3-iodo-L-tyrosine (CHEBI:27847)

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CHEBI:27847 - 3-iodo-L-tyrosine

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ChEBI Name	3-iodo-L-tyrosine

ChEBI ID	CHEBI:27847

ChEBI ASCII Name	3-iodo-L-tyrosine

Definition	The monoiodotyrosine that is L-tyrosine carrying an iodo-substituent at position C-3 of the benzyl group.

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

Secondary ChEBI IDs	CHEBI:1562, CHEBI:43609, CHEBI:20089

Supplier Information	ChemicalBook:CB5721061, eMolecules:523433, ZINC000000001575

Download	Molfile XML SDF

more structures >>

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IYR - Ideal conformer

RDKit 3D

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RDKit 3D

24 24 0 0 0 0 0 0 0 0999 V2000

0.9920 1.1940 3.5930 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.2350 0.4090 3.4060 C 0 0 1 0 0 0 0 0 0 0 0 0

0.0980 -0.8940 2.6780 C 0 0 0 0 0 0 0 0 0 0 0 0

0.7020 -0.5780 1.3340 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.1120 -0.4440 0.2260 C 0 0 0 0 0 0 0 0 0 0 0 0

0.4390 -0.1500 -1.0060 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.7970 0.0590 -2.6840 I 0 0 0 0 0 0 0 0 0 0 0 0

1.8120 0.0000 -1.1320 C 0 0 0 0 0 0 0 0 0 0 0 0

2.3580 0.2850 -2.3440 O 0 0 0 0 0 0 0 0 0 0 0 0

2.6280 -0.1390 -0.0190 C 0 0 0 0 0 0 0 0 0 0 0 0

2.0720 -0.4280 1.2110 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.8390 0.0930 4.7500 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.1270 -0.0280 5.7190 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.1680 -0.0510 4.8710 O 0 0 0 0 0 0 0 0 0 0 0 0

1.4150 1.2920 2.6830 H 0 0 0 0 0 0 0 0 0 0 0 0

1.6180 0.6260 4.1440 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.9470 0.9840 2.8140 H 0 0 0 0 0 0 0 0 0 0 0 0

0.8100 -1.4680 3.2710 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.8120 -1.4760 2.5400 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.1810 -0.5620 0.3250 H 0 0 0 0 0 0 0 0 0 0 0 0

2.5530 -0.5610 -2.7680 H 0 0 0 0 0 0 0 0 0 0 0 0

3.6980 -0.0210 -0.1140 H 0 0 0 0 0 0 0 0 0 0 0 0

2.7060 -0.5370 2.0780 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.5560 -0.2540 5.7340 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0

1 15 1 0

1 16 1 0

2 3 1 0

2 12 1 0

2 17 1 6

3 4 1 0

3 18 1 0

3 19 1 0

4 5 2 0

4 11 1 0

5 6 1 0

5 20 1 0

6 7 1 0

6 8 2 0

8 9 1 0

8 10 1 0

9 21 1 0

10 11 2 0

10 22 1 0

11 23 1 0

12 13 2 0

12 14 1 0

14 24 1 0

M END): 18 ms

reading 24 atoms

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Wikipedia	License
3-Iodotyrosine is an intermediate in the synthesis of thyroid hormones which is derived from iodination of tyrosine at the meta-position of the benzene ring. One unit can combine with diiodotyrosine to form triiodothyronine, as occurs in the colloid of the thyroid follicle. Two units can combine to form 3,3'-diiodothyronine. 3-Iodotyrosine is a reversible inhibitor of the enzyme tyrosine hydroxylase.
Read full article at Wikipedia

Formulae

C9H10INO3
C9H10INO3

Net Charge

Average Mass

307.087

Monoisotopic Mass

306.97054

InChI

InChI=1S/C9H10INO3/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14/h1-3,7,12H,4,11H2,(H,13,14)/t7-/m0/s1

