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Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:26:31 UTC |
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Update Date | 2020-06-04 22:23:45 UTC |
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BMDB ID | BMDB0000191 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | L-Aspartic acid |
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Description | L-Aspartic acid, also known as Asp or D, belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Aspartic acid exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Aspartic acid exists in all living species, ranging from bacteria to humans. L-Aspartic acid has been found to be associated with several diseases known as frontotemporal dementia, pancreatic cancer, cirrhosis, and perillyl alcohol administration for cancer treatment; also l-aspartic acid has been linked to the inborn metabolic disorders including growth hormone deficiency. |
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Structure | |
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Synonyms | Value | Source |
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(S)-2-Aminobutanedioic acid | ChEBI | (S)-2-Aminosuccinic acid | ChEBI | 2-Aminosuccinic acid | ChEBI | Asp | ChEBI | ASPARTIC ACID | ChEBI | D | ChEBI | L-Asparaginsaeure | ChEBI | L-Asp | Kegg | (S)-2-Aminobutanedioate | Generator | (S)-2-Aminosuccinate | Generator | 2-Aminosuccinate | Generator | ASPARTate | Generator | L-Aspartate | Generator | (+)-Aspartate | HMDB | (+)-Aspartic acid | HMDB | (2S)-Aspartate | HMDB | (2S)-Aspartic acid | HMDB | (L)-Aspartate | HMDB | (L)-Aspartic acid | HMDB | (R)-2-Aminosuccinate | HMDB | (S)-(+)-Aspartate | HMDB | (S)-(+)-Aspartic acid | HMDB | (S)-Amino-butanedioate | HMDB | (S)-Amino-butanedioic acid | HMDB | (S)-Aminobutanedioate | HMDB | (S)-Aminobutanedioic acid | HMDB | (S)-Aspartate | HMDB | (S)-Aspartic acid | HMDB | 2-Amino-3-methylsuccinate | HMDB | 2-Amino-3-methylsuccinic acid | HMDB | alpha-Aminosuccinate | HMDB | alpha-Aminosuccinic acid | HMDB | Aminosuccinate | HMDB | Asparagate | HMDB | Asparagic acid | HMDB | Asparaginate | HMDB | Asparaginic acid | HMDB | Asparatate | HMDB | H-Asp-OH | HMDB | L-(+)-Aspartate | HMDB | L-(+)-Aspartic acid | HMDB | L-Aminosuccinate | HMDB | L-Aminosuccinic acid | HMDB | L-Asparagate | HMDB | L-Asparagic acid | HMDB | L-Asparaginate | HMDB | L-Asparaginic acid | HMDB | (+-)-Aspartic acid | HMDB | (R,S)-Aspartic acid | HMDB | Aspartate, disodium | HMDB | Aspartate, magnesium | HMDB | Aspartate, monopotassium | HMDB | Aspartic acid, dipotassium salt | HMDB | Aspartic acid, hydrobromide | HMDB | Aspartic acid, monopotassium salt | HMDB | Aspartic acid, monosodium salt | HMDB | Aspartic acid, potassium salt | HMDB | L Aspartate | HMDB | MG5Longoral | HMDB | Potassium aspartate | HMDB | Polysuccinimide | HMDB | Ammonium aspartate | HMDB | Aspartate, ammonium | HMDB | Aspartate, calcium | HMDB | Aspartate, monosodium | HMDB | Aspartic acid, calcium salt | HMDB | Aspartic acid, disodium salt | HMDB | Aspartic acid, magnesium (1:1) salt, hydrochloride, trihydrate | HMDB | Dipotassium aspartate | HMDB | Disodium aspartate | HMDB | Hydrochloride, aspartate magnesium | HMDB | Monopotassium aspartate | HMDB | Sodium aspartate | HMDB | Aspartate, dipotassium | HMDB | Aspartic acid, magnesium (2:1) salt | HMDB | Aspartic acid, sodium salt | HMDB | Hydrobromide aspartic acid | HMDB | Magnesium aspartate | HMDB | MG 5 Longoral | HMDB | Monosodium aspartate | HMDB | Aspartate magnesium hydrochloride | HMDB | Aspartate, potassium | HMDB | Aspartate, sodium | HMDB | Aspartic acid, ammonium salt | HMDB | Aspartic acid, hydrochloride | HMDB | Aspartic acid, magnesium-potassium (2:1:2) salt | HMDB | Calcium aspartate | HMDB | Hydrochloride aspartic acid | HMDB | L Aspartic acid | HMDB | Magnesiocard | HMDB | MG-5-Longoral | HMDB | Poly-DL-succinimide | HMDB |
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Chemical Formula | C4H7NO4 |
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Average Molecular Weight | 133.1027 |
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Monoisotopic Molecular Weight | 133.037507717 |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 56-84-8 |
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SMILES | Not Available |
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InChI Identifier | InChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9)/t2-/m0/s1 |
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InChI Key | CKLJMWTZIZZHCS-REOHCLBHSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid 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 | Aspartic acid and derivatives |
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Alternative Parents | |
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Substituents | - Aspartic acid or derivatives
- Alpha-amino acid
- L-alpha-amino acid
- Dicarboxylic acid or derivatives
- Fatty acid
- Amino acid
- Carboxylic acid
- Organic oxide
- Organopnictogen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Organic oxygen compound
- Carbonyl group
- Amine
- Organic nitrogen compound
- Hydrocarbon derivative
- 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 | |
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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 | 270 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 5.39 mg/mL | YALKOWSKY,SH & DANNENFELSER,RM (1992) | LogP | -3.89 | 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 | |
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Biospecimen Locations | - All Tissues
- Blood
- Colostrum
- Liver
- Longissimus Thoracis Muscle
- 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 but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 14.5-16 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 31.9 uM | Not Specified | Both | Normal | | details | Blood | Detected and Quantified | 31-36 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 4.2-4.8 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 24 +/- 11 uM | 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 | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected and Quantified | 384 +/- 165 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Longissimus Thoracis Muscle | Detected and Quantified | 70 +/- 28 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 21787.687 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 21787.687 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 21787.687 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 21787.687 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 28.86 +/- 11.37 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 21036.388 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 21036.388 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 21036.388 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 10 - 77 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 19 +/- 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 | 20 +/- 1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 19 +/- 1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 19 +/- 3 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 21 +/- 2 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 19 +/- 3 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 21 +/- 3 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 | 28.63 +/- 13.11 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 20.35 +/- 7.08 uM | 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 | 26560 +/- 2480 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 26530 +/- 2600 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 24230 +/- 2800 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 25930 +/- 2200 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 14-54 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 | 153-925 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 | 122 +/- 35 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 185 +/- 50 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 180 +/- 69 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 115 +/- 47 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 115 +/- 47 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 68-228 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 164 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 201 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 | 123 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 | 157 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 | 132.7 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 196.4 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 179.6 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 126 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 124.71 +/- 40.5 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 566 +/- 204 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 | 57 +/- 28 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Testis | Detected and Quantified | 310-550 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 | 597 +/- 215 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 | 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 | Ruminal Fluid | Detected and Quantified | 192.08 +/- 65.33 uM | Not Specified | Not Specified | Rumen acidosis | | details |
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External Links |
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HMDB ID | HMDB0000191 |
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DrugBank ID | DB00128 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB012567 |
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KNApSAcK ID | C00001342 |
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Chemspider ID | 5745 |
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KEGG Compound ID | C00049 |
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BioCyc ID | L-ASPARTATE |
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BiGG ID | 33663 |
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Wikipedia Link | Aspartic acid |
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METLIN ID | 5206 |
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PubChem Compound | 5960 |
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PDB ID | Not Available |
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ChEBI ID | 17053 |
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References |
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Synthesis Reference | Pamfil, Maria; Lupescu, Irina; Savoiu, Valeria Gabriela. L-aspartic acid production from fumarate using Escherichia coli whole cells. Rom. (2005), 3pp. |
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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 ]
- Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
- 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 ]
- 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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