L-GLUTAMINE

Relevant Data

Food Additives Approved by WHO:

  • L-GLUTAMINE [show]

Flavouring Substances Approved by European Union:

  • Glutamine [show]

General Information

MaintermL-GLUTAMINE
Doc TypeASP
CAS Reg.No.(or other ID)56-85-9
Regnum 172.320

From www.fda.gov

Computed Descriptors

Download SDF
2D Structure
CID5961
IUPAC Name(2S)-2,5-diamino-5-oxopentanoic acid
InChIInChI=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
InChI KeyZDXPYRJPNDTMRX-VKHMYHEASA-N
Canonical SMILESC(CC(=O)N)C(C(=O)O)N
Molecular FormulaC5H10N2O3
Wikipediaglutamine

From Pubchem

Computed Properties

Property Name Property Value
Molecular Weight146.146
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Complexity146.0
CACTVS Substructure Key Fingerprint A A A D c c B j M A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A H g A Q C A A A C C j B g A Q A C A B A A g A I A A G Q G A A A A A A A A A A A A I G A A A A C A B I A g A A A Q A A E E A A A A A C c F w A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = =
Topological Polar Surface Area106.0
Monoisotopic Mass146.069
Exact Mass146.069
Compound Is CanonicalizedTrue
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

From Pubchem

Food Additives Biosynthesis/Degradation

ADMET Predicted Profile --- Classification

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

From admetSAR

ADMET Predicted Profile --- Regression

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

From admetSAR

Toxicity Profile

Route of ExposureAbsorption is efficient and occurs by an active transport mechanism
Mechanism of ToxicitySupplemental L-glutamine's possible immunomodulatory role may be accounted for in a number of ways. L-glutamine appears to play a major role in protecting the integrity of the gastrointestinal tract and, in particular, the large intestine. During catabolic states, the integrity of the intestinal mucosa may be compromised with consequent increased intestinal permeability and translocation of Gram-negative bacteria from the large intestine into the body. The demand for L-glutamine by the intestine, as well as by cells such as lymphocytes, appears to be much greater than that supplied by skeletal muscle, the major storage tissue for L-glutamine. L-glutamine is the preferred respiratory fuel for enterocytes, colonocytes and lymphocytes. Therefore, supplying supplemental L-glutamine under these conditions may do a number of things. For one, it may reverse the catabolic state by sparing skeletal muscle L-glutamine. It also may inhibit translocation of Gram-negative bacteria from the large intestine. L-glutamine helps maintain secretory IgA, which functions primarily by preventing the attachment of bacteria to mucosal cells. L-glutamine appears to be required to support the proliferation of mitogen-stimulated lymphocytes, as well as the production of interleukin-2 (IL-2) and interferon-gamma (IFN-gamma). It is also required for the maintenance of lymphokine-activated killer cells (LAK). L-glutamine can enhance phagocytosis by neutrophils and monocytes. It can lead to an increased synthesis of glutathione in the intestine, which may also play a role in maintaining the integrity of the intestinal mucosa by ameliorating oxidative stress. The exact mechanism of the possible immunomodulatory action of supplemental L-glutamine, however, remains unclear. It is conceivable that the major effect of L-glutamine occurs at the level of the intestine. Perhaps enteral L-glutamine acts directly on intestine-associated lymphoid tissue and stimulates overall immune function by that mechanism, without passing beyond the splanchnic bed.
MetabolismEnterocytes, Hepatic
Toxicity ValuesNone
Lethal DoseNone
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNone
Health EffectsNone
TreatmentNone
Reference
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762.[19212411 ]
  2. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7.[12097436 ]
  3. Subramanian A, Gupta A, Saxena S, Gupta A, Kumar R, Nigam A, Kumar R, Mandal SK, Roy R: Proton MR CSF analysis and a new software as predictors for the differentiation of meningitis in children. NMR Biomed. 2005 Jun;18(4):213-25.[15627241 ]
  4. Commodari F, Arnold DL, Sanctuary BC, Shoubridge EA: 1H NMR characterization of normal human cerebrospinal fluid and the detection of methylmalonic acid in a vitamin B12 deficient patient. NMR Biomed. 1991 Aug;4(4):192-200.[1931558 ]
  5. Boza JJ, Dangin M, Moennoz D, Montigon F, Vuichoud J, Jarret A, Pouteau E, Gremaud G, Oguey-Araymon S, Courtois D, Woupeyi A, Finot PA, Ballevre O: Free and protein-bound glutamine have identical splanchnic extraction in healthy human volunteers. Am J Physiol Gastrointest Liver Physiol. 2001 Jul;281(1):G267-74.[11408280 ]
  6. McAnena OJ, Moore FA, Moore EE, Jones TN, Parsons P: Selective uptake of glutamine in the gastrointestinal tract: confirmation in a human study. Br J Surg. 1991 Apr;78(4):480-2.[1903318 ]
