Identification

Name
L-Tyrosine
Accession Number
DB00135  (NUTR00059)
Type
Small Molecule
Groups
Approved, Nutraceutical
Description

A non-essential amino acid. In animals it is synthesized from phenylalanine. It is also the precursor of epinephrine; thyroid hormones; and melanin.

Structure
Thumb
Synonyms
  • (−)-α-amino-p-hydroxyhydrocinnamic acid
  • (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid
  • (S)-(-)-Tyrosine
  • (S)-2-Amino-3-(p-hydroxyphenyl)propionic acid
  • (S)-3-(p-Hydroxyphenyl)alanine
  • (S)-alpha-amino-4-Hydroxybenzenepropanoic acid
  • (S)-Tyrosine
  • (S)-α-amino-4-hydroxybenzenepropanoic acid
  • 4-hydroxy-L-phenylalanine
  • L-Tyrosin
  • Tyr
  • Tyrosine
  • Y
External IDs
FEMA NO. 3736
International/Other Brands
Rxosine
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
2.5% Travasol Amino Acid Injection With Electrolytes In 10% DextroseL-Tyrosine (10 mg) + Dipotassium phosphate (130.5 mg) + Glucose (10 g) + Glycine (260 mg) + L-Alanine (520 mg) + L-Arginine (290 mg) + L-Histidine (120 mg) + L-Isoleucine (150 mg) + L-Leucine (182.5 mg) + L-Lysine (145 mg) + L-Methionine (100 mg) + L-Phenylalanine (140 mg) + L-Proline (170 mg) + L-Serine (125 mg) + L-Threonine (105 mg) + L-Tryptophan (45 mg) + L-Valine (145 mg) + Magnesium chloride (25.5 mg) + Sodium Chloride (29.3 mg) + Sodium acetate (170 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada
2.5% Travasol Amino Acid Injection With Electrolytes In 10% Dextrose ClinimixL-Tyrosine (10 mg) + Dipotassium phosphate (130.5 mg) + Glucose (10 g) + Glycine (520 mg) + L-Alanine (520 mg) + L-Arginine (260 mg) + L-Histidine (110 mg) + L-Isoleucine (120 mg) + L-Leucine hydrochloride (155 mg) + L-Lysine hydrochloride (145 mg) + L-Methionine (145 mg) + L-Phenylalanine hydrochloride (155 mg) + L-Proline (105 mg) + L-Threonine (105 mg) + L-Tryptophan (45 mg) + L-Valine (115 mg) + Magnesium chloride (25.5 mg) + Sodium Chloride (29.3 mg) + Sodium acetate (170 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1993-12-312015-08-05Canada
2.5% Travasol Amino Acid Injection Without Electrolytes In 10% Dextrose QuickmixL-Tyrosine (10 mg) + Glucose (10 g) + Glycine (520 mg) + L-Alanine (520 mg) + L-Arginine (260 mg) + L-Histidine (110 mg) + L-Isoleucine (120 mg) + L-Leucine hydrochloride (155 mg) + L-Lysine hydrochloride (195 mg) + L-Methionine (195 mg) + L-Phenylalanine hydrochloride (155 mg) + L-Proline (105 mg) + L-Threonine (105 mg) + L-Tryptophan (45 mg) + L-Valine (115 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada
2.5%travasol Amino Acid InJ.W.eleC.W.25%dexL-Tyrosine (10 mg) + Dipotassium phosphate (130.5 mg) + Glucose (25 g) + Glycine (260 mg) + L-Alanine (520 mg) + L-Arginine (290 mg) + L-Histidine (120 mg) + L-Isoleucine (150 mg) + L-Leucine (182.5 mg) + L-Lysine (145 mg) + L-Methionine (100 mg) + L-Phenylalanine (140 mg) + L-Proline (170 mg) + L-Serine (125 mg) + L-Threonine (105 mg) + L-Tryptophan (45 mg) + L-Valine (145 mg) + Magnesium chloride (25.5 mg) + Sodium Chloride (29.3 mg) + Sodium acetate (170 mg)LiquidIntravenousClintec Nutrition Company1996-07-301998-08-13Canada
2.75% Travas. Amino Acid InJ.W.elecw.25%dexL-Tyrosine (11 mg) + Dipotassium phosphate (261 mg) + Glucose (25 g) + Glycine (283 mg) + L-Alanine (570 mg) + L-Arginine (316 mg) + L-Histidine (132 mg) + L-Isoleucine (165 mg) + L-Leucine (201 mg) + L-Lysine (159.5 mg) + L-Methionine (110 mg) + L-Phenylalanine (154 mg) + L-Proline (187 mg) + L-Serine (137.5 mg) + L-Threonine (115.5 mg) + L-Tryptophan (49.5 mg) + L-Valine (159.5 mg) + Magnesium chloride (51 mg) + Sodium Chloride (112 mg) + Sodium acetate (215.5 mg)LiquidIntravenousClintec Nutrition Company1996-07-301998-08-13Canada
