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Showing Compound L-(-)-Phenylalanine (FDB004940)

Record Information
Version1.0
Creation date2010-04-08 22:06:27 UTC
Update date2024-11-29 22:27:34 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
MOLSDFPDBSMILESInChI
Synonyms
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
    Physico-Chemical Properties - Experimental
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    EI-MSMass Spectrum (Electron Ionization)splash10-00dl-9300000000-4782928378caea601f9b2018-05-25View Spectrum
    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
    Predicted GC-MSL-(-)-Phenylalanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSL-(-)-Phenylalanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSL-(-)-Phenylalanine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSL-(-)-Phenylalanine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSL-(-)-Phenylalanine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0900000000-0f3b994108b8a9fd2a562012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0gb9-2900000000-c14d44c8a67621757f3d2012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9300000000-08c642dab7f49c00da432012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-7dce1e473976f7d2143e2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0f6x-9600000000-711557391093b0d8500a2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-0c25a5c116eac7bb059b2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-2804f79084ac4e67e1552012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-8a71bb1f8424064d7caf2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0f6x-9800000000-e027ff6bb67ce55e80a52012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-9f6185e9c7d54189f3692012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-df5f72fe2bba917424272012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0ir3-0988735721-bac229222fe7b52812a82012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0900000000-453477dec847a3672ffe2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0010963000-079a66bf710f6778bceb2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0000009000-62dbe98de4ecde484fb32012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-80558c17dc1845663c852012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0002-3900000000-e1ee31d41e48824e84b72012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0f6x-9500000000-cc11290a37615f24e16e2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-1a6020bce0e1a9a148322012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-38c044a112152626962e2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-014i-0900000000-9b908abfcb63153d60b32012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-1900000000-3ba5964e151bb1d561882012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-2900000000-20a7d24da0281f5b3b782012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0udi-5900000000-1800642a835b49f3398a2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0fb9-9300000000-f262384c85fb843f8a112012-08-31View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Spectrum
    2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
    2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
    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
    Processing...
    Biological Effects and Interactions
    Health Effects / BioactivitiesNot Available
    EnzymesNot Available
    Pathways
    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).