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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2020-11-24 22:13:41 UTC
NP-MRD IDNP0000208
Secondary Accession NumbersNone
Natural Product 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.
Structure
Thumb
Synonyms
ValueSource
4-(4-Hydroxyphenoxy)-L-phenylalanineChEBI
O-(4-Hydroxyphenyl)-L-tyrosineChEBI
b-(p-Hydroxyphenoxy)phenylalanineHMDB
beta-(p-Hydroxyphenoxy)phenylalanineHMDB
DesiodothyroxineHMDB
O-(4-Hydroxyphenyl)tyrosineHMDB
ThyronineHMDB
ThyroninesHMDB
Chemical FormulaC15H15NO4
Average Mass273.2839 Da
Monoisotopic Mass273.10011 Da
IUPAC Name(2S)-2-amino-3-[4-(4-hydroxyphenoxy)phenyl]propanoic acid
Traditional Namethyronine
CAS Registry Number1596-67-4
SMILES
N[C@@H](CC1=CC=C(OC2=CC=C(O)C=C2)C=C1)C(O)=O
InChI Identifier
InChI=1S/C15H15NO4/c16-14(15(18)19)9-10-1-5-12(6-2-10)20-13-7-3-11(17)4-8-13/h1-8,14,17H,9,16H2,(H,18,19)/t14-/m0/s1
InChI KeyKKCIOUWDFWQUBT-AWEZNQCLSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, simulated)Varshavi.d262021-08-01View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, simulated)V.dorna832021-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, experimental)V.dorna832021-08-23View Spectrum
Species
Species of Origin
  • Animalia
  • 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.
    KingdomOrganic compounds
    Super ClassOrganic acids and derivatives
    ClassCarboxylic acids and derivatives
    Sub ClassAmino acids, peptides, and analogues
    Direct ParentPhenylalanine and derivatives
    Alternative ParentsNot Available
    SubstituentsNot Available
    Molecular FrameworkAromatic homomonocyclic compounds
    External DescriptorsNot Available
    Physical Properties
    StateSolid
    Experimental Properties
    PropertyValueReference
    Melting Point255 °CNot Available
    Boiling PointNot AvailableNot Available
    Water SolubilityNot AvailableNot Available
    LogPNot AvailableNot Available
    Predicted Properties
    PropertyValueSource
    Water Solubility0.05 g/LALOGPS
    logP-0.27ALOGPS
    logP0.012ChemAxon
    logS-3.7ALOGPS
    pKa (Strongest Acidic)1.61ChemAxon
    pKa (Strongest Basic)9.26ChemAxon
    Physiological Charge0ChemAxon
    Hydrogen Acceptor Count4ChemAxon
    Hydrogen Donor Count3ChemAxon
    Polar Surface Area92.78 ŲChemAxon
    Rotatable Bond Count5ChemAxon
    Refractivity73.34 m³·mol⁻¹ChemAxon
    Polarizability27.72 ųChemAxon
    Number of Rings2ChemAxon
    BioavailabilityYesChemAxon
    Rule of FiveYesChemAxon
    Ghose FilterYesChemAxon
    Veber's RuleNoChemAxon
    MDDR-like RuleNoChemAxon
    External Links
    HMDB IDHMDB0000667
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB022172
    KNApSAcK IDNot Available
    Chemspider ID4574450
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkThyronine
    METLIN ID5637
    PubChem Compound5461103
    PDB IDNot Available
    ChEBI ID30662
    Good Scents IDNot Available
    References
    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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:11215512 ]