| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:38:43 UTC |
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| Update Date | 2020-06-04 21:21:54 UTC |
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| BMDB ID | BMDB0000929 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | L-Tryptophan |
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| Description | L-Tryptophan, also known as Trp or W, belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. L-Tryptophan exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Tryptophan exists in all living species, ranging from bacteria to humans. L-Tryptophan participates in a number of enzymatic reactions, within cattle. In particular, L-Tryptophan can be converted into n'-formylkynurenine; which is catalyzed by the enzyme tryptophan 2,3-dioxygenase. In addition, L-Tryptophan and tetrahydrobiopterin can be converted into 5-hydroxy-L-tryptophan and 4a-hydroxytetrahydrobiopterin through the action of the enzyme tryptophan 5-hydroxylase 1. In cattle, L-tryptophan is involved in the metabolic pathway called the tryptophan metabolism pathway. L-Tryptophan is a potentially toxic compound. L-Tryptophan has been found to be associated with several diseases known as pancreatic cancer, tryptophanuria with dwarfism, crohn's disease, and alzheimer's disease; also l-tryptophan has been linked to the inborn metabolic disorders including hartnup disease. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (2S)-2-Amino-3-(1H-indol-3-yl)propanoic acid | ChEBI | | (S)-alpha-Amino-1H-indole-3-propanoic acid | ChEBI | | (S)-alpha-Amino-beta-(3-indolyl)-propionic acid | ChEBI | | (S)-Tryptophan | ChEBI | | L-(-)-Tryptophan | ChEBI | | L-beta-3-Indolylalanine | ChEBI | | Trp | ChEBI | | Tryptophan | ChEBI | | W | ChEBI | | (2S)-2-Amino-3-(1H-indol-3-yl)propanoate | Generator | | (S)-a-Amino-1H-indole-3-propanoate | Generator | | (S)-a-Amino-1H-indole-3-propanoic acid | Generator | | (S)-alpha-Amino-1H-indole-3-propanoate | Generator | | (S)-Α-amino-1H-indole-3-propanoate | Generator | | (S)-Α-amino-1H-indole-3-propanoic acid | Generator | | (S)-a-Amino-b-(3-indolyl)-propionate | Generator | | (S)-a-Amino-b-(3-indolyl)-propionic acid | Generator | | (S)-alpha-Amino-beta-(3-indolyl)-propionate | Generator | | (S)-Α-amino-β-(3-indolyl)-propionate | Generator | | (S)-Α-amino-β-(3-indolyl)-propionic acid | Generator | | L-b-3-Indolylalanine | Generator | | L-Β-3-indolylalanine | Generator | | (-)-Tryptophan | HMDB | | (L)-Tryptophan | HMDB | | (S)-1H-Indole-3-alanine | HMDB | | (S)-2-Amino-3-(3-indolyl)propionic acid | HMDB | | (S)-a-Amino-b-indolepropionate | HMDB | | (S)-a-Amino-b-indolepropionic acid | HMDB | | (S)-a-Aminoindole-3-propionate | HMDB | | (S)-a-Aminoindole-3-propionic acid | HMDB | | (S)-alpha-Amino-beta-indolepropionate | HMDB | | (S)-alpha-Amino-beta-indolepropionic acid | HMDB | | (S)-alpha-Aminoindole-3-propionate | HMDB | | (S)-alpha-Aminoindole-3-propionic acid | HMDB | | 1-beta-3-Indolylalanine | HMDB | | 1beta-3-Indolylalanine | HMDB | | 1H-Indole-3-alanine | HMDB | | 2-Amino-3-indolylpropanoate | HMDB | | 2-Amino-3-indolylpropanoic acid | HMDB | | 3-(1H-indol-3-yl)-L-Alanine | HMDB | | 3-indol-3-Ylalanine | HMDB | | Alpha'-amino-3-indolepropionic acid | HMDB | | alpha-Aminoindole-3-propionic acid | HMDB | | Ardeytropin | HMDB | | H-TRP-OH | HMDB | | Indole-3-alanine | HMDB | | Kalma | HMDB | | L-alpha-Amino-3-indolepropionic acid | HMDB | | L-alpha-Aminoindole-3-propionic acid | HMDB | | L-Tryptofan | HMDB | | L-Tryptophane | HMDB | | Lopac-T-0254 | HMDB | | Lyphan | HMDB | | Optimax | HMDB | | Pacitron | HMDB | | Sedanoct | HMDB | | Triptofano | HMDB | | Trofan | HMDB | | Tryptacin | HMDB | | Tryptan | HMDB | | Tryptophane | HMDB | | Tryptophanum | HMDB | | Ardeydorm | HMDB | | L Tryptophan | HMDB | | L-Tryptophan-ratiopharm | HMDB | | Merck brand OF tryptophan | HMDB | | Niddapharm brand OF tryptophan | HMDB | | ICN brand OF tryptophan | HMDB | | Levotryptophan | HMDB | | PMS Tryptophan | HMDB | | PMS-Tryptophan | HMDB | | Ratiopharm brand OF tryptophan | HMDB | | Esparma brand OF tryptophan | HMDB | | Ratio-tryptophan | HMDB | | L Tryptophan ratiopharm | HMDB | | Naturruhe | HMDB | | Tryptophan metabolism alterations | HMDB | | Ardeypharm brand OF tryptophan | HMDB | | Kalma brand OF tryptophan | HMDB | | Pharmascience brand OF tryptophan | HMDB | | Upsher-smith brand OF tryptophan | HMDB | | Ratio tryptophan | HMDB |
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| Chemical Formula | C11H12N2O2 |
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| Average Molecular Weight | 204.2252 |
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| Monoisotopic Molecular Weight | 204.089877638 |
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| IUPAC Name | (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid |
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| Traditional Name | L-tryptophan |
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| CAS Registry Number | 73-22-3 |
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| SMILES | N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O |
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| InChI Identifier | InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1 |
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| InChI Key | QIVBCDIJIAJPQS-VIFPVBQESA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Indoles and derivatives |
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| Sub Class | Indolyl carboxylic acids and derivatives |
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| Direct Parent | Indolyl carboxylic acids and derivatives |
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| Alternative Parents | |
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| Substituents | - Indolyl carboxylic acid derivative
- Alpha-amino acid
