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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2014-12-01 23:18:16 UTC
HMDB IDHMDB00158
Secondary Accession Numbers
  • HMDB00647
Metabolite Identification
Common NameL-Tyrosine
DescriptionTyrosine is an essential amino acid that readily passes the blood-brain barrier. Once in the brain, it is a precursor for the neurotransmitters dopamine, norepinephrine and epinephrine, better known as adrenalin. These neurotransmitters are an important part of the body's sympathetic nervous system, and their concentrations in the body and brain are directly dependent upon dietary tyrosine. Tyrosine is not found in large concentrations throughout the body, probably because it is rapidly metabolized. Folic acid, copper and vitamin C are cofactor nutrients of these reactions. Tyrosine is also the precursor for hormones, thyroid, catecholestrogens and the major human pigment, melanin. Tyrosine is an important amino acid in many proteins, peptides and even enkephalins, the body's natural pain reliever. Valine and other branched amino acids, and possibly tryptophan and phenylalanine may reduce tyrosine absorption. A number of genetic errors of tyrosine metabolism occur. Most common is the increased amount of tyrosine in the blood of premature infants, which is marked by decreased motor activity, lethargy and poor feeding. Infection and intellectual deficits may occur. Vitamin C supplements reverse the disease. Some adults also develop elevated tyrosine in their blood. This indicates a need for more vitamin C. More tyrosine is needed under stress, and tyrosine supplements prevent the stress-induced depletion of norepinephrine and can cure biochemical depression. However, tyrosine may not be good for psychosis. Many antipsychotic medications apparently function by inhibiting tyrosine metabolism. L-dopa, which is directly used in Parkinson's, is made from tyrosine. Tyrosine, the nutrient, can be used as an adjunct in the treatment of Parkinson's. Peripheral metabolism of tyrosine necessitates large doses of tyrosine, however, compared to L-dopa. (http://www.dcnutrition.com).
Structure
Thumb
Synonyms
  1. (-)-a-Amino-p-hydroxyhydrocinnamate
  2. (-)-a-Amino-p-hydroxyhydrocinnamic acid
  3. (-)-alpha-Amino-p-hydroxyhydrocinnamate
  4. (-)-alpha-Amino-p-hydroxyhydrocinnamic acid
  5. (S)-(-)-Tyrosine
  6. (S)-2-Amino-3-(p-hydroxyphenyl)propionate
  7. (S)-2-Amino-3-(p-hydroxyphenyl)propionic acid
  8. (S)-3-(p-Hydroxyphenyl)alanine
  9. (S)-a-amino-4-hydroxy-Benzenepropanoate
  10. (S)-a-amino-4-hydroxy-Benzenepropanoic acid
  11. (S)-a-Amino-4-hydroxybenzenepropanoate
  12. (S)-a-Amino-4-hydroxybenzenepropanoic acid
  13. (S)-alpha-amino-4-hydroxy-Benzenepropanoate
  14. (S)-alpha-amino-4-hydroxy-Benzenepropanoic acid
  15. (S)-alpha-Amino-4-hydroxybenzenepropanoate
  16. (S)-alpha-Amino-4-hydroxybenzenepropanoic acid
  17. (S)-Tyrosine
  18. 2-Amino-3-(4-hydroxyphen yl)-2-amino-3-(4-hydroxyphenyl)-Propanoate
  19. 2-Amino-3-(4-hydroxyphen yl)-2-amino-3-(4-hydroxyphenyl)-Propanoic acid
  20. 3-(4-Hydroxyphenyl)-L-alanine
  21. 4-Hydroxy-L-Phenylalanine
  22. Benzenepropanoate
  23. Benzenepropanoic acid
  24. L-p-Tyrosine
  25. L-Tyrosine
  26. p-Tyrosine
  27. Tyr
  28. Tyrosine
Chemical FormulaC9H11NO3
Average Molecular Weight181.1885
Monoisotopic Molecular Weight181.073893223
IUPAC Name(2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid
Traditional NameL-tyrosine
CAS Registry Number60-18-4
SMILES
N[C@@H](CC1=CC=C(O)C=C1)C(O)=O
InChI Identifier
InChI=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)/t8-/m0/s1
InChI KeyOUYCCCASQSFEME-QMMMGPOBSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassAmino Acids and Derivatives
Sub ClassAlpha Amino Acids and Derivatives
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • alpha-amino acid(ChEBI)
  • aromatic amino acid(ChEBI)
Substituents
  • Amphetamine Or Derivative
  • Carboxylic Acid
  • Phenethylamine
  • Phenol
  • Phenol Derivative
  • Primary Aliphatic Amine (Alkylamine)
