Human Metabolome Database Version 3.5

Showing metabocard for L-Glutamine (HMDB00641)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:00 -0700
HMDB ID HMDB00641
Secondary Accession Numbers None
Metabolite Identification
Common Name L-Glutamine
Description 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. (http://en.wikipedia.org/wiki/glutamine).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (2S)-2,5-diamino-5-oxopentanoate
  2. (2S)-2,5-diamino-5-oxopentanoic acid
  3. (2S)-2-amino-4-carbamoylbutanoate
  4. (2S)-2-amino-4-carbamoylbutanoic acid
  5. (S)-2,5-Diamino-5-oxopentanoate
  6. (S)-2,5-Diamino-5-oxopentanoic acid
  7. 2-Aminoglutaramic acid
  8. Cebrogen
  9. gamma-Glutamine
  10. Glavamin
  11. Glumin
  12. Glutamic acid 5-amide
  13. Glutamic acid amide
  14. Glutamine
  15. L-(+)-Glutamine
  16. L-2-Aminoglutaramic acid
  17. L-2-Aminoglutaramidic acid
  18. L-Glutamic acid 5-amide
  19. L-Glutamic acid gamma-amide
  20. L-Glutamid
  21. L-Glutamide
  22. L-Glutamin
  23. L-Glutamine
  24. L-Glutaminsaeure-5-amid
  25. Levoglutamid
  26. Levoglutamida
  27. Levoglutamide
  28. Levoglutamidum
  29. Levoglutamina
  30. Polyglutamine
  31. Stimulina
Chemical Formula C5H10N2O3
Average Molecular Weight 146.1445
Monoisotopic Molecular Weight 146.069142196
IUPAC Name (2S)-2-amino-4-carbamoylbutanoic acid
Traditional IUPAC Name L-glutamine
CAS Registry Number 56-85-9
SMILES N[C@@H](CCC(N)=O)C(O)=O
InChI Identifier 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
InChI Key ZDXPYRJPNDTMRX-VKHMYHEASA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • alpha-amino acid(ChEBI)
Substituents
  • Carboxamide Group
  • Carboxylic Acid
  • Primary Aliphatic Amine (Alkylamine)
  • Primary Carboxylic Acid Amide
Direct Parent Alpha Amino Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Alanine and aspartate metabolism
  • Component of Aminoacyl-tRNA biosynthesis
  • Component of Aminosugars metabolism
  • Component of D-Glutamine and D-glutamate metabolism
  • Component of Glutamate metabolism
  • Component of Nitrogen metabolism
  • Component of Peptidoglycan biosynthesis
  • Component of Purine metabolism
  • Energy source
  • Essential amino acid
  • Non-essential amino acid
  • RNA component
Application Not Available
Cellular locations
  • Extracellular
  • Mitochondria
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 185 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 41.3 mg/mL YALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP -3.64 CHMELIK,J ET AL. (1991)
Predicted Properties
Property Value Source
Water Solubility 97.8 g/L ALOGPS
LogP -3.32 ALOGPS
LogP -4 ChemAxon
LogS -0.17 ALOGPS
pKa (strongest acidic) 2.15 ChemAxon
pKa (strongest basic) 9.31 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 106.41 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 33.11 ChemAxon
Polarizability 13.85 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Gas-MS Spectrum
13C NMR Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Muscle
  • Skeletal Muscle
  • Fibroblasts
  • Intestine
  • Neuron
  • Pancreas
  • Placenta
  • Testes
  • Kidney
  • Myelin
  • Prostate
  • Adipose Tissue
  • Gut
  • Spleen
  • Stratum Corneum
Pathways
Name SMPDB Link KEGG Link
Pyrimidine Metabolism SMP00046 map00240 Link_out
Glutamate Metabolism SMP00072 map00250 Link_out
Transcription/Translation SMP00019 Not Available
Purine Metabolism SMP00050 map00230 Link_out
Urea Cycle SMP00059 map00330 Link_out
Phenylacetate Metabolism SMP00126 map00360 Link_out
Ammonia Recycling SMP00009 map00910 Link_out
Amino Sugar Metabolism SMP00045 map00520 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
492.6 +/- 93.6 uM Adult (>18 years old) Not Specified Normal
Blood Detected and Quantified
542.5 (376.0-709.0) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
490.6 +/- 84.3 uM Adult (>18 years old) Male Normal
Blood Detected and Quantified
591.0 +/- 66.0 uM Children (1-13 year old) Female Normal
  • Geigy Scient...
