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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:10 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NameL-Thyronine
DescriptionIodide is actively absorbed from the bloodstream and concentrated in the thyroid follicles. (If there is a deficiency of dietary iodine, the thyroid enlarges in an attempt to trap more iodine, resulting in goitre.) Via a reaction with the enzyme thyroperoxidase, iodine is covalently bound to tyrosine residues in the thyroglobulin molecules, forming monoiodotyrosine (MIT) and diiodotyrosine (DIT). Linking two moieties of DIT produces thyroxine. Combining one particle of MIT and one particle of DIT produces triiodothyronine. The thyronamines function via some unknown mechanism to inhibit neuronal activity; this plays an important role in the hibernation cycles of mammals. One effect of administering the thyronamines is a severe drop in body temperature. Both T3 and T4 are used to treat thyroid hormone deficiency (hypothyroidism). They are both absorbed well by the gut, so can be given orally. Levothyroxine, the most commonly used synthetic thyroxine form, is a stereoisomer of physiological thyroxine, which is metabolised more slowly and hence usually only needs once-daily administration. Natural desiccated thyroid hormones, which are derived from pig thyroid glands, are a "natural" hypothyroid treatment containing 20% T3 and traces of T2, T1 and calcitonin. A group of metabolites derived from thyroxine and triiodothyronine via the peripheral enzymatic removal of iodines from the thyroxine nucleus. Thyronine is the thyroxine nucleus devoid of its four iodine atoms.
Chemical FormulaC15H15NO4
Average Molecular Weight273.2839
Monoisotopic Molecular Weight273.100107973
IUPAC Name(2S)-2-amino-3-[4-(4-hydroxyphenoxy)phenyl]propanoic acid
Traditional Namethyronine
CAS Registry Number1596-67-4
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylethers
Direct ParentDiphenylethers
Alternative Parents
  • Diphenylether
  • 3-phenylpropanoic-acid
  • Diaryl ether
  • L-alpha-amino acid
  • Amphetamine or derivatives
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Aralkylamine
  • Phenol
  • Amino fatty acid
  • Fatty acyl
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
StatusDetected and Quantified
  • Endogenous
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
Experimental Properties
Melting Point255 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.05 mg/mLALOGPS
pKa (Strongest Acidic)1.61ChemAxon
pKa (Strongest Basic)9.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.78 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity73.34 m3·mol-1ChemAxon
Polarizability27.72 Å3ChemAxon
Number of Rings2ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0adi-0090000000-0c68e00d57e7915b5486View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-2950000000-eb4bb2399809067f70a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-6900000000-9a61d9007b69a8a69798View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Spleen
  • Thyroid Gland
PathwaysNot Available
Normal Concentrations
BloodDetected and Quantified0.29 +/- 0.084 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0038 +/- 0.00048 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0010 +/- 0.00038 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BloodDetected and Quantified0.34 +/- 0.02 uMAdult (>18 years old)Both
Amyotrophic lateral sclerosis
UrineDetected and Quantified0.0069 +/- 0.0014 umol/mmol creatinineAdult (>18 years old)BothHyperthyroidism details
UrineDetected and Quantified0.00028 +/- 0.00017 umol/mmol creatinineAdult (>18 years old)Both
Chronic renal disease
Associated Disorders and Diseases
Disease References
Amyotrophic lateral sclerosis
  1. Malin JP, Kodding R, Fuhrmann H, von zur Muhlen A: T4, T3 and rT3 levels in serum and cerebrospinal fluid of patients with amyotrophic lateral sclerosis. J Neurol. 1989 Jan;236(1):57-9. [2915230 ]
Chronic kidney disease
  1. Ramsden DB, Farmer M, Mohammed MN, McGonigle RS, Sheppard MC: 3,5-Diiodotyrosine and thyronine in the urine of patients with chronic renal disease. Clin Endocrinol (Oxf). 1986 May;24(5):491-5. [3098453 ]
  1. Chopra IJ, Boado RJ, Geffner DL, Solomon DH: A radioimmunoassay for measurement of thyronine and its acetic acid analog in urine. J Clin Endocrinol Metab. 1988 Sep;67(3):480-7. [3410934 ]
Associated OMIM IDs
  • 105400 (Amyotrophic lateral sclerosis)
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022172
KNApSAcK IDNot Available
Chemspider ID4574450
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00667
Metagene LinkHMDB00667
PubChem Compound5461103
PDB IDNot Available
ChEBI ID30662
Synthesis ReferenceHarrington, C. R.; Rivers, Rosalind V. Pitt. New synthesis of thyronine. Journal of the Chemical Society (1940), 1101-3.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Chopra IJ, Wu SY, Teco GN, Santini F: A radioimmunoassay for measurement of 3,5,3'-triiodothyronine sulfate: studies in thyroidal and nonthyroidal diseases, pregnancy, and neonatal life. J Clin Endocrinol Metab. 1992 Jul;75(1):189-94. [1619009 ]
  2. Malin JP, Kodding R, Fuhrmann H, von zur Muhlen A: T4, T3 and rT3 levels in serum and cerebrospinal fluid of patients with amyotrophic lateral sclerosis. J Neurol. 1989 Jan;236(1):57-9. [2915230 ]
  3. Lomo LC, Zhang F, McCormick DJ, Giraldo AA, David CS, Kong YC: Flexibility of the thyroiditogenic T cell repertoire for murine autoimmune thyroiditis in CD8-deficient (beta2m -/-) and T cell receptor Vbeta(c) congenic mice. Autoimmunity. 1998;27(3):127-33. [9609129 ]
  4. LoPresti JS, Anderson KP, Nicoloff JT: Does a hidden pool of reverse triiodothyronine (rT3) production contribute to total thyroxine (T4) disposal in high T4 states in man. J Clin Endocrinol Metab. 1990 May;70(5):1479-84. [2335581 ]
  5. Ramsden DB, Farmer M, Mohammed MN, Willetts P: Mass spectral properties of volatile derivatives of thyronine (T0) and use of these in the study of thyronine excretion in eu-, hyper- and hypothyroidism. Biomed Mass Spectrom. 1984 Apr;11(4):193-8. [6733255 ]
  6. Morell M, Fernandez-Guillien FJ, Lopez-Garcia JM: Levels of L-T3 in maternal and foetal compartments following experimental modifications of the maternal thyroid state in rats. Arch Int Physiol Biochim Biophys. 1994 Jan-Feb;102(1):1-3. [7516725 ]
  7. Kohrle J: The deiodinase family: selenoenzymes regulating thyroid hormone availability and action. Cell Mol Life Sci. 2000 Dec;57(13-14):1853-63. [11215512 ]