| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:20:19 UTC |
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| Update Date | 2020-06-04 21:55:45 UTC |
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| BMDB ID | BMDB0000158 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | L-Tyrosine |
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| Description | L-Tyrosine, also known as (S)-tyrosine or para tyrosine, belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Tyrosine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Tyrosine exists in all living species, ranging from bacteria to humans. L-Tyrosine participates in a number of enzymatic reactions, within cattle. In particular, L-Tyrosine and oxoglutaric acid can be converted into 4-hydroxyphenylpyruvic acid and L-glutamic acid; which is mediated by the enzyme tyrosine aminotransferase. In addition, L-Tyrosine can be converted into tyramine through its interaction with the enzyme aromatic-L-amino-acid decarboxylase. In cattle, L-tyrosine is involved in a couple of metabolic pathways, which include thyroid hormone synthesis pathway and the tyrosine metabolism pathway. L-Tyrosine is a potentially toxic compound. L-Tyrosine has been found to be associated with several diseases known as irritable bowel syndrome, frontotemporal dementia, obesity, and leukemia; also l-tyrosine has been linked to the inborn metabolic disorders including hypermethioninemia. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (-)-alpha-Amino-p-hydroxyhydrocinnamic acid | ChEBI | | (2S)-2-Amino-3-(4-hydroxyphenyl)propanoic acid | ChEBI | | (S)-(-)-Tyrosine | ChEBI | | (S)-2-Amino-3-(p-hydroxyphenyl)propionic acid | ChEBI | | (S)-3-(p-Hydroxyphenyl)alanine | ChEBI | | (S)-alpha-Amino-4-hydroxybenzenepropanoic acid | ChEBI | | (S)-Tyrosine | ChEBI | | 4-Hydroxy-L-phenylalanine | ChEBI | | L-Tyrosin | ChEBI | | Tyr | ChEBI | | TYROSINE | ChEBI | | Y | ChEBI | | (-)-a-Amino-p-hydroxyhydrocinnamate | Generator | | (-)-a-Amino-p-hydroxyhydrocinnamic acid | Generator | | (-)-alpha-Amino-p-hydroxyhydrocinnamate | Generator | | (-)-Α-amino-p-hydroxyhydrocinnamate | Generator | | (-)-Α-amino-p-hydroxyhydrocinnamic acid | Generator | | (2S)-2-Amino-3-(4-hydroxyphenyl)propanoate | Generator | | (S)-2-Amino-3-(p-hydroxyphenyl)propionate | Generator | | (S)-a-Amino-4-hydroxybenzenepropanoate | Generator | | (S)-a-Amino-4-hydroxybenzenepropanoic acid | Generator | | (S)-alpha-Amino-4-hydroxybenzenepropanoate | Generator | | (S)-Α-amino-4-hydroxybenzenepropanoate | Generator | | (S)-Α-amino-4-hydroxybenzenepropanoic acid | Generator | | (S)-a-Amino-4-hydroxy-benzenepropanoate | HMDB | | (S)-a-Amino-4-hydroxy-benzenepropanoic acid | HMDB | | (S)-alpha-Amino-4-hydroxy-benzenepropanoate | HMDB | | (S)-alpha-Amino-4-hydroxy-benzenepropanoic acid | HMDB | | 2-Amino-3-(4-hydroxyphen yl)-2-amino-3-(4-hydroxyphenyl)-propanoate | HMDB | | 2-Amino-3-(4-hydroxyphen yl)-2-amino-3-(4-hydroxyphenyl)-propanoic acid | HMDB | | 3-(4-Hydroxyphenyl)-L-alanine | HMDB | | Benzenepropanoate | HMDB | | Benzenepropanoic acid | HMDB | | L-p-Tyrosine | HMDB | | p-Tyrosine | HMDB | | L Tyrosine | HMDB | | Tyrosine, L-isomer | HMDB | | Tyrosine, L isomer | HMDB | | Para tyrosine | HMDB | | Para-tyrosine | HMDB |
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| Chemical Formula | C9H11NO3 |
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| Average Molecular Weight | 181.1885 |
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| Monoisotopic Molecular Weight | 181.073893223 |
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| IUPAC Name | (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid |
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| Traditional Name | L-tyrosine |
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| CAS Registry Number | 60-18-4 |
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| SMILES | N[C@@H](CC1=CC=C(O)C=C1)C(O)=O |
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| InChI Identifier | InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m0/s1 |
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| InChI Key | OUYCCCASQSFEME-QMMMGPOBSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine 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 | Tyrosine and derivatives |
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| Alternative Parents | |
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| Substituents | - Tyrosine or derivatives
- Phenylalanine or derivatives
- 3-phenylpropanoic-acid
- Alpha-amino acid
- Amphetamine or derivatives
- L-alpha-amino acid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Aralkylamine
- Monocyclic benzene moiety
- Benzenoid
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Amine
- Primary aliphatic amine
- Organic nitrogen compound
- Carbonyl group
- Organopnictogen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Primary amine
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic 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 | 343 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 0.479 mg/mL | Not Available | | LogP | -2.26 | HANSCH,C ET AL. (1995) |
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| Predicted Properties | |
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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
- Mammary Gland
- Milk
- Muscle
- Placenta
- Prostate Tissue
- Ruminal Fluid
- Semen
- Semimembranosus Muscle
- Testis
- Urine
