Human Metabolome Database Version 3.5

Showing metabocard for L-Tyrosine (HMDB00158)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:00 -0700
HMDB ID HMDB00158
Secondary Accession Numbers
  • HMDB00647
Metabolite Identification
Common Name L-Tyrosine
Description Tyrosine 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C9H11NO3
Average Molecular Weight 181.1885
Monoisotopic Molecular Weight 181.073893223
IUPAC Name (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid
Traditional IUPAC Name L-tyrosine
CAS Registry Number 60-18-4
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 Key OUYCCCASQSFEME-QMMMGPOBSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha 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 Parent Alpha Amino Acids and Derivatives
Ontology
Status Detected 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
Application Not Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 343 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 0.479 mg/mL Not Available
LogP -2.26 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 7.67 g/L ALOGPS
LogP -2.39 ALOGPS
LogP -1.5 ChemAxon
LogS -1.37 ALOGPS
pKa (strongest acidic) 2 ChemAxon
pKa (strongest basic) 9.19 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 83.55 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 47.1 ChemAxon
Polarizability 18.19 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
13C NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • All Tissues
  • Prostate
Pathways
Name SMPDB Link KEGG Link
Tyrosine Metabolism SMP00006 map00350 Link_out
Transcription/Translation SMP00019 Not Available
Phenylalanine and Tyrosine Metabolism SMP00008 map00360 Link_out
Catecholamine Biosynthesis SMP00012 map00350 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
54.5 +/- 9.7 uM Adult (>18 years old) Not Specified Normal
Blood Detected and Quantified
143 +/- 35.3 uM Adult (>18 years old) Not Specified Normal
Blood Detected and Quantified
59.0 (47.0-71.0) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
120.0 +/- 100.0 uM Newborn (0-30 days old) Not Specified Normal
  • Geigy Scient...
Blood Detected and Quantified
68.0 +/- 10.0 uM Children (1-13 year old) Male Normal
  • Geigy Scient...
Blood Detected and Quantified
72.0 +/- 15.0 uM Adult (>18 years old) Male Normal
  • Geigy Scient...
Blood Detected and Quantified
61.0 +/- 13.0 uM Adult (>18 years old) Female Normal
  • Geigy Scient...
Blood Detected and Quantified
100.00 (55.00-147.00) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
142.0 +/- 4.0 uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
10.1 (6.37-13.8) uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
12.0 +/- 9.0 uM Not Specified Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
24.5 +/- 8.9 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
6.4 +/- 1.5 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
9.3 +/- 2.0 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
7.9 +/- 3.0 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
12.2 +/- 3.8 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
8.0 +/- 1.0 uM Adult (>18 years old) Both Normal
Saliva Detected and Quantified
>10 uM Adult (>18 years old) Both Normal
Saliva Detected and Quantified
1-127 uM Adult (>18 years old) Male Comment normal
Saliva Detected and Quantified
1-68 uM Adult (>18 years old) Male Comment normal
Urine Detected and Quantified
15.1 (6.1-23.2) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
21.0 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
5.52-38.66 umol/mmol creatinine Adult (>18 years old) Both Normal
  • David F. Put...
Urine Detected and Quantified
9.5 (4.1-23.5) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
6.72 umol/mmol creatinine Adult (>18 years old) Male Normal
  • Shaykhutdino...
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Comment Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Male Comment Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Male Comment Normal
Urine Detected and Quantified
27.35 +/- 13.98 umol/mmol creatinine Infant (0-1 year old) Both Normal
Urine Detected and Quantified
7.41 +/- 2.30 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
8.7 (3.0-20.1) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
0.72 (0.18-1.38) umol/mmol creatinine Newborn (0-30 days old) Both Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Urine Detected and Quantified
4.2 +/- 1.85 umol/mmol creatinine Children (1-13 year old) Male Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Urine Detected and Quantified
8.8 +/- 4.5 umol/mmol creatinine Adult (>18 years old) Male Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Urine Detected and Quantified
7.0 +/- 3.0 umol/mmol creatinine Adult (>18 years old) Female Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Urine Detected and Quantified
7.5 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
10.9 (2.566-19.1) umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 91.2 +/- 30.0 uM Adult (>18 years old) Male Schizophrenia
Blood Detected and Quantified 73.0 +/- 20.0 uM Adult (>18 years old) Female Schizophrenia
Blood Detected and Quantified 57.2 +/- 24.4 uM Adult (>18 years old) Not Specified Heart Transplant
Blood Detected and Quantified 50.7 (46.8-54.6) uM Adult (>18 years old) Both Comment Epilepsy
Blood Detected and Quantified 74.0 (71.0-77.0) uM Adult (>18 years old) Both Myocardial infarction
Blood Detected and Quantified 81.0 (75.9-86.1) uM Adult (>18 years old) Both Comment Epilepsy
Blood Detected and Quantified 90.0 (81.0-99.0) uM Adult (>18 years old) Both Viral Infection
Blood Detected and Quantified 300.0 (150.00-450.00) uM Children (1-13 year old) Both Hawkinsinuria
Blood Detected and Quantified 143.77 +/- 15.49 uM Elderly (>65 years old) Both Alzheimer's disease
Cerebrospinal Fluid (CSF) Detected and Quantified 15.3 (10.4-20.2) uM Adult (>18 years old) Both Hypothyroidism
Cerebrospinal Fluid (CSF) Detected and Quantified 14.2 +/-12.5 uM Adult (>18 years old) Not Specified Epilepsy
Cerebrospinal Fluid (CSF) Detected and Quantified 13.0 +/- 10.6 uM Adult (>18 years old) Not Specified Epilepsy
Cerebrospinal Fluid (CSF) Detected and Quantified 12.3 +/- 9.3 uM Adult (>18 years old) Not Specified Epilepsy
Cerebrospinal Fluid (CSF) Detected and Quantified 9.4 +/- 4.9 uM Adult (>18 years old) Not Specified Epilepsy
Cerebrospinal Fluid (CSF) Detected and Quantified 8.05 +/- 3.03 uM Adult (>18 years old) Not Specified Epilepsy
Cerebrospinal Fluid (CSF) Detected and Quantified 27.18 +/- 4.8 uM Adult (>18 years old) Both Alzheimer's disease
Cerebrospinal Fluid (CSF) Detected and Quantified 13.0 +/- 4.1 uM Children (1-13 year old) Both Leukemia
Cerebrospinal Fluid (CSF) Detected and Quantified 12.6 +/- 3.3 uM Children (1-13 year old) Both Comment Leukemia
Cerebrospinal Fluid (CSF) Detected and Quantified 15.3 +/- 4.9 uM Adult (>18 years old) Not Specified hypothyroidism
Cerebrospinal Fluid (CSF) Detected and Quantified 15.3 +/- 4.9 uM Adult (>18 years old) Both Hypothyroidism
Cerebrospinal Fluid (CSF) Detected and Quantified 7.8 +/- 1.38 uM Adult (>18 years old) Both Schizophrenia
Urine Detected and Quantified 10.5 +/- 1.5 umol/mmol creatinine Adult (>18 years old) Both Alzheimer's disease
Urine Detected and Quantified 10.72 +/- 4.63 umol/mmol creatinine Adult (>18 years old) Not Specified Cachexia
Associated Disorders and Diseases
Disease References
Cachexia
  • 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 Link_out
      Epilepsy
      • 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 Link_out
      • 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 Link_out
          Myocardial infarction
          • 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 Link_out
              Viral infection
              • 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 Link_out
                  Hypothyroidism
                  • 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 Link_out
                      Leukemia
                      • 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 Link_out
                          Schizophrenia
                          • 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 Link_out
                          • 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 Link_out
                              Alzheimer's disease
                              • 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 Link_out
                                  Hawkinsinuria
                                      Associated OMIM IDs
                                      DrugBank ID DB00135 Link_out
                                      DrugBank Metabolite ID Not Available
                                      Phenol Explorer Compound ID Not Available
                                      Phenol Explorer Metabolite ID Not Available
                                      FoodDB ID FDB000446
                                      KNApSAcK ID C00001397 Link_out
                                      Chemspider ID 5833 Link_out
                                      KEGG Compound ID C00082 Link_out
                                      BioCyc ID TYR Link_out
                                      BiGG ID 33785 Link_out
                                      Wikipedia Link L-Tyrosine Link_out
                                      NuGOwiki Link HMDB00158 Link_out
                                      Metagene Link HMDB00158 Link_out
                                      METLIN ID 34 Link_out
                                      PubChem Compound 6057 Link_out
                                      PDB ID TYR Link_out
                                      ChEBI ID 17895 Link_out
                                      References
                                      Synthesis Reference Enei, 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. 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 Link_out
                                      2. 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 Link_out
                                      3. 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 Link_out
                                      4. 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 Link_out
                                      5. 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 Link_out
                                      6. 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 Link_out
                                      7. 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 Link_out
                                      8. 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 Link_out
                                      9. 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 Link_out
                                      10. 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 Link_out
                                      11. 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 Link_out
                                      12. 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 Link_out
                                      13. 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 Link_out
                                      14. 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 Link_out
                                      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 Link_out
                                      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 Link_out
                                      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 Link_out

                                      Enzymes
                                      Name: Tyrosinase
                                      Reactions:
                                      L-Tyrosine + Oxygen unknown Dopaquinone + Water details
                                      L-Tyrosine + Oxygen unknown L-Dopa + Water details
                                      L-Dopa + L-Tyrosine + Oxygen unknown Dopaquinone + L-Dopa + Water details
                                      Gene Name: TYR
                                      Uniprot ID: P14679 Link_out
                                      Protein Sequence: FASTA
                                      Gene Sequence: FASTA
                                      Name: Tyrosine 3-monooxygenase
                                      Reactions:
                                      L-Tyrosine + L-erythro-tetrahydrobiopterin + Oxygen unknown L-Dopa + 4a-Hydroxytetrahydrobiopterin details
                                      L-erythro-tetrahydrobiopterin + L-Tyrosine + Oxygen unknown L-Dopa + 4a-Carbinolamine tetrahydrobiopterin + Water details
                                      Gene Name: TH
                                      Uniprot ID: P07101 Link_out
                                      Protein Sequence: FASTA
                                      Gene Sequence: FASTA
                                      Name: Thyroid peroxidase
                                      Reactions:
                                      I(-) + Iodotyrosine unknown Iodine + L-Tyrosine details
                                      Gene Name: TPO
                                      Uniprot ID: P07202 Link_out
                                      Protein Sequence: FASTA
                                      Gene Sequence: FASTA
                                      Name: Tyrosine aminotransferase
                                      Reactions:
                                      L-Tyrosine + Oxoglutaric acid unknown 4-Hydroxyphenylpyruvic acid + L-Glutamic acid details
                                      Gene Name: TAT
                                      Uniprot ID: P17735 Link_out
                                      Protein Sequence: FASTA
                                      Gene Sequence: FASTA
                                      Name: Aromatic-L-amino-acid decarboxylase
                                      Reactions:
                                      L-Tyrosine unknown Tyramine + Carbon dioxide details
                                      Gene Name: DDC
                                      Uniprot ID: P20711 Link_out
                                      Protein Sequence: FASTA
                                      Gene Sequence: FASTA
                                      Name: Phenylalanine-4-hydroxylase
                                      Reactions:
                                      L-Phenylalanine + L-erythro-tetrahydrobiopterin + Oxygen unknown L-Tyrosine + 4a-Hydroxytetrahydrobiopterin details
                                      L-erythro-tetrahydrobiopterin + L-Phenylalanine + Oxygen unknown 4a-Carbinolamine tetrahydrobiopterin + L-Tyrosine + Water details
                                      Gene Name: PAH
                                      Uniprot ID: P00439 Link_out
                                      Protein Sequence: FASTA
                                      Gene Sequence: FASTA
                                      Name: Aspartate aminotransferase, cytoplasmic
                                      Reactions:
                                      L-Tyrosine + Oxoglutaric acid unknown 4-Hydroxyphenylpyruvic acid + L-Glutamic acid details
                                      Gene Name: GOT1
                                      Uniprot ID: P17174 Link_out
                                      Protein Sequence: FASTA
                                      Gene Sequence: FASTA
                                      Name: Aspartate aminotransferase, mitochondrial
                                      Reactions:
                                      L-Tyrosine + Oxoglutaric acid unknown 4-Hydroxyphenylpyruvic acid + L-Glutamic acid details
                                      Gene Name: GOT2
                                      Uniprot ID: P00505 Link_out
                                      Protein Sequence: FASTA
                                      Gene Sequence: FASTA
                                      Name: Tyrosine--tRNA ligase, cytoplasmic
                                      Reactions:
                                      Adenosine triphosphate + L-Tyrosine + tRNA(Tyr) unknown Adenosine monophosphate + Pyrophosphate + L-tyrosyl-tRNA(Tyr) details
                                      Adenosine triphosphate + L-Tyrosine + tRNA(Tyr) unknown Adenosine monophosphate + Pyrophosphate + L-Tyrosyl-tRNA(Tyr) details
                                      Gene Name: YARS
                                      Uniprot ID: P54577 Link_out
                                      Protein Sequence: FASTA
                                      Gene Sequence: FASTA
                                      Name: Tyrosine--tRNA ligase, mitochondrial
                                      Reactions:
                                      Adenosine triphosphate + L-Tyrosine + tRNA(Tyr) unknown Adenosine monophosphate + Pyrophosphate + L-tyrosyl-tRNA(Tyr) details
                                      Adenosine triphosphate + L-Tyrosine + tRNA(Tyr) unknown Adenosine monophosphate + Pyrophosphate + L-Tyrosyl-tRNA(Tyr) details
                                      Gene Name: YARS2
                                      Uniprot ID: Q9Y2Z4 Link_out
                                      Protein Sequence: FASTA
                                      Gene Sequence: FASTA
                                      Name: Basic fibroblast growth factor receptor 1
                                      Reactions: Not Available
                                      Gene Name: FGFR1
                                      Uniprot ID: P11362 Link_out
                                      Protein Sequence: FASTA
                                      Gene Sequence: FASTA
                                      Name: Epidermal growth factor receptor
                                      Reactions: Not Available
                                      Gene Name: EGFR
                                      Uniprot ID: P00533 Link_out
                                      Protein Sequence: FASTA
                                      Gene Sequence: FASTA
                                      Name: L-amino-acid oxidase
                                      Reactions:
                                      L-Tyrosine + Water + Oxygen unknown 4-Hydroxyphenylpyruvic acid + Ammonia + Hydrogen peroxide details
                                      Gene Name: IL4I1
                                      Uniprot ID: Q96RQ9 Link_out
                                      Protein Sequence: FASTA
                                      Gene Sequence: FASTA
                                      Name: Iodotyrosine dehalogenase 1
                                      Reactions:
                                      L-Tyrosine + NADP + I(-) unknown 3,5-Diiodo-L-tyrosine + NADPH details
                                      Gene Name: IYD
                                      Uniprot ID: Q6PHW0 Link_out
                                      Protein Sequence: FASTA
                                      Gene Sequence: FASTA
                                      Name: Tubulin--tyrosine ligase
                                      Reactions:
                                      Adenosine triphosphate + detyrosinated alpha-tubulin + L-Tyrosine unknown alpha-tubulin + ADP + Phosphoric acid details
                                      Gene Name: TTL
                                      Uniprot ID: Q8NG68 Link_out
                                      Protein Sequence: FASTA
                                      Gene Sequence: FASTA
                                      Transporters
                                      Name: Monocarboxylate transporter 8
                                      Reactions: Not Available
                                      Gene Name: SLC16A2
                                      Uniprot ID: P36021 Link_out
                                      Protein Sequence: FASTA
                                      Gene Sequence: FASTA
                                      Name: Monocarboxylate transporter 10
                                      Reactions: Not Available
                                      Gene Name: SLC16A10
                                      Uniprot ID: Q8TF71 Link_out
                                      Protein Sequence: FASTA
                                      Gene Sequence: FASTA