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Identification
NameL-Tyrosine
Accession NumberDB00135  (NUTR00059)
Typesmall molecule
Groupsapproved, nutraceutical
Description

A non-essential amino acid. In animals it is synthesized from phenylalanine. It is also the precursor of epinephrine; thyroid hormones; and melanin. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
(−)-α-amino-p-hydroxyhydrocinnamic acidNot AvailableNot Available
(2S)-2-amino-3-(4-hydroxyphenyl)propanoic acidNot AvailableNot Available
(S)-(-)-TyrosineNot AvailableNot Available
(S)-2-Amino-3-(p-hydroxyphenyl)propionic acidNot AvailableNot Available
(S)-3-(p-Hydroxyphenyl)alanineNot AvailableNot Available
(S)-TyrosineNot AvailableNot Available
(S)-α-amino-4-hydroxybenzenepropanoic acidNot AvailableNot Available
4-hydroxy-L-phenylalanineNot AvailableNot Available
TyrNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
RxosineNot Available
Brand mixturesNot Available
Categories
CAS number60-18-4
WeightAverage: 181.1885
Monoisotopic: 181.073893223
Chemical FormulaC9H11NO3
InChI KeyOUYCCCASQSFEME-QMMMGPOBSA-N
InChI
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
IUPAC Name
(2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid
SMILES
N[C@@H](CC1=CC=C(O)C=C1)C(O)=O
Mass Specshow(7.36 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassPhenylpropanoids and Polyketides
ClassPhenylpropanoic Acids
SubclassNot Available
Direct parentPhenylpropanoic Acids
Alternative parentsAlpha Amino Acids and Derivatives; Amphetamines and Derivatives; Phenols and Derivatives; Amino Fatty Acids; Polyols; Enolates; Carboxylic Acids; Polyamines; Enols; Monoalkylamines
Substituentsphenol derivative; benzene; polyol; carboxylic acid derivative; polyamine; carboxylic acid; enol; enolate; amine; primary aliphatic amine; primary amine; organonitrogen compound
Classification descriptionThis compound belongs to the phenylpropanoic acids. These are compounds whose structure contain a benzene ring conjugated to a propanoic acid.
Pharmacology
IndicationTyrosine is claimed to act as an effective antidepressant, however results are mixed. Tyrosine has also been claimed to reduce stress and combat narcolepsy and chronic fatigue, however these claims have been refuted by some studies.
PharmacodynamicsTyrosine is a nonessential amino acid synthesized in the body from phenylalanine. Tyrosine is critical for the production of the body's proteins, enzymes and muscle tissue. Tyrosine is a precursor to the neurotransmitters norepinephrine and dopamine. It can act as a mood elevator and an anti-depressant. It may improve memory and increase mental alertness. Tyrosine aids in the production of melanin and plays a critical role in the production of thyroxin (thyroid hormones). Tyrosine deficiencies are manifested by hypothyroidism, low blood pressure and low body temperature. Supplemental tyrosine has been used to reduce stress and combat narcolepsy and chronic fatigue.
Mechanism of actionTyrosine is produced in cells by hydroxylating the essential amino acid phenylalanine. This relationship is much like that between cysteine and methionine. Half of the phenylalanine required goes into the production of tyrosine; if the diet is rich in tyrosine itself, the requirements for phenylalanine are reduced by about 50%. The mechanism of L-tyrosine's antidepressant activity can be accounted for by the precursor role of L-tyrosine in the synthesis of the neurotransmitters norepinephrine and dopamine. Elevated brain norepinephrine and dopamine levels are thought to be associated with antidepressant effects.
AbsorptionL-tyrosine is absorbed from the small intestine by a sodium-dependent active transport process.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

In the liver, L-tyrosine is involved in a number of biochemical reactions, including protein synthesis and oxidative catabolic reactions. L-tyrosine that is not metabolized in the liver is distributed via the systemic circulation to the various tissues of the body.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityL-Tyrosine has very low toxicity. There have been very few reports of toxicity. LD50 (oral, rat) > 5110 mg/kg.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Tyrosinemia Type 2 (or Richner-Hanhart syndrome)DiseaseSMP00369
Tyrosinemia Type 3 (TYRO3)DiseaseSMP00370
Monoamine oxidase-a deficiency (MAO-A)DiseaseSMP00533
Disulfiram Action PathwayDrug actionSMP00429
AlkaptonuriaDiseaseSMP00169
Aromatic L-Aminoacid Decarboxylase DeficiencyDiseaseSMP00170
Phenylalanine and Tyrosine MetabolismMetabolicSMP00008
Dopamine beta-hydroxylase deficiencyDiseaseSMP00498
Catecholamine BiosynthesisMetabolicSMP00012
Tyrosine hydroxylase deficiencyDiseaseSMP00497
HawkinsinuriaDiseaseSMP00190
Thyroid hormone synthesisMetabolicSMP00716
Tyrosinemia Type IDiseaseSMP00218
Tyrosine MetabolismMetabolicSMP00006
Tyrosinemia, transient, of the newbornDiseaseSMP00494
PhenylketonuriaDiseaseSMP00206
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption Not Available Not Available
Blood Brain Barrier Not Available Not Available
Caco-2 permeable Not Available Not Available
P-glycoprotein substrate Not Available Not Available
P-glycoprotein inhibitor I Not Available Not Available
P-glycoprotein inhibitor II Not Available Not Available
Renal organic cation transporter Not Available Not Available
CYP450 2C9 substrate Not Available Not Available
CYP450 2D6 substrate Not Available Not Available
CYP450 3A4 substrate Not Available Not Available
CYP450 1A2 substrate Not Available Not Available
CYP450 2C9 substrate Not Available Not Available
CYP450 2D6 substrate Not Available Not Available
CYP450 2C19 substrate Not Available Not Available
CYP450 3A4 substrate Not Available Not Available
CYP450 inhibitory promiscuity Not Available Not Available
Ames test Not Available Not Available
Carcinogenicity Not Available Not Available
Biodegradation Not Available Not Available
Rat acute toxicity Not Available Not applicable
hERG inhibition (predictor I) Not Available Not Available
hERG inhibition (predictor II) Not Available Not Available
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Tyrosine powder1.16USDg
L-tyrosine powder0.94USDg
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point343 dec °CPhysProp
water solubility479 mg/L (at 25 °C)SEIDELL,A (1941)
logP-2.26HANSCH,C ET AL. (1995)
logS-2.57ADME Research, USCD
pKa2.2 (at 25 °C)LEHNINGER,A (1975)
Predicted Properties
PropertyValueSource
water solubility7.67e+00 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 area83.55ChemAxon
rotatable bond count3ChemAxon
refractivity47.1ChemAxon
polarizability18.01ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
References
Synthesis Reference

Hai-quan Mao, Kam W. Leong, “Biodegradable poly (phosphoester-co-desaminotyrosyl L-tyrosine ester) compounds, compositions, articles and methods for making and using the same.” U.S. Patent US5912225, issued May, 1960.

US5912225
General Reference
  1. 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
  2. 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
  3. 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
External Links
ResourceLink
KEGG CompoundC01536
PubChem Compound6057
PubChem Substance46507885
ChemSpider5833
ChEBI17895
ChEMBLCHEMBL925
Therapeutic Targets DatabaseDAP000808
PharmGKBPA451822
HETTYR
PDRhealthhttp://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/lty_0256.shtml
WikipediaL-Tyrosine
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSshow(72.7 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Tyrosine 3-monooxygenase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Tyrosine 3-monooxygenase P07101 Details

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 Jun 29;. Pubmed
  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
  3. Rostrup M, Fossbakk A, Hauge A, Kleppe R, Gnaiger E, Haavik J: Oxygen dependence of tyrosine hydroxylase. Amino Acids. 2007 May 23;. Pubmed
  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
  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
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Tyrosine--tRNA ligase, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Tyrosine--tRNA ligase, mitochondrial Q9Y2Z4 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
  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
  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
  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
  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

3. Tyrosine--tRNA ligase, cytoplasmic

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Tyrosine--tRNA ligase, cytoplasmic P54577 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

4. Tyrosine aminotransferase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Tyrosine aminotransferase P17735 Details

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

Transporters

1. Monocarboxylate transporter 8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Monocarboxylate transporter 8 P36021 Details

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

2. Monocarboxylate transporter 10

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Monocarboxylate transporter 10 Q8TF71 Details

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
  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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:08