3,3',5-triiodo-L-thyronine (CHEBI:18258)

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CHEBI:18258 - 3,3',5-triiodo-L-thyronine

ChEBI ID	CHEBI:18258
ChEBI Name	3,3',5-triiodo-L-thyronine
Stars
ASCII Name	3,3',5-triiodo-L-thyronine
Definition	An iodothyronine compound having iodo substituents at the 3-, 3'- and 5-positions. 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. Its metabolic activity is about 3 to 5 times that of L-thyroxine. The sodium salt is used in the treatment of hypothyroidism.
Secondary ChEBI IDs	CHEBI:9722, CHEBI:11701, CHEBI:11702, CHEBI:13059, CHEBI:19894, CHEBI:45840
Last Modified	24 October 2024
Downloads	Molfile

Formula	C15H12I3NO4
Net Charge	0
Average Mass	650.976
Monoisotopic Mass	650.79005
SMILES	N[C@@H](Cc1cc(I)c(Oc2ccc(O)c(I)c2)c(I)c1)C(=O)O
InChI	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
InChIKey	AUYYCJSJGJYCDS-LBPRGKRZSA-N

Wikipedia

Species of Metabolite	Component	Source	Comments
Homo sapiens (ncbitaxon:9606)	-	DOI (10.1038/nbt.2488)
Mus musculus (ncbitaxon:10090)	-	PubMed (19425150)	Source: BioModels - MODEL1507180067

Roles Classification

Chemical Roles:	Bronsted base A molecular entity capable of accepting a hydron from a donor (Brønsted acid). Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:	immunosuppressive agent An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response. thyroid hormone Any hormone produced by the thyroid gland human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
Applications:	antidepressant Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. immunosuppressive agent An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response. antipsychotic agent Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. cardiovascular drug A drug that affects the rate or intensity of cardiac contraction, blood vessel diameter or blood volume. anti-arrhythmia drug A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.

ChEBI Ontology

Outgoing Relation(s)
	3,3',5-triiodo-L-thyronine (CHEBI:18258) has role anti-arrhythmia drug (CHEBI:38070)
	3,3',5-triiodo-L-thyronine (CHEBI:18258) has role antidepressant (CHEBI:35469)
	3,3',5-triiodo-L-thyronine (CHEBI:18258) has role antineoplastic agent (CHEBI:35610)
	3,3',5-triiodo-L-thyronine (CHEBI:18258) has role antipsychotic agent (CHEBI:35476)
	3,3',5-triiodo-L-thyronine (CHEBI:18258) has role cardiovascular drug (CHEBI:35554)
	3,3',5-triiodo-L-thyronine (CHEBI:18258) has role human metabolite (CHEBI:77746)
	3,3',5-triiodo-L-thyronine (CHEBI:18258) has role immunosuppressive agent (CHEBI:35705)
	3,3',5-triiodo-L-thyronine (CHEBI:18258) has role mouse metabolite (CHEBI:75771)
	3,3',5-triiodo-L-thyronine (CHEBI:18258) has role thyroid hormone (CHEBI:60311)
	3,3',5-triiodo-L-thyronine (CHEBI:18258) is a 2-halophenol (CHEBI:53291)
	3,3',5-triiodo-L-thyronine (CHEBI:18258) is a iodophenol (CHEBI:24863)
	3,3',5-triiodo-L-thyronine (CHEBI:18258) is a iodothyronine (CHEBI:24864)
	3,3',5-triiodo-L-thyronine (CHEBI:18258) is conjugate acid of 3,3',5-triiodo-L-thyroninate (CHEBI:60308)
	3,3',5-triiodo-L-thyronine (CHEBI:18258) is tautomer of 3,3',5-triiodo-L-thyronine zwitterion (CHEBI:533015)
Incoming Relation(s)
	3,3',5-triiodo-L-thyronine sulfate (CHEBI:35432) has functional parent 3,3',5-triiodo-L-thyronine (CHEBI:18258)
	desiccated thyroid extract (CHEBI:9584) has part 3,3',5-triiodo-L-thyronine (CHEBI:18258)
	3,3',5-triiodo-L-thyroninate (CHEBI:60308) is conjugate base of 3,3',5-triiodo-L-thyronine (CHEBI:18258)
	3,3',5-triiodo-L-thyronine residue (CHEBI:90874) is substituent group from 3,3',5-triiodo-L-thyronine (CHEBI:18258)
	3,3',5-triiodo-L-thyronine zwitterion (CHEBI:533015) is tautomer of 3,3',5-triiodo-L-thyronine (CHEBI:18258)

IUPAC Name
3,3',5-triiodo-L-thyronine

INNs	Source
liothyronine	ChemIDplus
liothyronine	ChEBI
liothyroninum	ChemIDplus
liotironina	ChemIDplus

Synonyms	Source
3,5,3'-Triiodo-L-thyronine	KEGG COMPOUND
3,5,3'TRIIODOTHYRONINE	PDBeChem
3,5,3'-Triiodothyronine	KEGG COMPOUND
3,5,3'-triiodothyronine, l-	ChEMBL
4-(4-hydroxy-3-iodophenoxy)-3,5-diiodo-L-phenylalanine	IUPAC
O-(4-hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine	IUPAC

Brand Names	Source
Tertroxin	DrugBank
Tresitope	DrugBank

Manual Xrefs	Databases
1585	DrugCentral
C02465	KEGG COMPOUND
D08128	KEGG DRUG
DB00279	DrugBank
HMDB0000265	HMDB
LSM-3991	LINCS
T3	PDBeChem
Triiodothyronine	Wikipedia

Registry Numbers	Sources
Reaxys:2710227	Reaxys
CAS:6893-02-3	ChemIDplus
CAS:6893-02-3	KEGG COMPOUND

Citations