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Record Information
Version1.0
Creation Date2016-09-30 22:20:20 UTC
Update Date2020-06-04 21:58:33 UTC
BMDB IDBMDB0000159
Secondary Accession Numbers
  • BMDB00159
Metabolite Identification
Common NameL-Phenylalanine
DescriptionL-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
Thumb
Synonyms
ValueSource
(S)-2-Amino-3-phenylpropionic acidChEBI
(S)-alpha-Amino-beta-phenylpropionic acidChEBI
3-Phenyl-L-alanineChEBI
beta-Phenyl-L-alanineChEBI
FChEBI
PheChEBI
PHENYLALANINEChEBI
(S)-2-Amino-3-phenylpropionateGenerator
(S)-a-Amino-b-phenylpropionateGenerator
(S)-a-Amino-b-phenylpropionic acidGenerator
(S)-alpha-Amino-beta-phenylpropionateGenerator
(S)-Α-amino-β-phenylpropionateGenerator
(S)-Α-amino-β-phenylpropionic acidGenerator
b-Phenyl-L-alanineGenerator
Β-phenyl-L-alanineGenerator
(-)-beta-PhenylalanineHMDB
(L)-PhenylalanineHMDB
(S)-(-)-PhenylalanineHMDB
(S)-2-Amino-3-phenylpropanoateHMDB
(S)-2-Amino-3-phenylpropanoic acidHMDB
(S)-alpha-Amino-benzenepropanoateHMDB
(S)-alpha-Amino-benzenepropanoic acidHMDB
(S)-alpha-AminobenzenepropanoateHMDB
(S)-alpha-Aminobenzenepropanoic acidHMDB
(S)-alpha-AminohydrocinnamateHMDB
(S)-alpha-Aminohydrocinnamic acidHMDB
(S)-PhenylalanineHMDB
alpha-AminohydrocinnamateHMDB
alpha-Aminohydrocinnamic acidHMDB
beta-Phenyl-alpha-alanineHMDB
beta-PhenylalanineHMDB
L-2-Amino-3-phenylpropionateHMDB
L-2-Amino-3-phenylpropionic acidHMDB
Phenyl-alanineHMDB
PhenylalamineHMDB
L-Isomer phenylalanineHMDB
Phenylalanine, L isomerHMDB
Phenylalanine, L-isomerHMDB
EndorphenylHMDB
(6S)-TetrahydrofolateHMDB
(6S)-Tetrahydrofolic acidHMDB
(6S)-THFAHMDB
5,6,7,8-TetrahydrofolateHMDB
TetrahydrofolateHMDB
THFHMDB
5,6,7,8-Tetrahydrofolic acidHMDB
Chemical FormulaC9H11NO2
Average Molecular Weight165.1891
Monoisotopic Molecular Weight165.078978601
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number63-91-2
SMILESNot 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 KeyCOLNVLDHVKWLRT-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPhenylalanine 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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point283 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility26.9 mg/mLNot Available
LogP-1.38AVDEEF,A (1997)
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
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
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified47.3 uMNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
    • Jiyuan Li, Everes...
details
BloodDetected and Quantified50.7 uMNot SpecifiedBothNormal details
BloodDetected and Quantified65-75 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified44-58 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified71 +/- 7 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
BloodDetected and Quantified45-48 uMNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Trabi M, Keller M...
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
ColostrumDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
ColostrumDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected and Quantified138 +/- 22 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Longissimus Thoracis MuscleDetected and Quantified55 +/- 12 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified10896.603 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified10896.603 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified10896.603 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified10896.603 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified10291.236 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified10291.236 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified10291.236 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified2 - 10 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified1.7 +/- 0.1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified1.9 +/- 0.1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified1.9 +/- 0.1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified1.99 +/- 0.01 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified3.4 +/- 0.3 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MuscleDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified105.7 +/- 18.05 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified242.58 +/- 15.65 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified51-258 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified54.02 +/- 3.36 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified240 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
MuscleDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • S. F. Graham, T. ...