2.75% Travasol Amino Acid Injection With Electrolytes In 25% Dextrose QuickmixL-Tyrosine (11 mg) + Dipotassium phosphate (261 mg) + Glucose (25 g) + Glycine (570 mg) + L-Alanine (570 mg) + L-Arginine (285 mg) + L-Histidine (120.5 mg) + L-Isoleucine (131.5 mg) + L-Leucine hydrochloride (170 mg) + L-Lysine hydrochloride (159 mg) + L-Methionine (159 mg) + L-Phenylalanine hydrochloride (170 mg) + L-Proline (115 mg) + L-Threonine (115 mg) + L-Tryptophan (49.5 mg) + L-Valine (126 mg) + Magnesium chloride (51 mg) + Sodium Chloride (112 mg) + Sodium acetate (215.5 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-02-022007-08-02Canada
2.75% Travasol Amino Acid Injection With Electrolytes In 5% Dextrose QuickmixL-Tyrosine (11 mg) + Dipotassium phosphate (215.5 mg) + Glucose (5 g) + Glycine (570 mg) + L-Alanine (570 mg) + L-Arginine (285 mg) + L-Histidine (120.5 mg) + L-Isoleucine (131.5 mg) + L-Leucine hydrochloride (170 mg) + L-Lysine hydrochloride (159 mg) + L-Methionine (159 mg) + L-Phenylalanine hydrochloride (170 mg) + L-Proline (115 mg) + L-Threonine (115 mg) + L-Tryptophan (49.5 mg) + L-Valine (126 mg) + Magnesium chloride (51 mg) + Sodium Chloride (112 mg) + Sodium acetate (256 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1993-12-312007-08-02Canada
2.75%travasol Amino Acid InJ.W.eleC.W.5%dex.L-Tyrosine (11 mg) + Dipotassium phosphate (261 mg) + Glucose (5 g) + Glycine (283 mg) + L-Alanine (570 mg) + L-Arginine (316 mg) + L-Histidine (132 mg) + L-Isoleucine (165 mg) + L-Leucine (201 mg) + L-Lysine (159.5 mg) + L-Methionine (110 mg) + L-Phenylalanine (154 mg) + L-Proline (187 mg) + L-Serine (137.5 mg) + L-Threonine (115.5 mg) + L-Tryptophan (49.5 mg) + L-Valine (159.5 mg) + Magnesium chloride (51 mg) + Sodium Chloride (112 mg) + Sodium acetate (215 mg)LiquidIntravenousClintec Nutrition Company1996-12-311999-08-10Canada
4.25% Amino Acid Injection Without Electrolytes In 20% Dextrose QuickmixL-Tyrosine (17 mg) + Glucose (20 g) + Glycine (880 mg) + L-Alanine (880 mg) + L-Arginine (440 mg) + L-Histidine (186 mg) + L-Isoleucine (203 mg) + L-Leucine hydrochloride (263 mg) + L-Lysine hydrochloride (246 mg) + L-Methionine (246 mg) + L-Phenylalanine hydrochloride (263 mg) + L-Proline (178 mg) + L-Threonine (178 mg) + L-Tryptophan (76 mg) + L-Valine (195 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada
4.25% Travasol Amino Acid Injection With Electrolytes In 10% DextroseL-Tyrosine (17 mg) + Dipotassium phosphate (261 mg) + Glucose (10 g) + Glycine (438 mg) + L-Alanine (880 mg) + L-Arginine (489 mg) + L-Histidine (204 mg) + L-Isoleucine (255 mg) + L-Leucine (310 mg) + L-Lysine hydrochloride (246.5 mg) + L-Methionine (170 mg) + L-Phenylalanine (238 mg) + L-Proline (289 mg) + L-Serine (212.5 mg) + L-Threonine (178.5 mg) + L-Tryptophan (76.5 mg) + L-Valine (246.5 mg) + Magnesium chloride (51 mg) + Sodium Chloride (77 mg) + Sodium acetate (297 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada
Categories
UNII
42HK56048U
CAS number
60-18-4
Weight
Average: 181.1885
Monoisotopic: 181.073893223
Chemical Formula
C9H11NO3
InChI Key
OUYCCCASQSFEME-QMMMGPOBSA-N
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
IUPAC Name
(2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid
SMILES
N[[email protected]@H](CC1=CC=C(O)C=C1)C(O)=O