Direct ParentAlpha Amino Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Aminoacyl-tRNA biosynthesis
  • Component of Novobiocin biosynthesis
  • Component of Phenylalanine metabolism
  • Component of Phenylalanine, tyrosine and tryptophan biosynthesis
  • Component of Riboflavin metabolism
  • Component of Stilbene, coumarine and lignin biosynthesis
  • Component of Tyrosine metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point343 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.479 mg/mLNot Available
LogP-2.26HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility7.67ALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.1 m3·mol-1ChemAxon
Polarizability18.19 Å3ChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Location
  • All Tissues
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Catecholamine BiosynthesisSMP00012map00350
Phenylalanine and Tyrosine MetabolismSMP00008map00360
Transcription/TranslationSMP00019Not Available
Tyrosine MetabolismSMP00006map00350
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified54.5 +/- 9.7 uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified143 +/- 35.3 uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified59.0 (47.0-71.0) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified120.0 +/- 100.0 uMNewborn (0-30 days old)Not SpecifiedNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified68.0 +/- 10.0 uMChildren (1-13 years old)MaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified72.0 +/- 15.0 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified61.0 +/- 13.0 uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified100.00 (55.00-147.00) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified142.0 +/- 4.0 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified10.1 (6.37-13.8) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified12.0 +/- 9.0 uMNot SpecifiedBothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified24.5 +/- 8.9 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified6.4 +/- 1.5 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified9.3 +/- 2.0 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified7.9 +/- 3.0 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified12.2 +/- 3.8 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified8.0 +/- 1.0 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified114.246 +/- 94.322 uMNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
SalivaDetected and Quantified36.17 +/- 15.02 uMAdult (>18 years old)FemaleNormal details
SalivaDetected and Quantified>10 uMAdult (>18 years old)BothNormal details
SalivaDetected and Quantified5 (<1-78) uMAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified1-77 uMAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified30 (<1-91) uMAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified12 (<1-49) uMAdult (>18 years old)Female
Normal
details
SalivaDetected and Quantified11.1 +/- 7.65 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified15.1 +/- 10.3 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
SalivaDetected and Quantified1-127 uMAdult (>18 years old)Male
normal
details
SalivaDetected and Quantified1-68 uMAdult (>18 years old)Male
normal
details
SalivaDetected and Quantified13.7 +/- 3.6 uMAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified12.0 +/- 5.8 uMAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified11.8 +/- 6.2 uMAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected and Quantified39.85 +/- 24.71 uMAdult (>18 years old)BothNormal
    • Dame, ZT. et al. ...
details
SalivaDetected and Quantified12.2 +/- 3.8 uMAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified15.1 (6.1-23.2) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified21.0 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified5.52-38.66 umol/mmol creatinineAdult (>18 years old)BothNormal
    • David F. Putnam C...
details
UrineDetected and Quantified9.5 (4.1-23.5) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified6.72 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Shaykhutdinov RA,...
