L-Glutamine
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Basic Info
Common Name | L-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 ID | F05338 |
CAS Number | 56-85-9 |
PubChem CID | 5961 |
Formula | C5H10N2O3 |
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 |
Wikipedia | L-Glutamine |
Synonyms | Levoglutamid L-glutamine glutamine 56-85-9 Levoglutamide L-(+)-Glutamine Glutamic acid amide Stimulina Cebrogen glumin |
Classifies | Animal Toxin |
Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Organic acids and derivatives |
Class | Carboxylic acids and derivatives |
Subclass | Amino acids, peptides, and analogues |
Intermediate Tree Nodes | Amino acids and derivatives - Alpha amino acids and derivatives - Alpha amino acids |
Direct Parent | L-alpha-amino acids |
Alternative Parents | |
Molecular Framework | Aliphatic acyclic compounds |
Substituents | L-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 |
Description | This 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 Name | Property Value |
---|---|
Molecular Weight | 146.146 |
Hydrogen Bond Donor Count | 3 |
Hydrogen Bond Acceptor Count | 4 |
Rotatable Bond Count | 4 |
Complexity | 146 |
Monoisotopic Mass | 146.069 |
Exact Mass | 146.069 |
XLogP | -3.1 |
Formal Charge | 0 |
Heavy Atom Count | 10 |
Defined Atom Stereocenter Count | 1 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB+ | 0.9604 |
Human Intestinal Absorption | HIA- | 0.5588 |
Caco-2 Permeability | Caco2- | 0.8957 |
P-glycoprotein Substrate | Non-substrate | 0.7302 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.9640 |
Non-inhibitor | 0.9919 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.9610 |
Distribution | ||
Subcellular localization | Mitochondria | 0.7313 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.8450 |
CYP450 2D6 Substrate | Non-substrate | 0.8496 |
CYP450 3A4 Substrate | Non-substrate | 0.7544 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.9583 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.9741 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9600 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.9761 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.8936 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9932 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9953 |
Non-inhibitor | 0.9828 | |
AMES Toxicity | Non AMES toxic | 0.7849 |
Carcinogens | Non-carcinogens | 0.9136 |
Fish Toxicity | Low FHMT | 0.9272 |
Tetrahymena Pyriformis Toxicity | Low TPT | 0.9965 |
Honey Bee Toxicity | Low HBT | 0.8173 |
Biodegradation | Ready biodegradable | 0.8854 |
Acute Oral Toxicity | IV | 0.6418 |
Carcinogenicity (Three-class) | Non-required | 0.6980 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -0.6129 | LogS |
Caco-2 Permeability | -0.0182 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 1.2587 | LD50, mol/kg |
Fish Toxicity | 2.7940 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | -1.2818 | pIGC50, ug/L |
References
Title | Journal | Date | Pubmed 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 Sci | 2018 May | 29753376 |
Characterization of H9N2 avian influenza viruses from the Middle Eastdemonstrates heterogeneity at amino acid position 226 in the hemagglutinin andpotential for transmission to mammals. | Virology | 2018 May | 29524835 |
A novel calcium-binding peptide from Antarctic krill protein hydrolysates andidentification of binding sites of calcium-peptide complex. | Food Chem | 2018 Mar 15 | 29146354 |
Maternal N-Carbamylglutamate Supply during Early Pregnancy Enhanced PregnancyOutcomes in Sows through Modulations of Targeted Genes and Metabolism Pathways. | J Agric Food Chem | 2018 Jun 13 | 29804448 |
Nigella sativa L. as an alternative antibiotic feed supplement and effect ongrowth performance in weanling pigs. | J Sci Food Agric | 2018 Jun | 29230814 |
Genomic, Biochemical, and Modeling Analyses of Asparagine Synthetases from Wheat. | Front Plant Sci | 2018 Jan 15 | 29379512 |
Metabolomic analysis of CSF indicates brain metabolic impairment precedeshematological indices of anemia in the iron-deficient infant monkey. | Nutr Neurosci | 2018 Jan | 27499134 |
Influence of differently processed yeast (Kluyveromyces fragilis) on feed intake and gut physiology in weaned pigs. | J Anim Sci | 2018 Feb 15 | 29385459 |
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 Sci | 2018 Feb | 29248224 |
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 Feb | 28503899 |
H9N2 avian influenza virus retained low pathogenicity after serial passage inchickens. | Can J Vet Res | 2018 Apr | 29755193 |
Effects of multi-carbohydrase and phytase on standardized ileal digestibility of amino acids and apparent metabolizable energy in canola meal fed to broilerchicks. | Poult Sci | 2017 Sep 1 | 28854754 |
Enterocyte glycosylation is responsive to changes in extracellular conditions:implications for membrane functions. | Glycobiology | 2017 Sep 1 | 28486580 |
Dietary glutamine, glutamic acid and nucleotides increase the carbon turnover (δ 13C) on the intestinal mucosa of weaned piglets. | Animal | 2017 Sep | 28183385 |
Damage to the microbial cell membrane during pyrolytic sugar utilization andstrategies for increasing resistance. | J Ind Microbiol Biotechnol | 2017 Sep | 28551747 |
Physio-biochemical basis of iron-sulfide nanoparticle induced growth and seedyield enhancement in B. juncea. | Plant Physiol Biochem | 2017 Sep | 28666234 |
The effects of prebiotics on microbial dysbiosis, butyrate production andimmunity in HIV-infected subjects. | Mucosal Immunol | 2017 Sep | 28000678 |
Metabolic Characterization of Dairy Cows Treated with Gossypol by BloodBiochemistry and Body Fluid Untargeted Metabolome Analyses. | J Agric Food Chem | 2017 Oct 25 | 28965405 |
Changes in Amino Acid Profile in Roots of Glyphosate Resistant and SusceptibleSoybean (Glycine max) Induced by Foliar Glyphosate Application. | J Agric Food Chem | 2017 Oct 11 | 28920676 |
Influence of l-pyroglutamic acid on the color formation process of non-enzymatic browning reactions. | Food Chem | 2017 Oct 1 | 28490097 |
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
- 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
- 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
- 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 ]