TYROSINE

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 Search

SMILES

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

InChI

InChIKey=OUYCCCASQSFEME-QMMMGPOBSA-N

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

HIDE SMILES / InChI

Molecular Formula	C9H11NO3
Molecular Weight	181.1885
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=02597da7-70bc-44f5-50a5-d67934125b7f | https://www.ncbi.nlm.nih.gov/pubmed/20046338

Tyrosine (L-form) is a non-essential amino acid, which is primarily required for the protein synthesis. This amino acid is the precursor of dopamine, norepinephrine, and epinephrine; therefore the lower concentration of tyrosine could be a peripheral marker of the hyperdopaminergic condition hypothesized to explain psychosis. Tyrosine supplements can improve cognition, increase energy, reduce anxiety, reduce depression, reduce levels of pain.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Protein biosynthesis 8 Target ID: Protein biosynthesis Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=02597da7-70bc-44f5-50a5-d67934125b7f	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Negative nitrogen balance 4 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=02597da7-70bc-44f5-50a5-d67934125b7f	Primary		Approved 8583	AMINOSYN Approved Use Aminosyn, Sulfite-Free, (a crystalline amino acid solution) infused with dextrose by peripheral vein infusion is indicated as a source of nitrogen in the nutritional support of patients with adequate stores of body fat, in whom, for short periods of time, oral nutrition cannot be tolerated, is undesirable, or inadequate. Launch Date 1975

C_max

Value	Dose	Co-administered	Analyte	Population
154 nmol/mL REVIEW https://chiro.org/Graphics_Box_NUTRITION/L-Tyrosine_Monograph.pdf	100 mg/kg single, oral dose: 100 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		TYROSINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
203 nmol/mL REVIEW https://chiro.org/Graphics_Box_NUTRITION/L-Tyrosine_Monograph.pdf	150 mg/kg single, oral dose: 150 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		TYROSINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 inducer 1087	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP19A1 429 CYP2C19 2057	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/6057#section=BioAssay-Results Page: 9.0	inconclusive [IC50 6.3261 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/6057#section=BioAssay-Results Page: 78.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/6057#section=BioAssay-Results Page: 134.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/6057#section=BioAssay-Results Page: 135.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/6057#section=BioAssay-Results Page: 129.0	no
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/6057#section=BioAssay-Results Page: 124.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/6057#section=BioAssay-Results Page: 125.0	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/6057#section=BioAssay-Results Page: 123 \| 125	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/6057#section=BioAssay-Results Page: 48 \| 133

