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Human Metabolome Database Version 3.5

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Showing metabocard for Liothyronine (HMDB00265)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:12 -0700
HMDB ID HMDB00265
Secondary Accession Numbers
  • HMDB06780
Metabolite Identification
Common Name Liothyronine
Description Liothyronine 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 Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 3,3',5'-Triiodo-L-thyronine
  2. 3,3',5'-Triiodothyronine
  3. 3,3',5-Triiodo-L-thyronine
  4. 3,3',5-Triiodothyronine
  5. 3,5,3'-Triiodothyronine
  6. 4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenylalanine
  7. Cyronine
  8. L-3,3',5-Triiodo-Thyronine
  9. L-3,3',5-Triiodothyronine
  10. L-3-[4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenyl]-Alanine
  11. L-Liothyronine
  12. L-T3
  13. L-Triiodothyronine
  14. Liothyronin
  15. Liothyronine
  16. O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-Tyrosine
  17. T3
  18. Tresitope
  19. Triiodo-L-thyronine
  20. Triiodothyronine
Chemical Formula C15H12I3NO4
Average Molecular Weight 650.9735
Monoisotopic Molecular Weight 650.790038137
IUPAC Name (2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid
Traditional IUPAC Name liothyronine
CAS Registry Number 6893-02-3
SMILES N[C@@H](CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C1)C(O)=O
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
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha Amino Acids and Derivatives
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Aromatic Homopolycyclic Compounds
  • Other amino acids(KEGG)
  • Thyroxine(KEGG)
  • amino acid zwitterion(ChEBI)
Substituents
  • Amphetamine Or Derivative
  • Aryl Iodide
  • Carboxylic Acid
  • Iodobenzene
  • Methoxyphenol
  • Organoiodide
  • Phenethylamine
  • Phenol
  • Phenol Derivative
  • Primary Aliphatic Amine (Alkylamine)
Direct Parent Alpha Amino Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
Application Not Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.019 g/L ALOGPS
LogP 0.82 ALOGPS
LogP 2.8 ChemAxon
LogS -4.52 ALOGPS
pKa (strongest acidic) 0.3 ChemAxon
pKa (strongest basic) 9.48 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 92.78 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 113.43 ChemAxon
Polarizability 44.07 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue Location
  • Skeletal Muscle
  • Fibroblasts
  • Intestine
  • Neuron
  • Placenta
  • Testes
  • Epidermis
  • Thyroid Gland
  • Adrenal Gland
  • Adipose Tissue
  • Nerve Cells
  • Platelet
Pathways
Name SMPDB Link KEGG Link
Tyrosine Metabolism SMP00006 map00350 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.0029 +/- 0.00019 uM Children (1-13 year old) Both Normal Not Available
Blood Detected and Quantified
Article_icon
0.002 +/- 0.0006 uM Adolescent (13-18 years old) Female Normal Not Available
Saliva Detected and Quantified
Article_icon
0.0 - 1.0 uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.0011 +/- 0.00024 uM Children (1-13 year old) Both Severly malnourished children Not Available
Blood Detected and Quantified
Article_icon
0.0014 +/- 0.0004 uM Adolescent (13-18 years old) Female Anorexia nervosa Not Available
Urine Detected and Quantified
Article_icon
0.00075 +/- 0.00033 umol/mmol creatinine Adult (>18 years old) Both Hyperthyroidism Not Available
Urine Detected and Quantified
Article_icon
0.000014 +/- 0.000015 umol/mmol creatinine Adult (>18 years old) Both Hypothyroidism Not Available
Associated Disorders and Diseases
Disease References
Anorexia nervosa
  • 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 Link_out
    Hyperthyroidism
    • 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 Link_out
      Hypothyroidism
      • 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 Link_out
        Associated OMIM IDs
        DrugBank ID Not Available
        Phenol Explorer Compound ID Not Available
        Phenol Explorer Metabolite ID Not Available
        FoodDB ID FDB021810
        KNApSAcK ID Not Available
        Chemspider ID 5707 Link_out
        KEGG Compound ID C02465 Link_out
        BioCyc ID LIOTHYRONINE Link_out
        BiGG ID 39878 Link_out
        Wikipedia Link Liothyronine Link_out
        NuGOwiki Link HMDB00265 Link_out
        Metagene Link HMDB00265 Link_out
        METLIN ID 5265 Link_out
        PubChem Compound 5920 Link_out
        PDB ID T3 Link_out
        ChEBI ID 18258 Link_out
        References
        Synthesis Reference Salamonczyk, 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 Link_out
        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 Link_out
        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 Link_out
        4. Holt PJ: In vitro responses of the epidermis to triiodothyronine. J Invest Dermatol. 1978 Sep;71(3):202-4. Pubmed: 690484 Link_out
        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 Link_out
        6. Himms-Hagen J: Brown adipose tissue thermogenesis: interdisciplinary studies. FASEB J. 1990 Aug;4(11):2890-8. Pubmed: 2199286 Link_out
        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 Link_out
        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 Link_out
        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 Link_out
        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 Link_out
        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 Link_out
        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 Link_out
        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 Link_out
        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 Link_out
        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 Link_out
        16. Iwao H, Abe Y: [Expression of the renin and angiotensinogen genes] Nippon Yakurigaku Zasshi. 1991 Jan;97(1):1-11. Pubmed: 2045011 Link_out
        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 Link_out
        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 Link_out
        Enzymes
        Name: Thyroid peroxidase
        Reactions:
        • 2 iodide + H2O2 + 2 H+ = diiodine + 2 H2O [RN:R02810]
        Gene Name: TPO
        Uniprot ID: P07202 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Type I iodothyronine deiodinase
        Reactions:
        • 3,5,3'-triiodo-L-thyronine + iodide + A + H+ = L-thyroxine + AH2 [RN:R03734]
        Gene Name: DIO1
        Uniprot ID: P49895 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Type II iodothyronine deiodinase
        Reactions:
        • 3,5,3'-triiodo-L-thyronine + iodide + A + H+ = L-thyroxine + AH2 [RN:R03734]
        Gene Name: DIO2
        Uniprot ID: Q92813 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Transthyretin
        Reactions:
          Gene Name: TTR
          Uniprot ID: P02766 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Serum albumin
          Reactions:
            Gene Name: ALB
            Uniprot ID: P02768 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Thyroxine-binding globulin
            Reactions:
              Gene Name: SERPINA7
              Uniprot ID: P05543 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Thyroid hormone receptor beta
              Reactions:
                Gene Name: THRB
                Uniprot ID: P10828 Link_out
                Protein Sequence: FASTA
                Gene Sequence: FASTA
                Name: Thyroid hormone receptor alpha
                Reactions:
                  Gene Name: THRA
                  Uniprot ID: P10827 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA