Record Information
Version1.0
Creation date2010-04-08 22:04:34 UTC
Update date2018-01-23 18:44:19 UTC
Primary IDFDB000446
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Tyrosine
DescriptionDietary supplement, nutrient. Flavouring ingredient. L-Tyrosine is found in many foods, some of which are blue crab, sweet rowanberry, lemon sole, and alpine sweetvetch.
CAS Number60-18-4
Structure
Thumb
Synonyms
SynonymSource
2-Amino-3-(4-hydroxyphenyl)propanoic acidChEBI
2-Amino-3-(p-hydroxyphenyl)propionic acidChEBI
3-(p-Hydroxyphenyl)alanineChEBI
TirosinaChEBI
TyrChEBI
TyrosinChEBI
YChEBI
2-Amino-3-(4-hydroxyphenyl)propanoateGenerator
2-Amino-3-(p-hydroxyphenyl)propionateGenerator
(-)-α-amino-p-hydroxyhydrocinnamic acidbiospider
(-)-a-amino-p-hydroxyhydrocinnamatebiospider
(-)-a-amino-p-hydroxyhydrocinnamic acidbiospider
(-)-alpha-amino-p-hydroxyhydrocinnamatebiospider
(-)-alpha-amino-p-hydroxyhydrocinnamic acidbiospider
(-)-α-amino-P-hydroxyhydrocinnamateGenerator
(-)-α-amino-P-hydroxyhydrocinnamic acidGenerator
(2S)-2-amino-3-(4-Hydroxyphenyl)propanoateGenerator
(2S)-2-amino-3-(4-hydroxyphenyl)propanoic acidbiospider
(s)-(-)-tyrosinebiospider
(S)-2-Amino-3-(4-hydroxyphenyl)propionic acidbiospider
(S)-2-Amino-3-(p-hydroxyphenyl)propionatebiospider
(S)-2-Amino-3-(p-hydroxyphenyl)propionic acidbiospider
(S)-3-(p-Hydroxyphenyl)alaninebiospider
(S)-a-amino-4-hydroxy-Benzenepropanoatebiospider
(S)-a-amino-4-hydroxy-Benzenepropanoic acidbiospider
(S)-a-Amino-4-hydroxybenzenepropanoatebiospider
(S)-a-Amino-4-hydroxybenzenepropanoic acidbiospider
(S)-alpha-amino-4-hydroxy-Benzenepropanoatebiospider
(S)-alpha-amino-4-hydroxy-Benzenepropanoic acidbiospider
(S)-alpha-Amino-4-hydroxybenzenepropanoatebiospider
(S)-alpha-Amino-4-hydroxybenzenepropanoic acidbiospider
(s)-tyrosinebiospider
(S)-α-amino-4-hydroxybenzenepropanoateGenerator
(S)-α-amino-4-hydroxybenzenepropanoic acidGenerator
α-amino-α-amino-p-hydroxyhydrocinnamic acidbiospider
α-Amino-β-(4-hydroxyphenyl)propionic acidbiospider
2-amino-3-(4-Hydroxyphen yl)-2-amino-3-(4-hydroxyphenyl)-propanoateHMDB
2-amino-3-(4-Hydroxyphen yl)-2-amino-3-(4-hydroxyphenyl)-propanoic acidHMDB
2-Amino-3-(4-hydroxyphenyl)propanoic acid-(S)-biospider
2-Amino-3-(4-hydroxyphenyl)propanoic acid, (S)-biospider
3-(4-Hydroxyphenyl)-L-alaninebiospider
4-Hydroxy-L-phenylalanineChEBI
alpha-Amino-4-hydroxybenzenepropanoic acid, (S)-biospider
Alpha-amino-p-hydroxyhydrocinnamic acid, (-)-biospider
BenzenepropanoateHMDB
Benzenepropanoic acid, α-amino-4-hydroxy-, (S)-biospider
Benzenepropanoic acid, alpha-amino-4-hydroxy-, (S)-biospider
FEMA 3736db_source
L-2-Amino-3-p-hydroxyphenylpropanoic acidbiospider
L-p-tyrosinebiospider
L-Phenylalanine-4-hydroxy-biospider
L-Phenylalanine, 4-hydroxy-biospider
L-TyrosinChEBI
L-Tyrosinemanual
L-Tyrosine (9CI)biospider
P-TyrosineHMDB
Propanoic acid, 2-amino-3-(4-hydroxyphenyl)-, (S)-biospider
TYRbiospider
TYROSINEChEBI
Tyrosine, 9CI, 8CI; L-formdb_source
Tyrosine, L- (8CI)biospider
Predicted Properties
PropertyValueSource
Water Solubility7.67 g/LALOGPS
logP-2.4ALOGPS
logP-1.5ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)2ChemAxon
pKa (Strongest Basic)9.19ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.1 m³·mol⁻¹ChemAxon
Polarizability18.01 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC9H11NO3
IUPAC name(2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid
InChI IdentifierInChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)
InChI KeyOUYCCCASQSFEME-UHFFFAOYSA-N
Isomeric SMILESNC(CC1=CC=C(O)C=C1)C(O)=O
Average Molecular Weight181.1885
Monoisotopic Molecular Weight181.073893223
