L-thyroxine (CHEBI:18332)

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CHEBI:18332 - L-thyroxine

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ChEBI Name	L-thyroxine

ChEBI ID	CHEBI:18332

ChEBI ASCII Name	L-thyroxine

Definition	The L-enantiomer of thyroxine.

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

Secondary ChEBI IDs	CHEBI:7663, CHEBI:45848, CHEBI:13177, CHEBI:21406

Supplier Information	ChemicalBook:CB7852954, eMolecules:478134, ZINC000000895323

Download	Molfile XML SDF

more structures >>

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Wikipedia	License
Phenylacetaldehyde is an organic compound used in the synthesis of fragrances and polymers. Phenylacetaldehyde is an aldehyde that consists of acetaldehyde bearing a phenyl substituent; the parent member of the phenylacetaldehyde class of compounds. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is an alpha-CH2-containing aldehyde and a member of phenylacetaldehydes. Phenylacetaldehyde is one important oxidation-related aldehyde. Exposure to styrene gives phenylacetaldehyde as a secondary metabolite. Styrene has been implicated as reproductive toxicant, neurotoxicant, or carcinogen in vivo or in vitro. Phenylacetaldehyde could be formed by diverse thermal reactions during the cooking process together with C8 compounds is identified as a major aroma–active compound in cooked pine mushroom. Phenylacetaldehyde is readily oxidized to phenylacetic acid. Therefore will eventually be hydrolyzed and oxidized to yield phenylacetic acid that will be excreted primarily in the urine in conjugated form.
Read full article at Wikipedia

Formula

C15H11I4NO4

Net Charge

Average Mass

776.87006

Monoisotopic Mass

776.68669

InChI

InChI=1S/C15H11I4NO4/c16-8-4-7(5-9(17)13(8)21)24-14-10(18)1-6(2-11(14)19)3-12(20)15(22)23/h1-2,4-5,12,21H,3,20H2,(H,22,23)/t12-/m0/s1

InChIKey

XUIIKFGFIJCVMT-LBPRGKRZSA-N

SMILES

N[C@@H](Cc1cc(I)c(Oc2cc(I)c(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):	antithyroid drug A drug used to treat hyperthyroidism by reducing the excessive production of thyroid hormones. human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). thyroid hormone Any hormone produced by the thyroid gland mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). mitogen A chemical substance that encourages a cell to commence cell division, triggering mitosis. (via thyroxine )

Application(s):	antithyroid drug A drug used to treat hyperthyroidism by reducing the excessive production of thyroid hormones.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	L-thyroxine (CHEBI:18332) has role antithyroid drug (CHEBI:50671) L-thyroxine (CHEBI:18332) has role human metabolite (CHEBI:77746) L-thyroxine (CHEBI:18332) has role mouse metabolite (CHEBI:75771) L-thyroxine (CHEBI:18332) has role thyroid hormone (CHEBI:60311) L-thyroxine (CHEBI:18332) is a 2-halophenol (CHEBI:53291) L-thyroxine (CHEBI:18332) is a L-phenylalanine derivative (CHEBI:84144) L-thyroxine (CHEBI:18332) is a iodophenol (CHEBI:24863) L-thyroxine (CHEBI:18332) is a non-proteinogenic L-α-amino acid (CHEBI:83822) L-thyroxine (CHEBI:18332) is a thyroxine (CHEBI:30660) L-thyroxine (CHEBI:18332) is conjugate acid of L-thyroxine(1−) (CHEBI:60302) L-thyroxine (CHEBI:18332) is enantiomer of D-thyroxine (CHEBI:30659) L-thyroxine (CHEBI:18332) is tautomer of L-thyroxine zwitterion (CHEBI:58448)

Incoming	desiccated thyroid extract (CHEBI:9584) has part L-thyroxine (CHEBI:18332) L-thyroxine(1−) (CHEBI:60302) is conjugate base of L-thyroxine (CHEBI:18332) D-thyroxine (CHEBI:30659) is enantiomer of L-thyroxine (CHEBI:18332) L-thyroxine residue (CHEBI:90872) is substituent group from L-thyroxine (CHEBI:18332) L-thyroxine zwitterion (CHEBI:58448) is tautomer of L-thyroxine (CHEBI:18332)

IUPAC Name

L-thyroxine

Synonyms	Sources
3,3',5,5'-tetraiodo-L-thyronine	ChemIDplus
3,5,3',5'-TETRAIODO-L-THYRONINE	PDBeChem
3,5,3',5'-tetraiodo-L-thyronine	ChemIDplus
4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodo-L-phenylalanine	IUPAC
L-T₄	ChemIDplus
L-Thyroxine	KEGG COMPOUND
Levothyroxin	KEGG COMPOUND
levothyroxine	ChemIDplus
LT₄	ChEBI
O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine	PDBeChem
T4	KEGG COMPOUND
T₄	ChEBI

Manual Xrefs	Databases
2646	DrugCentral
3004	VSDB
C01829	KEGG COMPOUND
D08125	KEGG DRUG
DB00451	DrugBank
Levothyroxine	Wikipedia
LSM-5447	LINCS
T44	PDBeChem
View more database links

Registry Numbers	Types	Sources
2228515	Beilstein Registry Number	Beilstein
51-48-9	CAS Registry Number	KEGG COMPOUND
51-48-9	CAS Registry Number	ChemIDplus
7002831	Beilstein Registry Number	Beilstein

Citations

Alzoubi KH, Alkadhi KA (2014)
Levothyroxin replacement therapy restores hypothyroidism induced impairment of L-LTP induction: critical role of CREB.
Brain research bulletin 100, 29-37 [PubMed:24216002]
[show Abstract]

Ianiro G, Mangiola F, Di Rienzo TA, Bibbò S, Franceschi F, Greco AV, Gasbarrini A (2014)
Levothyroxine absorption in health and disease, and new therapeutic perspectives.
European review for medical and pharmacological sciences 18, 451-456 [PubMed:24610609]
[show Abstract]

Anagnostis P, Efstathiadou ZA, Slavakis A, Selalmatzidou D, Poulasouchidou M, Katergari S, Karathanasi E, Dogramatzi F, Kita M (2014)
The effect of L-thyroxine substitution on lipid profile, glucose homeostasis, inflammation and coagulation in patients with subclinical hypothyroidism.
International journal of clinical practice 68, 857-863 [PubMed:24548294]
[show Abstract]

Prasad BB, Madhuri R, Tiwari MP, Sharma PS (2010)
Layer-by-layer assembled molecularly imprinted polymer modified silver electrode for enantioselective detection of D- and L-thyroxine.
Analytica chimica acta 681, 16-26 [PubMed:21035598]
[show Abstract]

Prasad BB, Tiwari MP, Madhuri R, Sharma PS (2010)
Enatioselective quantitative separation of D- and L-thyroxine by molecularly imprinted micro-solid phase extraction silver fiber coupled with complementary molecularly imprinted polymer-sensor.
Journal of chromatography. A 1217, 4255-4266 [PubMed:20483419]
[show Abstract]

Pabla D, Akhlaghi F, Zia H (2009)
A comparative pH-dissolution profile study of selected commercial levothyroxine products using inductively coupled plasma mass spectrometry.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 72, 105-110 [PubMed:18996189]
[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]

Sandhu GS, Steele R, Gonnella NC (1991)
Effect of L-thyroxine (LT4) and D-thyroxine (DT4) on cardiac function and high-energy phosphate metabolism: a 31P NMR study.
Magnetic resonance in medicine 18, 237-243 [PubMed:2062236]
[show Abstract]

Last Modified

18 February 2021

ChEBI

CHEBI:18332 - L-thyroxine

Aims

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Results

Conclusions

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