details
MuscleDetected and Quantified80.81 +/- 10.96 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified36-48 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified103-496 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified36 +/- 13 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified64 +/- 17 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified65 +/- 20 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified34 +/- 17 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified34 +/- 17 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified31-80 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified35.7 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified64.5 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified77.7 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified28.9 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified17 - 29 uMNot SpecifiedBothNormal details
Ruminal FluidDetected and Quantified310 +/- 129 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Ruminal FluidDetected and Quantified35.37 +/- 13.73 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
details
SemenDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
SemenDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Semimembranosus MuscleDetected and Quantified58 +/- 10 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
TestisDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
TestisDetected and Quantified56 +/- 12 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Treated with growth-promoting hormones
details
BloodDetected and Quantified51.7 uMNot SpecifiedNot Specified
Bovine spongiform encephalopathy negative
details
BloodDetected and Quantified54.3 uMNot SpecifiedNot Specified
Bovine spongiform encephalopathy positive
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
All Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
High dose Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Low dose Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Mycobacterium avium subsp. paratuberculosis infection
details
ColostrumDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Commercial Product/bacterial growth on ground beef
details
MuscleDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Commercial Product/bacterial growth on ground beef
details
Ruminal FluidDetected and Quantified74.13 +/- 13.28 uMNot SpecifiedNot SpecifiedRumen acidosis
    • Fozia Saleem, Sou...
details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Fed pasture vs barley-based concentrate
details
HMDB IDHMDB0000159
DrugBank IDDB00120
Phenol Explorer Compound IDNot Available
FooDB IDFDB004940
KNApSAcK IDC00001386
Chemspider ID5910
KEGG Compound IDC00079
BioCyc IDPHE
BiGG ID33775
Wikipedia LinkPhenylalanine
METLIN ID28
PubChem Compound6140
PDB IDNot Available
ChEBI ID17295
References
Synthesis ReferenceZhou, 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
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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.
  7. 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.
  8. Fooddata+, The Technical University of Denmark (DTU) [Link]

Enzymes

General function:
Amino acid transport and metabolism
Specific function:
Catalyzes the hydroxylation of L-phenylalanine to L-tyrosine.
Gene Name:
PAH
Uniprot ID:
Q2KIH7
Molecular weight:
51727.0
General function:
Amino acid transport and metabolism
Specific function:
Biosynthesis of L-glutamate from L-aspartate or L-cysteine. Important regulator of levels of glutamate, the major excitatory neurotransmitter of the vertebrate central nervous system. Acts as a scavenger of glutamate in brain neuroprotection. The aspartate aminotransferase activity is involved in hepatic glucose synthesis during development and in adipocyte glyceroneogenesis. Using L-cysteine as substrate, regulates levels of mercaptopyruvate, an important source of hydrogen sulfide. Mercaptopyruvate is converted into H(2)S via the action of 3-mercaptopyruvate sulfurtransferase (3MST). Hydrogen sulfide is an important synaptic modulator and neuroprotectant in the brain (By similarity).
Gene Name:
GOT1
Uniprot ID:
P33097
Molecular weight:
46399.0
Reactions
L-Phenylalanine + Oxoglutaric acid → Phenylpyruvic acid + L-Glutamic aciddetails
General function:
Amino acid transport and metabolism
Specific function:
Transaminase involved in tyrosine breakdown. Converts tyrosine to p-hydroxyphenylpyruvate. Can catalyze the reverse reaction, using glutamic acid, with 2-oxoglutarate as cosubstrate (in vitro). Has much lower affinity and transaminase activity for phenylalanine (By similarity).
Gene Name:
TAT
Uniprot ID:
Q58CZ9
Molecular weight:
49691.0
Reactions
L-Phenylalanine + Oxoglutaric acid → Phenylpyruvic acid + L-Glutamic aciddetails
General function:
Involved in protein binding
Specific function:
Mediates tetrahydrobiopterin inhibition of GTP cyclohydrolase 1. This inhibition is reversed by L-phenylalanine (By similarity).
Gene Name:
GCHFR
Uniprot ID:
Q32L41
Molecular weight:
9557.0
General function:
Amino acid transport and metabolism
Specific function:
Not Available
Gene Name:
SLC7A5
Uniprot ID:
Q9TU26
Molecular weight:
55110.0
General function:
Not Available
Specific function:
Not Available
Gene Name:
IL4I1
Uniprot ID:
F1N191
Molecular weight:
64479.0
Reactions
L-Phenylalanine + Water + Oxygen → Phenylpyruvic acid + Ammonia + Hydrogen peroxidedetails