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Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:20:22 UTC |
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Update Date | 2020-06-04 22:35:59 UTC |
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BMDB ID | BMDB0000162 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | L-Proline |
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Description | L-Proline, also known as L-prolin, belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Proline exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Proline exists in all living species, ranging from bacteria to humans. L-Proline is a potentially toxic compound. L-Proline has been found to be associated with several diseases known as rheumatoid arthritis, perillyl alcohol administration for cancer treatment, colorectal cancer, and pregnancy; also l-proline has been linked to the inborn metabolic disorders including iminoglycinuria. |
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Structure | |
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Synonyms | Value | Source |
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(-)-(S)-Proline | ChEBI | (-)-2-Pyrrolidinecarboxylic acid | ChEBI | (-)-Proline | ChEBI | (2S)-Pyrrolidine-2-carboxylic acid | ChEBI | (S)-2-Carboxypyrrolidine | ChEBI | (S)-2-Pyrrolidinecarboxylic acid | ChEBI | (S)-Pyrrolidine-2-carboxylic acid | ChEBI | 2-Pyrrolidinecarboxylic acid | ChEBI | L-(-)-Proline | ChEBI | L-alpha-Pyrrolidinecarboxylic acid | ChEBI | L-Prolin | ChEBI | L-Pyrrolidine-2-carboxylic acid | ChEBI | P | ChEBI | Prolina | ChEBI | PROLINE | ChEBI | Prolinum | ChEBI | (-)-2-Pyrrolidinecarboxylate | Generator | (2S)-Pyrrolidine-2-carboxylate | Generator | (S)-2-Pyrrolidinecarboxylate | Generator | (S)-Pyrrolidine-2-carboxylate | Generator | 2-Pyrrolidinecarboxylate | Generator | L-a-Pyrrolidinecarboxylate | Generator | L-a-Pyrrolidinecarboxylic acid | Generator | L-alpha-Pyrrolidinecarboxylate | Generator | L-Α-pyrrolidinecarboxylate | Generator | L-Α-pyrrolidinecarboxylic acid | Generator | L-Pyrrolidine-2-carboxylate | Generator | (S)-(-)-Proline | HMDB | (S)-(-)-Pyrrolidine-2-carboxylate | HMDB | (S)-(-)-Pyrrolidine-2-carboxylic acid | HMDB | (S)-2-Pyrralidinecarboxylate | HMDB | (S)-2-Pyrralidinecarboxylic acid | HMDB | (S)-Proline | HMDB | L Proline | HMDB |
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Chemical Formula | C5H9NO2 |
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Average Molecular Weight | 115.1305 |
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Monoisotopic Molecular Weight | 115.063328537 |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 147-85-3 |
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SMILES | Not Available |
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InChI Identifier | InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1 |
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InChI Key | ONIBWKKTOPOVIA-BYPYZUCNSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
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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 | Proline and derivatives |
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Alternative Parents | |
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Substituents | - Proline or derivatives
- Alpha-amino acid
- L-alpha-amino acid
- Pyrrolidine carboxylic acid
- Pyrrolidine carboxylic acid or derivatives
- Pyrrolidine
- Amino acid
- Carboxylic acid
- Secondary aliphatic amine
- Monocarboxylic acid or derivatives
- Secondary amine
- Organoheterocyclic compound
- Azacycle
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Amine
- Organopnictogen compound
- Organic oxide
- Carbonyl group
- Organic nitrogen compound
- Hydrocarbon derivative
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic 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
- Endoplasmic reticulum
- Lysosome
- Mitochondria
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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 | 221 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 162.0 mg/mL | Not Available | LogP | -2.54 | 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
- Endoplasmic reticulum
- Lysosome
- Mitochondria
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Biospecimen Locations | - All Tissues
- Blood
- Colostrum
- Liver
- Longissimus Thoracis Muscle
- Mammary Gland
- Milk
- Muscle
- Placenta
- Prostate Tissue
- Ruminal Fluid
- Semen
- Semimembranosus Muscle
- Testis
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Pathways | |
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Normal Concentrations |
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All Tissues | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 45.7 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 but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 84-110 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 45-68 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 103 +/- 15 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 72-78 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 | 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 | 352 +/- 67 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 | 174 +/- 59 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 | 25 +/- 1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 30 +/- 1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 27 +/- 3 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 82.350 +/- 29.96 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 27 +/- 5 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 11 - 47 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 29531.705 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 29531.705 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 29531.705 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 29531.705 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 28663.126 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 28663.126 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 28663.126 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 27 +/- 2 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 30 +/- 2 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 29 +/- 2 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 30 +/- 1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 19.2 +/- 5.6 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 29.0 +/- 9.5 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 55.55 +/- 12.68 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 60.57 +/- 15.15 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 and Quantified | 5950 +/- 1890 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 6670 +/- 2850 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 5120 +/- 1460 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 5590 +/- 1450 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 240-365 nmol/g of tissue | 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 | 158 +/- 33 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 220 +/- 31 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 173 +/- 29 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 159.6 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 158 +/- 24 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 220.4 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 158 +/- 24 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 173.2 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 154.6 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 240-1275 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 50-174 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 117 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 165 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 141 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 130 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 and Quantified | 834 +/- 377 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 154.56 +/- 24.18 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 | 203 +/- 60 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Testis | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Testis | Detected and Quantified | 191 +/- 40 nmol/g of tissue | Not Specified | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 48.9 uM | Not Specified | Not Specified | Bovine spongiform encephalopathy negative | | details | Blood | Detected and Quantified | 55.3 uM | Not Specified | Not Specified | Bovine spongiform encephalopathy positive | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Sub/clinical ketosis | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Heat stress | | 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 | 173.23 +/- 28.4 uM | Not Specified | Not Specified | Rumen acidosis | | details |
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External Links |
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HMDB ID | HMDB0000162 |
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DrugBank ID | DB00172 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB000570 |
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KNApSAcK ID | C00001388 |
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Chemspider ID | 128566 |
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KEGG Compound ID | C00148 |
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BioCyc ID | PRO |
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BiGG ID | 34042 |
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Wikipedia Link | L-proline |
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METLIN ID | 29 |
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PubChem Compound | 145742 |
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PDB ID | Not Available |
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ChEBI ID | 17203 |
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References |
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Synthesis Reference | Itoh, Tamio. Synthesis of L-proline from L-glutamine. Bulletin of the Chemical Society of Japan (1963), 36(1), 25-9 |
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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 ]
- 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 ]
- O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
- Klein MS, Almstetter MF, Nurnberger N, Sigl G, Gronwald W, Wiedemann S, Dettmer K, Oefner PJ: Correlations between milk and plasma levels of amino and carboxylic acids in dairy cows. J Proteome Res. 2013 Nov 1;12(11):5223-32. doi: 10.1021/pr4006537. Epub 2013 Aug 23. [PubMed:23931703 ]
- 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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