Basic Info

Common NameL-Glutamine(F05338)
2D Structure
Description

L-Glutamine (Gln) is one of the 20 amino acids encoded by the standard genetic code. Its side chain is an amide; it is formed by replacing a side-chain hydroxyl of glutamic acid with an amine functional group. glutamine is found in foods high in proteins, such as fish, red meat, beans, and dairy products. glutamine is a supplement that is used in weightlifting, bodybuilding, endurance and other sports, as well as by those who suffer from muscular cramps or pain particularly elderly people. The main use of glutamine within the diet of either group is as a means of replenishing the body's stores of amino acids that have been used during exercise or everyday activities. Studies which are looking into problems with excessive consumption of glutamine thus far have proved inconclusive. However, normal supplementation is healthy mainly because glutamine is supposed to be supplemented after prolonged periods of exercise (for example, a workout or exercise in which amino acids are required for use) and replenishes amino acid stores; this being the main reason glutamine is recommended during fasting or for people who suffer from physical trauma, immune deficiencies, or cancer. There is a significant body of evidence that links glutamine-enriched diets with intestinal effects; aiding maintenance of gut barrier function, intestinal cell proliferation and differentiation, as well as generally reducing septic morbidity and the symptoms of Irritable Bowel Syndrome. The reason for such cleansing properties is thought to stem from the fact that the intestinal extraction rate of glutamine is higher than that for other amino acids, and is therefore thought to be the most viable option when attempting to alleviate conditions relating to the gastrointestinal tract. These conditions were discovered after comparing plasma concentration within the gut between glutamine-enriched and non glutamine-enriched diets. However, even though glutamine is thought to have cleansing properties and effects, it is unknown to what extent glutamine has clinical benefits, due to the varied concentrations of glutamine in varieties of food. It is also known that glutamine has various effects in reducing healing time after operations. Hospital waiting times after abdominal surgery are reduced by providing parenteral nutrition regimens containing amounts of glutamine to patients. Clinical trials have revealed that patients on supplementation regimes containing glutamine have improved nitrogen balances, generation of cysteinyl-leukotrienes from polymorphonuclear neutrophil granulocytes and improved lymphocyte recovery and intestinal permeability (in postoperative patients) - in comparison to those who had no glutamine within their dietary regime; all without any side-effects. It is synthesized from glutamic acid and ammonia. It is the principal carrier of nitrogen in the body and is an important energy source for many cells.

FRCD IDF05338
CAS Number56-85-9
PubChem CID5961
FormulaC5H10N2O3
IUPAC Name

(2S)-2,5-diamino-5-oxopentanoic acid

InChI Key

ZDXPYRJPNDTMRX-VKHMYHEASA-N

InChI

InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m0/s1

Canonical SMILES

C(CC(=O)N)C(C(=O)O)N

Isomeric SMILES

C(CC(=O)N)[C@@H](C(=O)O)N

WikipediaL-Glutamine
Synonyms
        
            Levoglutamid
        
            L-glutamine
        
            glutamine
        
            56-85-9
        
            Levoglutamide
        
            L-(+)-Glutamine
        
            Glutamic acid amide
        
            Stimulina
        
            Cebrogen
        
            glumin
        
Classifies
                

                  
                    Animal Toxin
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
SubclassAmino acids, peptides, and analogues
Intermediate Tree NodesAmino acids and derivatives - Alpha amino acids and derivatives - Alpha amino acids
Direct ParentL-alpha-amino acids
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsL-alpha-amino acid - Fatty acid - Amino acid - Carboximidic acid - Carboximidic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Amine - Hydrocarbon derivative - Primary amine - Organooxygen compound - Organonitrogen compound - Organic oxide - Primary aliphatic amine - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Carbonyl group - Aliphatic acyclic compound
DescriptionThis compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Properties

Property NameProperty Value
Molecular Weight146.146
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Complexity146
Monoisotopic Mass146.069
Exact Mass146.069
XLogP-3.1
Formal Charge0
Heavy Atom Count10
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9604
Human Intestinal AbsorptionHIA-0.5588
Caco-2 PermeabilityCaco2-0.8957
P-glycoprotein SubstrateNon-substrate0.7302
P-glycoprotein InhibitorNon-inhibitor0.9640
Non-inhibitor0.9919
Renal Organic Cation TransporterNon-inhibitor0.9610
Distribution
Subcellular localizationMitochondria0.7313
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8450
CYP450 2D6 SubstrateNon-substrate0.8496
CYP450 3A4 SubstrateNon-substrate0.7544
CYP450 1A2 InhibitorNon-inhibitor0.9583
CYP450 2C9 InhibitorNon-inhibitor0.9741
CYP450 2D6 InhibitorNon-inhibitor0.9600
CYP450 2C19 InhibitorNon-inhibitor0.9761
CYP450 3A4 InhibitorNon-inhibitor0.8936
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9932
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9953
Non-inhibitor0.9828
AMES ToxicityNon AMES toxic0.7849
CarcinogensNon-carcinogens0.9136
Fish ToxicityLow FHMT0.9272
Tetrahymena Pyriformis ToxicityLow TPT0.9965
Honey Bee ToxicityLow HBT0.8173
BiodegradationReady biodegradable0.8854
Acute Oral ToxicityIV0.6418
Carcinogenicity (Three-class)Non-required0.6980

Model Value Unit
Absorption
Aqueous solubility-0.6129LogS
Caco-2 Permeability-0.0182LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.2587LD50, mol/kg
Fish Toxicity2.7940pLC50, mg/L
Tetrahymena Pyriformis Toxicity-1.2818pIGC50, ug/L

