ChemFOnt: Showing chemical card for Iodotyrosine (CFc000000018)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:36:24 UTC

Chemfont ID

CFc000000018

Molecule Identification

Common Name

Iodotyrosine

Definition

Iodotyrosine is an iodated derivative of L-tyrosine. This is an early precursor to L-thyroxine, one of the primary thyroid hormones. In the thyroid gland, iodide is trapped, transported, and concentrated in the follicular lumen for thyroid hormone synthesis. Before trapped iodide can react with tyrosine residues, it must be oxidized by thyroid peroxidase. Iodotyrosine is made from tyrosine via thyroid peroxidase and then further iodinated by this enzyme to make the di-iodo and tri-iodo variants. Two molecules of di-iodotyrosine combine to form T4, and one molecule of mono-iodotyrosine combines with one molecule of di-iodotyrosine to form T3.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S)-2-Amino-3-(4-hydroxy-3-iodophenyl)propanoic acid	ChEBI
3-IODO-tyrosine	ChEBI
MIT	ChEBI
(2S)-2-Amino-3-(4-hydroxy-3-iodophenyl)propanoate	Generator
3-Iodo-4-hydroxyphenylalanine	HMDB
3-Iodo-L-tyrosine	HMDB
3-Iodotyrosine	HMDB
3-Monoiodo-L-tyrosine	HMDB
4-Hydroxy-3-iodophenylalanine	HMDB
IYR	HMDB
L-Tyrosine-3-iodo	HMDB
Monoiodotyrosine	HMDB

Chemical Formula

C₉H₁₀INO₃

Average Molecular Weight

307.0851

Monoisotopic Molecular Weight

306.970536611

IUPAC Name

(2S)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoic acid

Traditional Name

iodotyrosine

CAS Registry Number

70-78-0

SMILES

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

InChI Identifier

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

InChI Key

UQTZMGFTRHFAAM-ZETCQYMHSA-N

Chemical Taxonomy

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
Alpha-amino acid
Amphetamine or derivatives
L-alpha-amino acid
2-iodophenol
2-halophenol
1-hydroxy-2-unsubstituted benzenoid
Iodobenzene
Halobenzene
Phenol
Aralkylamine
Aryl iodide
Aryl halide
Benzenoid
Monocyclic benzene moiety
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organohalogen compound
Primary aliphatic amine
Organoiodide
Organonitrogen compound
Organooxygen compound
Primary amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:27847 )
L-tyrosine derivative (CHEBI:27847 )
monoiodotyrosine (CHEBI:27847 )
Other amino acids (C02515 )

Functional Ontology

Physiological effect

Health effect

Endocrine system disorder

Thyroidal or parathyroidal disorder

Athyreosis (HMDB: HMDB0000021)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 2225717)

Organ

Gland

Thyroid gland (HMDB: HMDB0000021)
Thyroid gland (HMDB: HMDB0000021)

Cellular substructure

Cytoplasm (HMDB: HMDB0000021)

Source

Exogenous

Exogenous (HMDB: HMDB0000021)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0000021)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Thyroid hormone synthesis (PathBank: SMP0087269)
Thyroid hormone synthesis (HMDB: HMDB0000021)
Thyroid hormone synthesis (PathBank: SMP0063679)
Tyrosine Metabolism (HMDB: HMDB0000021)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0000021)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.94 g/L	ALOGPS
logP	-1.5	ALOGPS
logP	-0.56	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	0.99	ChemAxon
pKa (Strongest Basic)	9.5	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	60.46 m³·mol⁻¹	ChemAxon
Polarizability	23.54 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

External Links

HMDB ID

HMDB0000021

DrugBank ID

DB01758

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021875

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

Not Available

PubChem Compound

439744

PDB ID

Not Available

ChEBI ID

27847

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Hillmann, Gunther; Hillmann-Elies, Anneliese. Synthesis of 3-iodo-L-tyrosine. Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie (1956), 305 177-81.

Showing chemical card for Iodotyrosine (CFc000000018)

MOL for CFc000000018 (Iodotyrosine)

3D MOL for CFc000000018 (Iodotyrosine)

3D SDF for CFc000000018 (Iodotyrosine)

3D-SDF for CFc000000018 (Iodotyrosine)

PDB for CFc000000018 (Iodotyrosine)

3D PDB for CFc000000018 (Iodotyrosine)

SMILES for CFc000000018 (Iodotyrosine)

INCHI for CFc000000018 (Iodotyrosine)

Structure for CFc000000018 (Iodotyrosine)

3D Structure for CFc000000018 (Iodotyrosine)