InChIKey

UQTZMGFTRHFAAM-ZETCQYMHSA-N

SMILES

IC1=CC(C[C@@H](C(O)=O)N)=CC=C1O

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI

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):	human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). EC 1.14.16.2 (tyrosine 3-monooxygenase) inhibitor An EC 1.14.16.* (oxidoreductase acting on paired donors, reduced pteridine as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosine 3-monooxygenase (EC 1.14.16.2). mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	3-iodo-L-tyrosine (CHEBI:27847) has role EC 1.14.16.2 (tyrosine 3-monooxygenase) inhibitor (CHEBI:63932) 3-iodo-L-tyrosine (CHEBI:27847) has role human metabolite (CHEBI:77746) 3-iodo-L-tyrosine (CHEBI:27847) has role mouse metabolite (CHEBI:75771) 3-iodo-L-tyrosine (CHEBI:27847) is a L-tyrosine derivative (CHEBI:27177) 3-iodo-L-tyrosine (CHEBI:27847) is a monoiodotyrosine (CHEBI:25400) 3-iodo-L-tyrosine (CHEBI:27847) is a non-proteinogenic L-α-amino acid (CHEBI:83822) 3-iodo-L-tyrosine (CHEBI:27847) is tautomer of 3-iodo-L-tyrosine zwitterion (CHEBI:59898)

Incoming	3-iodo-L-tyrosine residue (CHEBI:90870) is substituent group from 3-iodo-L-tyrosine (CHEBI:27847) 3-iodo-L-tyrosine zwitterion (CHEBI:59898) is tautomer of 3-iodo-L-tyrosine (CHEBI:27847)

IUPAC Name

3-iodo-L-tyrosine

Synonyms	Sources
(2S)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoic acid	IUPAC
3-Iodo-L-tyrosine	KEGG COMPOUND
3-IODO-TYROSINE	PDBeChem
MIT	ChemIDplus

Manual Xrefs	Databases
3-Iodotyrosine	Wikipedia
C02515	KEGG COMPOUND
CPD-12288	MetaCyc
DB01758	DrugBank
HMDB0000021	HMDB
IYR	PDBeChem
View more database links

Registry Numbers	Types	Sources
2110934	Gmelin Registry Number	Gmelin
2941266	Reaxys Registry Number	Reaxys
70-78-0	CAS Registry Number	KEGG COMPOUND
70-78-0	CAS Registry Number	ChemIDplus

Citations

Hayashi A, Hino N, Kobayashi T, Arai R, Shirouzu M, Yokoyama S, Sakamoto K (2011)
Dissecting cell signaling pathways with genetically encoded 3-iodo-L-tyrosine.
Chembiochem : a European journal of chemical biology 12, 387-389 [PubMed:21290538]

Sakamoto K, Murayama K, Oki K, Iraha F, Kato-Murayama M, Takahashi M, Ohtake K, Kobayashi T, Kuramitsu S, Shirouzu M, Yokoyama S (2009)
Genetic encoding of 3-iodo-L-tyrosine in Escherichia coli for single-wavelength anomalous dispersion phasing in protein crystallography.
Structure (London, England : 1993) 17, 335-344 [PubMed:19278648]
[show Abstract]

Shionoya H, Sugihara Y, Okano K, Sagami F, Mikami T, Katayama K (2004)
Studies on experimental iodine allergy: 1. Antigen recognition of guinea pig anti-iodine antibody.
The Journal of toxicological sciences 29, 131-136 [PubMed:15206581]
[show Abstract]

Walker WH, Rokita SE (2003)
Use of a boroxazolidone complex of 3-iodo-L-tyrosine for palladium-catalyzed cross-coupling.
The Journal of organic chemistry 68, 1563-1566 [PubMed:12585904]
[show Abstract]

Ness DK, Foley GL, Villar D, Hansen LG (1996)
Effects of 3-iodo-L-tyrosine, a tyrosine hydroxylase inhibitor, on eye pigmentation and biogenic amines in the planarian, Dugesia dorotocephala.
Fundamental and applied toxicology : official journal of the Society of Toxicology 30, 153-161 [PubMed:8812261]
[show Abstract]

Last Modified

21 November 2019

CHEBI:27847 - 3-iodo-L-tyrosine

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