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified27.35 +/- 13.98 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified7.41 +/- 2.30 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified8.7 (3.0-20.1) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.72 (0.18-1.38) umol/mmol creatinineNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified4.2 +/- 1.85 umol/mmol creatinineChildren (1-13 years old)MaleNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified8.8 +/- 4.5 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified7.0 +/- 3.0 umol/mmol creatinineAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified7.5 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified10.9 (2.566-19.1) umol/mmol creatinineAdult (>18 years old)BothNormal
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    BloodDetected and Quantified91.2 +/- 30.0 uMAdult (>18 years old)MaleSchizophrenia details
    BloodDetected and Quantified73.0 +/- 20.0 uMAdult (>18 years old)FemaleSchizophrenia details
    BloodDetected and Quantified57.2 +/- 24.4 uMAdult (>18 years old)Not SpecifiedHeart Transplant details
    BloodDetected and Quantified50.7 (46.8-54.6) uMAdult (>18 years old)Both
    Epilepsy
    details
    BloodDetected and Quantified74.0 (71.0-77.0) uMAdult (>18 years old)BothMyocardial infarction details
    BloodDetected and Quantified81.0 (75.9-86.1) uMAdult (>18 years old)Both
    Epilepsy
    details
    BloodDetected and Quantified90.0 (81.0-99.0) uMAdult (>18 years old)BothViral Infection details
    BloodDetected and Quantified300.0 (150.00-450.00) uMChildren (1-13 years old)BothHawkinsinuria details
    BloodDetected and Quantified143.77 +/- 15.49 uMElderly (>65 years old)BothAlzheimer's disease details
    Cerebrospinal Fluid (CSF)Detected and Quantified15.3 (10.4-20.2) uMAdult (>18 years old)BothHypothyroidism details
    Cerebrospinal Fluid (CSF)Detected and Quantified14.2 +/-12.5 uMAdult (>18 years old)Not SpecifiedEpilepsy details
    Cerebrospinal Fluid (CSF)Detected and Quantified13.0 +/- 10.6 uMAdult (>18 years old)Not SpecifiedEpilepsy details
    Cerebrospinal Fluid (CSF)Detected and Quantified12.3 +/- 9.3 uMAdult (>18 years old)Not SpecifiedEpilepsy details
    Cerebrospinal Fluid (CSF)Detected and Quantified9.4 +/- 4.9 uMAdult (>18 years old)Not SpecifiedEpilepsy details
    Cerebrospinal Fluid (CSF)Detected and Quantified8.05 +/- 3.03 uMAdult (>18 years old)Not SpecifiedEpilepsy details
    Cerebrospinal Fluid (CSF)Detected and Quantified27.18 +/- 4.8 uMAdult (>18 years old)BothAlzheimer's disease details
    Cerebrospinal Fluid (CSF)Detected and Quantified13.0 +/- 4.1 uMChildren (1-13 years old)BothLeukemia details
    Cerebrospinal Fluid (CSF)Detected and Quantified12.6 +/- 3.3 uMChildren (1-13 years old)Both
    Leukemia
    details
    Cerebrospinal Fluid (CSF)Detected and Quantified15.3 +/- 4.9 uMAdult (>18 years old)Not Specifiedhypothyroidism details
    Cerebrospinal Fluid (CSF)Detected and Quantified15.3 +/- 4.9 uMAdult (>18 years old)BothHypothyroidism details
    Cerebrospinal Fluid (CSF)Detected and Quantified7.8 +/- 1.38 uMAdult (>18 years old)BothSchizophrenia details
    FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
    Irritable bowel syndrome
    details
    FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
    Ulcerative colitis
    details
    SalivaDetected and Quantified21.64 +/- 9.24 uMAdult (>18 years old)MaleAlzheimer's disease details
    SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothOral cancer details
    SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)FemaleBreast cancer details
    SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedPancreatic cancer details
    SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedPeriodontal diseases details
    SalivaDetected and Quantified25.82 +/- 9.25 uMAdult (>18 years old)MaleFrontotemporal lobe dementia details
    SalivaDetected and Quantified25.05 +/- 8.02 uMAdult (>18 years old)BothLewy body disease details
    UrineDetected and Quantified10.5 +/- 1.5 umol/mmol creatinineAdult (>18 years old)BothAlzheimer's disease details
    UrineDetected and Quantified10.72 +/- 4.63 umol/mmol creatinineAdult (>18 years old)Not SpecifiedCachexia details
    Associated Disorders and Diseases
    Disease References
    Alzheimer's disease
    1. Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. Pubmed: 17031479
    Cachexia
    1. Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2008 Oct 25. Pubmed: 18953024
    Epilepsy
    1. Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. Pubmed: 14992292
    2. Botez MI, Young SN: Effects of anticonvulsant treatment and low levels of folate and thiamine on amine metabolites in cerebrospinal fluid. Brain. 1991 Feb;114 ( Pt 1A):333-48. Pubmed: 1705463
    Schizophrenia
    1. Alfredsson G, Wiesel FA: Monoamine metabolites and amino acids in serum from schizophrenic patients before and during sulpiride treatment. Psychopharmacology (Berl). 1989;99(3):322-7. Pubmed: 2480613