  7. Morlion BJ, Stehle P, Wachtler P, Siedhoff HP, Koller M, Konig W, Furst P, Puchstein C: Total parenteral nutrition with glutamine dipeptide after major abdominal surgery: a randomized, double-blind, controlled study. Ann Surg. 1998 Feb;227(2):302-8.[9488531 ]
  8. Jian ZM, Cao JD, Zhu XG, Zhao WX, Yu JC, Ma EL, Wang XR, Zhu MW, Shu H, Liu YW: The impact of alanyl-glutamine on clinical safety, nitrogen balance, intestinal permeability, and clinical outcome in postoperative patients: a randomized, double-blind, controlled study of 120 patients. JPEN J Parenter Enteral Nutr. 1999 Sep-Oct;23(5 Suppl):S62-6.[10483898 ]
  9. Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6.[12297216 ]
  10. Nicholson JK, O'Flynn MP, Sadler PJ, Macleod AF, Juul SM, Sonksen PH: Proton-nuclear-magnetic-resonance studies of serum, plasma and urine from fasting normal and diabetic subjects. Biochem J. 1984 Jan 15;217(2):365-75.[6696735 ]
  11. Redjems-Bennani N, Jeandel C, Lefebvre E, Blain H, Vidailhet M, Gueant JL: Abnormal substrate levels that depend upon mitochondrial function in cerebrospinal fluid from Alzheimer patients. Gerontology. 1998;44(5):300-4.[9693263 ]
  12. Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14.[15911239 ]
  13. Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24.[14992292 ]
  14. Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7.[6198473 ]
  15. Melis GC, Boelens PG, van der Sijp JR, Popovici T, De Bandt JP, Cynober L, van Leeuwen PA: The feeding route (enteral or parenteral) affects the plasma response of the dipetide Ala-Gln and the amino acids glutamine, citrulline and arginine, with the administration of Ala-Gln in preoperative patients. Br J Nutr. 2005 Jul;94(1):19-26.[16115328 ]
  16. Frayn KN, Khan K, Coppack SW, Elia M: Amino acid metabolism in human subcutaneous adipose tissue in vivo. Clin Sci (Lond). 1991 May;80(5):471-4.[1851687 ]
  17. Rutten EP, Engelen MP, Wouters EF, Schols AM, Deutz NE: Metabolic effects of glutamine and glutamate ingestion in healthy subjects and in persons with chronic obstructive pulmonary disease. Am J Clin Nutr. 2006 Jan;83(1):115-23.[16400059 ]
  18. Szebenyi G, Morfini GA, Babcock A, Gould M, Selkoe K, Stenoien DL, Young M, Faber PW, MacDonald ME, McPhaul MJ, Brady ST: Neuropathogenic forms of huntingtin and androgen receptor inhibit fast axonal transport. Neuron. 2003 Sep 25;40(1):41-52.[14527432 ]
  19. Wada A, Yoshida R, Oda K, Fukuba E, Uchida N, Kitagaki H: Acute encephalopathy associated with intravenous immunoglobulin therapy. AJNR Am J Neuroradiol. 2005 Oct;26(9):2311-5.[16219838 ]
  20. Pennisi P, Gavrilova O, Setser-Portas J, Jou W, Santopietro S, Clemmons D, Yakar S, LeRoith D: Recombinant human insulin-like growth factor-I treatment inhibits gluconeogenesis in a transgenic mouse model of type 2 diabetes mellitus. Endocrinology. 2006 Jun;147(6):2619-30. Epub 2006 Mar 2.[16513827 ]
  21. Avila J, Barbaro B, Gangemi A, Romagnoli T, Kuechle J, Hansen M, Shapiro J, Testa G, Sankary H, Benedetti E, Lakey J, Oberholzer J: Intra-ductal glutamine administration reduces oxidative injury during human pancreatic islet isolation. Am J Transplant. 2005 Dec;5(12):2830-7.[16302995 ]
  22. Cooper AJ: Ammonia metabolism in normal and portacaval-shunted rats. Adv Exp Med Biol. 1990;272:23-46.[2103690 ]
  23. Choudry HA, Pan M, Karinch AM, Souba WW: Branched-chain amino acid-enriched nutritional support in surgical and cancer patients. J Nutr. 2006 Jan;136(1 Suppl):314S-8S.[16365105 ]
  24. Coeffier M, Miralles-Barrachina O, Le Pessot F, Lalaude O, Daveau M, Lavoinne A, Lerebours E, Dechelotte P: Influence of glutamine on cytokine production by human gut in vitro. Cytokine. 2001 Feb 7;13(3):148-54.[11161457 ]
  25. van der Hulst RR, von Meyenfeldt MF, Deutz NE, Soeters PB: Glutamine extraction by the gut is reduced in depleted [corrected] patients with gastrointestinal cancer. Ann Surg. 1997 Jan;225(1):112-21.[8998127 ]

From T3DB

Taxonomic Classification

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.

From ClassyFire

Targets

Target Details

Glutamine synthetase

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. Tan S, Evans R, Singh B: Herbicidal inhibitors of amino acid biosynthesis and herbicide-tolerant crops. Amino Acids. 2006 Mar;30(2):195-204. Epub 2006 Mar 20. [16547651 ]
Target Details

CTP synthase 1

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. Fijolek A, Hofer A, Thelander L: Expression, purification, characterization, and in vivo targeting of trypanosome CTP synthetase for treatment of African sleeping sickness. J Biol Chem. 2007 Apr 20;282(16):11858-65. Epub 2007 Feb 28. [17331943 ]
Target Details

Amidophosphoribosyltransferase

General Function:
Metal ion binding
Gene Name:
PPAT
Uniprot ID:
Q06203
Molecular Weight:
57398.52 Da
References
  1. Jiang P, Mayo AE, Ninfa AJ: Escherichia coli glutamine synthetase adenylyltransferase (ATase, EC 2.7.7.49): kinetic characterization of regulation by PII, PII-UMP, glutamine, and alpha-ketoglutarate. Biochemistry. 2007 Apr 3;46(13):4133-46. Epub 2007 Mar 14. [17355125 ]

From T3DB