FComEx: L-Thyronine (PC000775)

Record Information

Version

1.0

Creation date

2015-10-09 22:32:38 UTC

Update date

2017-01-19 02:36:35 UTC

FoodComEx ID

PC000775

FoodDB Record

FDB022172

Chemical Information

Name

L-Thyronine

Description

Iodide is actively absorbed from the bloodstream and concentrated in the thyroid follicles. (If there is a deficiency of dietary iodine, the thyroid enlarges in an attempt to trap more iodine, resulting in goitre.) Via a reaction with the enzyme thyroperoxidase, iodine is covalently bound to tyrosine residues in the thyroglobulin molecules, forming monoiodotyrosine (MIT) and diiodotyrosine (DIT). Linking two moieties of DIT produces thyroxine. Combining one particle of MIT and one particle of DIT produces triiodothyronine. The thyronamines function via some unknown mechanism to inhibit neuronal activity; this plays an important role in the hibernation cycles of mammals. One effect of administering the thyronamines is a severe drop in body temperature. Both T3 and T4 are used to treat thyroid hormone deficiency (hypothyroidism). They are both absorbed well by the gut, so can be given orally. Levothyroxine, the most commonly used synthetic thyroxine form, is a stereoisomer of physiological thyroxine, which is metabolised more slowly and hence usually only needs once-daily administration. Natural desiccated thyroid hormones, which are derived from pig thyroid glands, are a "natural" hypothyroid treatment containing 20% T3 and traces of T2, T1 and calcitonin. A group of metabolites derived from thyroxine and triiodothyronine via the peripheral enzymatic removal of iodines from the thyroxine nucleus. Thyronine is the thyroxine nucleus devoid of its four iodine atoms. [HMDB]

CAS Number

1596-67-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
4-(4-Hydroxyphenoxy)-L-phenylalanine	ChEBI
b-(p-Hydroxyphenoxy)phenylalanine	hmdb
beta-(p-Hydroxyphenoxy)phenylalanine	hmdb
Desiodothyroxine	hmdb
L-Thyronine	hmdb
O-(4-Hydroxyphenyl)-L-tyrosine	ChEBI
O-(4-Hydroxyphenyl)tyrosine	hmdb
Thyronine	hmdb

Chemical Formula

C15H15NO4

IUPAC name

(2S)-2-amino-3-[4-(4-hydroxyphenoxy)phenyl]propanoic acid

InChI Identifier

InChI=1S/C15H15NO4/c16-14(15(18)19)9-10-1-5-12(6-2-10)20-13-7-3-11(17)4-8-13/h1-8,14,17H,9,16H2,(H,18,19)/t14-/m0/s1

InChI Key

KKCIOUWDFWQUBT-AWEZNQCLSA-N

Isomeric SMILES

N[C@@H](CC1=CC=C(OC2=CC=C(O)C=C2)C=C1)C(O)=O

Average Molecular Weight

273.2839

Monoisotopic Molecular Weight

273.100107973

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine 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

Phenylalanine and derivatives

Alternative Parents