Pharmacology

Indication

Tyrosine is claimed to act as an effective antidepressant, however results are mixed. Tyrosine has also been claimed to reduce stress and combat narcolepsy and chronic fatigue, however these claims have been refuted by some studies.

Structured Indications
Not Available
Pharmacodynamics

Tyrosine is a nonessential amino acid synthesized in the body from phenylalanine. Tyrosine is critical for the production of the body's proteins, enzymes and muscle tissue. Tyrosine is a precursor to the neurotransmitters norepinephrine and dopamine. It can act as a mood elevator and an anti-depressant. It may improve memory and increase mental alertness. Tyrosine aids in the production of melanin and plays a critical role in the production of thyroxin (thyroid hormones). Tyrosine deficiencies are manifested by hypothyroidism, low blood pressure and low body temperature. Supplemental tyrosine has been used to reduce stress and combat narcolepsy and chronic fatigue.

Mechanism of action

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.

TargetActionsOrganism
UTyrosine 3-monooxygenase
binder
Human
UTyrosine--tRNA ligase, mitochondrialNot AvailableHuman
UTyrosine--tRNA ligase, cytoplasmicNot AvailableHuman
UTyrosine aminotransferaseNot AvailableHuman
Absorption

L-tyrosine is absorbed from the small intestine by a sodium-dependent active transport process.

Volume of distribution
Not Available
Protein binding
Not Available
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.

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

L-Tyrosine has very low toxicity. There have been very few reports of toxicity. LD50 (oral, rat) > 5110 mg/kg.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Aromatic L-Aminoacid Decarboxylase DeficiencyDisease
PhenylketonuriaDisease
Tyrosine MetabolismMetabolic
Tyrosinemia, transient, of the newbornDisease
Catecholamine BiosynthesisMetabolic
Tyrosinemia Type 2 (or Richner-Hanhart syndrome)Disease
Tyrosinemia Type 3 (TYRO3)Disease
Tyrosinemia Type IDisease
Disulfiram Action PathwayDrug action
Tyrosine hydroxylase deficiencyDisease
Thyroid hormone synthesisMetabolic
Phenylalanine and Tyrosine MetabolismMetabolic
AlkaptonuriaDisease
HawkinsinuriaDisease
Dopamine beta-hydroxylase deficiencyDisease
Monoamine oxidase-a deficiency (MAO-A)Disease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Hai-quan Mao, Kam W. Leong, "Biodegradable poly (phosphoester-co-desaminotyrosyl L-tyrosine ester) compounds, compositions, articles and methods for making and using the same." U.S. Patent US5912225, issued May, 1960.

