ChemFOnt: Showing chemical card for 2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid (CFc000166560)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 23:59:53 UTC

Chemfont ID

CFc000166560

Molecule Identification

Common Name

2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid

Definition

Liothyronine, also known as T3 or liotironina, 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. An iodothyronine compound having iodo substituents at the 3-, 3'- and 5-positions. The sodium salt is used in the treatment of hypothyroidism. Liothyronine is a very strong basic compound (based on its pKa). Its metabolic activity is about 3 to 5 times that of L-thyroxine. Liothyronine exists in all living organisms, ranging from bacteria to humans. In humans, liothyronine is involved in thyroid hormone synthesis. Liothyronine is a potentially toxic compound. Although some is produced in the thyroid, most of the 3,3',5-triiodo-L-thyronine in the body is generated by mono-deiodination of L-thyroxine in the peripheral tissues.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,5,3'-Triiodo-L-thyronine	ChEBI
3,5,3'-Triiodothyronine	ChEBI
3,5,3'TRIIODOTHYRONINE	ChEBI
4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodo-L-phenylalanine	ChEBI
L-3,5,3'-Triiodothyronine	ChEBI
L-T3	ChEBI
Liothyroninum	ChEBI
Liotironina	ChEBI
O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine	ChEBI
T3	ChEBI
Tertroxin	ChEBI
Tresitope	ChEBI
Triiodothyronine	ChEBI
3,3',5-Triiodo-L-thyronine	Kegg
Thyrolar	Kegg
3,3',5-Triiodothyronine	HMDB
Cytomel	HMDB
T3 Thyroid hormone	HMDB
Thyroid hormone, T3	HMDB
Liothyronine sodium	HMDB
3,3',5'-Triiodo-L-thyronine	HMDB
3,3',5'-Triiodothyronine	HMDB
4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenylalanine	HMDB
Cyronine	HMDB
L-3,3',5-Triiodo-thyronine	HMDB
L-3,3',5-Triiodothyronine	HMDB
L-3-[4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenyl]-alanine	HMDB
L-Liothyronine	HMDB
L-Triiodothyronine	HMDB
Liothyronin	HMDB
Triiodo-L-thyronine	HMDB

Chemical Formula

C₁₅H₁₂I₃NO₄

Average Molecular Weight

650.9735

Monoisotopic Molecular Weight

650.790038137

IUPAC Name

(2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid

Traditional Name

liothyronine

CAS Registry Number

6893-02-3

SMILES

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

InChI Identifier

InChI=1S/C15H12I3NO4/c16-9-6-8(1-2-13(9)20)23-14-10(17)3-7(4-11(14)18)5-12(19)15(21)22/h1-4,6,12,20H,5,19H2,(H,21,22)/t12-/m0/s1

InChI Key

AUYYCJSJGJYCDS-LBPRGKRZSA-N

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

Substituents

Phenylalanine or derivatives
Diphenylether
Diaryl ether
3-phenylpropanoic-acid
Alpha-amino acid
Amphetamine or derivatives
L-alpha-amino acid
Phenoxy compound
2-iodophenol
2-halophenol
Phenol ether
Iodobenzene
1-hydroxy-2-unsubstituted benzenoid
Halobenzene
Phenol
Aralkylamine
Aryl iodide
Aryl halide
Monocyclic benzene moiety
Benzenoid
Amino acid
Ether
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Primary aliphatic amine
Organohalogen compound
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

iodothyronine (CHEBI:18258 )
iodophenol (CHEBI:18258 )
2-halophenol (CHEBI:18258 )
thyroxine (C02465 )
Other amino acids (C02465 )

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.02 g/L	ALOGPS
logP	0.82	ALOGPS
logP	2.8	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	0.3	ChemAxon
pKa (Strongest Basic)	9.48	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.78 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	113.43 m³·mol⁻¹	ChemAxon
Polarizability	43.92 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000265

DrugBank ID

DB00279

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C02465

BioCyc ID

CPD-10813

BiGG ID

Not Available

Wikipedia Link

Triiodothyronine

METLIN ID

Not Available

PubChem Compound

5920

PDB ID

Not Available

ChEBI ID

18258

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid (CFc000166560)

MOL for CFc000166560 (2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid)

3D MOL for CFc000166560 (2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid)

3D SDF for CFc000166560 (2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid)

3D-SDF for CFc000166560 (2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid)

PDB for CFc000166560 (2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid)

3D PDB for CFc000166560 (2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid)

SMILES for CFc000166560 (2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid)

INCHI for CFc000166560 (2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid)

Structure for CFc000166560 (2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid)

3D Structure for CFc000166560 (2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid)