You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Bovine Metabolome Database.
Record Information |
---|
Version | 1.0 |
---|
Creation Date | 2016-09-30 22:20:20 UTC |
---|
Update Date | 2020-06-04 21:58:33 UTC |
---|
BMDB ID | BMDB0000159 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | L-Phenylalanine |
---|
Description | L-Phenylalanine, also known as F or endorphenyl, belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Phenylalanine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Phenylalanine exists in all living species, ranging from bacteria to humans. L-Phenylalanine is a potentially toxic compound. |
---|
Structure | |
---|
Synonyms | Value | Source |
---|
(S)-2-Amino-3-phenylpropionic acid | ChEBI | (S)-alpha-Amino-beta-phenylpropionic acid | ChEBI | 3-Phenyl-L-alanine | ChEBI | beta-Phenyl-L-alanine | ChEBI | F | ChEBI | Phe | ChEBI | PHENYLALANINE | ChEBI | (S)-2-Amino-3-phenylpropionate | Generator | (S)-a-Amino-b-phenylpropionate | Generator | (S)-a-Amino-b-phenylpropionic acid | Generator | (S)-alpha-Amino-beta-phenylpropionate | Generator | (S)-Α-amino-β-phenylpropionate | Generator | (S)-Α-amino-β-phenylpropionic acid | Generator | b-Phenyl-L-alanine | Generator | Β-phenyl-L-alanine | Generator | (-)-beta-Phenylalanine | HMDB | (L)-Phenylalanine | HMDB | (S)-(-)-Phenylalanine | HMDB | (S)-2-Amino-3-phenylpropanoate | HMDB | (S)-2-Amino-3-phenylpropanoic acid | HMDB | (S)-alpha-Amino-benzenepropanoate | HMDB | (S)-alpha-Amino-benzenepropanoic acid | HMDB | (S)-alpha-Aminobenzenepropanoate | HMDB | (S)-alpha-Aminobenzenepropanoic acid | HMDB | (S)-alpha-Aminohydrocinnamate | HMDB | (S)-alpha-Aminohydrocinnamic acid | HMDB | (S)-Phenylalanine | HMDB | alpha-Aminohydrocinnamate | HMDB | alpha-Aminohydrocinnamic acid | HMDB | beta-Phenyl-alpha-alanine | HMDB | beta-Phenylalanine | HMDB | L-2-Amino-3-phenylpropionate | HMDB | L-2-Amino-3-phenylpropionic acid | HMDB | Phenyl-alanine | HMDB | Phenylalamine | HMDB | L-Isomer phenylalanine | HMDB | Phenylalanine, L isomer | HMDB | Phenylalanine, L-isomer | HMDB | Endorphenyl | HMDB | (6S)-Tetrahydrofolate | HMDB | (6S)-Tetrahydrofolic acid | HMDB | (6S)-THFA | HMDB | 5,6,7,8-Tetrahydrofolate | HMDB | Tetrahydrofolate | HMDB | THF | HMDB | 5,6,7,8-Tetrahydrofolic acid | HMDB |
|
---|
Chemical Formula | C9H11NO2 |
---|
Average Molecular Weight | 165.1891 |
---|
Monoisotopic Molecular Weight | 165.078978601 |
---|
IUPAC Name | Not Available |
---|
Traditional Name | Not Available |
---|
CAS Registry Number | 63-91-2 |
---|
SMILES | Not Available |
---|
InChI Identifier | InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m0/s1 |
---|
InChI Key | COLNVLDHVKWLRT-QMMMGPOBSA-N |
---|
Chemical Taxonomy |
---|
Description | belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic acids and derivatives |
---|
Class | Carboxylic acids and derivatives |
---|
Sub Class | Amino acids, peptides, and analogues |
---|
Direct Parent | Phenylalanine and derivatives |
---|
Alternative Parents | |
---|
Substituents | - Phenylalanine or derivatives
- 3-phenylpropanoic-acid
- Alpha-amino acid
- Amphetamine or derivatives
- L-alpha-amino acid
- Aralkylamine
- Monocyclic benzene moiety
- Benzenoid
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic nitrogen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Primary aliphatic amine
- Organic oxide
- Carbonyl group
- Organopnictogen compound
- Organic oxygen compound
- Amine
- Aromatic homomonocyclic compound
|
---|
Molecular Framework | Aromatic homomonocyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
Status | Detected and Quantified |
---|
Origin | |
---|
Biofunction | Not Available |
---|
Application | Not Available |
---|
Cellular locations | |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | 283 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 26.9 mg/mL | Not Available | LogP | -1.38 | AVDEEF,A (1997) |
|
---|
Predicted Properties | Not Available |
---|
Spectra |
---|
Spectra | |
---|
Biological Properties |
---|
Cellular Locations | |
---|
Biospecimen Locations | - All Tissues
- Blood
- Colostrum
- Liver
- Longissimus Thoracis Muscle
- Mammary Gland
- Milk
- Muscle
- Placenta
- Prostate Tissue
- Ruminal Fluid
- Semen
- Semimembranosus Muscle
- Testis
- Urine
|
---|
Pathways | |
---|
Normal Concentrations |
---|
| |
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 | 47.3 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 | 50.7 uM | Not Specified | Both | Normal | | details | Blood | Detected and Quantified | 65-75 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 44-58 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 71 +/- 7 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 45-48 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 | 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 | 138 +/- 22 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 | 55 +/- 12 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 | 10896.603 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 10896.603 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 10896.603 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 10896.603 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 10291.236 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 10291.236 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 10291.236 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 2 - 10 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 1.7 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 1.9 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 1.9 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 1.99 +/- 0.01 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 3.4 +/- 0.3 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 | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 105.7 +/- 18.05 uM | Not Specified | Not Specified | Normal | | details | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 242.58 +/- 15.65 uM | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 51-258 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 54.02 +/- 3.36 uM | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 240 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 80.81 +/- 10.96 uM | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 36-48 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 103-496 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 | 36 +/- 13 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 64 +/- 17 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 65 +/- 20 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 34 +/- 17 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 34 +/- 17 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 | 31-80 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 35.7 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 64.5 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 77.7 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 28.9 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 17 - 29 uM | Not Specified | Both | Normal | | details | Ruminal Fluid | Detected and Quantified | 310 +/- 129 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 35.37 +/- 13.73 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 | 58 +/- 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 | 56 +/- 12 nmol/g of tissue | Not Specified | Not Specified | Normal | | details |
|
---|
Abnormal Concentrations |
---|
| |
Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Treated with growth-promoting hormones | | details | Blood | Detected and Quantified | 51.7 uM | Not Specified | Not Specified | Bovine spongiform encephalopathy negative | | details | Blood | Detected and Quantified | 54.3 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 | 74.13 +/- 13.28 uM | Not Specified | Not Specified | Rumen acidosis | | details | Urine | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Fed pasture vs barley-based concentrate | | details |
|
---|
External Links |
---|
HMDB ID | HMDB0000159 |
---|
DrugBank ID | DB00120 |
---|
Phenol Explorer Compound ID | Not Available |
---|
FooDB ID | FDB004940 |
---|
KNApSAcK ID | C00001386 |
---|
Chemspider ID | 5910 |
---|
KEGG Compound ID | C00079 |
---|
BioCyc ID | PHE |
---|
BiGG ID | 33775 |
---|
Wikipedia Link | Phenylalanine |
---|
METLIN ID | 28 |
---|
PubChem Compound | 6140 |
---|
PDB ID | Not Available |
---|
ChEBI ID | 17295 |
---|
References |
---|
Synthesis Reference | Zhou, Hua; Zhong, Yao; Sun, Guanghai; Wei, Ping. Preparation of L-phenylalanine by an aqueous two-phase system. Huaxue Fanying Gongcheng Yu Gongyi (2006), 22(2), 146-150. |
---|
Material Safety Data Sheet (MSDS) | Not Available |
---|
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 ]
- 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]
|
---|