PubMed

Title	Date	PubMed
The Src kinase p56(lck) up-regulates VLA-4 integrin affinity. Implications for rapid spontaneous and chemokine-triggered T cell adhesion to VCAM-1 and fibronectin.	2001-04-27	11102438
ATM is required for IkappaB kinase (IKKk) activation in response to DNA double strand breaks.	2001-03-23	11114307
Cloning of ACP33 as a novel intracellular ligand of CD4.	2001-03-23	11113139
Contrasting localizations of MALS/LIN-7 PDZ proteins in brain and molecular compensation in knockout mice.	2001-03-23	11104771
Differential regulation of alternatively spliced endothelial cell myosin light chain kinase isoforms by p60(Src).	2001-03-16	11113114
Cellular stress induces the tyrosine phosphorylation of caveolin-1 (Tyr(14)) via activation of p38 mitogen-activated protein kinase and c-Src kinase. Evidence for caveolae, the actin cytoskeleton, and focal adhesions as mechanical sensors of osmotic stress.	2001-03-16	11094059
Functional relationships between capacitation-dependent cell signaling and compartmentalized metabolic pathways in murine spermatozoa.	2001-03-09	11115497
PU.1 is a lineage-specific regulator of tyrosine phosphatase CD45.	2001-03-09	11114304
Regulation of ROMK1 channels by protein-tyrosine kinase and -tyrosine phosphatase.	2001-03-09	11114300
An interaction between ricin and calreticulin that may have implications for toxin trafficking.	2001-03-09	11113144
Stimulation of extracellular signal-regulated kinases and proliferation in rat osteoblastic cells by parathyroid hormone is protein kinase C-dependent.	2001-03-09	11108712
Inhibition of osteoclast function by adenovirus expressing antisense protein-tyrosine kinase 2.	2001-03-09	11102447
The basis of prostaglandin synthesis in coral: molecular cloning and expression of a cyclooxygenase from the Arctic soft coral Gersemia fruticosa.	2001-03-09	11085996
Mechanism of stimulation of osteoclastic bone resorption through Gas6/Tyro 3, a receptor tyrosine kinase signaling, in mouse osteoclasts.	2001-03-09	11084030
CD44 interaction with c-Src kinase promotes cortactin-mediated cytoskeleton function and hyaluronic acid-dependent ovarian tumor cell migration.	2001-03-09	11084024
The two major plant plasma membrane H+-ATPases display different regulatory properties.	2001-03-09	11080498
The rat liver Na(+)/bile acid cotransporter. Importance of the cytoplasmic tail to function and plasma membrane targeting.	2001-03-02	11112779
Essential tyrosine residues for interaction of the non-receptor protein-tyrosine phosphatase PTP1B with N-cadherin.	2001-03-02	11106648
Multiple regions of MAP kinase phosphatase 3 are involved in its recognition and activation by ERK2.	2001-03-02	11104775
Insufficient phosphorylation prevents fc gamma RIIB from recruiting the SH2 domain-containing protein-tyrosine phosphatase SHP-1.	2001-03-02	11099496
Altered regulation of cell cycle machinery involved in interleukin-1-induced G(1) and G(2) phase growth arrest of A375S2 human melanoma cells.	2001-03-02	11098059
Epidermal growth factor receptor-dependent control of keratinocyte survival and Bcl-xL expression through a MEK-dependent pathway.	2001-03-02	11098053
Fibrin clot retraction by human platelets correlates with alpha(IIb)beta(3) integrin-dependent protein tyrosine dephosphorylation.	2001-03-02	11084040
Effects of tumor necrosis factor alpha on taurine uptake in cultured rat astrocytes.	2001-03	11099784
The molecular adapter SLP-76 relays signals from platelet integrin alphaIIbbeta3 to the actin cytoskeleton.	2001-02-23	11113155
T Cell Receptor Binding to a pMHCII Ligand Is Kinetically Distinct from and Independent of CD4.	2001-02-23	11106664
A model of platelet aggregation involving multiple interactions of thrombospondin-1, fibrinogen, and GPIIbIIIa receptor.	2001-02-23	11094060
Stimulation of M3 muscarinic receptors induces phosphorylation of the Cdc42 effector activated Cdc42Hs-associated kinase-1 via a Fyn tyrosine kinase signaling pathway.	2001-02-23	11087735
The plant isoflavenoid genistein activates p53 and Chk2 in an ATM-dependent manner.	2001-02-16	11096068
Glycosylation-induced conformational modification positively regulates receptor-receptor association: a study with an aberrant epidermal growth factor receptor (EGFRvIII/DeltaEGFR) expressed in cancer cells.	2001-02-16	11087732
Divergent roles of SHP-2 in ERK activation by leptin receptors.	2001-02-16	11085989
Inhibitory role for dual specificity phosphatase VHR in T cell antigen receptor and CD28-induced Erk and Jnk activation.	2001-02-16	11085983
Role of dynamin, Src, and Ras in the protein kinase C-mediated activation of ERK by gonadotropin-releasing hormone.	2001-02-16	11083862
Integrin-independent tyrosine phosphorylation of p125(fak) in human platelets stimulated by collagen.	2001-02-02	11110790
Activation of Rho is required for ligand-independent oncogenic signaling by a mutant epidermal growth factor receptor.	2001-02-02	11110781
EPR studies of the water oxidizing complex in the S1 and the higher S states: the manganese cluster and Y(Z) radical.	2001-01-05	11115628
EPR/ENDOR characterization of the physical and electronic structure of the OEC Mn cluster.	2001-01-05	11115627
Vibrational spectroscopy of the oxygen-evolving complex and of manganese model compounds.	2001-01-05	11115625
Metallo-radical hypothesis for photoassembly of (Mn)4-cluster of photosynthetic oxygen evolving complex.	2001-01-05	11115623
Okadaic acid-induced upregulation of nitrotyrosine and heme oxygenase-1 in rat cortical neuron cultures.	2001-01-05	11114478
IDA-1, a Caenorhabditis elegans homolog of the diabetic autoantigens IA-2 and phogrin, is expressed in peptidergic neurons in the worm.	2001-01-01	11086294
Structure of longitudinal brain zones that provide the origin for the substantia nigra and ventral tegmental area in human embryos, as revealed by cytoarchitecture and tyrosine hydroxylase, calretinin, calbindin, and GABA immunoreactions.	2001-01-01	11086287
Biochemical and immunohistological changes in the brain of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-treated mouse.	2001-01	11113642
Abnormal localisation and hyperclustering of (alpha)(V)(beta)(3) integrins and associated proteins in Src-deficient or tyrphostin A9-treated osteoclasts.	2001-01	11112699
The common Arg972 polymorphism in insulin receptor substrate-1 causes apoptosis of human pancreatic islets.	2001-01	11099486
Phosphatidylinositol-3 kinase acts in parallel to the ERK MAP kinase in the FGF pathway during Xenopus mesoderm induction.	2001-01	11092809
Identification of receptor tyrosine kinase associating proteins using the yeast two-hybrid system.	2001	11100481
Identification of receptor tyrosine kinase (RTK) substrates by the cloning of receptor targets (CORT) strategy.	2001	11100480
Cloning protein tyrosine kinases by screening cDNA libraries with antiphosphotyrosine antibodies.	2001	11100465
Synthesis and use of DNA containing a 5'-bridging phosphorothioate as a suicide substrate for type I DNA topoisomerases.	2001	11089225

