MiMeDB: Showing metabocard for Liothyronine (MMDBc0031978)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:57:18 UTC

Update Date

2024-10-09 20:37:18 UTC

Metabolite ID

MMDBc0031978

Metabolite Identification

Common Name

Liothyronine

Description

NULL

Structure

MOL SDF PDB SMILES InChI

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

Molecular Formula

C₁₅H₁₂I₃NO₄

Average Mass

650.9735

Monoisotopic Mass

650.790038137

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

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

iodothyronine (CHEBI:18258 )
iodophenol (CHEBI:18258 )
2-halophenol (CHEBI:18258 )
thyroxine (C02465 )
Other amino acids (C02465 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Adipose Tissue
Adrenal Gland
Blood
Epidermis
Feces
Fibroblasts
Intestine
Neuron
Placenta
Platelet
Saliva
Skeletal Muscle
Testis
Thyroid Gland
Urine

Tissue Locations

Adipose Tissue
Adrenal Gland
Epidermis
Fibroblasts
Intestine
Neuron
Placenta
Platelet
Skeletal Muscle
Testis
Thyroid Gland

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191946	Thyroid peroxidase	Unknown	P07202	Homo sapiens
MMDBp0192670	Type I iodothyronine deiodinase	Enzyme	P49895	Homo sapiens
MMDBp0192671	Type II iodothyronine deiodinase	Enzyme	Q92813	Homo sapiens
MMDBp0193289	Transthyretin	Enzyme	P02766	Homo sapiens
MMDBp0193408	Serum albumin	Unknown	P02768	Homo sapiens
MMDBp0193712	Thyroxine-binding globulin	Enzyme	P05543	Homo sapiens
MMDBp0193718	Thyroid hormone receptor beta	Enzyme	P10828	Homo sapiens
MMDBp0196040	Type III iodothyronine deiodinase	Enzyme	P55073	Homo sapiens
MMDBp0196296	Thyroid hormone receptor alpha	Unknown	P10827	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0001497	3,5-Diiodo-L-tyrosine	2-Aminoacrylic acid	thyroid peroxidase	VMH	2997169 3153466 3475693
MMDBr0002272	Phosphoadenosine phosphosulfate	Adenosine 3',5'-diphosphate	sulfotransferase family, cytosolic, 1A, phenol-preferring, member 1	VMH	11535246 15293241
MMDBr0003914	Liothyronine	3,5,3-Triiodo-L-Thyronine-Beta-D-Glucuronoside	UDP glucuronosyltransferase 1 family, polypeptide A8	VMH	7263841 8405382
MMDBr0003915	Liothyronine	3,5,3-Triiodo-L-Thyronine-Beta-D-Glucuronoside	UDP glucuronosyltransferase 1 family, polypeptide A10	VMH	7263841 8405382
MMDBr0010424	3,3-Diiodo-L-Thyronine	Liothyronine	deiodinase, iodothyronine, type I	VMH	30371894
MMDBr0010425	3,3-Diiodo-L-Thyronine	Liothyronine	deiodinase, iodothyronine, type I	VMH	30371894
MMDBr0010430	3,5-Diiodo-L-Thyronine	Liothyronine	deiodinase, iodothyronine, type I	VMH	30371894
MMDBr0010431	3,5-Diiodo-L-Thyronine	Liothyronine	deiodinase, iodothyronine, type I	VMH	30371894
MMDBr0010436	Iodide	Thyroxine	deiodinase, iodothyronine, type I	VMH; KEGG	30371894
MMDBr0010437	Iodide	Thyroxine	deiodinase, iodothyronine, type I	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Anorexia nervosa	Slight Decrease	Association	Human Blood	HMDB	10197568
Hyperthyroidism		Association	Human Urine	HMDB	7256725
Hypothyroidism		Association	Human Urine	HMDB	7256725