References

TitleJournalDatePubmed ID
Effectiveness of Sofosbuvir, Ribavirin and PEG-IFNα-2a in the Treatment of Naïve Egyptian Patients With Chronic Hepatitis C Virus Genotype 4.Am J Med Sci2018 May29753376
Characterization of H9N2 avian influenza viruses from the Middle Eastdemonstrates heterogeneity at amino acid position 226 in the hemagglutinin andpotential for transmission to mammals.Virology2018 May29524835
A novel calcium-binding peptide from Antarctic krill protein hydrolysates andidentification of binding sites of calcium-peptide complex.Food Chem2018 Mar 1529146354
Maternal N-Carbamylglutamate Supply during Early Pregnancy Enhanced PregnancyOutcomes in Sows through Modulations of Targeted Genes and Metabolism Pathways.J Agric Food Chem2018 Jun 1329804448
Nigella sativa L. as an alternative antibiotic feed supplement and effect ongrowth performance in weanling pigs.J Sci Food Agric2018 Jun29230814
Genomic, Biochemical, and Modeling Analyses of Asparagine Synthetases from Wheat.Front Plant Sci2018 Jan 1529379512
Metabolomic analysis of CSF indicates brain metabolic impairment precedeshematological indices of anemia in the iron-deficient infant monkey.Nutr Neurosci2018 Jan27499134
Influence of differently processed yeast (Kluyveromyces fragilis) on feed intake and gut physiology in weaned pigs.J Anim Sci2018 Feb 1529385459
Varying the ratio of Lys:Met while maintaining the ratios of Thr:Phe, Lys:Thr,Lys:His, and Lys:Val alters mammary cellular metabolites, mammalian target ofrapamycin signaling, and gene transcription.J Dairy Sci2018 Feb29248224
Effects of maternal treatment with β-hydroxy-β-metylbutyrate and 2-oxoglutaricacid on femur development in offspring of minks of the standard dark brown type.J Anim Physiol Anim Nutr (Berl)2018 Feb28503899
H9N2 avian influenza virus retained low pathogenicity after serial passage inchickens.Can J Vet Res2018 Apr29755193
Effects of multi-carbohydrase and phytase on standardized ileal digestibility of amino acids and apparent metabolizable energy in canola meal fed to broilerchicks.Poult Sci2017 Sep 128854754
Enterocyte glycosylation is responsive to changes in extracellular conditions:implications for membrane functions.Glycobiology2017 Sep 128486580
Dietary glutamine, glutamic acid and nucleotides increase the carbon turnover (δ 13C) on the intestinal mucosa of weaned piglets.Animal2017 Sep28183385
Damage to the microbial cell membrane during pyrolytic sugar utilization andstrategies for increasing resistance.J Ind Microbiol Biotechnol2017 Sep28551747
Physio-biochemical basis of iron-sulfide nanoparticle induced growth and seedyield enhancement in B. juncea.Plant Physiol Biochem2017 Sep28666234
The effects of prebiotics on microbial dysbiosis, butyrate production andimmunity in HIV-infected subjects.Mucosal Immunol2017 Sep28000678
Metabolic Characterization of Dairy Cows Treated with Gossypol by BloodBiochemistry and Body Fluid Untargeted Metabolome Analyses.J Agric Food Chem2017 Oct 2528965405
Changes in Amino Acid Profile in Roots of Glyphosate Resistant and SusceptibleSoybean (Glycine max) Induced by Foliar Glyphosate Application.J Agric Food Chem2017 Oct 1128920676
Influence of l-pyroglutamic acid on the color formation process of non-enzymatic browning reactions.Food Chem2017 Oct 128490097

Targets

General Function:
Manganese ion binding
Specific Function:
This enzyme has 2 functions: it catalyzes the production of glutamine and 4-aminobutanoate (gamma-aminobutyric acid, GABA), the latter in a pyridoxal phosphate-independent manner (By similarity). Essential for proliferation of fetal skin fibroblasts.
Gene Name:
GLUL
Uniprot ID:
P15104
Molecular Weight:
42064.15 Da
References
  1. Mong JA, Blutstein T: Estradiol modulation of astrocytic form and function: implications for hormonal control of synaptic communication. Neuroscience. 2006;138(3):967-75. Epub 2005 Dec 2. [16326016 ]
General Function:
Metal ion binding
Gene Name:
PPAT
Uniprot ID:
Q06203
Molecular Weight:
57398.52 Da
References
  1. Jiang P, Pioszak AA, Ninfa AJ: Structure-function analysis of glutamine synthetase adenylyltransferase (ATase, EC 2.7.7.49) of Escherichia coli. Biochemistry. 2007 Apr 3;46(13):4117-32. Epub 2007 Mar 14. [17355124 ]
General Function:
Ctp synthase activity
Specific Function:
This enzyme is involved in the de novo synthesis of CTP, a precursor of DNA, RNA and phospholipids. Catalyzes the ATP-dependent amination of UTP to CTP with either L-glutamine or ammonia as a source of nitrogen. This enzyme and its product, CTP, play a crucial role in the proliferation of activated lymphocytes and therefore in immunity.
Gene Name:
CTPS1
Uniprot ID:
P17812
Molecular Weight:
66689.9 Da
References
  1. MacLeod TJ, Lunn FA, Bearne SL: The role of lysine residues 297 and 306 in nucleoside triphosphate regulation of E. coli CTP synthase: inactivation by 2',3'-dialdehyde ATP and mutational analyses. Biochim Biophys Acta. 2006 Feb;1764(2):199-210. Epub 2005 Dec 27. [16427816 ]