Blood Detected and Quantified
645.0 +/- 64.0 uM Adult (>18 years old) Male Normal
  • Geigy Scient...
Blood Detected and Quantified
578.0 +/- 85.0 uM Adult (>18 years old) Female Normal
  • Geigy Scient...
Blood Detected and Quantified
905.0 +/- 250.0 uM Newborn (0-30 days old) Not Specified Normal
  • Geigy Scient...
Blood Detected and Quantified
600.0 +/- 70.0 uM Children (1-13 year old) Male Normal
  • Geigy Scient...
Blood Detected and Quantified
586.0 (502.0-670.0) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
510.4 +/- 118.2 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
432 +/- 204 uM Not Specified Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
570.0 +/- 240.0 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
623.6 +/- 71.6 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
518.0 +/- 81.0 uM Adult (>18 years old) Male Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
425.0 +/- 70.5 uM Adult (>18 years old) Female Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
444.0 +/- 84.0 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
363.3 +/- 97.6 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
627.0 (482.0-772.0) uM Adult (>18 years old) Both Normal
Saliva Detected and Quantified
>10 uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
36.8 (14.5-59.2) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.0024 - 0.0148 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
33.98 umol/mmol creatinine Adult (>18 years old) Male Normal
  • Shaykhutdino...
Urine Detected and Quantified
118.96 +/- 89.94 umol/mmol creatinine Infant (0-1 year old) Both Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Comment Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Male Comment Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Male Comment Normal
Urine Detected and Quantified
33.32 +/- 10.78 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
39.9 (18.4-72.5) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
37.2 (19.1-77.9) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
20.0 (9.0-33.0) umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 376.8 +/- 114.3 uM Adult (>18 years old) Not Specified Heart Transplant
Blood Detected and Quantified 650.0 +/- 98.0 uM Adult (>18 years old) Male Schizophrenia
Blood Detected and Quantified 673.0 +/- 96.0 uM Adult (>18 years old) Female Schizophrenia
Blood Detected and Quantified 900.0 (700.0-1100.0) uM Children (1-13 year old) Both Carbamoyl Phosphate Synthetase Deficiency
Blood Detected and Quantified 228.34 +/- 12.00 uM Elderly (>65 years old) Both Alzheimer's disease
Blood Detected and Quantified 476.0 (455.0-498.0) uM Adult (>18 years old) Both Comment Epilepsy
Blood Detected and Quantified 495.0 (477.0-513.0) uM Children (1-13 year old) Both Comment Epilepsy
Blood Detected and Quantified 611.0 (591.0-630.0) uM Adult (>18 years old) Both Comment Epilepsy
Cerebrospinal Fluid (CSF) Detected and Quantified 1875.3 +/- 285.8 uM Children (1-13 year old) Not Specified Comment Leukemia
Cerebrospinal Fluid (CSF) Detected and Quantified 1061.0 +/- 230.2 uM Children (1-13 year old) Not Specified Leukemia
Cerebrospinal Fluid (CSF) Detected and Quantified 902 uM Not Specified Not Specified propionic acidemia
Cerebrospinal Fluid (CSF) Detected and Quantified 1146.6 +/- 10.6 uM Adult (>18 years old) Both Alzheimer's disease
Cerebrospinal Fluid (CSF) Detected and Quantified 254.0 (152.0-356.0) uM Adult (>18 years old) Both Alzheimer's disease
Urine Detected and Quantified 0.0029 - 0.0048 umol/mmol creatinine Adult (>18 years old) Both ADPKD
Urine Detected and Quantified 1.17 +/- 0.49 umol/mmol creatinine Adult (>18 years old) Both Alzheimer's disease
Urine Detected and Quantified 31.4 +/- 2.3 umol/mmol creatinine Adult (>18 years old) Both 3-Hydroxy-3- methylglutaryl-CoA lyase (HL) deficency
Urine Detected and Quantified 37.5 +/- 0.6 umol/mmol creatinine Adult (>18 years old) Both Propionic acidemia
Urine Detected and Quantified 52.8 +/- 26.3 umol/mmol creatinine Adult (>18 years old) Both Maple syrup urine disease
Urine Detected and Quantified 319.9 +/- 47.1 umol/mmol creatinine Adult (>18 years old) Both Aminoaciduria
Associated Disorders and Diseases
Disease References
Epilepsy
  • 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. Pubmed: 14992292 Link_out
      Alzheimer's disease
      • 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. Pubmed: 9693263 Link_out
      • Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. Pubmed: 17031479 Link_out
          Leukemia
          • 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. Pubmed: 15911239 Link_out
              Schizophrenia
              • Alfredsson G, Wiesel FA: Monoamine metabolites and amino acids in serum from schizophrenic patients before and during sulpiride treatment. Psychopharmacology (Berl). 1989;99(3):322-7. Pubmed: 2480613 Link_out