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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 | 47.9 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 | 69.6 uM | Not Specified | Both | Normal | | details | | Blood | Detected and Quantified | 68-75 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 47-60 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 25-42 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 91 +/- 10 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 40-44 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 | | 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 | 84 +/- 27 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 | 54 +/- 14 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 | 4.71 +/- 0.96 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 4 +/- 1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2.6 +/- 0.3 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 3 +/- 1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2 - 11 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 4 +/- 1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2.6 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 5.8 +/- 2.6 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 1.6 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2.30 +/- 0.04 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2.4 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2.3 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 8.11 +/- 1.97 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 8.65 +/- 2.51 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 8278.671 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 8278.671 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 8278.671 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 8278.671 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 8278.671 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 8278.671 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 8278.671 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 251.11 +/- 17.54 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 44-269 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 48.4 +/- 4.1 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 530 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 81.35 +/- 11.06 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 97.9 +/- 13.13 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 31-41 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 82-422 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 | 35 +/- 13 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 50 +/- 24 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 61 +/- 21 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 49 +/- 12 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 49 +/- 12 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 68-471 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 36 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 49.1 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 60.9 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 42.2 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 26-77 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 41.3 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 52.2 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 50.6 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 46.5 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 | 8 - 12 uM | Not Specified | Both | Normal | | details | | Ruminal Fluid | Detected and Quantified | 295 +/- 136 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 42.17 +/- 8.29 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 | 52 +/- 10 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 | 43 +/- 9 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Urine | Detected 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 and Quantified | 34.9 uM | Not Specified | Not Specified | Bovine spongiform encephalopathy negative | | details | | Blood | Detected and Quantified | 43.4 uM | Not Specified | Not Specified | Bovine spongiform encephalopathy positive | | 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 | Mycobacterium avium subsp. paratuberculosis infection | | 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 | 60.86 +/- 20.13 uM | Not Specified | Not Specified | Rumen acidosis | | details |
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| External Links |
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| HMDB ID | HMDB0000158 |
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| DrugBank ID | DB00135 |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB000446 |
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| KNApSAcK ID | C00001397 |
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| Chemspider ID | 5833 |
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| KEGG Compound ID | C00082 |
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| BioCyc ID | TYR |
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| BiGG ID | 33785 |
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| Wikipedia Link | Tyrosine |
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| METLIN ID | 34 |
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| PubChem Compound | 6057 |
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| PDB ID | Not Available |
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| ChEBI ID | 17895 |
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| References |
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| Synthesis Reference | Enei, Hitoshi; Matsui, Hiroshi; Yamashita, Koichi; Okumura, Shinji; Yamada, Hideaki. Microbiological synthesis of L-tyrosine and 3,4-dihydroxyphenyl-L-alanine. I. Distribution of tyrosine phenol lyase in microorganisms. Agricultural and Biological Chemist 1972, 36:11, 1861-1868, DOI: 10.1080/00021369.1972.10860505 |
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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 ]
- 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 ]
- 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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