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L-Phenylalanine (FDB014705)

Record Information
Version1.0
Creation date2010-04-08 22:11:25 UTC
Update date2019-08-01 18:42:28 UTC
Primary IDFDB014705
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Phenylalanine
DescriptionFound in many foods. It is used in cocoa substitutes. Flavouring ingredient; dietary supplement L-phenylalanine can also be converted into L-tyrosine, another one of the DNA-encoded amino acids. L-tyrosine in turn is converted into L-DOPA, which is further converted into dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline). The latter three are known as the catecholamines.; Phenylalanine (abbreviated as Phe or F) is an ?-amino acid with the formula HO2CCH(NH2)CH2C6H5, which is found naturally in the breast milk of mammals and manufactured for food and drink products and are also sold as nutritional supplements for their reputed analgesic and antidepressant effects. Phenylalanine is structurally closely related to dopamine, epinephrine (adrenaline) and tyrosine. It is a direct precursor to the neuromodulator phenylethylamine, a commonly used dietary supplement.; Phenylalanine is an essential amino acid and the precursor for the amino acid tyrosine. Like tyrosine, it is the precursor of catecholamines in the body (tyramine, dopamine, epinephrine and norepinephrine). The psychotropic drugs (mescaline, morphine, codeine, and papaverine) also have phenylalanine as a constituent. Phenylalanine is a precursor of the neurotransmitters called catecholamines, which are adrenalin-like substances. Phenylalanine is highly concentrated in the human brain and plasma. Normal metabolism of phenylalanine requires biopterin, iron, niacin, vitamin B6, copper and vitamin C. An average adult ingests 5 g of phenylalanine per day and may optimally need up to 8 g daily. Phenylalanine is highly concentrated in high protein foods, such as meat, cottage cheese and wheat germ. A new dietary source of phenylalanine is artificial sweeteners containing aspartame. Aspartame appears to be nutritious except in hot beverages; This essential amino acid is classified as nonpolar because of the hydrophobic nature of the benzyl side chain. The codons for L-phenylalanine are UUU and UUC. It is a white, powdery solid. L-Phenylalanine (LPA) is an electrically-neutral amino acid, one of the twenty common amino acids used to biochemically form proteins, coded for by DNA.; It is used by the brain to produce Norepinephrine, a chemical that transmits signals between nerve cells and the brain; however, it should be avoided by phenylketonurics and pregnant women. Phenylketonurics, who have a genetic error of phenylalanine metabolism, have elevated serum plasma levels of phenylalanine up to 400 times normal. Mild phenylketonuria can be an unsuspected cause of hyperactivity, learning problems, and other developmental problems in children. Phenylalanine can be an effective pain reliever. Its use in premenstrual syndrome and Parkinson's may enhance the effects of acupuncture and electric transcutaneous nerve stimulation (TENS). Phenylalanine and tyrosine, like L-dopa, produce a catecholamine effect. Phenylalanine is better absorbed than tyrosine and may cause fewer headaches. Low phenylalanine diets have been prescribed for certain cancers with mixed results. Some tumors use more phenylalanine (particularly melatonin-producing tumors called melanoma). One strategy is to exclude this amino acid from the diet, i.e., a Phenylketonuria (PKU) diet (compliance is a difficult issue; it is hard to quantify and is under-researched). The other strategy is just to increase phenylalanine's competing amino acids, i.e., tryptophan, valine, isoleucine and leucine, but not tyrosine. (http://www.dcnutrition.com)
CAS Number63-91-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted PropertiesNot Available
Chemical FormulaC9H11NO2
IUPAC name
InChI IdentifierInChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)
InChI KeyCOLNVLDHVKWLRT-UHFFFAOYSA-N
Isomeric SMILESNC(CC1=CC=CC=C1)C(O)=O
Average Molecular Weight165.1891
Monoisotopic Molecular Weight165.078978601
Classification
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
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Primary amine
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 65.44%; H 6.71%; N 8.48%; O 19.37%DFC
Melting PointMp 283-284° (rapid heat)DFC
Boiling PointNot Available
Experimental Water Solubility26.9 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-1.38AVDEEF,A (1997)
Experimental pKapKa2 9.13 (NH2)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -34.3 (c, 1 in H2O) (98% op)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MSNot Available
NMRNot Available
ChemSpider ID5910
ChEMBL IDCHEMBL301523
KEGG Compound IDC00079
Pubchem Compound ID6140
Pubchem Substance IDNot Available
ChEBI ID17295
Phenol-Explorer IDNot Available
DrugBank IDDB00120
HMDB IDHMDB00159
CRC / DFC (Dictionary of Food Compounds) IDJVC81-S:JVC67-S
EAFUS ID2995
Dr. Duke IDPHENYLALANINE
BIGG ID33775
KNApSAcK IDC00001386
HET IDPHE
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1036921
SuperScent IDNot Available
Wikipedia IDL-Phenylalanine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti ADDDUKE
anti depressant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti Parkinsonian48407 A drug used in the treatment of Parkinson's disease.DUKE
anti sicklingDUKE
anti vitiligicDUKE
monoamine precursorDUKE
tremorigenicDUKE
Enzymes
NameGene NameUniProt ID
Aromatic-L-amino-acid decarboxylaseDDCP20711
Tyrosine 3-monooxygenaseTHP07101
Tyrosine aminotransferaseTATP17735
Phenylalanine-4-hydroxylasePAHP00439
Aspartate aminotransferase, cytoplasmicGOT1P17174
Aspartate aminotransferase, mitochondrialGOT2P00505
Peroxiredoxin-6PRDX6P30041
Kynurenine--oxoglutarate transaminase 1CCBL1Q16773
Phenylalanine--tRNA ligase, mitochondrialFARS2O95363
Phenylalanine--tRNA ligase beta subunitFARSBQ9NSD9
FARSLA proteinFARSLAQ6IBR2
Phenylalanine--tRNA ligase alpha subunitFARSAQ9Y285
Pathways
NameSMPDB LinkKEGG Link
Phenylalanine and Tyrosine MetabolismSMP00008 map00360
Transcription/TranslationSMP00019 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.