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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:00 UTC
HMDB IDHMDB0000265
Secondary Accession Numbers
  • HMDB0006780
  • HMDB00265
  • HMDB06780
Metabolite Identification
Common NameLiothyronine
DescriptionLiothyronine is a T3 thyroid hormone normally synthesized and secreted by the thyroid gland in much smaller quantities than thyroxine (T4). Most T3 is derived from peripheral monodeiodination of T4 at the 5' position of the outer ring of the iodothyronine nucleus. The hormone finally delivered and used by the tissues is mainly T3. Mildly toxic by ingestion. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx, I(-), and Cl(-). (Sax's Dangerous Properties of Industrial Materials).
Structure
Data?1563860640
SynonymsNot Available
Chemical FormulaC15H12I3NO4
Average Molecular Weight650.9735
Monoisotopic Molecular Weight650.790038137
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number6893-02-3
SMILESNot 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 KeyAUYYCJSJGJYCDS-LBPRGKRZSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05a9-5090378000-014ef55558b58a3d38f2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-000i-0009001000-1d47041336da63b556e4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-000i-1009001000-15f70073b9018f013c9cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-000i-0009000000-71c231d7a3ab505815ffJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0000009000-f932659d1e6d8a622985JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-0000009000-6506a7a71dab928abfb0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0fc0-0700119000-1df6db0e3031eb2739faJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-0900000000-973fc871534b19242cc8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-0900000000-ac3c4a198bb017dc7cccJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0udi-0000009000-2770ece749a9fa1042f4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0udi-0000009000-881174c66da97022d645JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a4i-0000019000-6f798ae76702a3053339JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4i-0000219000-d2ca9f0cc3c1b47176b5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-056r-0021915000-6f3810619f383bce651aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0000009000-f932659d1e6d8a622985JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0000009000-6506a7a71dab928abfb0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0fc0-0700119000-1df6db0e3031eb2739faJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-973fc871534b19242cc8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-ac3c4a198bb017dc7cccJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0000009000-2770ece749a9fa1042f4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pb9-0000009000-4d60e144164273111464JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000149000-87babecf610c68223da5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-016r-0039010000-b57f6dd23e6456cf7c1eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0010009000-50e441d89395debe176bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-0050139000-a259e39ad1204b60b373JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00e9-9262431000-bcc1f7554c4e309cef17JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Saliva
  • Urine
Tissue Locations
  • Adipose Tissue
  • Adrenal Gland
  • Epidermis
  • Fibroblasts
  • Intestine
  • Nerve Cells
  • Neuron
  • Placenta
  • Platelet
  • Skeletal Muscle
  • Testes
  • Thyroid Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0029 +/- 0.00019 uMChildren (1-13 years old)BothNormal details
BloodDetected and Quantified0.002 +/- 0.0006 uMAdolescent (13-18 years old)FemaleNormal details
BloodDetected and Quantified0.000013 - 0.000028 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0000038 - 0.0000060 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0000031-0.0000077 uMAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected and Quantified0.0 - 1.0 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0011 +/- 0.00024 uMChildren (1-13 years old)BothMalnutrition (type kwashiorkor and marasmus) details
BloodDetected and Quantified0.0014 +/- 0.0004 uMAdolescent (13-18 years old)FemaleAnorexia nervosa details
BloodDetected and Quantified0.00169 uMAdult (>18 years old)Female
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified0.0000041 uMAdult (>18 years old)FemaleProprotein Convertase 1/3 Deficiency details
UrineDetected and Quantified0.00075 +/- 0.00033 umol/mmol creatinineAdult (>18 years old)BothHyperthyroidism details
UrineDetected and Quantified0.000014 +/- 0.000015 umol/mmol creatinineAdult (>18 years old)BothHypothyroidism details
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease References
Anorexia nervosa
  1. Capo-chichi CD, Gueant JL, Lefebvre E, Bennani N, Lorentz E, Vidailhet C, Vidailhet M: Riboflavin and riboflavin-derived cofactors in adolescent girls with anorexia nervosa. Am J Clin Nutr. 1999 Apr;69(4):672-8. [PubMed:10197568 ]
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
  1. Hattori N, Ishihara T, Moridera K, Hino M, Ikekubo K, Kurahachi H: A case of late-onset congenital adrenal hyperplasia due to partial 3 beta-hydroxysteroid dehydrogenase deficiency. Endocr J. 1993 Feb;40(1):107-9. [PubMed:7951484 ]
Proprotein Convertase 1/3 Deficiency
