L-tyrosine (CHEBI:17895)

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CHEBI:17895 - L-tyrosine

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ChEBI Name	L-tyrosine

ChEBI ID	CHEBI:17895

ChEBI ASCII Name	L-tyrosine

Definition	An optically active form of tyrosine having L-configuration.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:46070, CHEBI:46161, CHEBI:6313, CHEBI:13181, CHEBI:21411

Supplier Information	ChemicalBook:CB1269334, ChemicalBook:CB41381672, eMolecules:514474, eMolecules:26757083, ZINC000000266964

Download	Molfile XML SDF

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Molfile

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Marvin 10140721123D

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Marvin 10140721123D

24 24 0 0 0 0 999 V2000

0.3015 2.0988 0.4380 N 0 0 0 0 0 0 0 0 0 0 0 0

1.3178 1.1996 -0.1242 C 0 0 2 0 0 0 0 0 0 0 0 0

2.3333 2.0066 -0.8917 C 0 0 0 0 0 0 0 0 0 0 0 0

2.0050 3.0368 -1.4282 O 0 0 0 0 0 0 0 0 0 0 0 0

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0.0091 -1.7922 0.3142 C 0 0 0 0 0 0 0 0 0 0 0 0

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3.6030 1.5794 -0.9772 O 0 0 0 0 0 0 0 0 0 0 0 0

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1.8154 0.6635 0.6849 H 0 0 0 0 0 0 0 0 0 0 0 0

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1 14 1 0 0 0 0

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2 5 1 0 0 0 0

2 16 1 0 0 0 0

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13 22 1 0 0 0 0

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reading 24 atoms

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Wikipedia	License
L-Tyrosine or tyrosine (symbol Tyr or Y) or 4-hydroxyphenylalanine is one of the 20 standard amino acids that are used by cells to synthesize proteins. It is a conditionally essential amino acid with a polar side group. The word "tyrosine" is from the Greek tyrós, meaning cheese, as it was first discovered in 1846 by German chemist Justus von Liebig in the protein casein from cheese. It is called tyrosyl when referred to as a functional group or side chain. While tyrosine is generally classified as a hydrophobic amino acid, it is more hydrophilic than phenylalanine. It is encoded by the codons UAC and UAU in messenger RNA. The one-letter symbol Y was assigned to tyrosine for being alphabetically nearest of those letters available. Note that T was assigned to the structurally simpler threonine, U was avoided for its similarity with V for valine, W was assigned to tryptophan, while X was reserved for undetermined or atypical amino acids. The mnemonic tYrosine was also proposed.
Read full article at Wikipedia

Formula

C9H11NO3

Net Charge

Average Mass

181.18858

Monoisotopic Mass

181.07389

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

InChIKey

OUYCCCASQSFEME-QMMMGPOBSA-N

SMILES

N[C@@H](Cc1ccc(O)cc1)C(O)=O

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Mycoplasma genitalium (NCBI:txid2097)	See: PubMed
Chlamydomonas reinhardtii (NCBI:txid3055)	See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932)	Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI
Homo sapiens (NCBI:txid9606)	Found in blood serum (BTO:0000133). See: MetaboLights Study

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	micronutrient Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions. fundamental metabolite Any metabolite produced by all living cells. EC 1.3.1.43 (arogenate dehydrogenase) inhibitor An EC 1.3.1.* (oxidoreductase acting on CH-CH group of donor, NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of arogenate dehydrogenase (EC 1.3.1.43). Daphnia magna metabolite A Daphnia metabolite produced by the species Daphnia magna. (via tyrosine )

Application(s):	nutraceutical A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	L-tyrosine (CHEBI:17895) has functional parent L-tyrosinal (CHEBI:46209) L-tyrosine (CHEBI:17895) has role EC 1.3.1.43 (arogenate dehydrogenase) inhibitor (CHEBI:64416) L-tyrosine (CHEBI:17895) has role fundamental metabolite (CHEBI:78675) L-tyrosine (CHEBI:17895) has role micronutrient (CHEBI:27027) L-tyrosine (CHEBI:17895) has role nutraceutical (CHEBI:50733) L-tyrosine (CHEBI:17895) is a L-α-amino acid (CHEBI:15705) L-tyrosine (CHEBI:17895) is a erythrose 4-phosphate/phosphoenolpyruvate family amino acid (CHEBI:73690) L-tyrosine (CHEBI:17895) is a proteinogenic amino acid (CHEBI:83813) L-tyrosine (CHEBI:17895) is a tyrosine (CHEBI:18186) L-tyrosine (CHEBI:17895) is conjugate acid of L-tyrosinate(1−) (CHEBI:32760) L-tyrosine (CHEBI:17895) is conjugate base of L-tyrosinium (CHEBI:32762) L-tyrosine (CHEBI:17895) is enantiomer of D-tyrosine (CHEBI:28479) L-tyrosine (CHEBI:17895) is tautomer of L-tyrosine zwitterion (CHEBI:58315)

