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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
2D NMR[1H, 13C]-HSQC 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
Species NameSourceReference
Anas platyrhynchos
Anatidae
Anser anser
Bison bison
Bos taurus
Bos taurus X Bison bison
Bubalus bubalis
Capra aegagrus hircus
Cervidae
Cervus canadensis
Columba
Columbidae
Dromaius novaehollandiae
Equus caballus
Gallus gallus
Lagopus muta
Leporidae
Lepus timidus
Melanitta fusca
Meleagris gallopavo
Numida meleagris
Odocoileus
Oryctolagus
Ovis aries
Phasianidae
Phasianus colchicus
Struthio camelus
Sus scrofa
Sus scrofa domestica
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 Parents
Substituents
  • Phenylalanine or derivatives
  • Diphenylether
  • Diaryl ether
  • 3-phenylpropanoic-acid
  • Amphetamine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Phenol ether
  • Phenoxy compound
  • Aralkylamine
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Primary aliphatic amine
  • Amine
  • Organic oxide
  • Primary amine
  • Carbonyl group
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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
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 ]