    2. Do KQ, Lauer CJ, Schreiber W, Zollinger M, Gutteck-Amsler U, Cuenod M, Holsboer F: gamma-Glutamylglutamine and taurine concentrations are decreased in the cerebrospinal fluid of drug-naive patients with schizophrenic disorders. J Neurochem. 1995 Dec;65(6):2652-62. Pubmed: 7595563
    Hawkinsinuria
    1. MetaGene
    Hypothyroidism
    1. Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. Pubmed: 9849813
    Leukemia
    1. Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. Pubmed: 15911239
    Myocardial infarction
    1. Wannemacher RW Jr, Klainer AS, Dinterman RE, Beisel WR: The significance and mechanism of an increased serum phenylalanine-tyrosine ratio during infection. Am J Clin Nutr. 1976 Sep;29(9):997-1006. Pubmed: 822705
    Viral infection
    1. Wannemacher RW Jr, Klainer AS, Dinterman RE, Beisel WR: The significance and mechanism of an increased serum phenylalanine-tyrosine ratio during infection. Am J Clin Nutr. 1976 Sep;29(9):997-1006. Pubmed: 822705
    Associated OMIM IDs
    DrugBank IDDB00135
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB000446
    KNApSAcK IDC00001397
    Chemspider ID5833
    KEGG Compound IDC00082
    BioCyc IDTYR
    BiGG ID33785
    Wikipedia LinkL-Tyrosine
    NuGOwiki LinkHMDB00158
    Metagene LinkHMDB00158
    METLIN ID34
    PubChem Compound6057
    PDB IDTYR
    ChEBI ID17895
    References
    Synthesis ReferenceEnei, Hitoshi; Matsui, Hiroshi; Yamashita, Koichi; Okumura, Shinji; Yamada, Hideaki. Microbiological synthesis of L-tyrosine and 3,4-dihydroxyphenyl-L-alanine. I. Distribution of tyrosine phenol lyase in microorganisms. Agricultural and Biological Chemist
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
    2. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. Pubmed: 12097436
    3. Nicholson JK, O'Flynn MP, Sadler PJ, Macleod AF, Juul SM, Sonksen PH: Proton-nuclear-magnetic-resonance studies of serum, plasma and urine from fasting normal and diabetic subjects. Biochem J. 1984 Jan 15;217(2):365-75. Pubmed: 6696735
    4. Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50. Pubmed: 12834252
    5. Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. Pubmed: 9849813
    6. Eklundh T, Eriksson M, Sjoberg S, Nordin C: Monoamine precursors, transmitters and metabolites in cerebrospinal fluid: a prospective study in healthy male subjects. J Psychiatr Res. 1996 May-Jun;30(3):201-8. Pubmed: 8884658
    7. Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7. Pubmed: 6198473
    8. Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. Pubmed: 15911239
    9. Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. Pubmed: 12297216
    10. Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. Pubmed: 14992292
    11. Deng C, Shang C, Hu Y, Zhang X: Rapid diagnosis of phenylketonuria and other aminoacidemias by quantitative analysis of amino acids in neonatal blood spots by gas chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Jul 25;775(1):115-20. Pubmed: 12101068
    12. Flamen P, Bernheim N, Deron P, Caveliers V, Chavatte K, Franken PR, Bossuyt A: Iodine-123 alpha-methyl-l-tyrosine single-photon emission tomography for the visualization of head and neck squamous cell carcinomas. Eur J Nucl Med. 1998 Feb;25(2):177-81. Pubmed: 9473267
    13. Ishiwata K, Tsukada H, Kubota K, Nariai T, Harada N, Kawamura K, Kimura Y, Oda K, Iwata R, Ishii K: Preclinical and clinical evaluation of O-[11C]methyl-L-tyrosine for tumor imaging by positron emission tomography. Nucl Med Biol. 2005 Apr;32(3):253-62. Pubmed: 15820760
    14. Wannemacher RW Jr, Klainer AS, Dinterman RE, Beisel WR: The significance and mechanism of an increased serum phenylalanine-tyrosine ratio during infection. Am J Clin Nutr. 1976 Sep;29(9):997-1006. Pubmed: 822705
    15. Molnar GA, Wagner Z, Marko L, Ko Szegi T, Mohas M, Kocsis B, Matus Z, Wagner L, Tamasko M, Mazak I, Laczy B, Nagy J, Wittmann I: Urinary ortho-tyrosine excretion in diabetes mellitus and renal failure: evidence for hydroxyl radical production. Kidney Int. 2005 Nov;68(5):2281-7. Pubmed: 16221230
    16. Molnar GA, Nemes V, Biro Z, Ludany A, Wagner Z, Wittmann I: Accumulation of the hydroxyl free radical markers meta-, ortho-tyrosine and DOPA in cataractous lenses is accompanied by a lower protein and phenylalanine content of the water-soluble phase. Free Radic Res. 2005 Dec;39(12):1359-66. Pubmed: 16298866
    17. Hoffhines AJ, Damoc E, Bridges KG, Leary JA, Moore KL: Detection and purification of tyrosine-sulfated proteins using a novel anti-sulfotyrosine monoclonal antibody. J Biol Chem. 2006 Dec 8;281(49):37877-87. Epub 2006 Oct 17. Pubmed: 17046811

    Enzymes

    General function:
    Involved in oxidoreductase activity
    Specific function:
    This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
    Gene Name:
    TYR
    Uniprot ID:
    P14679
    Molecular weight:
    60392.69
    Reactions
    L-Tyrosine + Oxygen → Dopaquinone + Waterdetails
    L-Tyrosine + Oxygen → L-Dopa + Waterdetails
    L-Dopa + L-Tyrosine + Oxygen → Dopaquinone + L-Dopa + Waterdetails
    General function:
    Involved in monooxygenase activity
    Specific function:
    Plays an important role in the physiology of adrenergic neurons.
