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Record Information
Version3.6
Creation Date2007-04-12 21:16:46 UTC
Update Date2016-09-22 21:06:51 UTC
HMDB IDHMDB06050
Secondary Accession NumbersNone
Metabolite Identification
Common Nameo-Tyrosine
Descriptiono-Tyrosine is a normal human metabolite. Its presence is possible due to the hydroxylation of l-phenylalanine by hydroxyl radical (*OH), and is proposed as an hydroxy radical biomarker of oxidative damage to proteins. o-Tyrosine might also be included in the diet and absorbed. It has been associated with disease such as Kwashiorkor, a severe form of protein-energy malnutrition. However, many publications mention that the results are inconclusive, and o-tyrosine is not selectively altered by antioxidant intervention, exercise training or age. (PMID: 14670743 , 10969271 , 9887186 ).
Structure
Thumb
Synonyms
ValueSource
2-TyrosineMetaCyc
DL-O-TyrosineMetaCyc
ortho-TyrosineMetaCyc
O-TyrosineMetaCyc
DL-3-(O-Hydroxyphenyl)alanineMetaCyc
2-amino-3-(2-Hydroxyphenyl)propanoateGenerator
2-Hydroxy-DL-phenylalanineHMDB
2-Hydroxy-phenylalanineHMDB
2-HydroxyphenylalanineHMDB
3-(O-Hydroxyphenyl)DL-alanineHMDB
DL- O-TyrosineHMDB
Chemical FormulaC9H11NO3
Average Molecular Weight181.1885
Monoisotopic Molecular Weight181.073893223
IUPAC Name2-amino-3-(2-hydroxyphenyl)propanoic acid
Traditional Name2-tyrosine
CAS Registry Number2370-61-8
SMILES
NC(CC1=CC=CC=C1O)C(O)=O
InChI Identifier
InChI=1S/C9H11NO3/c10-7(9(12)13)5-6-3-1-2-4-8(6)11/h1-4,7,11H,5,10H2,(H,12,13)
InChI KeyInChIKey=WRFPVMFCRNYQNR-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • Amphetamine or derivatives
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Aralkylamine
  • Phenol
  • Amino fatty acid
  • Fatty acyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point262 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2 mg/mL at 17 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.57 mg/mLALOGPS
logP-2.3ALOGPS
logP-1.5ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)2.01ChemAxon
pKa (Strongest Basic)8.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.1 m3·mol-1ChemAxon
Polarizability17.76 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0900000000-ebb473b1eb9270c27a26View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-015i-0900000000-d3b4c59468db65e33b80View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00kf-9700000000-cf7cdfd040ca5a451fa2View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)FemaleNormal details
UrineDetected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023822
KNApSAcK IDNot Available
Chemspider ID82607
KEGG Compound IDNot Available
BioCyc IDCPD0-923
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06050
Metagene LinkHMDB06050
METLIN IDNot Available
PubChem Compound91482
PDB IDNot Available
ChEBI ID278475
References
Synthesis ReferenceKokotos, George; Tzougraki, Chrysa. Synthesis and study of substituted coumarins. A facile preparation of D,L-o-tyrosine. Journal of Heterocyclic Chemistry (1986), 23(1), 87-92
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Orhan H, Vermeulen NP, Tump C, Zappey H, Meerman JH: Simultaneous determination of tyrosine, phenylalanine and deoxyguanosine oxidation products by liquid chromatography-tandem mass spectrometry as non-invasive biomarkers for oxidative damage. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Jan 25;799(2):245-54. [14670743 ]
  2. Manary MJ, Leeuwenburgh C, Heinecke JW: Increased oxidative stress in kwashiorkor. J Pediatr. 2000 Sep;137(3):421-4. [10969271 ]
  3. Leeuwenburgh C, Hansen PA, Holloszy JO, Heinecke JW: Oxidized amino acids in the urine of aging rats: potential markers for assessing oxidative stress in vivo. Am J Physiol. 1999 Jan;276(1 Pt 2):R128-35. [9887186 ]