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Source Type	Activity	Data Source	Reference
Not Available	Neurodevelopment effects	U.S. Environmental Protection Agency	CompTox
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	0.00169				uM	Adult (>18 years old)	Female	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	7951484
Human Blood	Detected and Quantified	0.0014	0.0004			uM	Adolescent (13-18 years old)	Female	Anorexia nervosa	HMDB	10197568
Human Urine	Detected and Quantified	0.00075	0.00033			umol/mmol creatinine	Adult (>18 years old)	Both	Hyperthyroidism	HMDB	7256725
Human Urine	Detected and Quantified	0.000014	0.000015			umol/mmol creatinine	Adult (>18 years old)	Both	Hypothyroidism	HMDB	7256725
Human Blood	Detected and Quantified	0.0000041				uM	Adult (>18 years old)	Female	Proprotein Convertase 1/3 Deficiency	HMDB	7477119
Human Saliva	Detected and Quantified			0.0	1.0	uM	Adult (>18 years old)	Both	Normal	HMDB	15179829
Human Blood	Detected and Quantified			0.0000031	0.0000077	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	7477119
Human Blood	Detected and Quantified	0.002	0.0006			uM	Adolescent (13-18 years old)	Female	Normal	HMDB	10197568
Human Blood	Detected and Quantified	0.0029	0.00019			uM	Children (1-13 years old)	Both	Normal	HMDB	10731506
Human Blood	Detected and Quantified			0.0000038	0.0000060	uM	Adult (>18 years old)	Both	Normal	HMDB	K&S Clinical Diagnostics (http://www.ksdiagnostics.com)
Human Blood	Detected and Quantified			0.000013	0.000028	uM	Adult (>18 years old)	Both	Normal	HMDB	K&S Clinical Diagnostics (http://www.ksdiagnostics.com)
Human Adipose tissue	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Adrenal gland	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Testis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Thyroid gland	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0000265