US5912225
General References
  1. Hoffhines AJ, Damoc E, Bridges KG, Leary JA, Moore KL: Detection and purification of tyrosine-sulfated proteins using a novel anti-sulfotyrosine monoclonal antibody. J Biol Chem. 2006 Dec 8;281(49):37877-87. Epub 2006 Oct 17. [PubMed:17046811]
  2. Molnar GA, Wagner Z, Marko L, Ko Szegi T, Mohas M, Kocsis B, Matus Z, Wagner L, Tamasko M, Mazak I, Laczy B, Nagy J, Wittmann I: Urinary ortho-tyrosine excretion in diabetes mellitus and renal failure: evidence for hydroxyl radical production. Kidney Int. 2005 Nov;68(5):2281-7. [PubMed:16221230]
  3. Molnar GA, Nemes V, Biro Z, Ludany A, Wagner Z, Wittmann I: Accumulation of the hydroxyl free radical markers meta-, ortho-tyrosine and DOPA in cataractous lenses is accompanied by a lower protein and phenylalanine content of the water-soluble phase. Free Radic Res. 2005 Dec;39(12):1359-66. [PubMed:16298866]
External Links
Human Metabolome Database
HMDB00158
KEGG Drug
D00022
KEGG Compound
C00082
PubChem Compound
6057
PubChem Substance
46507885
ChemSpider
5833
BindingDB
18129
ChEBI
58315
ChEMBL
CHEMBL925
Therapeutic Targets Database
DAP000808
PharmGKB
PA451822
HET
TYR
PDRhealth
PDRhealth Drug Page
Wikipedia
Tyrosine
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
FDA label
Not Available
MSDS
Download (72.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingSupportive CareProtein Feeding in Post-traumatic Injury Patients1
2Unknown StatusTreatmentNemaline Myopathy1
3CompletedTreatmentCritical Illness1
3CompletedTreatmentHypersensitivity, Immediate1
3CompletedTreatmentInfant, Low Birth Weight / Infant, Small for Gestational Age / Infants, Premature / Newborn Infants / Sepsis1
Not AvailableTerminatedBasic ScienceHealthy Volunteers1
Not AvailableTerminatedTreatmentFibromyalgia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
Injection, solutionIntravenous
Kit
Injection, solution, concentrateIntravenous
EmulsionIntravenous
SolutionIntravenous
LiquidIntravenous
InjectionIntravenous
Prices
Unit descriptionCostUnit
Tyrosine powder1.16USD g
L-tyrosine powder0.94USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)343 dec °CPhysProp
water solubility479 mg/L (at 25 °C)SEIDELL,A (1941)
logP-2.26HANSCH,C ET AL. (1995)
logS-2.57ADME Research, USCD
pKa2.2 (at 25 °C)LEHNINGER,A (1975)
Predicted Properties
PropertyValueSource
Water Solubility7.67 mg/mLALOGPS
logP-2.4ALOGPS
logP-1.5ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)2ChemAxon
pKa (Strongest Basic)9.19ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.1 m3·mol-1ChemAxon
Polarizability18.01 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Download (7.36 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-014i-0690000000-cbbf40bb26fc84f2aead
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-014i-0890000000-ca45f993f95c8b0cee44
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-014i-0890000000-5749069211ba15d713ef
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-00xr-9240000000-2c87373c0d964e0edef5
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-014i-0890000000-848b2a4f247a0b3f14e8
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-00xr-9450000000-6d4550940f4dde6f18ff
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-004i-1910000000-5cc19cad5dc24b3b9b11
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-014i-1790000000-de22041357aadf60a06b
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-0690000000-cbbf40bb26fc84f2aead
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-0890000000-ca45f993f95c8b0cee44
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-0890000000-5749069211ba15d713ef
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00xr-9240000000-2c87373c0d964e0edef5
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-0890000000-848b2a4f247a0b3f14e8
GC-MS Spectrum - GC-EI-QQGC-MSsplash10-0udi-3319000000-1d3d28a67f82366fff22
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00xr-9450000000-6d4550940f4dde6f18ff
GC-MS Spectrum - GC-MSGC-MSsplash10-004i-1910000000-5cc19cad5dc24b3b9b11
GC-MS Spectrum - GC-MSGC-MSsplash10-014i-1790000000-de22041357aadf60a06b
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-01p9-0900000000-580de2c16cd24559cd5c
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-0006-9400000000-f233fbc6c58236ee4aeb
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-002f-9100000000-8b5e12eba034bcfdf8a1
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0920000000-b43356ad3da227b488cb
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-014i-0900000000-c04f0be6515621dda5ac
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-0900000000-3ed8b68bfade9194763b
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0udi-0900000000-fe6a1ce69851a8c5db00
