Record Information
Version1.0
Creation date2010-04-08 22:06:27 UTC
Update date2020-09-17 15:30:54 UTC
Primary IDFDB004940
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-(-)-Phenylalanine
DescriptionPhenylalanine, abbreviated Phe or F, is a neutral, nonpolar, hydrophobic, essential amino acid. It is the precursor of the amino acid tyrosine, a precursor of the skin pigment melanin and a precursor of catecholamines that include tyramine, dopamine, epinephrine, and norepinephrine. Catecholamines are neurotransmitters that act as adrenalin-like substances. Interestingly, several psychotropic drugs (mescaline, morphine, codeine, and papaverine) also have phenylalanine as a constituent. Phenylalanine is highly concentrated in the human brain and plasma and is found naturally in mammalian breast milk. 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 several high protein foods, such as meat, cottage cheese, and wheat germ. An additional dietary source of phenylalanine is artificial sweeteners containing aspartame. Generally, aspartame should be avoided by phenylketonurics and pregnant women. When present in sufficiently high levels, phenylalanine can act as a neurotoxin and a metabotoxin. A neurotoxin is a compound that disrupts or attacks neural cells and neural tissue. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of phenylalanine are associated with at least five inborn errors of metabolism, including Hartnup disorder, hyperphenylalaninemia due to guanosine triphosphate cyclohydrolase deficiency, phenylketonuria (PKU), tyrosinemia type 2 (or Richner-Hanhart syndrome), and tyrosinemia type III (TYRO3). Phenylalanine also has some potential benefits. Phenylalanine can act as an analgesic, providing relief for premenstrual syndrome and may enhance the effects of acupuncture and electric transcutaneous nerve stimulation (TENS) for Parkinson's patients. Phenylalanine and tyrosine, like L-DOPA, produce a catecholamine-like effect. Phenylalanine is better absorbed than tyrosine and may cause fewer headaches. Low phenylalanine diets have been prescribed for certain cancers with mixed results. For some tumours that use more phenylalanine than others (such as melatonin-producing tumours called melanomas) may benefit from low phenylalanine diets.
CAS Number63-91-2
Structure
Thumb
Synonyms
SynonymSource
(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
Predicted Properties
PropertyValueSource
Water Solubility4.14 g/LALOGPS
logP-1.4ALOGPS
logP-1.2ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2.47ChemAxon
pKa (Strongest Basic)9.45ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.12 m³·mol⁻¹ChemAxon
Polarizability17.03 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H11NO2
IUPAC name(2S)-2-amino-3-phenylpropanoic acid
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)/t8-/m0/s1
InChI KeyCOLNVLDHVKWLRT-QMMMGPOBSA-N
Isomeric SMILESN[C@@H](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
  • 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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Industrial application:

Biological role:

Foods
  • Dairy products
  • Eggs
  • Meats
  • Grains:

    Nuts and legumes:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateNot Available
    Physical DescriptionNot Available
    Mass CompositionNot Available
    Melting PointNot Available
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    EI-MSMass Spectrum (Electron Ionization)splash10-00dl-9300000000-4782928378caea601f9bSpectrum
    GC-MSL-(-)-Phenylalanine, 2 TMS, GC-MS Spectrumsplash10-0fr6-1930000000-a37fbccaf826443ef70cSpectrum
    GC-MSL-(-)-Phenylalanine, non-derivatized, GC-MS Spectrumsplash10-014l-1940000000-537e2725d621246630c1Spectrum
    GC-MSL-(-)-Phenylalanine, 2 TMS, GC-MS Spectrumsplash10-00di-9630000000-ead0919f9a19d2352d80Spectrum
    GC-MSL-(-)-Phenylalanine, 1 TMS, GC-MS Spectrumsplash10-00di-2900000000-cb2d6dc4bf9515150328Spectrum
    GC-MSL-(-)-Phenylalanine, 2 TMS, GC-MS Spectrumsplash10-014l-2960000000-f77489792f0652dd5613Spectrum
    GC-MSL-(-)-Phenylalanine, non-derivatized, GC-MS Spectrumsplash10-014l-0970000000-792b341dd28b9e30bac2Spectrum
    GC-MSL-(-)-Phenylalanine, non-derivatized, GC-MS Spectrumsplash10-0fr6-1930000000-a37fbccaf826443ef70cSpectrum
    GC-MSL-(-)-Phenylalanine, non-derivatized, GC-MS Spectrumsplash10-014l-1940000000-537e2725d621246630c1Spectrum
    GC-MSL-(-)-Phenylalanine, non-derivatized, GC-MS Spectrumsplash10-0ul9-3659000000-b85be4e71798e2fdc47bSpectrum
    GC-MSL-(-)-Phenylalanine, non-derivatized, GC-MS Spectrumsplash10-00di-9630000000-ead0919f9a19d2352d80Spectrum
    GC-MSL-(-)-Phenylalanine, non-derivatized, GC-MS Spectrumsplash10-00di-2900000000-cb2d6dc4bf9515150328Spectrum
    GC-MSL-(-)-Phenylalanine, non-derivatized, GC-MS Spectrumsplash10-014l-2960000000-f77489792f0652dd5613Spectrum
    Predicted GC-MSL-(-)-Phenylalanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006x-9600000000-df38fcb743d8f44fb876Spectrum
    Predicted GC-MSL-(-)-Phenylalanine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-7900000000-f21569d2ec75b88e1bdaSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0900000000-0f3b994108b8a9fd2a56Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0gb9-2900000000-c14d44c8a67621757f3dSpectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9300000000-08c642dab7f49c00da43Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-7dce1e473976f7d2143eSpectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0f6x-9600000000-711557391093b0d8500aSpectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-0c25a5c116eac7bb059bSpectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-2804f79084ac4e67e155Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-8a71bb1f8424064d7cafSpectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0f6x-9800000000-e027ff6bb67ce55e80a5Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-9f6185e9c7d54189f369Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-df5f72fe2bba91742427Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0ir3-0988735721-bac229222fe7b52812a8Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0900000000-453477dec847a3672ffeSpectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0010963000-079a66bf710f6778bcebSpectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0000009000-62dbe98de4ecde484fb3Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-80558c17dc1845663c85Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0002-3900000000-e1ee31d41e48824e84b7Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0f6x-9500000000-cc11290a37615f24e16eSpectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-1a6020bce0e1a9a14832Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-38c044a112152626962eSpectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-014i-0900000000-9b908abfcb63153d60b3Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-1900000000-3ba5964e151bb1d56188Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-2900000000-20a7d24da0281f5b3b78Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0udi-5900000000-1800642a835b49f3398aSpectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0fb9-9300000000-f262384c85fb843f8a11Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    2D NMR[1H,1H] 2D NMR SpectrumSpectrum
    2D NMR[1H,13C] 2D NMR SpectrumSpectrum
    ChemSpider IDNot Available
    ChEMBL IDNot Available
    KEGG Compound IDNot Available
    Pubchem Compound IDNot Available
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer IDNot Available
    DrugBank IDNot Available
    HMDB IDNot Available
    CRC / DFC (Dictionary of Food Compounds) IDNot Available
    EAFUS IDNot Available
    Dr. Duke IDL-(-)-PHENYLALANINE
    BIGG IDNot Available
    KNApSAcK IDNot Available
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite IDNot Available
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / BioactivitiesNot Available
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSNot Available
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).