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

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

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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:	thyroid hormone Any hormone produced by the thyroid gland mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).

ChEBI Ontology

Outgoing Relation(s)
	3,3',5-triiodo-L-thyronine (CHEBI:18258) has role human metabolite (CHEBI:77746)
	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
liothyroninum	ChemIDplus
liotironina	ChemIDplus
liothyronine	ChEBI
liothyronine	ChemIDplus

Synonyms	Source
Triiodothyronine	KEGG COMPOUND
L-3,5,3'-Triiodothyronine	KEGG COMPOUND
3,5,3'-Triiodothyronine	KEGG COMPOUND
Liothyronine	KEGG COMPOUND
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
Tresitope	DrugBank
Tertroxin	DrugBank

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

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

Citations