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

ChEBI ID	CHEBI:18258

ChEBI 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.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:11701, CHEBI:45840, CHEBI:11702, CHEBI:9722, CHEBI:13059, CHEBI:19894

Supplier Information	ChemicalBook:CB8221269, eMolecules:521934, ZINC000003830999

Download	Molfile XML SDF

more structures >>

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reading 35 atoms

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Wikipedia	License
Triiodothyronine, also known as T3, is a thyroid hormone. It affects almost every physiological process in the body, including growth and development, metabolism, body temperature, and heart rate. Production of T3 and its prohormone thyroxine (T4) is activated by thyroid-stimulating hormone (TSH), which is released from the anterior pituitary gland. This pathway is part of a closed-loop feedback process: Elevated concentrations of T3, and T4 in the blood plasma inhibit the production of TSH in the anterior pituitary gland. As concentrations of these hormones decrease, the anterior pituitary gland increases production of TSH, and by these processes, a feedback control system stabilizes the level of thyroid hormones in the bloodstream. At the cellular level, T3 is the body's more active and potent thyroid hormone. T3 helps deliver oxygen and energy to all of the body's cells, its effects on target tissues being roughly four times more potent than those of T4. Of the thyroid hormone that is produced, just about 20% is T3, whereas 80% is produced as T4. Roughly 85% of the circulating T3 is later formed in the liver and anterior pituitary by removal of the iodine atom from the carbon atom number five of the outer ring of T4. In any case, the concentration of T3 in the human blood plasma is about one-fortieth that of T4. The half-life of T3 is about 2.5 days. The half-life of T4 is about 6.5 days. T3 levels start to rise 45 minutes after administration and peak at about 2.5 hours. Although manufacturer of Cytomel states half-life to be 2.5 days the half-life variability is great and can vary depending on the thyroid status of the patient. Newer studies have found the pharmakokinetics of T3 to be complex and the half-life to vary between 10 – 22 hours.
Read full article at Wikipedia

Formula

C15H12I3NO4

Net Charge

Average Mass

650.97350

Monoisotopic Mass

650.79004

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

SMILES

N[C@@H](Cc1cc(I)c(Oc2ccc(O)c(I)c2)c(I)c1)C(O)=O

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	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).

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	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	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	Sources
liothyronine	ChEBI
liothyronine	ChemIDplus
liothyroninum	ChemIDplus
liotironina	ChemIDplus

Synonyms	Sources
3,5,3'-Triiodo-L-thyronine	KEGG COMPOUND
3,5,3'-Triiodothyronine	KEGG COMPOUND
3,5,3'TRIIODOTHYRONINE	PDBeChem
4-(4-hydroxy-3-iodophenoxy)-3,5-diiodo-L-phenylalanine	IUPAC
L-3,3',5-triiodothyronine	HMDB
L-3,5,3'-Triiodothyronine	KEGG COMPOUND
L-T₃	ChemIDplus
L-triiodothyronine	HMDB
Liothyronine	KEGG COMPOUND
O-(4-hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine	IUPAC
T3	KEGG COMPOUND
T₃	ChEBI
Triiodothyronine	KEGG COMPOUND

Brand Names	Sources
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
View more database links

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

Citations

Swenne I, Stridsberg M, Thurfjell B, Rosling A (2009)
Triiodothyronine is an indicator of nutritional status in adolescent girls with eating disorders.
Hormone research 71, 268-275 [PubMed:19339791]
[show Abstract]

Shionoya H, Sugihara Y, Okano K, Sagami F, Mikami T, Katayama K (2004)
Studies on experimental iodine allergy: 1. Antigen recognition of guinea pig anti-iodine antibody.
The Journal of toxicological sciences 29, 131-136 [PubMed:15206581]
[show Abstract]

Power DM, Llewellyn L, Faustino M, Nowell MA, Björnsson BT, Einarsdottir IE, Canario AV, Sweeney GE (2001)
Thyroid hormones in growth and development of fish.
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP 130, 447-459 [PubMed:11738632]
[show Abstract]

Last Modified

24 October 2024

ChEBI

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

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