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
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
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2096905 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4633120 |
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Target ID: CHEMBL2095205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4633120 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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The formation of 3,4-dihydroxy-L-phenylalanine from L-meta-tyrosine by rat liver and beef adrenal medulla. | 1971 May 21 |
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Comparison of two independent aromatic hydroxylation assays in combination with intracerebral microdialysis to determine hydroxyl free radicals. | 2001 Jul 15 |
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Intimal redox stress: accelerated atherosclerosis in metabolic syndrome and type 2 diabetes mellitus. Atheroscleropathy. | 2002 Sep 27 |
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Demonstration of a peroxide shunt in the tetrahydropterin-dependent aromatic amino acid monooxygenases. | 2009 Apr 8 |
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Eukaryotic cytosolic and mitochondrial phenylalanyl-tRNA synthetases catalyze the charging of tRNA with the meta-tyrosine. | 2009 Jul 7 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/518579
5 mg/kg
Route of Administration:
Oral
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NCI_THESAURUS |
C231
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C61817
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SUBSTANCE RECORD