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-aafdcea07be221817fd4
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0002-0900000000-66a5b9a0a48bdc0a2b47
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-014i-0900000000-13eb4252ca23455a58da
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-014i-0900000000-fb85798746829bac3f3d
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-03e9-0839226000-5504e667281c746669ec
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-03di-0900000000-f65cb3ad2fa730c922f7
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-001i-0900000000-a9276fe43ef61b4693e6
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0a59-0039210000-21b4bd9870bf4965a6d1
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-001i-0848491200-aae99eb0b66dd1c7036d
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-03di-0900000000-4104a2ca5d5ef5f22f6d
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-001i-0900000000-f309996d57a95c719deb
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-03di-0013090000-112cd9c2eea42dbc079b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-001i-0900000000-c7f95918d936586f633d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-03yi-1900000000-d1682546c1e0893c71e4
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-014i-2900000000-a0cc78ed35e56dd812a5
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-00kf-9500000000-d3f399f5dd10e338e25a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0006-9200000000-8acd8d370f194bfe28ed
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-001i-0900000000-6b26ce2f5b326ace12a4
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-00ri-0900000000-6f6f9222a3132279b0b3
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-00r6-5900000000-5038b0b81cef20042492
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-0006-9200000000-39be21ca2f5d4dc1d587
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-0006-9000000000-7de0309922df1d7c61b5
MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , PositiveLC-MS/MSsplash10-001i-0900000000-a13dba0f14c43b2439d5
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-001i-0900000000-e7947aa74e53285a8038
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, PositiveLC-MS/MSsplash10-001i-0900000000-6f37258e3b8ec12255a9
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-001i-1900000000-571c365754ff408549e4
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-0900000000-c7f95918d936586f633d
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03yi-1900000000-644614c00b6e9f6aef94
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-2900000000-a0cc78ed35e56dd812a5
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00kf-9500000000-d3f399f5dd10e338e25a
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9200000000-8acd8d370f194bfe28ed
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-03di-0900000000-f65cb3ad2fa730c922f7
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-001i-0900000000-a9276fe43ef61b4693e6
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a59-0039210000-21b4bd9870bf4965a6d1
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-03di-0900000000-972f236da42e07f9af17
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-001i-0900000000-f309996d57a95c719deb
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-03di-0013090000-112cd9c2eea42dbc079b
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-001i-1900000000-571c365754ff408549e4
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-0900000000-dae93349deb73168ad0f
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00ri-0900000000-b536ea8de6f7d020ec0e
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00r6-5900000000-5038b0b81cef20042492
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-9200000000-39be21ca2f5d4dc1d587
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-9000000000-7de0309922df1d7c61b5
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-014i-0900000000-e698098d8d8b04bbcc40
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-c04f0be6515621dda5ac
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-3ed8b68bfade9194763b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0900000000-fe6a1ce69851a8c5db00
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-66a5b9a0a48bdc0a2b47
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-13eb4252ca23455a58da
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-fb85798746829bac3f3d
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-0900000000-e7947aa74e53285a8038
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001r-0900000000-78c6ce0af62aa6010bcf
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

