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Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:34:08 UTC |
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Update Date | 2020-06-04 21:03:49 UTC |
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BMDB ID | BMDB0000641 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | L-Glutamine |
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Description | L-Glutamine, also known as levoglutamide or Q, 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. L-Glutamine is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. It is used to reduce the acute complications of sickle cell disease in adult and pediatric patients 5 years of age and older [fda label]. L-Glutamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Glutamine exists in all living species, ranging from bacteria to humans. L-Glutamine can be converted into phenylacetylglutamine; which is mediated by the enzyme glycine N-acyltransferase. In cattle, L-glutamine is involved in the metabolic pathway called the phenylacetate metabolism pathway. L-Glutamine is a potentially toxic compound. |
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Structure | |
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Synonyms | Value | Source |
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(2S)-2,5-Diamino-5-oxopentanoic acid | ChEBI | (2S)-2-Amino-4-carbamoylbutanoic acid | ChEBI | (S)-2,5-Diamino-5-oxopentanoic acid | ChEBI | Glutamic acid 5-amide | ChEBI | Glutamic acid amide | ChEBI | GLUTAMINE | ChEBI | L-(+)-Glutamine | ChEBI | L-2-Aminoglutaramic acid | ChEBI | L-Glutamic acid gamma-amide | ChEBI | L-Glutamin | ChEBI | L-Glutaminsaeure-5-amid | ChEBI | Levoglutamide | ChEBI | Q | ChEBI | Endari | Kegg | Nutrestore | Kegg | (2S)-2,5-Diamino-5-oxopentanoate | Generator | (2S)-2-Amino-4-carbamoylbutanoate | Generator | (S)-2,5-Diamino-5-oxopentanoate | Generator | Glutamate 5-amide | Generator | Glutamate amide | Generator | L-2-Aminoglutaramate | Generator | L-Glutamate g-amide | Generator | L-Glutamate gamma-amide | Generator | L-Glutamate γ-amide | Generator | L-Glutamic acid g-amide | Generator | L-Glutamic acid γ-amide | Generator | 2-Aminoglutaramic acid | HMDB | Cebrogen | HMDB | gamma-Glutamine | HMDB | Glavamin | HMDB | Glumin | HMDB | L-2-Aminoglutaramidic acid | HMDB | L-Glutamic acid 5-amide | HMDB | L-Glutamid | HMDB | L-Glutamide | HMDB | Levoglutamid | HMDB | Levoglutamida | HMDB | Levoglutamidum | HMDB | Levoglutamina | HMDB | Polyglutamine | HMDB | Stimulina | HMDB | D-Glutamine | HMDB | D Glutamine | HMDB | L Glutamine | HMDB |
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Chemical Formula | C5H10N2O3 |
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Average Molecular Weight | 146.1445 |
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Monoisotopic Molecular Weight | 146.069142196 |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 56-85-9 |
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SMILES | Not Available |
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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 |
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InChI Key | ZDXPYRJPNDTMRX-VKHMYHEASA-N |
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Chemical Taxonomy |
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Description | 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. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | L-alpha-amino acids |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Status | Detected and Quantified |
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Origin | |
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Biofunction | Not Available |
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Application | Not Available |
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Cellular locations | - Cytoplasm
- Mitochondria
- Myelin sheath
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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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) |
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Predicted Properties | Not Available |
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Spectra |
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Spectra | |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Mitochondria
- Myelin sheath
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Biospecimen Locations | - Adipose Tissue
- Blood
- Colostrum
- Epidermis
- Fibroblasts
- Intestine
- Kidney
- Liver
- Longissimus Thoracis Muscle
- Mammary Gland
- Milk
- Muscle
- Neuron
- Pancreas
- Placenta
- Prostate Tissue
- Ruminal Fluid
- Semimembranosus Muscle
- Spleen
- Testis
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Pathways | |
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Normal Concentrations |
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Adipose Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 95-126 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 35.2 uM | Not Specified | Both | Normal | | details | Blood | Detected and Quantified | 330 +/- 42 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 246-260 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Colostrum | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Epidermis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Fibroblasts | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Intestine | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Kidney | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected and Quantified | 1433 +/- 231 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Liver | Detected and Quantified | 1911-2576 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Longissimus Thoracis Muscle | Detected and Quantified | 2841 +/- 828 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 17.0 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 20 +/- 2 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 10.0 +/- 0.3 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 17 +/- 1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 1148.18 +/- 201.58 uM | Not Specified | Not Specified | Normal | | details | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 1508.29 +/- 185.39 uM | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 1582.02 +/- 237.99 uM | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 412-1820 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 9330 +/- 960 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 6470 +/- 1360 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 6060 +/- 680 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 6180 +/- 650 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 476.93 +/- 64.67 uM | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 910 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 277-443 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 3051-4834 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Neuron | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Pancreas | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 830.5 +/- 251.38 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 945.3 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 993.6 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 907.6 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 830.5 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 946 +/- 239 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 994 +/- 358 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 907 +/- 255 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 831 +/- 252 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 831 +/- 251 uM | Not Specified | Not Specified | Normal | | details | Semimembranosus Muscle | Detected and Quantified | 2492 +/- 668 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Spleen | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Testis | Detected and Quantified | 1517 +/- 338 nmol/g of tissue | Not Specified | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Treated with growth-promoting hormones | | details | Blood | Detected and Quantified | 1342 +/- 416 uM | Not Specified | Not Specified | Right displaced abomasum (RDA) | | details | Blood | Detected and Quantified | 2978 +/- 411 uM | Not Specified | Not Specified | Left displaced abomasum (LDA) | | details | Blood | Detected and Quantified | 2050 +/- 692 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | All Mycobacterium avium subsp. paratuberculosis-infected | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | High dose Mycobacterium avium subsp. paratuberculosis-infected | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Low dose Mycobacterium avium subsp. paratuberculosis-infected | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Hepatic lipidosis | | details | Colostrum | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Fed pasture vs barley-based concentrate | | details | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Fed pasture vs barley-based concentrate | | details | Ruminal Fluid | Detected and Quantified | 907.56 +/- 247.09 uM | Not Specified | Not Specified | Rumen acidosis | | details |
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External Links |
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HMDB ID | HMDB0000641 |
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DrugBank ID | DB00130 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB030965 |
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KNApSAcK ID | C00001359 |
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Chemspider ID | 5746 |
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KEGG Compound ID | C00064 |
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BioCyc ID | GLN |
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BiGG ID | 33714 |
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Wikipedia Link | Glutamine |
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METLIN ID | 5614 |
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PubChem Compound | 5961 |
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PDB ID | Not Available |
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ChEBI ID | 18050 |
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References |
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Synthesis Reference | Jiao, Qingcai; Qian, Shaosong; Chen, Ran; Wu, Xiaoyan. Synthesis of L-glutamine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 7 pp. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6. [PubMed:25108860 ]
- Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
- Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
- Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
- A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
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