| Record Information |
|---|
| Version | 1.0 |
|---|
| Creation Date | 2016-09-30 22:27:36 UTC |
|---|
| Update Date | 2020-06-04 20:57:12 UTC |
|---|
| BMDB ID | BMDB0000265 |
|---|
| Secondary Accession Numbers | |
|---|
| Metabolite Identification |
|---|
| Common Name | Liothyronine |
|---|
| Description | 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. Liothyronine is a drug which is used as replacement or supplemental therapy in patients with hypothyroidism of any etiology, except transient hypothyrodism during the recovery phase of subacute thyroiditis. Liothyronine is possibly soluble (in water) and a very strong basic compound (based on its pKa). Liothyronine exists in all living organisms, ranging from bacteria to humans. In cattle, liothyronine is involved in the metabolic pathway called thyroid hormone synthesis pathway. Liothyronine is a potentially toxic compound. |
|---|
| Structure | |
|---|
| 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 | |
|---|
| Ontology |
|---|
| Status | Detected and Quantified |
|---|
| Origin | |
|---|
| Biofunction | Not Available |
|---|
| Application | Not Available |
|---|
| Cellular locations | - Cell membrane
- Cytoplasm
- Membrane
|
|---|
| Physical Properties |
|---|
| State | Solid |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
|
|---|
| Predicted Properties | |
|---|
| Spectra |
|---|
| Spectra | |
|---|
| Synthesis Reference | Salamonczyk, Grzegorz M.; Oza, Vibha B.; Sih, Charles J. A concise synthesis of thyroxine (T4) and 3,5,3'-triiodo-L-thyronine (T3). Tetrahedron Letters (1997), 38(40), 6965-69 |
|---|