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.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Tyrosine and derivatives
Alternative Parents
Phenylalanine and derivatives / Phenylpropanoic acids / L-alpha-amino acids / Amphetamines and derivatives / Aralkylamines / 1-hydroxy-2-unsubstituted benzenoids / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds
show 4 more
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
show 16 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
proteinogenic amino acid, L-alpha-amino acid, tyrosine, erythrose 4-phosphate/phosphoenolpyruvate family amino acid (CHEBI:17895) / Common amino acids (C00082)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Binder
General Function
Tyrosine 3-monooxygenase activity
Specific Function
Plays an important role in the physiology of adrenergic neurons.
Gene Name
TH
Uniprot ID
P07101
Uniprot Name
Tyrosine 3-monooxygenase
Molecular Weight
58599.545 Da
References
  1. Olsovska J, Novotna J, Flieger M, Spizek J: Assay of tyrosine hydroxylase based on high-performance liquid chromatography separation and quantification of L-dopa and L-tyrosine. Biomed Chromatogr. 2007 Dec;21(12):1252-8. [PubMed:17604359]
  2. Bodnar I, Hechtl D, Szekacs D, Olah M, Nagy GM: Effect of local (intracerebral and intracerebroventricular) administration of tyrosine hydroxylase inhibitor on the neuroendocrine dopaminergic neurons and prolactin release. Ideggyogy Sz. 2007 Mar 30;60(3-4):177-81. [PubMed:17451064]
  3. Rostrup M, Fossbakk A, Hauge A, Kleppe R, Gnaiger E, Haavik J: Oxygen dependence of tyrosine hydroxylase. Amino Acids. 2008 Apr;34(3):455-64. Epub 2007 May 23. [PubMed:17520326]
  4. Richards AB, Scheel TA, Wang K, Henkemeyer M, Kromer LF: EphB1 null mice exhibit neuronal loss in substantia nigra pars reticulata and spontaneous locomotor hyperactivity. Eur J Neurosci. 2007 May;25(9):2619-28. [PubMed:17561836]
  5. Ugriumov MV: [Brain neurons partly expressing monoaminergic phenotype: distribution, development, and functional significance]. Usp Fiziol Nauk. 2007 Apr-Jun;38(2):3-25. [PubMed:17578016]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
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
Uniprot Name
Tyrosine--tRNA ligase, mitochondrial
Molecular Weight
53198.56 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Zhang Y, Wang L, Schultz PG, Wilson IA: Crystal structures of apo wild-type M. jannaschii tyrosyl-tRNA synthetase (TyrRS) and an engineered TyrRS specific for O-methyl-L-tyrosine. Protein Sci. 2005 May;14(5):1340-9. [PubMed:15840835]
  4. Kiga D, Sakamoto K, Kodama K, Kigawa T, Matsuda T, Yabuki T, Shirouzu M, Harada Y, Nakayama H, Takio K, Hasegawa Y, Endo Y, Hirao I, Yokoyama S: An engineered Escherichia coli tyrosyl-tRNA synthetase for site-specific incorporation of an unnatural amino acid into proteins in eukaryotic translation and its application in a wheat germ cell-free system. Proc Natl Acad Sci U S A. 2002 Jul 23;99(15):9715-20. Epub 2002 Jul 3. [PubMed:12097643]
  5. 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. [PubMed:12754495]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
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
Uniprot Name
Tyrosine--tRNA ligase, cytoplasmic
Molecular Weight
59143.025 Da
References
  1. 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. [PubMed:17401211]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
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...
Gene Name
TAT
Uniprot ID
P17735
Uniprot Name
Tyrosine aminotransferase
Molecular Weight
50398.895 Da
References
  1. 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. [PubMed:17389761]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Very active and specific thyroid hormone transporter. Stimulates cellular uptake of thyroxine (T4), triiodothyronine (T3), reverse triiodothyronine (rT3) and diidothyronine. Does not transport Leu,...
Gene Name
SLC16A2
Uniprot ID
P36021
Uniprot Name
Monocarboxylate transporter 8
Molecular Weight
59510.86 Da
References
  1. Friesema EC, Ganguly S, Abdalla A, Manning Fox JE, Halestrap AP, Visser TJ: Identification of monocarboxylate transporter 8 as a specific thyroid hormone transporter. J Biol Chem. 2003 Oct 10;278(41):40128-35. Epub 2003 Jul 18. [PubMed:12871948]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells (By similarity).
Gene Name
SLC16A10
Uniprot ID
Q8TF71
Uniprot Name
Monocarboxylate transporter 10
Molecular Weight
55492.07 Da
References
  1. Kim DK, Kanai Y, Matsuo H, Kim JY, Chairoungdua A, Kobayashi Y, Enomoto A, Cha SH, Goya T, Endou H: The human T-type amino acid transporter-1: characterization, gene organization, and chromosomal location. Genomics. 2002 Jan;79(1):95-103. [PubMed:11827462]
  2. Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. [PubMed:11278508]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 04:31