Classification
Description belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine 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 ParentTyrosine and derivatives
Alternative Parents
Substituents
  • Tyrosine or derivatives
  • Phenylalanine or derivatives
  • 3-phenylpropanoic-acid
  • Amphetamine or derivatives
  • Alpha-amino acid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Foods
  • Dairy products
  • Eggs
  • Meats
  • Grains:

    Nuts and legumes:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionC 59.66%; H 6.12%; N 7.73%; O 26.49%DFC
    Melting PointMp 314-318 dec. approx. (rapid heat)DFC
    Boiling PointNot Available
    Experimental Water Solubility0.479 mg/mL at 25 oCSEIDELL,A (1941)
    Experimental logP-2.26HANSCH,C ET AL. (1995)
    Experimental pKapKa3 10.07 (phenolic OH)DFC
    Isoelectric pointNot Available
    ChargeNot Available
    Optical Rotation[a]D -9.01 (11.6% KOH)DFC
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    Spectrum TypeDescriptionSplash Key
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-4900000000-fb040ac104208d200d8cView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q0-0900000000-64b5df3e494e5df5c1beView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-c38735d64e2a16bd0c68View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-6900000000-6696908ff67c37922f99View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-941af648c85b3f0f7c66View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-1900000000-b7d3075f2496303aeb37View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9700000000-c242deae91617b5e8735View in MoNA
    MSMass Spectrum (Electron Ionization)splash10-0a4i-3900000000-7a26097fda66f2f445b5View in MoNA
    ChemSpider ID5833
    ChEMBL IDCHEMBL925
    KEGG Compound IDC00082
    Pubchem Compound ID6057
    Pubchem Substance IDNot Available
    ChEBI ID17895
    Phenol-Explorer IDNot Available
    DrugBank IDDB03839
    HMDB IDHMDB00158
    CRC / DFC (Dictionary of Food Compounds) IDBCN92-M:BCK50-J
    EAFUS ID3789
    Dr. Duke IDTYROSINE|L-(-)-TYROSINE
    BIGG ID33785
    KNApSAcK IDC00001397
    HET IDTYR
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDrw1037771
    SuperScent IDNot Available
    Wikipedia IDL-Tyrosine
    Phenol-Explorer Metabolite IDNot Available
    Duplicate IDS
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / Bioactivities
    DescriptorIDDefinitionReference
    anti depressant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti encephalopathic52217 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 phenylketonuric52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
    cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    monoamine precursorDUKE
    Enzymes
    NameGene NameUniProt ID
    Aromatic-L-amino-acid decarboxylaseDDCP20711
    Tyrosine 3-monooxygenaseTHP07101
    Tyrosine aminotransferaseTATP17735
    Phenylalanine-4-hydroxylasePAHP00439
    Aspartate aminotransferase, cytoplasmicGOT1P17174
    Aspartate aminotransferase, mitochondrialGOT2P00505
    Tyrosine--tRNA ligase, cytoplasmicYARSP54577
    Tyrosine--tRNA ligase, mitochondrialYARS2Q9Y2Z4
    Basic fibroblast growth factor receptor 1FGFR1P11362
    Epidermal growth factor receptorEGFRP00533
    Pathways
    NameSMPDB LinkKEGG Link
    Catecholamine BiosynthesisSMP00012 map00350
    Phenylalanine and Tyrosine MetabolismSMP00008 map00360
    Transcription/TranslationSMP00019 Not Available
    Tyrosine MetabolismSMP00006 map00350
    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.
    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.