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Bovine Metabolome Database



Showing metabocard for Iodotyrosine (BMDB00021)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:57:38
Accession Number BMDB00021
Common Name Iodotyrosine
Description An iodated derivative of L-tyrosine. This is an early precursor to L-thyroxine, one of the primary thyroid hormones. In the thyroid gland, iodide is trapped, transported, and concentrated in the follicular lumen for thyroid hormone synthesis. Before trapped iodide can react with tyrosine residues, it must be oxidized by thyroid peroxidase. Iodotyrosine is made from tyrosine via thyroid peroxidase and then further iodinated by this enzyme to make the di-iodo and tri-iodo variants. Two molecules of di-iodotyrosine combine to form T4, and one molecule of mono-iodotyrosine combines with one molecule of di-iodotyrosine to form T3.
Synonyms
  1. Monoiodotyrosine
  2. 3-Iodo-L-tyrosine
  3. MIT
  4. 3-Monoiodo-L-tyrosine
  5. 3-Iodotyrosine
  6. 3-Iodo-4-hydroxyphenylalanine
  7. IYR
  8. 3-iodo-tyrosine
  9. (2S)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoic acid
  10. 4-Hydroxy-3-iodophenylalanine
  11. L-Tyrosine-3-iodo
  12. (2S)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoate
Chemical IUPAC Name (2S)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoic acid
Chemical Formula C9H10INO3
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Amino acids and Amino Acid conjugates
Class
  • Amino Acids
Sub Class
  • NA
Family
  • Mammalian_Metabolite
Species
  • phenol or hydroxyhetarene; primary amine; primary aliphatic amine (alkylamine); aryl iodide; carboxylic acid; aromatic compound; alpha-aminoacid
Biofunction
  • Protein synthesis, amino acid biosynthesis
Application
Source
  • Endogenous
Average Molecular Weight 307.085
Monoisotopic Molecular Weight 306.970551
Isomeric SMILES N[C@@H](CC1=CC=C(O)C(I)=C1)C(O)=O
Canonical SMILES NC(CC1=CC=C(O)C(I)=C1)C(O)=O
KEGG Compound ID C02515 Link Image
BioCyc ID IODO-L-TYROSINE Link Image
BiGG ID 39998 Link Image
Wikipedia Link Monoiodotyrosine Link Image
METLIN ID Not Available
PubChem Compound 439744 Link Image
PubChem Substance 7888504 Link Image
ChEBI ID 27847 Link Image
CAS Registry Number 70-78-0
InChI Identifier InChI=1/C9H10INO3/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14/h1-3,7,12H,4,11H2,(H,13,14)/t7-/m0/s1
Synthesis Reference Hillmann, Gunther; Hillmann-Elies, Anneliese. Synthesis of 3-iodo-L-tyrosine. Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie (1956), 305 177-81.
Melting Point (Experimental) 205 oC
Experimental Water Solubility 3 mg/mL [HMP experimental] Source: PhysProp
Predicted Water Solubility 124.0 mg/mL [MEYLAN,WM et al. (1996)]; 0.937 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -0.7 [Predicted by PubChem via XLOGP]; -1.51 [Predicted by ALOGPS]; -0.60 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
Biofluid Location Not Available
Tissue Location
Tissue References
Thyroid Gland
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Tyrosine Metabolism
HMDB Pathways
Name Tyrosine Metabolism
Image Show Link Image
KEGG Pathways
Name Tyrosine Metabolism
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SimCell Pathways
Name Tyrosine Metabolism
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Graph
SBML
General References
  1. Wikipedia Link Image