Patents

Sample Use Guides

In Vivo Use Guide

In adults, tyrosine (Aminosyn solution) is given for nutritional maintenance via peripheral vein at a final amino acid concentration of 3.5, 4.25 or 5% together with dextrose in concentrations of 5% to 10%. 5%, 7%, 8.5% and 10% solutions should only be infused via a central vein when admixed with sufficient dextrose. In pediatric patients, the amino acid mixture is administered in a 2.5% concentration.

Route of Administration: Intravenous

In Vitro Use Guide

Human melanoma cell line IIB-MEL-J was treated with 3 mM tyrosine. The amino acid produced a great decrease in the cell growth rate, a loss of the anchor-age-independent growth capacity, and a change in the morphology of the cells to a fibroblastoid aspect.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:36:58 GMT 2025` Edited by `admin` on `Mon Mar 31 17:36:58 GMT 2025`
Record UNII	42HK56048U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

L-TYROSINE

Preferred Name

English

TYROSINE

Official Name

English

TYROSINE [ORANGE BOOK]

Common Name

English

N-ACETYLTYROSINE IMPURITY A [EP IMPURITY]

Common Name

English

TYROSINE [MART.]

Common Name

English

TYROSINE [USAN]

Common Name

English

FEMA NO. 3736

Code

English

tyrosine [INN]

Common Name

English

TYROSINE [EP MONOGRAPH]

Common Name

English

LEVODOPA IMPURITY, L-TYROSINE- [USP IMPURITY]

Common Name

English

TYROSINE [II]

Common Name

English

Tyrosine [WHO-DD]

Common Name

English

(2S)-2-AMINO-3-(4-HYDROXYPHENYL)PROPANOIC ACID

Common Name

English

L-TYROSINE [FHFI]

Common Name

English

TYROSINE [HSDB]

Common Name

English

L-TYROSINE [USP-RS]

Common Name

English

L-TYROSINE [FCC]

Common Name

English

L-TYROSINE [JAN]

Common Name

English

(-)-.ALPHA.-AMINO-P-HYDROXYHYDROCINNAMIC ACID

Common Name

English

TYROSINE, L-

Systematic Name

English

TYROSINE [MI]

Common Name

English

LEVODOPA IMPURITY B [EP IMPURITY]

Common Name

English

TYROSINE [USP MONOGRAPH]

Common Name

English

TYROSINE [VANDF]

Common Name

English

2-AMINO-3-(4-HYDROXYPHENYL)PROPANOIC ACID, (S)-

Common Name

English

NSC-82624

Code

English

Classification Tree Code System Code

LOINC

47795-0