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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(O)=CC=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
The formation of 3,4-dihydroxy-L-phenylalanine from L-meta-tyrosine by rat liver and beef adrenal medulla.
1971 May 21
The metabolism of L-m-tyrosine in man.
1979 Oct
A hydroxyl radical-like species oxidizes cynomolgus monkey artery wall proteins in early diabetic vascular disease.
2001 Apr
Comparison of two independent aromatic hydroxylation assays in combination with intracerebral microdialysis to determine hydroxyl free radicals.
2001 Jul 15
Measurements of protein carbonyls, ortho- and meta-tyrosine and oxidative phosphorylation complex activity in mitochondria from young and old rats.
2001 Jul 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 Jun
In vivo production of hydroxyl radical by Enterococcus faecalis colonizing the intestinal tract using aromatic hydroxylation.
2002 Sep 15
Intimal redox stress: accelerated atherosclerosis in metabolic syndrome and type 2 diabetes mellitus. Atheroscleropathy.
2002 Sep 27
Non-protein-bound transition metals and hydroxyl radical generation in cerebrospinal fluid of newborn infants with hypoxic ischemic encephalopathy.
2003 Apr
Reactive oxidative and nitrogen species in the nigrostriatal system following striatal 6-hydroxydopamine lesion in rats.
2005 Aug 2
Reactive carbonyls and polyunsaturated fatty acids produce a hydroxyl radical-like species: a potential pathway for oxidative damage of retinal proteins in diabetes.
2005 Jun 17
Trace analysis of oxidized, nitrated, and chlorinated aromatic amino acids by capillary electrophoresis with electroosmotic flow modification allowing large-volume sample stacking.
2005 May
Ingredients contribute to variation in production of reactive oxygen species by areca quid.
2006 Jun
Characterization of oxidative pathways in chronic rhinosinusitis and sinonasal polyposis.
2006 May-Jun
Quantitative determination of ortho- and meta-tyrosine as biomarkers of protein oxidative damage in beta-thalassemia.
2007
Taking ecological function seriously: soil microbial communities can obviate allelopathic effects of released metabolites.
2009
Demonstration of a peroxide shunt in the tetrahydropterin-dependent aromatic amino acid monooxygenases.
2009 Apr 8
Eukaryotic cytosolic and mitochondrial phenylalanyl-tRNA synthetases catalyze the charging of tRNA with the meta-tyrosine.
2009 Jul 7
Patents

Sample Use Guides

In Vivo Use Guide
5 mg/kg
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
L-META-TYROSINE
Common Name English
3-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 Fri Dec 15 15:08:26 GMT 2023 , Edited by admin on Fri Dec 15 15:08:26 GMT 2023
Code System Code Type Description
CHEBI
44303
Created by admin on Fri Dec 15 15:08:26 GMT 2023 , Edited by admin on Fri Dec 15 15:08:26 GMT 2023
PRIMARY
FDA UNII
D5YF57V4QW
Created by admin on Fri Dec 15 15:08:26 GMT 2023 , Edited by admin on Fri Dec 15 15:08:26 GMT 2023
PRIMARY
MERCK INDEX
m11291
Created by admin on Fri Dec 15 15:08:26 GMT 2023 , Edited by admin on Fri Dec 15 15:08:26 GMT 2023
PRIMARY Merck Index
PUBCHEM
6950577
Created by admin on Fri Dec 15 15:08:26 GMT 2023 , Edited by admin on Fri Dec 15 15:08:26 GMT 2023
PRIMARY
NCI_THESAURUS
C61817
Created by admin on Fri Dec 15 15:08:26 GMT 2023 , Edited by admin on Fri Dec 15 15:08:26 GMT 2023
PRIMARY
CAS
587-33-7
Created by admin on Fri Dec 15 15:08:26 GMT 2023 , Edited by admin on Fri Dec 15 15:08:26 GMT 2023
PRIMARY
EPA CompTox
DTXSID60871778
Created by admin on Fri Dec 15 15:08:26 GMT 2023 , Edited by admin on Fri Dec 15 15:08:26 GMT 2023
PRIMARY
DRUG BANK
DB03552
Created by admin on Fri Dec 15 15:08:26 GMT 2023 , Edited by admin on Fri Dec 15 15:08:26 GMT 2023
PRIMARY
CHEBI
78290
Created by admin on Fri Dec 15 15:08:26 GMT 2023 , Edited by admin on Fri Dec 15 15:08:26 GMT 2023
PRIMARY