    Gene Name:
    TH
    Uniprot ID:
    P07101
    Molecular weight:
    55611.26
    Reactions
    L-Tyrosine + L-erythro-tetrahydrobiopterin + Oxygen → L-Dopa + 4a-Hydroxytetrahydrobiopterindetails
    L-erythro-tetrahydrobiopterin + L-Tyrosine + Oxygen → L-Dopa + 4a-Carbinolamine tetrahydrobiopterin + Waterdetails
    References
    1. Olsovska J, Novotna J, Flieger M, Spizek J: Assay of tyrosine hydroxylase based on high-performance liquid chromatography separation and quantification of L-dopa and L-tyrosine. Biomed Chromatogr. 2007 Dec;21(12):1252-8. Pubmed: 17604359
    2. Bodnar I, Hechtl D, Szekacs D, Olah M, Nagy GM: Effect of local (intracerebral and intracerebroventricular) administration of tyrosine hydroxylase inhibitor on the neuroendocrine dopaminergic neurons and prolactin release. Ideggyogy Sz. 2007 Mar 30;60(3-4):177-81. Pubmed: 17451064
    3. Rostrup M, Fossbakk A, Hauge A, Kleppe R, Gnaiger E, Haavik J: Oxygen dependence of tyrosine hydroxylase. Amino Acids. 2008 Apr;34(3):455-64. Epub 2007 May 23. Pubmed: 17520326
    4. Richards AB, Scheel TA, Wang K, Henkemeyer M, Kromer LF: EphB1 null mice exhibit neuronal loss in substantia nigra pars reticulata and spontaneous locomotor hyperactivity. Eur J Neurosci. 2007 May;25(9):2619-28. Pubmed: 17561836
    5. Ugriumov MV: [Brain neurons partly expressing monoaminergic phenotype: distribution, development, and functional significance]. Usp Fiziol Nauk. 2007 Apr-Jun;38(2):3-25. Pubmed: 17578016
    6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed: 11752352
    General function:
    Involved in calcium ion binding
    Specific function:
    Iodination and coupling of the hormonogenic tyrosines in thyroglobulin to yield the thyroid hormones T(3) and T(4).
    Gene Name:
    TPO
    Uniprot ID:
    P07202
    Molecular weight:
    102961.63
    Reactions
    I(-) + Iodotyrosine → Iodine + L-Tyrosinedetails
    General function:
    Involved in 1-aminocyclopropane-1-carboxylate synthase activity
    Specific function:
    Transaminase involved in tyrosine breakdown. Converts tyrosine to p-hydroxyphenylpyruvate. Can catalyze the reverse reaction, using glutamic acid, with 2-oxoglutarate as cosubstrate (in vitro). Has much lower affinity and transaminase activity towards phenylalanine.