Incoming	γ-Glu-Tyr (CHEBI:82969) has functional parent L-tyrosine (CHEBI:17895) (2S)-3-(4-hydroxyphenyl)-2-isocyanopropanoate (CHEBI:140647) has functional parent L-tyrosine (CHEBI:17895) L-tyrosine derivative (CHEBI:27177) has functional parent L-tyrosine (CHEBI:17895) L-tyrosinyl radical (CHEBI:32759) has functional parent L-tyrosine (CHEBI:17895) L-tyrosinyl radical cation (CHEBI:32763) has functional parent L-tyrosine (CHEBI:17895) Ala-Gly-Tyr (CHEBI:73351) has functional parent L-tyrosine (CHEBI:17895) Ala-Met-Asp-Tyr (CHEBI:176849) has functional parent L-tyrosine (CHEBI:17895) Ala-Tyr (CHEBI:73395) has functional parent L-tyrosine (CHEBI:17895) Ala-Val-Asp-Tyr (CHEBI:73391) has functional parent L-tyrosine (CHEBI:17895) Arg-Trp-Ser-Tyr (CHEBI:73405) has functional parent L-tyrosine (CHEBI:17895) Asn-Tyr (CHEBI:73427) has functional parent L-tyrosine (CHEBI:17895) Asp-Phe-Val-Tyr (CHEBI:73293) has functional parent L-tyrosine (CHEBI:17895) Asp-Tyr (CHEBI:73455) has functional parent L-tyrosine (CHEBI:17895) Cys-Met-Thr-Tyr (CHEBI:73459) has functional parent L-tyrosine (CHEBI:17895) DON-10-tyrosine (CHEBI:149459) has functional parent L-tyrosine (CHEBI:17895) Gln-Phe-Trp-Tyr (CHEBI:73464) has functional parent L-tyrosine (CHEBI:17895) Gln-Phe-Tyr (CHEBI:156250) has functional parent L-tyrosine (CHEBI:17895) Gln-Tyr (CHEBI:141432) has functional parent L-tyrosine (CHEBI:17895) Glu-Thr-Thr-Tyr (CHEBI:73489) has functional parent L-tyrosine (CHEBI:17895) Glu-Tyr (CHEBI:73513) has functional parent L-tyrosine (CHEBI:17895) Glu-Val-Thr-Leu-Tyr peptide residue (CHEBI:85622) has functional parent L-tyrosine (CHEBI:17895) Gly-Tyr (CHEBI:73517) has functional parent L-tyrosine (CHEBI:17895) Ile-Leu-Val-Tyr (CHEBI:73519) has functional parent L-tyrosine (CHEBI:17895) Leu-Asp-Tyr (CHEBI:73564) has functional parent L-tyrosine (CHEBI:17895) Leu-enkephalin (CHEBI:89656) has functional parent L-tyrosine (CHEBI:17895) Leu-Leu-Tyr (CHEBI:6415) has functional parent L-tyrosine (CHEBI:17895) Leu-Pro-Tyr (CHEBI:73581) has functional parent L-tyrosine (CHEBI:17895) Leu-Ser-Ser-Tyr (CHEBI:73522) has functional parent L-tyrosine (CHEBI:17895) Leu-Tyr (CHEBI:73591) has functional parent L-tyrosine (CHEBI:17895) Lys-Asp-Tyr (CHEBI:73598) has functional parent L-tyrosine (CHEBI:17895) Lys-Thr-Trp-Tyr (CHEBI:73597) has functional parent L-tyrosine (CHEBI:17895) Lys-Tyr (CHEBI:73608) has functional parent L-tyrosine (CHEBI:17895) Lys-Tyr-Glu (CHEBI:140742) has functional parent L-tyrosine (CHEBI:17895) maculosin (CHEBI:6631) has functional parent L-tyrosine (CHEBI:17895) Met-enkephalin (CHEBI:6618) has functional parent L-tyrosine (CHEBI:17895) Met-Tyr (CHEBI:73615) has functional parent L-tyrosine (CHEBI:17895) Phe-Tyr (CHEBI:73637) has functional parent L-tyrosine (CHEBI:17895) Phe-Tyr-Asp (CHEBI:84102) has functional parent L-tyrosine (CHEBI:17895) Ser-Tyr (CHEBI:73652) has functional parent L-tyrosine (CHEBI:17895) Thr-Pro-Tyr (CHEBI:73661) has functional parent L-tyrosine (CHEBI:17895) Thr-Tyr (CHEBI:73667) has functional parent L-tyrosine (CHEBI:17895) Tyr-Asn (CHEBI:141452) has functional parent L-tyrosine (CHEBI:17895) Tyr-Asp (CHEBI:141455) has functional parent L-tyrosine (CHEBI:17895) Tyr-Cys (CHEBI:157903) has functional parent L-tyrosine (CHEBI:17895) Tyr-FMDP (CHEBI:74501) has functional parent L-tyrosine (CHEBI:17895) Tyr-His (CHEBI:73695) has functional parent L-tyrosine (CHEBI:17895) Tyr-Ile-Leu (CHEBI:165121) has functional parent L-tyrosine (CHEBI:17895) Tyr-Pro (CHEBI:141456) has functional parent L-tyrosine (CHEBI:17895) Tyr-Ser (CHEBI:141457) has functional parent L-tyrosine (CHEBI:17895) Tyr-Thr (CHEBI:141458) has functional parent L-tyrosine (CHEBI:17895) Val-Tyr (CHEBI:73703) has functional parent L-tyrosine (CHEBI:17895) L-tyrosine-d4 (CHEBI:192085) is a L-tyrosine (CHEBI:17895) L-tyrosinium (CHEBI:32762) is conjugate acid of L-tyrosine (CHEBI:17895) L-tyrosinate(1−) (CHEBI:32760) is conjugate base of L-tyrosine (CHEBI:17895) D-tyrosine (CHEBI:28479) is enantiomer of L-tyrosine (CHEBI:17895) L-tyrosin-O⁴-yl group (CHEBI:32768) is substituent group from L-tyrosine (CHEBI:17895) L-tyrosine residue (CHEBI:46858) is substituent group from L-tyrosine (CHEBI:17895) L-tyrosino group (CHEBI:46857) is substituent group from L-tyrosine (CHEBI:17895) L-tyrosyl group (CHEBI:32764) is substituent group from L-tyrosine (CHEBI:17895) L-tyrosine zwitterion (CHEBI:58315) is tautomer of L-tyrosine (CHEBI:17895)