                  Carbamoyl Phosphate Synthetase Deficiency
                      Associated OMIM IDs
                      DrugBank ID DB00130 Link_out
                      DrugBank Metabolite ID Not Available
                      Phenol Explorer Compound ID Not Available
                      Phenol Explorer Metabolite ID Not Available
                      FoodDB ID FDB012164
                      KNApSAcK ID C00001359 Link_out
                      Chemspider ID 5746 Link_out
                      KEGG Compound ID C00064 Link_out
                      BioCyc ID GLN Link_out
                      BiGG ID 33714 Link_out
                      Wikipedia Link L-Glutamine Link_out
                      NuGOwiki Link HMDB00641 Link_out
                      Metagene Link HMDB00641 Link_out
                      METLIN ID 5614 Link_out
                      PubChem Compound 5961 Link_out
                      PDB ID GLN Link_out
                      ChEBI ID 18050 Link_out
                      References
                      Synthesis Reference Jiao, Qingcai; Qian, Shaosong; Chen, Ran; Wu, Xiaoyan. Synthesis of L-glutamine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 7 pp.
                      Material Safety Data Sheet (MSDS) Download (PDF)
                      General References
                      1. 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. Pubmed: 14527432 Link_out
                      2. 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. Pubmed: 16219838 Link_out
                      3. 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. Pubmed: 16513827 Link_out
                      4. 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. Pubmed: 15911239 Link_out
                      5. Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. Pubmed: 12297216 Link_out
                      6. 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. Pubmed: 14992292 Link_out
                      7. 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. Pubmed: 15627241 Link_out
                      8. 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. Pubmed: 9693263 Link_out
                      9. 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. Pubmed: 16302995 Link_out
                      10. Cooper AJ: Ammonia metabolism in normal and portacaval-shunted rats. Adv Exp Med Biol. 1990;272:23-46. Pubmed: 2103690 Link_out
                      11. 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. Pubmed: 16115328 Link_out
                      12. 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. Pubmed: 16365105 Link_out
                      13. 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. Pubmed: 1931558 Link_out
                      14. 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. Pubmed: 1851687 Link_out
                      15. 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. Pubmed: 12097436 Link_out
                      16. 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. Pubmed: 11161457 Link_out
                      17. 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. Pubmed: 6696735 Link_out
                      18. 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. Pubmed: 16400059 Link_out
                      19. 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. Pubmed: 8998127 Link_out
                      20. 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. Pubmed: 6198473 Link_out
                      21. 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. Pubmed: 19212411 Link_out
                      22. 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. Pubmed: 1903318 Link_out
                      23. 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. Pubmed: 9488531 Link_out
                      24. 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. Pubmed: 10483898 Link_out
                      25. 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. Pubmed: 11408280 Link_out

                      Enzymes
                      Name: Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 2
                      Reactions:
                      L-Glutamine + Fructose 6-phosphate unknown L-Glutamic acid + Glucosamine 6-phosphate details
                      Gene Name: GFPT2
                      Uniprot ID: O94808 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 1
                      Reactions:
                      L-Glutamine + Fructose 6-phosphate unknown L-Glutamic acid + Glucosamine 6-phosphate details
                      Gene Name: GFPT1