    Gene Name:
    TAT
    Uniprot ID:
    P17735
    Molecular weight:
    50398.895
    Reactions
    L-Tyrosine + Oxoglutaric acid → 4-Hydroxyphenylpyruvic acid + L-Glutamic aciddetails
    References
    1. Dong S, Kang S, Gu TL, Kardar S, Fu H, Lonial S, Khoury HJ, Khuri F, Chen J: 14-3-3 Integrates prosurvival signals mediated by the AKT and MAPK pathways in ZNF198-FGFR1-transformed hematopoietic cells. Blood. 2007 Jul 1;110(1):360-9. Epub 2007 Mar 27. Pubmed: 17389761
    General function:
    Involved in carboxy-lyase activity
    Specific function:
    Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
    Gene Name:
    DDC
    Uniprot ID:
    P20711
    Molecular weight:
    53893.755
    Reactions
    L-Tyrosine → Tyramine + Carbon dioxidedetails
    General function:
    Involved in amino acid binding
    Specific function:
    Not Available
    Gene Name:
    PAH
    Uniprot ID:
    P00439
    Molecular weight:
    51861.565
    Reactions
    L-Phenylalanine + L-erythro-tetrahydrobiopterin + Oxygen → L-Tyrosine + 4a-Hydroxytetrahydrobiopterindetails
    L-erythro-tetrahydrobiopterin + L-Phenylalanine + Oxygen → 4a-Carbinolamine tetrahydrobiopterin + L-Tyrosine + Waterdetails
    General function:
    Involved in transferase activity, transferring nitrogenous groups
    Specific function:
    Plays a key role in amino acid metabolism (By similarity).
    Gene Name:
    GOT1
    Uniprot ID:
    P17174
    Molecular weight:
    46247.14
    Reactions
    L-Tyrosine + Oxoglutaric acid → 4-Hydroxyphenylpyruvic acid + L-Glutamic aciddetails
    General function:
    Involved in transferase activity, transferring nitrogenous groups
    Specific function:
    Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
    Gene Name:
    GOT2
    Uniprot ID:
    P00505
    Molecular weight:
    47517.285
    Reactions
    L-Tyrosine + Oxoglutaric acid → 4-Hydroxyphenylpyruvic acid + L-Glutamic aciddetails
    General function:
    Involved in nucleotide binding
    Specific function:
    Catalyzes the attachment of tyrosine to tRNA(Tyr) in a two-step reaction: tyrosine is first activated by ATP to form Tyr-AMP and then transferred to the acceptor end of tRNA(Tyr) (By similarity).
    Gene Name:
    YARS
    Uniprot ID:
    P54577
    Molecular weight:
    59143.025
    Reactions
    Adenosine triphosphate + L-Tyrosine + tRNA(Tyr) → Adenosine monophosphate + Pyrophosphate + L-tyrosyl-tRNA(Tyr)details
    Adenosine triphosphate + L-Tyrosine + tRNA(Tyr) → Adenosine monophosphate + Pyrophosphate + L-Tyrosyl-tRNA(Tyr)details
    References
    1. Bonnefond L, Frugier M, Touze E, Lorber B, Florentz C, Giege R, Rudinger-Thirion J, Sauter C: Tyrosyl-tRNA synthetase: the first crystallization of a human mitochondrial aminoacyl-tRNA synthetase. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2007 Apr 1;63(Pt 4):338-41. Epub 2007 Mar 30. Pubmed: 17401211
    General function:
    Involved in nucleotide binding
    Specific function:
    Catalyzes the attachment of tyrosine to tRNA(Tyr) in a two-step reaction: tyrosine is first activated by ATP to form Tyr-AMP and then transferred to the acceptor end of tRNA(Tyr) (By similarity).
    Gene Name:
    YARS2
    Uniprot ID:
    Q9Y2Z4
    Molecular weight:
    53198.56
    Reactions
    Adenosine triphosphate + L-Tyrosine + tRNA(Tyr) → Adenosine monophosphate + Pyrophosphate + L-tyrosyl-tRNA(Tyr)details
    Adenosine triphosphate + L-Tyrosine + tRNA(Tyr) → Adenosine monophosphate + Pyrophosphate + L-Tyrosyl-tRNA(Tyr)details
    References
    1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
    2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423
    3. Zhang Y, Wang L, Schultz PG, Wilson IA: Crystal structures of apo wild-type M. jannaschii tyrosyl-tRNA synthetase (TyrRS) and an engineered TyrRS specific for O-methyl-L-tyrosine. Protein Sci. 2005 May;14(5):1340-9. Pubmed: 15840835
    4. Kiga D, Sakamoto K, Kodama K, Kigawa T, Matsuda T, Yabuki T, Shirouzu M, Harada Y, Nakayama H, Takio K, Hasegawa Y, Endo Y, Hirao I, Yokoyama S: An engineered Escherichia coli tyrosyl-tRNA synthetase for site-specific incorporation of an unnatural amino acid into proteins in eukaryotic translation and its application in a wheat germ cell-free system. Proc Natl Acad Sci U S A. 2002 Jul 23;99(15):9715-20. Epub 2002 Jul 3. Pubmed: 12097643
    5. Kobayashi T, Nureki O, Ishitani R, Yaremchuk A, Tukalo M, Cusack S, Sakamoto K, Yokoyama S: Structural basis for orthogonal tRNA specificities of tyrosyl-tRNA synthetases for genetic code expansion. Nat Struct Biol. 2003 Jun;10(6):425-32. Pubmed: 12754495
    General function:
    Involved in protein kinase activity
    Specific function:
    Receptor for basic fibroblast growth factor. Receptor for FGF23 in the presence of KL. A shorter form of the receptor could be a receptor for FGF1 (aFGF)
    Gene Name:
    FGFR1
    Uniprot ID:
    P11362
    Molecular weight:
    91866.9
    General function:
    Involved in transmembrane receptor protein tyrosine kinase activity
    Specific function:
    Isoform 2 may act as an antagonist of EGF action
    Gene Name:
    EGFR
    Uniprot ID:
    P00533
    Molecular weight:
    134276.2
    General function:
    Involved in oxidoreductase activity
    Specific function:
    Lysosomal L-amino-acid oxidase with highest specific activity with phenylalanine. May play a role in lysosomal antigen processing and presentation (By similarity).
    Gene Name:
    IL4I1
    Uniprot ID:
    Q96RQ9
    Molecular weight:
    65327.26
    Reactions
    L-Tyrosine + Water + Oxygen → 4-Hydroxyphenylpyruvic acid + Ammonia + Hydrogen peroxidedetails
    General function:
    Involved in oxidoreductase activity
    Specific function:
    Catalyzes the oxidative NADPH-dependent deiodination of monoiodotyrosine (L-MIT) or diiodotyrosine (L-DIT). Acts during the hydrolysis of thyroglobulin to liberate iodide, which can then reenter the hormone-producing pathways. Acts more efficiently on monoiodotyrosine than on diiodotyrosine.
    Gene Name:
    IYD
    Uniprot ID:
    Q6PHW0
    Molecular weight:
    33781.22
    Reactions
    L-Tyrosine + NADP + I(-) → 3,5-Diiodo-L-tyrosine + NADPHdetails
    General function:
    Involved in catalytic activity
    Specific function:
    Catalyzes the post-translational addition of a tyrosine to the C-terminal end of detyrosinated alpha-tubulin (By similarity).
    Gene Name:
    TTL
    Uniprot ID:
    Q8NG68
    Molecular weight:
    43211.94
    Reactions
    Adenosine triphosphate + detyrosinated alpha-tubulin + L-Tyrosine → alpha-tubulin + ADP + Phosphoric aciddetails

    Transporters

    General function:
    Involved in transmembrane transport
    Specific function:
    Very active and specific thyroid hormone transporter. Stimulates cellular uptake of thyroxine (T4), triiodothyronine (T3), reverse triiodothyronine (rT3) and diidothyronine. Does not transport Leu, Phe, Trp or Tyr
    Gene Name:
    SLC16A2
    Uniprot ID:
    P36021
    Molecular weight:
    59510.9
    References
    1. Friesema EC, Ganguly S, Abdalla A, Manning Fox JE, Halestrap AP, Visser TJ: Identification of monocarboxylate transporter 8 as a specific thyroid hormone transporter. J Biol Chem. 2003 Oct 10;278(41):40128-35. Epub 2003 Jul 18. Pubmed: 12871948
    General function:
    Involved in transmembrane transport
    Specific function:
    Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells
    Gene Name:
    SLC16A10
    Uniprot ID:
    Q8TF71
    Molecular weight:
    55492.1
    References
    1. Kim DK, Kanai Y, Matsuo H, Kim JY, Chairoungdua A, Kobayashi Y, Enomoto A, Cha SH, Goya T, Endou H: The human T-type amino acid transporter-1: characterization, gene organization, and chromosomal location. Genomics. 2002 Jan;79(1):95-103. Pubmed: 11827462
    2. Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. Pubmed: 11278508