- Alpha-amino acid or derivatives
- L-alpha-amino acid
- 3-alkylindole
- Indole
- Aralkylamine
- Benzenoid
- Substituted pyrrole
- Heteroaromatic compound
- Pyrrole
- Amino acid or derivatives
- Amino acid
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Azacycle
- Amine
- Primary aliphatic amine
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Organic nitrogen compound
- Carbonyl group
- Organonitrogen compound
- Organooxygen compound
- Primary amine
- Organopnictogen compound
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic 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 | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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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 | - Blood
- Colostrum
- Fibroblasts
- Liver
- Longissimus Thoracis Muscle
- Mammary Gland
- Milk
- Muscle
- Neuron
- Placenta
- Prostate Tissue
- Ruminal Fluid
- Semimembranosus Muscle
- Testis
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| Pathways | |
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| Normal Concentrations |
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| Blood | Detected and Quantified | 37-42 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 22-25 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 47 +/- 7 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Fibroblasts | 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 but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected and Quantified | 44 +/- 7 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Longissimus Thoracis Muscle | Detected and Quantified | 19 +/- 5 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 | 3 +/- 1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 3 +/- 2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 3 +/- 2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 3 +/- 1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 1 - 5 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2301.381 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2301.381 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 3.2 +/- 1.1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2.1 +/- 0.6 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2301.381 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2.0 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2.0 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2301.381 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2.18 +/- 0.02 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2.1 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2252.415 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2252.415 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2252.415 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 50 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 35-95 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Neuron | 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 | 9.26 +/- 3.06 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 4.41 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 6.59 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 9.5 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 8.68 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 4-12 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 5 - 8 uM | Not Specified | Both | Normal | | details | | Ruminal Fluid | Detected and Quantified | 7 +/- 3 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 10 +/- 3 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 17 +/- 9 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 11 +/- 5 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 11 +/- 5 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 24 +/- 14 uM | Not Specified | Not Specified | Normal | | details | | Semimembranosus Muscle | Detected and Quantified | 21 +/- 3 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Testis | Detected and Quantified | 18 +/- 4 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 | | 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 | 9.48 +/- 2.92 uM | Not Specified | Not Specified | Rumen acidosis | | details |
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| External Links |
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| HMDB ID | HMDB0000929 |
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| DrugBank ID | DB00150 |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB002250 |
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| KNApSAcK ID | C00001396 |
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| Chemspider ID | 6066 |
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| KEGG Compound ID | C00078 |
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| BioCyc ID | TRP |
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| BiGG ID | 33772 |
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| Wikipedia Link | Tryptophan |
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| METLIN ID | 5879 |
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| PubChem Compound | 6305 |
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| PDB ID | Not Available |
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| ChEBI ID | 16828 |
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| References |
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| Synthesis Reference | Amir-Heidari, Bagher; Thirlway, Jenny; Micklefield, Jason. Stereochemical course of tryptophan dehydrogenation during biosynthesis of the calcium-dependent lipopeptide antibiotics. Organic Letters (2007), 9(8), 1513-1516. |
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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 ]
- 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 ]
- 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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