DrugBank ID

DB00279

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C02465

BioCyc ID

CPD-10813

BiGG ID

Not Available

Wikipedia Link

Triiodothyronine

METLIN ID

Not Available

PubChem Compound

5920

PDB ID

Not Available

ChEBI ID

18258

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Holt PJ: In vitro responses of the epidermis to triiodothyronine. J Invest Dermatol. 1978 Sep;71(3):202-4. doi: 10.1111/1523-1747.ep12547158. [PubMed:690484 ]
Gledhill RF, Dessein PH, Van der Merwe CA: Treatment of Raynaud's phenomenon with triiodothyronine corrects co-existent autonomic dysfunction: preliminary findings. Postgrad Med J. 1992 Apr;68(798):263-7. doi: 10.1136/pgmj.68.798.263. [PubMed:1409189 ]
Iwao H, Abe Y: [Expression of the renin and angiotensinogen genes]. Nihon Yakurigaku Zasshi. 1991 Jan;97(1):1-11. doi: 10.1254/fpj.97.1_1. [PubMed:2045011 ]
Himms-Hagen J: Brown adipose tissue thermogenesis: interdisciplinary studies. FASEB J. 1990 Aug;4(11):2890-8. [PubMed:2199286 ]
Calvo R, Obregon MJ, Ruiz de Ona C, Escobar del Rey F, Morreale de Escobar G: Congenital hypothyroidism, as studied in rats. Crucial role of maternal thyroxine but not of 3,5,3'-triiodothyronine in the protection of the fetal brain. J Clin Invest. 1990 Sep;86(3):889-99. doi: 10.1172/JCI114790. [PubMed:2394838 ]
Dutkiewicz S, Witeska A, Nauman A: The deiodination of thyroxine to triiodothyronine in the testes of patients with prostate cancer. Int Urol Nephrol. 1995;27(1):81-5. doi: 10.1007/BF02575224. [PubMed:7615374 ]
Llewellyn L, Ramsurn VP, Wigham T, Sweeney GE, Power DM: Cloning, characterisation and expression of the apolipoprotein A-I gene in the sea bream (Sparus aurata). Biochim Biophys Acta. 1998 Nov 8;1442(2-3):399-404. doi: 10.1016/s0167-4781(98)00171-7. [PubMed:9804999 ]
Zimmermann-Belsing T, Dreyer M, Holst JJ, Feldt-Rasmussen U: The relationship between the serum leptin concentrations of thyrotoxic patients during treatment and their total fat mass is different from that of normal subjects. Clin Endocrinol (Oxf). 1998 Nov;49(5):589-95. doi: 10.1046/j.1365-2265.1998.00627.x. [PubMed:10197073 ]
Kassem M, Brixen K, Mosekilde L, Blum WF, Flyvbjerg A: Effects of growth hormone treatment on serum levels of insulin-like growth factors (IGFs) and IGF binding proteins 1-4 in postmenopausal women. Clin Endocrinol (Oxf). 1998 Dec;49(6):747-56. doi: 10.1046/j.1365-2265.1998.00606.x. [PubMed:10209562 ]
Urcelay E, Jareno MA, Menaya J, Parrilla R, Ayuso MS, Martin-Requero A: Cloning and functional characterization of the 5' regulatory region of the human mitochondrial glycerol-3-phosphate dehydrogenase gene. Lack of 3,5,3'-triiodothyronine responsiveness in adipose tissue. Eur J Biochem. 2000 Dec;267(24):7209-17. doi: 10.1046/j.1432-1327.2000.01832.x. [PubMed:11106433 ]
Mizuma H, Murakami M, Mori M: Thyroid hormone activation in human vascular smooth muscle cells: expression of type II iodothyronine deiodinase. Circ Res. 2001 Feb 16;88(3):313-8. doi: 10.1161/01.res.88.3.313. [PubMed:11179199 ]
Lebon V, Dufour S, Petersen KF, Ren J, Jucker BM, Slezak LA, Cline GW, Rothman DL, Shulman GI: Effect of triiodothyronine on mitochondrial energy coupling in human skeletal muscle. J Clin Invest. 2001 Sep;108(5):733-7. doi: 10.1172/JCI11775. [PubMed:11544279 ]
Stalenheim EG: Long-term validity of biological markers of psychopathy and criminal recidivism: follow-up 6-8 years after forensic psychiatric investigation. Psychiatry Res. 2004 Jan 1;121(3):281-91. doi: 10.1016/j.psychres.2003.07.002. [PubMed:14675747 ]
Gil'miiarova FN, Pervova IuV, Radomskaia VM, Gergel' NI, Tarasova SV: [Levels of unified metabolites and thyroid hormones in blood and oral fluid of children with minimal brain dysfunction]. Biomed Khim. 2004 Mar-Apr;50(2):204-10. [PubMed:15179829 ]
Haas MJ, Fishman M, Mreyoud A, Mooradian AD: Thyroid hormone responsive protein (THRP) mediates thyroid hormone-induced cytotoxicity in primary neuronal cultures. Exp Brain Res. 2005 Jan;160(4):424-32. doi: 10.1007/s00221-004-2027-6. Epub 2004 Oct 15. [PubMed:15490139 ]
Escobar-Morreale HF, Botella-Carretero JI, Gomez-Bueno M, Galan JM, Barrios V, Sancho J: Thyroid hormone replacement therapy in primary hypothyroidism: a randomized trial comparing L-thyroxine plus liothyronine with L-thyroxine alone. Ann Intern Med. 2005 Mar 15;142(6):412-24. doi: 10.7326/0003-4819-142-6-200503150-00007. [PubMed:15767619 ]
Schwartz CE, May MM, Carpenter NJ, Rogers RC, Martin J, Bialer MG, Ward J, Sanabria J, Marsa S, Lewis JA, Echeverri R, Lubs HA, Voeller K, Simensen RJ, Stevenson RE: Allan-Herndon-Dudley syndrome and the monocarboxylate transporter 8 (MCT8) gene. Am J Hum Genet. 2005 Jul;77(1):41-53. doi: 10.1086/431313. Epub 2005 May 11. [PubMed:15889350 ]
Rosenbaum M, Goldsmith R, Bloomfield D, Magnano A, Weimer L, Heymsfield S, Gallagher D, Mayer L, Murphy E, Leibel RL: Low-dose leptin reverses skeletal muscle, autonomic, and neuroendocrine adaptations to maintenance of reduced weight. J Clin Invest. 2005 Dec;115(12):3579-86. doi: 10.1172/JCI25977. [PubMed:16322796 ]

Showing metabocard for Liothyronine (MMDBc0031978)

MOL for #<Metabolite:0x00007fdb4838c9a0>

3D MOL for #<Metabolite:0x00007fdb4838c9a0>

3D SDF for #<Metabolite:0x00007fdb4838c9a0>

3D-SDF for #<Metabolite:0x00007fdb4838c9a0>

PDB for #<Metabolite:0x00007fdb4838c9a0>

3D PDB for #<Metabolite:0x00007fdb4838c9a0>

SMILES for #<Metabolite:0x00007fdb4838c9a0>

INCHI for #<Metabolite:0x00007fdb4838c9a0>

Structure for #<Metabolite:0x00007fdb4838c9a0>

3D Structure for #<Metabolite:0x00007fdb4838c9a0>