                      Uniprot ID: Q06210 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Amidophosphoribosyltransferase
                      Reactions:
                      5-Phosphoribosylamine + Pyrophosphate + L-Glutamic acid unknown L-Glutamine + Phosphoribosyl pyrophosphate + Water details
                      Gene Name: PPAT
                      Uniprot ID: Q06203 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Kynurenine--oxoglutarate transaminase 1
                      Reactions:
                      L-Glutamine + Phenylpyruvic acid unknown 2-Keto-glutaramic acid + L-Phenylalanine details
                      Gene Name: CCBL1
                      Uniprot ID: Q16773 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Glutamine--tRNA ligase
                      Reactions:
                      Adenosine triphosphate + L-Glutamine + tRNA(Gln) unknown Adenosine monophosphate + Pyrophosphate + L-glutaminyl-tRNA(Gln) details
                      Adenosine triphosphate + L-Glutamine + tRNA(Gln) unknown Adenosine monophosphate + Pyrophosphate + Glutaminyl-tRNA details
                      Gene Name: QARS
                      Uniprot ID: P47897 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Asparagine synthetase [glutamine-hydrolyzing]
                      Reactions:
                      Adenosine triphosphate + L-Aspartic acid + L-Glutamine + Water unknown Adenosine monophosphate + Pyrophosphate + L-Asparagine + L-Glutamic acid details
                      Gene Name: ASNS
                      Uniprot ID: P08243 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: GMP synthase [glutamine-hydrolyzing]
                      Reactions:
                      Adenosine triphosphate + Xanthylic acid + L-Glutamine + Water unknown Adenosine monophosphate + Pyrophosphate + Guanosine monophosphate + L-Glutamic acid details
                      6-Thioxanthine 5'-monophosphate + Adenosine triphosphate + L-Glutamine + Water unknown 6-Thioguanosine monophosphate + Adenosine monophosphate + Pyrophosphate + L-Glutamic acid details
                      Gene Name: GMPS
                      Uniprot ID: P49915 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Protein-glutamine gamma-glutamyltransferase E
                      Reactions: Not Available
                      Gene Name: TGM3
                      Uniprot ID: Q08188 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Protein-glutamine gamma-glutamyltransferase 2
                      Reactions: Not Available
                      Gene Name: TGM2
                      Uniprot ID: P21980 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Glutamine synthetase
                      Reactions:
                      Adenosine triphosphate + L-Glutamic acid + Ammonia unknown ADP + Phosphoric acid + L-Glutamine details
                      Gene Name: GLUL
                      Uniprot ID: P15104 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Coagulation factor XIII A chain
                      Reactions: Not Available
                      Gene Name: F13A1
                      Uniprot ID: P00488 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Glutaminase liver isoform, mitochondrial
                      Reactions:
                      L-Glutamine + Water unknown L-Glutamic acid + Ammonia details
                      Gene Name: GLS2
                      Uniprot ID: Q9UI32 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: CTP synthase 1
                      Reactions:
                      Adenosine triphosphate + Uridine triphosphate + L-Glutamine + Water unknown ADP + Phosphoric acid + Cytidine triphosphate + L-Glutamic acid details
                      Gene Name: CTPS1
                      Uniprot ID: P17812 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Protein-glutamine gamma-glutamyltransferase 5
                      Reactions: Not Available
                      Gene Name: TGM5
                      Uniprot ID: O43548 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Glutaminase kidney isoform, mitochondrial
                      Reactions:
                      L-Glutamine + Water unknown L-Glutamic acid + Ammonia details
                      Gene Name: GLS
                      Uniprot ID: O94925 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Protein-glutamine gamma-glutamyltransferase 4
                      Reactions: Not Available
                      Gene Name: TGM4
                      Uniprot ID: P49221 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Protein-glutamine gamma-glutamyltransferase K
                      Reactions: Not Available
                      Gene Name: TGM1
                      Uniprot ID: P22735 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Protein-glutamine gamma-glutamyltransferase 6
