AFCDB: L-Tyrosine (FDB000446)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:34 UTC

Update date

2019-11-26 02:54:49 UTC

Primary ID

FDB000446

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

L-Tyrosine

Description

L-Tyrosine, also known as Tyr or tirosina, belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives 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. L-Tyrosine is an odorless tasting compound. L-Tyrosine is found, on average, in the highest concentration within a few different foods, such as casein, milk (cow), and other soy product and in a lower concentration in waffle, cracker, and garden tomato (var.). L-Tyrosine has also been detected, but not quantified in, several different foods, such as hawthorns (Crataegus), sourdough, root vegetables, ohelo berries (Vaccinium reticulatum), and black raisin. This could make L-tyrosine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on L-Tyrosine.

CAS Number

60-18-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	7.67 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-1.5	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	2	ChemAxon
pKa (Strongest Basic)	9.19	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	83.55 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	47.1 m³·mol⁻¹	ChemAxon
Polarizability	18.18 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C9H11NO3

IUPAC name

2-amino-3-(4-hydroxyphenyl)propanoic acid

InChI Identifier

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)

InChI Key

OUYCCCASQSFEME-UHFFFAOYSA-N

Isomeric SMILES

NC(CC1=CC=C(O)C=C1)C(O)=O

Average Molecular Weight

181.1885

Monoisotopic Molecular Weight

181.073893223

Classification

Description

Belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives 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

Substituents

Tyrosine or derivatives
Phenylalanine or derivatives
3-phenylpropanoic-acid
Amphetamine or derivatives
Alpha-amino acid
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Monocyclic benzene moiety
Benzenoid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

alpha-amino acid (CHEBI:18186 )
aromatic amino acid (CHEBI:18186 )

Ontology

Whole grain cereal products

Nuts and legumes:

Nuts

Legumes:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 59.66%; H 6.12%; N 7.73%; O 26.49%	DFC
Melting Point	Mp 314-318 dec. approx. (rapid heat)	DFC
Boiling Point	Not Available
Experimental Water Solubility	0.479 mg/mL at 25 oC	SEIDELL,A (1941)
Experimental logP	-2.26	HANSCH,C ET AL. (1995)
Experimental pKa	pKa3 10.07 (phenolic OH)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]D -9.01 (11.6% KOH)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-3900000000-7a26097fda66f2f445b5	2014-09-20	View Spectrum
Predicted GC-MS	L-Tyrosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4r-4900000000-fb040ac104208d200d8c	Spectrum
Predicted GC-MS	L-Tyrosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Tyrosine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Tyrosine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Tyrosine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Tyrosine, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Tyrosine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Tyrosine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Tyrosine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Tyrosine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Tyrosine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Tyrosine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Tyrosine, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Tyrosine, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Tyrosine, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Tyrosine, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9200000000-2547dae1665803f38bd1	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00rf-6900000000-b2b0f8f68423fbfd602c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Negative	splash10-001i-0900000000-3a614a31d778b5df1dc5	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-014r-0900000000-e0fcbbd1a3428bca9ec3	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-000i-0900000000-68cd9dcfb64ff4fab197	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00kr-0900000000-03fe77841e11d74f5df7	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0900000000-4a714f9a050c975b9c94	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-014i-0900000000-dceaa0a6a4997d0a9e6d	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 25V, Positive	splash10-014r-0900000000-4c7edd239a412ca97d14	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-2c0f9a585c243ecc645f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-ecbde0599ce71965579a	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-39abc09c5fc3d275d44b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-00kr-0900000000-00cb1ae859c330a9a3be	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-0900000000-4902904e7400106e84d5	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9200000000-290ac7df2e0f388c56ae	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9700000000-194f27fb6aa928ff0650	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-002f-9000000000-d55fb2db34d35408a084	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00rf-6900000000-f692bfce6e48ce195419	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 25V, Positive	splash10-00kr-0900000000-87801ed16c51bc9eea00	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q0-0900000000-64b5df3e494e5df5c1be	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-c38735d64e2a16bd0c68	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-6900000000-6696908ff67c37922f99	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-941af648c85b3f0f7c66	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01q9-1900000000-b7d3075f2496303aeb37	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fr-9700000000-c242deae91617b5e8735	2015-05-27	View Spectrum

NMR

Type	Description		View

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

17895

Phenol-Explorer ID

Not Available

DrugBank ID

DB03839

HMDB ID

HMDB00158

CRC / DFC (Dictionary of Food Compounds) ID

BCN92-M:BCK50-J

EAFUS ID

3789

Dr. Duke ID

TYROSINE|L-(-)-TYROSINE

BIGG ID

33785

KNApSAcK ID

C00001397

HET ID

TYR

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1037771

SuperScent ID

Not Available

Wikipedia ID

L-Tyrosine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Pubchem compound: 5460822

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti depressant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti encephalopathic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti Parkinsonian	48407	A drug used in the treatment of Parkinson's disease.	DUKE
anti phenylketonuric	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti ulcer	49201	One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
monoamine precursor			DUKE

Enzymes

Name	Gene Name	UniProt ID
Aromatic-L-amino-acid decarboxylase	DDC	P20711
Tyrosine 3-monooxygenase	TH	P07101
Tyrosine aminotransferase	TAT	P17735
Phenylalanine-4-hydroxylase	PAH	P00439
Aspartate aminotransferase, cytoplasmic	GOT1	P17174
Aspartate aminotransferase, mitochondrial	GOT2	P00505
Tyrosine--tRNA ligase, cytoplasmic	YARS	P54577
Tyrosine--tRNA ligase, mitochondrial	YARS2	Q9Y2Z4
Basic fibroblast growth factor receptor 1	FGFR1	P11362
Epidermal growth factor receptor	EGFR	P00533

Pathways

Name	SMPDB Link	KEGG Link
Catecholamine Biosynthesis	SMP00012	map00350
Phenylalanine and Tyrosine Metabolism	SMP00008	map00360
Transcription/Translation	SMP00019	Not Available
Tyrosine Metabolism	SMP00006	map00350

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
odorless	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

L-Tyrosine (FDB000446)

Structure for FDB000446 (L-Tyrosine)