  1. O'Rahilly S, Gray H, Humphreys PJ, Krook A, Polonsky KS, White A, Gibson S, Taylor K, Carr C: Brief report: impaired processing of prohormones associated with abnormalities of glucose homeostasis and adrenal function. N Engl J Med. 1995 Nov 23;333(21):1386-90. doi: 10.1056/NEJM199511233332104. [PubMed:7477119 ]
Hyperthyroidism
  1. Yoshida K, Sakurada T, Kaise N, Yamamoto M, Kaise K, Saito S, Yoshinaga K: Measurement of triiodothyronine in urine. Tohoku J Exp Med. 1980 Dec;132(4):389-95. [PubMed:7256725 ]
Hypothyroidism
  1. Yoshida K, Sakurada T, Kaise N, Yamamoto M, Kaise K, Saito S, Yoshinaga K: Measurement of triiodothyronine in urine. Tohoku J Exp Med. 1980 Dec;132(4):389-95. [PubMed:7256725 ]
Associated OMIM IDs
  • 606788 (Anorexia nervosa)
  • 201810 (Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency)
  • 600955 (Proprotein Convertase 1/3 Deficiency)
External LinksNot Available
References
Synthesis ReferenceSalamonczyk, Grzegorz M.; Oza, Vibha B.; Sih, Charles J. A concise synthesis of thyroxine (T4) and 3,5,3'-triiodo-L-thyronine (T3). Tetrahedron Letters (1997), 38(40), 6965-69
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [PubMed:14675747 ]
  2. 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. Epub 2005 May 11. [PubMed:15889350 ]
  3. 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. [PubMed:10197073 ]
  4. Holt PJ: In vitro responses of the epidermis to triiodothyronine. J Invest Dermatol. 1978 Sep;71(3):202-4. [PubMed:690484 ]
  5. 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. [PubMed:11179199 ]
  6. Himms-Hagen J: Brown adipose tissue thermogenesis: interdisciplinary studies. FASEB J. 1990 Aug;4(11):2890-8. [PubMed:2199286 ]
  7. 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. [PubMed:1409189 ]
  8. 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. [PubMed:10209562 ]
  9. 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. [PubMed:9804999 ]
  10. 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. [PubMed:7615374 ]
  11. 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 ]
  12. 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. [PubMed:16322796 ]
  13. 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. [PubMed:11106433 ]
  14. 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. [PubMed:15767619 ]
  15. 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. [PubMed:11544279 ]
  16. Iwao H, Abe Y: [Expression of the renin and angiotensinogen genes]. Nihon Yakurigaku Zasshi. 1991 Jan;97(1):1-11. [PubMed:2045011 ]
  17. 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. [PubMed:2394838 ]
  18. 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. Epub 2004 Oct 15. [PubMed:15490139 ]

Enzymes

General function:
Involved in calcium ion binding
Specific function:
Iodination and coupling of the hormonogenic tyrosines in thyroglobulin to yield the thyroid hormones T(3) and T(4).
Gene Name:
TPO
Uniprot ID:
P07202
Molecular weight:
102961.63
Reactions
Iodotyrosine + 3,5-Diiodo-L-tyrosine + Hydrogen peroxide → Liothyronine + 2-Aminoacrylic acid + Waterdetails
General function:
Involved in thyroxine 5'-deiodinase activity
Specific function:
Responsible for the deiodination of T4 (3,5,3',5'-tetraiodothyronine) into T3 (3,5,3'-triiodothyronine) and of T3 into T2 (3,3'-diiodothyronine). Plays a role in providing a source of plasma T3 by deiodination of T4 in peripheral tissues such as liver and kidney.
Gene Name:
DIO1
Uniprot ID:
P49895
Molecular weight:
28924.21
Reactions
Liothyronine + I(-) + A + Hydrogen Ion → Thyroxine + AH(2)details
General function:
Involved in thyroxine 5'-deiodinase activity
Specific function:
Responsible for the deiodination of T4 (3,5,3',5'-tetraiodothyronine) into T3 (3,5,3'-triiodothyronine). Essential for providing the brain with appropriate levels of T3 during the critical period of development.
Gene Name:
DIO2
Uniprot ID:
Q92813
Molecular weight:
30551.48
Reactions
Liothyronine + I(-) + A + Hydrogen Ion → Thyroxine + AH(2)details
General function:
Involved in hormone activity
Specific function:
Thyroid hormone-binding protein. Probably transports thyroxine from the bloodstream to the brain
Gene Name:
TTR
Uniprot ID:
P02766
Molecular weight:
15886.9
General function:
Involved in transport
Specific function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc
Gene Name:
ALB
Uniprot ID:
P02768
Molecular weight:
69365.9
General function:
Involved in serine-type endopeptidase inhibitor activity
Specific function:
Major thyroid hormone transport protein in serum
Gene Name:
SERPINA7
Uniprot ID:
P05543
Molecular weight:
46324.1
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
High affinity receptor for triiodothyronine
Gene Name:
THRB
Uniprot ID:
P10828
Molecular weight:
52787.2
General function:
Involved in thyroxine 5'-deiodinase activity
Specific function:
Responsible for the deiodination of T4 (3,5,3',5'-tetraiodothyronine) into RT3 (3,3',5'-triiodothyronine) and of T3 (3,5,3'-triiodothyronine) into T2 (3,3'-diiodothyronine). RT3 and T2 are inactive metabolites. May play a role in preventing premature exposure of developing fetal tissues to adult levels of thyroid hormones. Can regulate circulating fetal thyroid hormone concentrations throughout gestation. Essential role for regulation of thyroid hormone inactivation during embryological development.
Gene Name:
DIO3
Uniprot ID:
P55073
Molecular weight:
33947.175
Reactions
Liothyronine + I(-) + A + Hydrogen Ion → Thyroxine + AH(2)details
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Nuclear hormone receptor. High affinity receptor for triiodothyronine
Gene Name:
THRA
Uniprot ID:
P10827
Molecular weight:
54815.1