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Record Information
Version3.6
Creation Date2006-08-12 21:39:17 UTC
Update Date2013-02-09 00:12:35 UTC
HMDB IDHMDB03474
Secondary Accession NumbersNone
Metabolite Identification
Common Name3,5-Diiodo-L-tyrosine
Description3,5-Diiodo-L-tyrosine is a product from the iodination of monoiodotyrosine. In the biosynthesis of thyroid hormones, diiodotyrosine residues are coupled with other monoiodotyrosine or diiodotyrosine residues to form T4 or T3 thyroid hormones (thyroxine and triiodothyronine).
Structure
Thumb
Synonyms
  1. 3,5-Diiodotyrocine
  2. 3,5-Iodo-L-tyrosine
  3. 3,5-L-Diiodotyrosine
  4. 4-Hydroxy-3,5-diiodophenylalanine
  5. L-3,5-DiioDOTyrosine
  6. L-Diiodotyrosine
Chemical FormulaC9H9I2NO3
Average Molecular Weight432.9816
Monoisotopic Molecular Weight432.867179999
IUPAC Name(2S)-2-amino-3-(4-hydroxy-3,5-diiodophenyl)propanoic acid
Traditional Name3,5-diiodotyrosine
CAS Registry Number300-39-0
SMILES
N[C@@H](CC1=CC(I)=C(O)C(I)=C1)C(O)=O
InChI Identifier
InChI=1S/C9H9I2NO3/c10-5-1-4(2-6(11)8(5)13)3-7(12)9(14)15/h1-2,7,13H,3,12H2,(H,14,15)/t7-/m0/s1
InChI KeyNYPYHUZRZVSYKL-ZETCQYMHSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassAmino Acids and Derivatives
Sub ClassAlpha Amino Acids and Derivatives
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Other amino acids(KEGG)
  • dihalogenated L-tyrosine(ChEBI)
  • diiodotyrosine(ChEBI)
Substituents
  • Amphetamine Or Derivative
  • Aryl Iodide
  • Carboxylic Acid
  • Iodobenzene
  • Organoiodide
  • Phenethylamine
  • Phenol
  • Phenol Derivative
  • Primary Aliphatic Amine (Alkylamine)
Direct ParentAlpha Amino Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.617 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.52 g/LALOGPS
logP-0.7ALOGPS
logP0.37ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)0.48ChemAxon
pKa (Strongest Basic)9.45ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity73.82ChemAxon
Polarizability28.94ChemAxon
Spectra
SpectraGC-MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Tyrosine MetabolismSMP00006map00350
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0036 (0.0014-0.0099) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.000049 +/- 0.000027 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0036 (0.0010-0.0134) uMAdult (>18 years old)BothHyperthyroidism details
UrineDetected and Quantified0.00013 +/- 0.000098 umol/mmol creatinineAdult (>18 years old)BothChronic renal disease details
Associated Disorders and Diseases
Disease References
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. Pubmed: 3098453
Hyperthyroidism
  1. Nelson JC, Weiss RM, Lewis JE, Wilcox RB, Palmer FJ: A multiple ligand-binding radioimmunoassay of diiodotyrosine. J Clin Invest. 1974 Feb;53(2):416-22. Pubmed: 11344555
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023181
KNApSAcK IDNot Available
Chemspider ID8946
KEGG Compound IDC01060
BioCyc IDDIIODO-L-TYROSINE
BiGG ID36719
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03474
Metagene LinkHMDB03474
METLIN ID6940
PubChem Compound9305
PDB IDTYI
ChEBI ID15768
References
Synthesis ReferenceSavitskii, A. Ya. The preparation and properties of 3,5-diiodo-l-tyrosine. Zhurnal Obshchei Khimii (1939), 9 1342-4.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Ismail-Beigi F, Rahimifar M: A variant of iodotyrosine-dehalogenase deficiency. J Clin Endocrinol Metab. 1977 Mar;44(3):499-506. Pubmed: 838849
  2. Bismuth J, Castay M, Lissitzky S: Binding of 3,5-diiodotyrosine to serum proteins. Clin Chim Acta. 1976 Jun 15;69(3):417-22. Pubmed: 59643
  3. Tompkins RK, Croke JC: Bile acids inhibit pepsin activity against a refined substrate. Am J Surg. 1980 Feb;139(2):237-9. Pubmed: 6766680

Enzymes

General function:
Involved in calcium ion binding
Specific function:
Iodination and coupling of the hormonogenic tyrosines in thyroglobulin to yield the thyroid hormones T(3) and T(4).
Gene Name:
TPO
Uniprot ID:
P07202
Molecular weight:
102961.63
Reactions
3,5-Diiodo-L-tyrosine + Hydrogen peroxide → Thyroxine + 2-Aminoacrylic acid + Waterdetails
Iodotyrosine + 3,5-Diiodo-L-tyrosine + Hydrogen peroxide → Liothyronine + 2-Aminoacrylic acid + Waterdetails
I(-) + 3,5-Diiodo-L-tyrosine → Iodotyrosine + Iodinedetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative NADPH-dependent deiodination of monoiodotyrosine (L-MIT) or diiodotyrosine (L-DIT). Acts during the hydrolysis of thyroglobulin to liberate iodide, which can then reenter the hormone-producing pathways. Acts more efficiently on monoiodotyrosine than on diiodotyrosine.
Gene Name:
IYD
Uniprot ID:
Q6PHW0
Molecular weight:
33781.22
Reactions
L-Tyrosine + NADP + I(-) → 3,5-Diiodo-L-tyrosine + NADPHdetails