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Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:19:50 UTC |
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Update Date | 2020-06-04 21:57:34 UTC |
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BMDB ID | BMDB0000123 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Glycine |
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Description | Glycine, also known as Gly or aminoessigsaeure, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Glycine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Glycine exists in all living species, ranging from bacteria to humans. Glycine is a potentially toxic compound. Glycine has been found to be associated with several diseases known as crohn's disease, leukemia, phosphoserine aminotransferase deficiency, and hyperglycinemia, lactic acidosis, and seizures; also glycine has been linked to the inborn metabolic disorders including n-acetylglutamate synthetase deficiency. |
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Structure | |
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Synonyms | Value | Source |
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Aminoacetic acid | ChEBI | Aminoessigsaeure | ChEBI | Aminoethanoic acid | ChEBI | G | ChEBI | Gly | ChEBI | Glycin | ChEBI | Glycocoll | ChEBI | Glykokoll | ChEBI | Glyzin | ChEBI | H2N-CH2-COOH | ChEBI | Hgly | ChEBI | Leimzucker | ChEBI | Aminoacetate | Generator | Aminoethanoate | Generator | 2-Aminoacetate | HMDB | 2-Aminoacetic acid | HMDB | Aciport | HMDB | Amino-acetate | HMDB | Amino-acetic acid | HMDB | Glicoamin | HMDB | Glycolixir | HMDB | Glycosthene | HMDB | Gyn-hydralin | HMDB | Padil | HMDB | Glycine carbonate (1:1), monosodium salt | HMDB | Glycine carbonate (2:1), monopotassium salt | HMDB | Glycine sulfate (3:1) | HMDB | Glycine, monoammonium salt | HMDB | Glycine, monosodium salt | HMDB | Glycine, sodium hydrogen carbonate | HMDB | Monoammonium salt glycine | HMDB | Calcium salt glycine | HMDB | Glycine hydrochloride (2:1) | HMDB | Glycine phosphate (1:1) | HMDB | Glycine, monopotasssium salt | HMDB | Monopotasssium salt glycine | HMDB | Monosodium salt glycine | HMDB | Glycine carbonate (2:1), monolithium salt | HMDB | Glycine carbonate (2:1), monosodium salt | HMDB | Glycine hydrochloride | HMDB | Glycine, copper salt | HMDB | Hydrochloride, glycine | HMDB | Salt glycine, monoammonium | HMDB | Acid, aminoacetic | HMDB | Cobalt salt glycine | HMDB | Copper salt glycine | HMDB | Glycine phosphate | HMDB | Glycine, calcium salt | HMDB | Glycine, calcium salt (2:1) | HMDB | Glycine, cobalt salt | HMDB | Phosphate, glycine | HMDB | Salt glycine, monosodium | HMDB |
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Chemical Formula | C2H5NO2 |
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Average Molecular Weight | 75.0666 |
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Monoisotopic Molecular Weight | 75.032028409 |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 56-40-6 |
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SMILES | Not Available |
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InChI Identifier | InChI=1S/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5) |
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InChI Key | DHMQDGOQFOQNFH-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). |
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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 | Alpha amino acids |
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Alternative Parents | |
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Substituents | - Alpha-amino acid
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic nitrogen compound
- Organic oxide
- Hydrocarbon derivative
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Primary aliphatic amine
- Organic oxygen compound
- Carbonyl group
- Amine
- 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
- Lysosome
- Mitochondria
- Myelin sheath
- Peroxisome
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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 | 262.2 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 249.0 mg/mL | Not Available | LogP | -3.21 | HANSCH,C ET AL. (1995) |
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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
- Lysosome
- Mitochondria
- Myelin sheath
- Peroxisome
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Biospecimen Locations | - Bladder
- Blood
- Brain
- Colostrum
- Epidermis
- Fibroblasts
- Intestine
- Kidney
- Liver
- Longissimus Thoracis Muscle
- Mammary Gland
- Milk
- Muscle
- Neuron
- Pancreas
- Placenta
- Platelet
- Prostate Tissue
- Ruminal Fluid
- Semen
- Semimembranosus Muscle
- Spleen
- Testis
- Thyroid Gland
- Urine
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Pathways | |
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Normal Concentrations |
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Bladder | 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 and Quantified | 287 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 | 326.5 uM | Not Specified | Both | Normal | | details | Blood | Detected and Quantified | 162-185 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 513-760 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 398 +/- 65 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 405-428 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 | Brain | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Colostrum | 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 but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected and Quantified | 3201 +/- 499 nmol/g of tissue | 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 | 576 +/- 215 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 | 33 - 1100 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 163 - 855 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 33 - 1109 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 68 +/- 3 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 77 +/- 3 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 65 +/- 3 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 72 +/- 2 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 and Quantified | 9591.483 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 9591.483 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 9458.268 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 9458.268 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 9325.0527 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 9325.0527 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 9325.0527 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 342-570 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 368.34 +/- 26.45 uM | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 379.36 +/- 32.68 uM | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 402.07 +/- 29.8 uM | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 551.88 +/- 18.61 uM | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 1068-1336 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 | Platelet | 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 | 50-696 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 80-220 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 | 105 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 158 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 150 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 104 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected but not Quantified | Not Quantified | 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 | 974 +/- 315 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 119.75 +/- 24.37 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 129 +/- 17 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 130 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 165 +/- 55 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 177.6 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 168 +/- 70 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 189.8 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 113 +/- 27 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 119.8 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 113 +/- 27 uM | Not Specified | Not Specified | Normal | | details | Semen | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Semen | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Semimembranosus Muscle | Detected and Quantified | 538 +/- 147 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 | 930-1250 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Testis | Detected and Quantified | 1247 +/- 251 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Testis | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Thyroid Gland | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Urine | Detected but not Quantified | Not Quantified | 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 | Sub/clinical ketosis | | details | Blood | Detected and Quantified | 294 uM | Not Specified | Not Specified | Bovine spongiform encephalopathy positive | | details | Blood | Detected and Quantified | 321 uM | Not Specified | Not Specified | Bovine spongiform encephalopathy negative | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Hepatic lipidosis | | 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 | Colostrum | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Commercial Product/bacterial growth on ground beef | | details | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Commercial Product/bacterial growth on ground beef | | details | Ruminal Fluid | Detected and Quantified | 189.78 +/- 69.73 uM | Not Specified | Not Specified | Rumen acidosis | | details |
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External Links |
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HMDB ID | HMDB0000123 |
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DrugBank ID | DB00145 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB000484 |
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KNApSAcK ID | C00001361 |
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Chemspider ID | 730 |
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KEGG Compound ID | C00037 |
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BioCyc ID | GLY |
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BiGG ID | 33610 |
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Wikipedia Link | Glycine |
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METLIN ID | 20 |
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PubChem Compound | 750 |
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PDB ID | Not Available |
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ChEBI ID | 15428 |
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References |
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Synthesis Reference | Anslow, Winston K.; King, Harold. Synthesis of glycine. Journal of the Chemical Society (1929), 2163-6. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
- Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. [PubMed:22098372 ]
- 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.
- Fooddata+, The Technical University of Denmark (DTU) [Link]
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