L-TYROSINE
Relevant Data
Food Additives Approved in the United States
Flavouring Substances Approved by European Union:
General Information
| Synonyms: | L-beta-(p-HYDROXYPHENYL)ALANINE |
| Chemical Names: | L-TYROSINE |
| CAS number: | 60-18-4 |
| JECFA number: | 1434 |
| FEMA number: | 3736 |
| Functional Class: |
Flavouring Agent FLAVOURING_AGENT |
From apps.who.int
Evaluations
| Evaluation year: | 2004 |
| ADI: | No safety concern at current levels of intake when used as a flavouring agent |
| Comments: | Not evaluated using the Procedure for the Safety Evaluation of Flavouring Agents; the substance is a macronutrient and a normal component of protein and, as such, human exposure through food is orders of magnitude higher than the anticipated level of exposure from use as a flavouring agent |
| Report: | TRS 928-JECFA 63/98 |
| Tox Monograph: | FAS 54-JECFA 63/435 |
| Specification: | COMPENDIUM ADDENDUM 12/FNP 52 Add. 12/90 |
From apps.who.int
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 6057 |
| IUPAC Name | (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid |
| 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 |
| InChI Key | OUYCCCASQSFEME-QMMMGPOBSA-N |
| Canonical SMILES | C1=CC(=CC=C1CC(C(=O)O)N)O |
| Molecular Formula | C9H11NO3 |
| Wikipedia | L-Tyrosine |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 181.191 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 3 |
| Complexity | 176.0 |
| CACTVS Substructure Key Fingerprint | A A A D c c B y M A A A A A A A A A A A A A A A A A A A A A A A A A A w A A A A A A A A A A A B A A A A H g A Q C A A A D C z B m A Q w D o B A A g C I A i D S C A A C A A A g I A A I i I G G C I g K J j K C k R O A c A A k 0 B E I m A e Y y K C O I A A A A A A A A A B A A A A A A A A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 83.6 |
| Monoisotopic Mass | 181.074 |
| Exact Mass | 181.074 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 13 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB- | 0.8760 |
| Human Intestinal Absorption | HIA+ | 0.9821 |
| Caco-2 Permeability | Caco2- | 0.6180 |
| P-glycoprotein Substrate | Non-substrate | 0.6478 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9925 |
| Non-inhibitor | 0.9937 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9126 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5547 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8458 |
| CYP450 2D6 Substrate | Non-substrate | 0.7971 |
| CYP450 3A4 Substrate | Non-substrate | 0.7817 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9649 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9862 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9760 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9324 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9128 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9807 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9690 |
| Non-inhibitor | 0.9692 | |
| AMES Toxicity | Non AMES toxic | 0.9132 |
| Carcinogens | Non-carcinogens | 0.9118 |
| Fish Toxicity | High FHMT | 0.7643 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.6264 |
| Honey Bee Toxicity | Low HBT | 0.5179 |
| Biodegradation | Ready biodegradable | 0.7630 |
| Acute Oral Toxicity | III | 0.6091 |
| Carcinogenicity (Three-class) | Non-required | 0.7041 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.5075 | LogS |
| Caco-2 Permeability | 0.1509 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.2474 | LD50, mol/kg |
| Fish Toxicity | 2.3101 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -1.0252 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | L-tyrosine is absorbed from the small intestine by a sodium-dependent active transport process. |
|---|---|
| Mechanism of Toxicity | Tyrosine 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. |
| 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. |
| Toxicity Values | LD<sub>50</sub> (oral, rat) > 5110 mg/kg |
| Lethal Dose | None |
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
| Minimum Risk Level | None |
| Health Effects | None |
| Treatment | None |
| Reference |
|
From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic acids and derivatives |
| Class | Carboxylic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Intermediate Tree Nodes | Amino acids and derivatives - Alpha amino acids and derivatives |
| Direct Parent | Tyrosine and derivatives |
| Alternative Parents |
|
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Tyrosine or derivatives - Phenylalanine or derivatives - 3-phenylpropanoic-acid - Alpha-amino acid - Amphetamine or derivatives - L-alpha-amino acid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Aralkylamine - Monocyclic benzene moiety - Benzenoid - Amino acid - Carboxylic acid - Monocarboxylic acid or derivatives - Organic oxide - Organooxygen compound - Organonitrogen compound - Amine - Primary aliphatic amine - Organic nitrogen compound - Carbonyl group - Organopnictogen compound - Organic oxygen compound - Hydrocarbon derivative - Primary amine - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as tyrosine and derivatives. These are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
From ClassyFire
Targets
- General Function:
- Tyrosine 3-monooxygenase activity
- Specific Function:
- Plays an important role in the physiology of adrenergic neurons.
- Gene Name:
- TH
- Uniprot ID:
- P07101
- Molecular Weight:
- 58599.545 Da
References
- Ugriumov MV: [Brain neurons partly expressing monoaminergic phenotype: distribution, development, and functional significance]. Usp Fiziol Nauk. 2007 Apr-Jun;38(2):3-25. [17578016 ]
- General Function:
- Tyrosine-trna ligase activity
- Specific Function:
- Catalyzes the attachment of tyrosine to tRNA(Tyr) in a two-step reaction: tyrosine is first activated by ATP to form Tyr-AMP and then transferred to the acceptor end of tRNA(Tyr).
- Gene Name:
- YARS2
- Uniprot ID:
- Q9Y2Z4
- Molecular Weight:
- 53198.56 Da
References
- 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. [12754495 ]
- General Function:
- Tubulin-tyrosine ligase activity
- Specific Function:
- Catalyzes the post-translational addition of a tyrosine to the C-terminal end of detyrosinated alpha-tubulin.
- Gene Name:
- TTL
- Uniprot ID:
- Q8NG68
- Molecular Weight:
- 43211.94 Da
References
- Banerjee A, Panosian TD, Mukherjee K, Ravindra R, Gal S, Sackett DL, Bane S: Site-specific orthogonal labeling of the carboxy terminus of alpha-tubulin. ACS Chem Biol. 2010 Aug 20;5(8):777-85. doi: 10.1021/cb100060v. [20545322 ]
- General Function:
- Pyridoxal phosphate binding
- Specific Function:
- Transaminase involved in tyrosine breakdown. Converts tyrosine to p-hydroxyphenylpyruvate. Can catalyze the reverse reaction, using glutamic acid, with 2-oxoglutarate as cosubstrate (in vitro). Has much lower affinity and transaminase activity towards phenylalanine.
- Gene Name:
- TAT
- Uniprot ID:
- P17735
- Molecular Weight:
- 50398.895 Da
References
- 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. [17389761 ]
- General Function:
- Tyrosine-trna ligase activity
- Specific Function:
- Catalyzes the attachment of tyrosine to tRNA(Tyr) in a two-step reaction: tyrosine is first activated by ATP to form Tyr-AMP and then transferred to the acceptor end of tRNA(Tyr).
- Gene Name:
- YARS
- Uniprot ID:
- P54577
- Molecular Weight:
- 59143.025 Da
References
- 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. [17401211 ]
From T3DB