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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2007-04-12 21:16:46 UTC
Update Date2023-02-21 17:17:14 UTC
HMDB IDHMDB0006050
Secondary Accession Numbers
  • HMDB06050
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-Amino-3-(2-hydroxyphenyl)propanoic acidChEBI
2-Amino-3-(2-hydroxyphenyl)propanoateGenerator
2-Hydroxy-DL-phenylalanineHMDB
2-Hydroxy-phenylalanineHMDB
2-HydroxyphenylalanineHMDB
2-TyrosineHMDB
3-(O-Hydroxyphenyl)DL-alanineHMDB
DL- O-TyrosineHMDB
DL-3-(O-Hydroxyphenyl)alanineHMDB
DL-O-TyrosineHMDB
Ortho-tyrosineHMDB
2-Tyrosine, (D)-isomerHMDB
2-Tyrosine, (DL)-isomerHMDB
2-Tyrosine, (L)-isomerHMDB
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 KeyWRFPVMFCRNYQNR-UHFFFAOYSA-N
Chemical Taxonomy
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
  • Amphetamine or derivatives
  • Alpha-amino acid
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point262 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2 mg/mL at 17 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available134.252http://allccs.zhulab.cn/database/detail?ID=AllCCS00000065
[M+H]+Not Available141.898http://allccs.zhulab.cn/database/detail?ID=AllCCS00000065
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleNormal details
UrineDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023822
KNApSAcK IDNot Available
Chemspider ID82607
KEGG Compound IDNot Available
BioCyc IDCPD0-923
BiGG IDNot Available
Wikipedia LinkTyrosine
METLIN IDNot Available
PubChem Compound91482
PDB IDNot Available
ChEBI ID91038
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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)Not Available
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. [PubMed:14670743 ]
  2. Manary MJ, Leeuwenburgh C, Heinecke JW: Increased oxidative stress in kwashiorkor. J Pediatr. 2000 Sep;137(3):421-4. [PubMed: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. [PubMed:9887186 ]