo sapiens (human)
negative regulation of glucose importAngiotensin-converting enzyme Homo sapiens (human)
regulation of synaptic plasticityAngiotensin-converting enzyme Homo sapiens (human)
lung alveolus developmentAngiotensin-converting enzyme Homo sapiens (human)
amyloid-beta metabolic processAngiotensin-converting enzyme Homo sapiens (human)
arachidonic acid secretionAngiotensin-converting enzyme Homo sapiens (human)
positive regulation of neurogenesisAngiotensin-converting enzyme Homo sapiens (human)
heart contractionAngiotensin-converting enzyme Homo sapiens (human)
regulation of angiotensin metabolic processAngiotensin-converting enzyme Homo sapiens (human)
hematopoietic stem cell differentiationAngiotensin-converting enzyme Homo sapiens (human)
angiogenesis involved in coronary vascular morphogenesisAngiotensin-converting enzyme Homo sapiens (human)
cellular response to glucose stimulusAngiotensin-converting enzyme Homo sapiens (human)
response to dexamethasoneAngiotensin-converting enzyme Homo sapiens (human)
cell proliferation in bone marrowAngiotensin-converting enzyme Homo sapiens (human)
regulation of heart rate by cardiac conductionAngiotensin-converting enzyme Homo sapiens (human)
negative regulation of calcium ion importAngiotensin-converting enzyme Homo sapiens (human)
response to thyroid hormoneAngiotensin-converting enzyme Homo sapiens (human)
blood vessel diameter maintenanceAngiotensin-converting enzyme Homo sapiens (human)
regulation of hematopoietic stem cell proliferationAngiotensin-converting enzyme Homo sapiens (human)
negative regulation of gap junction assemblyAngiotensin-converting enzyme Homo sapiens (human)
cellular response to aldosteroneAngiotensin-converting enzyme Homo sapiens (human)
positive regulation of peptidyl-cysteine S-nitrosylationAngiotensin-converting enzyme Homo sapiens (human)
positive regulation of systemic arterial blood pressureAngiotensin-converting enzyme Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (16)

Processvia Protein(s)Taxonomy
endopeptidase activityAngiotensin-converting enzyme Homo sapiens (human)
carboxypeptidase activityAngiotensin-converting enzyme Homo sapiens (human)
metalloendopeptidase activityAngiotensin-converting enzyme Homo sapiens (human)
calmodulin bindingAngiotensin-converting enzyme Homo sapiens (human)
peptidase activityAngiotensin-converting enzyme Homo sapiens (human)
metallopeptidase activityAngiotensin-converting enzyme Homo sapiens (human)
exopeptidase activityAngiotensin-converting enzyme Homo sapiens (human)
tripeptidyl-peptidase activityAngiotensin-converting enzyme Homo sapiens (human)
peptidyl-dipeptidase activityAngiotensin-converting enzyme Homo sapiens (human)
zinc ion bindingAngiotensin-converting enzyme Homo sapiens (human)
chloride ion bindingAngiotensin-converting enzyme Homo sapiens (human)
mitogen-activated protein kinase kinase bindingAngiotensin-converting enzyme Homo sapiens (human)
bradykinin receptor bindingAngiotensin-converting enzyme Homo sapiens (human)
mitogen-activated protein kinase bindingAngiotensin-converting enzyme Homo sapiens (human)
metallodipeptidase activityAngiotensin-converting enzyme Homo sapiens (human)
heterocyclic compound bindingAngiotensin-converting enzyme Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (10)

Processvia Protein(s)Taxonomy
extracellular spaceAngiotensin-converting enzyme Homo sapiens (human)
extracellular regionAngiotensin-converting enzyme Homo sapiens (human)
extracellular spaceAngiotensin-converting enzyme Homo sapiens (human)
lysosomeAngiotensin-converting enzyme Homo sapiens (human)
endosomeAngiotensin-converting enzyme Homo sapiens (human)
plasma membraneAngiotensin-converting enzyme Homo sapiens (human)
external side of plasma membraneAngiotensin-converting enzyme Homo sapiens (human)
basal plasma membraneAngiotensin-converting enzyme Homo sapiens (human)
brush border membraneAngiotensin-converting enzyme Homo sapiens (human)
extracellular exosomeAngiotensin-converting enzyme Homo sapiens (human)
sperm midpieceAngiotensin-converting enzyme Homo sapiens (human)
plasma membraneAngiotensin-converting enzyme Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID196773Compound (1 mM) evaluated to block the increase in the permeability of the neuronal sodium ions in rat striatum slices by excitatory 30 uM of N-methyl-D-aspartic acid1985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
A dipeptide derived from kainic and L-glutamic acids: a selective antagonist of amino acid induced neuroexcitation with anticonvulsant properties.
AID38876Biological activity was measured against Angiotensin I converting enzyme1995Journal of medicinal chemistry, Jul-07, Volume: 38, Issue:14
Amino acid side chain descriptors for quantitative structure-activity relationship studies of peptide analogues.
AID114204Effective dose required to protect mice from picrotoxin-induced seizures1985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
A dipeptide derived from kainic and L-glutamic acids: a selective antagonist of amino acid induced neuroexcitation with anticonvulsant properties.
AID386057Activity of human PepT1 expressed in xenopus laevis oocyte assessed as induction of inward current at 5 mM2007The Journal of biological chemistry, Sep-28, Volume: 282, Issue:39
Tripeptides of RS1 (RSC1A1) inhibit a monosaccharide-dependent exocytotic pathway of Na+-D-glucose cotransporter SGLT1 with high affinity.
AID196775Compound (1 mM) to block the increase in the permeability of the neuronal sodium ions in rat striatum slices by excitatory 0.1 M of Quis qulalic acid.1985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
A dipeptide derived from kainic and L-glutamic acids: a selective antagonist of amino acid induced neuroexcitation with anticonvulsant properties.
AID196777Compound (1 mM) to block the increase in the permeability of the neuronal sodium ions in rat striatum slices by excitatory 0.5 mM of L-GLutamic acid1985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
A dipeptide derived from kainic and L-glutamic acids: a selective antagonist of amino acid induced neuroexcitation with anticonvulsant properties.
AID680664TP_TRANSPORTER: upregulation of mRNA and protein in Caco-2 cells1998The Journal of physiology, Mar-15, Volume: 507 ( Pt 3)Substrate upregulation of the human small intestinal peptide transporter, hPepT1.
AID196780Evaluated at 1 mM to block the increase in the permeability of the neuronal sodium ions in rat striatum slices by excitatory 0.1 mM of Kainic Acid1985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
A dipeptide derived from kainic and L-glutamic acids: a selective antagonist of amino acid induced neuroexcitation with anticonvulsant properties.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (93)

TimeframeStudies, This Drug (%)All Drugs %
pre-199017 (18.28)18.7374
1990's31 (33.33)18.2507
2000's30 (32.26)29.6817
2010's12 (12.90)24.3611
2020's3 (3.23)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 9.83

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 Index9.83 (24.57)
Research Supply Index4.73 (2.92)
Research Growth Index4.56 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (9.83)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials8 (7.69%)5.53%
Reviews6 (5.77%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other90 (86.54%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]