IUPAC Name

L-tyrosine

Synonyms	Sources
(−)-α-amino-p-hydroxyhydrocinnamic acid	NIST Chemistry WebBook
(2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid	IUPAC
(S)-(-)-Tyrosine	HMDB
(S)-2-Amino-3-(p-hydroxyphenyl)propionic acid	KEGG COMPOUND
(S)-3-(p-Hydroxyphenyl)alanine	KEGG COMPOUND
(S)-α-amino-4-hydroxybenzenepropanoic acid	NIST Chemistry WebBook
(S)-Tyrosine	HMDB
4-hydroxy-L-phenylalanine	NIST Chemistry WebBook
L-Tyrosin	ChEBI
L-Tyrosine	KEGG COMPOUND
Tyr	ChEBI
TYROSINE	PDBeChem
Tyrosine	KEGG COMPOUND
Y	ChEBI

Manual Xrefs	Databases
2786	DrugCentral
C00001397	KNApSAcK
C00082	KEGG COMPOUND
c0234	UM-BBD
D00022	KEGG DRUG
DB00135	DrugBank
ECMDB00158	ECMDB
HMDB0000158	HMDB
TYR	MetaCyc
TYR	PDBeChem
Tyrosine	Wikipedia
YMDB00364	YMDB
View more database links

Registry Numbers	Types	Sources
392441	Reaxys Registry Number	Reaxys
50929	Gmelin Registry Number	Gmelin
60-18-4	CAS Registry Number	KEGG COMPOUND
60-18-4	CAS Registry Number	NIST Chemistry WebBook
60-18-4	CAS Registry Number	ChemIDplus

Citations

Liu X, Luo L, Ding Y, Kang Z, Ye D (2012)
Simultaneous determination of L-cysteine and L-tyrosine using Au-nanoparticles/poly-eriochrome black T film modified glassy carbon electrode.
Bioelectrochemistry (Amsterdam, Netherlands) 86, 38-45 [PubMed:22360849]
[show Abstract]

Sa M, Ying L, Tang AG, Xiao LD, Ren YP (2012)
Simultaneous determination of tyrosine, tryptophan and 5-hydroxytryptamine in serum of MDD patients by high performance liquid chromatography with fluorescence detection.
Clinica chimica acta; international journal of clinical chemistry 413, 973-977 [PubMed:22402312]
[show Abstract]

Bonner CA, Jensen RA, Gander JE, Keyhani NO (2004)
A core catalytic domain of the TyrA protein family: arogenate dehydrogenase from Synechocystis.
The Biochemical journal 382, 279-291 [PubMed:15171683]
[show Abstract]

Last Modified

08 April 2022

ChEBI

CHEBI:17895 - L-tyrosine

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