                      Reactions: Not Available
                      Gene Name: TGM6
                      Uniprot ID: O95932 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Protein-glutamine gamma-glutamyltransferase Z
                      Reactions: Not Available
                      Gene Name: TGM7
                      Uniprot ID: Q96PF1 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Phosphoribosylformylglycinamidine synthase
                      Reactions:
                      Adenosine triphosphate + N(2)-formyl-N(1)-(5-phospho-D-ribosyl)glycinamide + L-Glutamine + Water unknown ADP + Phosphoric acid + 2-(formamido)-N(1)-(5-phospho-D-ribosyl)acetamidine + L-Glutamic acid details
                      Adenosine triphosphate + 5'-Phosphoribosyl-N-formylglycinamide + L-Glutamine + Water unknown ADP + Phosphoric acid + Phosphoribosylformylglycineamidine + L-Glutamic acid details
                      Gene Name: PFAS
                      Uniprot ID: O15067 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Glutamyl-tRNA(Gln) amidotransferase subunit B, mitochondrial
                      Reactions:
                      Adenosine triphosphate + L-glutamyl-tRNA(Gln) + L-Glutamine unknown ADP + Phosphoric acid + L-glutaminyl-tRNA(Gln) + L-Glutamic acid details
                      Gene Name: PET112
                      Uniprot ID: O75879 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Glutamine-dependent NAD(+) synthetase
                      Reactions:
                      Adenosine triphosphate + Nicotinic acid adenine dinucleotide + L-Glutamine + Water unknown Adenosine monophosphate + Pyrophosphate + NAD + L-Glutamic acid details
                      Gene Name: NADSYN1
                      Uniprot ID: Q6IA69 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: CAD protein
                      Reactions:
                      Adenosine triphosphate + L-Glutamine + Carbonic acid + Water unknown ADP + Phosphoric acid + L-Glutamic acid + Carbamoyl phosphate details
                      Gene Name: CAD
                      Uniprot ID: P27708 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: CTP synthase 2
                      Reactions:
                      Adenosine triphosphate + Uridine triphosphate + L-Glutamine + Water unknown ADP + Phosphoric acid + Cytidine triphosphate + L-Glutamic acid details
                      Gene Name: CTPS2
                      Uniprot ID: Q9NRF8 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Glycine N-acyltransferase-like protein 1
                      Reactions:
                      Acyl-CoA + L-Glutamine unknown Coenzyme A + N-acyl-L-glutamine details
                      Gene Name: GLYATL1
                      Uniprot ID: Q969I3 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Glutamine synthetase
                      Reactions: Not Available
                      Gene Name: PIG59
                      Uniprot ID: A8YXX4 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Glutamyl-tRNA(Gln) amidotransferase subunit A, mitochondrial
                      Reactions:
                      Adenosine triphosphate + L-glutamyl-tRNA(Gln) + L-Glutamine unknown ADP + Phosphoric acid + L-glutaminyl-tRNA(Gln) + L-Glutamic acid details
                      Gene Name: QRSL1
                      Uniprot ID: Q9H0R6 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Glutamyl-tRNA(Gln) amidotransferase subunit C, mitochondrial
                      Reactions:
                      Adenosine triphosphate + L-glutamyl-tRNA(Gln) + L-Glutamine unknown ADP + Phosphoric acid + L-glutaminyl-tRNA(Gln) + L-Glutamic acid details
                      Gene Name: GATC
                      Uniprot ID: O43716 Link_out
                      Protein Sequence: FASTA
                      Transporters
                      Name: Neutral amino acid transporter B(0)
                      Reactions: Not Available
                      Gene Name: SLC1A5
                      Uniprot ID: Q15758 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Large neutral amino acids transporter small subunit 2
                      Reactions: Not Available
                      Gene Name: SLC7A8
                      Uniprot ID: Q9UHI5 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Sodium-coupled neutral amino acid transporter 3
                      Reactions: Not Available
                      Gene Name: SLC38A3
                      Uniprot ID: Q99624 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Monocarboxylate transporter 10
                      Reactions: Not Available
                      Gene Name: SLC16A10
                      Uniprot ID: Q8TF71 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA