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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H11NO3
Molecular Weight 181.1885
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of L-META-TYROSINE

SMILES

N[C@@H](CC1=CC=CC(O)=C1)C(O)=O

InChI

InChIKey=JZKXXXDKRQWDET-QMMMGPOBSA-N
InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-2-1-3-7(11)4-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m0/s1

HIDE SMILES / InChI
3-Tyrosine, in contrast to the para isomer, is readily racemized. The majority of the load was metabolized to m-hydroxyphenylacetic acid but m-hydroxymandelic acid and 3,4-dihydroxyphenylacetic acid were also detected. Low circulating levels of m-tyrosine in the plasma suggest that most of the load is held due to a first pass effect somewhere in the enterohepatic system and that this portion of the load is not in equilibrium with the plasma m-tyrosine. The metabolism of a m-tyrosine may give further insight into the deficiencies of the phenylalanine hydroxylating system found in the various phenotypes of phenylketonuria. 3-Tyrosine has been used experimentally as a substitute for L-DOPA in the treatment of Parkinsonism. 3-tyrosine mimics the action of Dopa in two experimental animal models. It was also obvious from the experiments with d,l- and l-m-tyrosine that only the l-isomer (3-Tyrosine) is active.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Eukaryotic cytosolic and mitochondrial phenylalanyl-tRNA synthetases catalyze the charging of tRNA with the meta-tyrosine.
2009-07-07
Demonstration of a peroxide shunt in the tetrahydropterin-dependent aromatic amino acid monooxygenases.
2009-04-08
Taking ecological function seriously: soil microbial communities can obviate allelopathic effects of released metabolites.
2009
Quantitative determination of ortho- and meta-tyrosine as biomarkers of protein oxidative damage in beta-thalassemia.
2007
Characterization of oxidative pathways in chronic rhinosinusitis and sinonasal polyposis.
2006-07-29
Ingredients contribute to variation in production of reactive oxygen species by areca quid.
2006-06
Reactive oxidative and nitrogen species in the nigrostriatal system following striatal 6-hydroxydopamine lesion in rats.
2005-08-02
Reactive carbonyls and polyunsaturated fatty acids produce a hydroxyl radical-like species: a potential pathway for oxidative damage of retinal proteins in diabetes.
2005-06-17
Trace analysis of oxidized, nitrated, and chlorinated aromatic amino acids by capillary electrophoresis with electroosmotic flow modification allowing large-volume sample stacking.
2005-05
Non-protein-bound transition metals and hydroxyl radical generation in cerebrospinal fluid of newborn infants with hypoxic ischemic encephalopathy.
2003-04
Intimal redox stress: accelerated atherosclerosis in metabolic syndrome and type 2 diabetes mellitus. Atheroscleropathy.
2002-09-27
In vivo production of hydroxyl radical by Enterococcus faecalis colonizing the intestinal tract using aromatic hydroxylation.
2002-09-15
Comparison of two independent aromatic hydroxylation assays in combination with intracerebral microdialysis to determine hydroxyl free radicals.
2001-07-15
Measurements of protein carbonyls, ortho- and meta-tyrosine and oxidative phosphorylation complex activity in mitochondria from young and old rats.
2001-07-15
Inhibitory effect of a two day fast on reactive oxygen species (ROS) generation by leucocytes and plasma ortho-tyrosine and meta-tyrosine concentrations.
2001-06
A hydroxyl radical-like species oxidizes cynomolgus monkey artery wall proteins in early diabetic vascular disease.
2001-04
The metabolism of L-m-tyrosine in man.
1979-10
The formation of 3,4-dihydroxy-L-phenylalanine from L-meta-tyrosine by rat liver and beef adrenal medulla.
1971-05-21
Patents

Sample Use Guides

In Vivo Use Guide
5 mg/kg
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
3-TYROSINE
Preferred Name English
L-META-TYROSINE
Common Name English
3-TYROSINE L-
Common Name English
L-M-TYROSINE
Common Name English
M-TYROSINE, L-
Common Name English
3-(M-HYDROXYPHENYL)ALANINE
Systematic Name English
L-PHENYLALANINE, 3-HYDROXY-
Systematic Name English
3-HYDROXY-L-PHENYLALANINE
Systematic Name English
3-HYDROXYPHENYLALANINE
Systematic Name English
M-L-TYROSINE
Common Name English
M-TYROSINE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C231
Created by admin on Mon Mar 31 17:47:48 GMT 2025 , Edited by admin on Mon Mar 31 17:47:48 GMT 2025
Code System Code Type Description
CHEBI
44303
Created by admin on Mon Mar 31 17:47:48 GMT 2025 , Edited by admin on Mon Mar 31 17:47:48 GMT 2025
PRIMARY
FDA UNII
D5YF57V4QW
Created by admin on Mon Mar 31 17:47:48 GMT 2025 , Edited by admin on Mon Mar 31 17:47:48 GMT 2025
PRIMARY
MERCK INDEX
m11291
Created by admin on Mon Mar 31 17:47:48 GMT 2025 , Edited by admin on Mon Mar 31 17:47:48 GMT 2025
PRIMARY Merck Index
PUBCHEM
6950577
Created by admin on Mon Mar 31 17:47:48 GMT 2025 , Edited by admin on Mon Mar 31 17:47:48 GMT 2025
PRIMARY
NCI_THESAURUS
C61817
Created by admin on Mon Mar 31 17:47:48 GMT 2025 , Edited by admin on Mon Mar 31 17:47:48 GMT 2025
PRIMARY
CAS
587-33-7
Created by admin on Mon Mar 31 17:47:48 GMT 2025 , Edited by admin on Mon Mar 31 17:47:48 GMT 2025
PRIMARY
EPA CompTox
DTXSID60871778
Created by admin on Mon Mar 31 17:47:48 GMT 2025 , Edited by admin on Mon Mar 31 17:47:48 GMT 2025
PRIMARY
DRUG BANK
DB03552
Created by admin on Mon Mar 31 17:47:48 GMT 2025 , Edited by admin on Mon Mar 31 17:47:48 GMT 2025
PRIMARY
CHEBI
78290
Created by admin on Mon Mar 31 17:47:48 GMT 2025 , Edited by admin on Mon Mar 31 17:47:48 GMT 2025
PRIMARY