Human Metabolome Database Version 3.5

Showing metabocard for 3,5-Diiodo-L-tyrosine (HMDB03474)

Record Information
Version 3.5
Creation Date 2006-08-12 15:39:17 -0600
Update Date 2013-02-08 17:12:35 -0700
HMDB ID HMDB03474
Secondary Accession Numbers None
Metabolite Identification
Common Name 3,5-Diiodo-L-tyrosine
Description 3,5-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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C9H9I2NO3
Average Molecular Weight 432.9816
Monoisotopic Molecular Weight 432.867179999
IUPAC Name (2S)-2-amino-3-(4-hydroxy-3,5-diiodophenyl)propanoic acid
Traditional IUPAC Name 3,5-diiodotyrosine
CAS Registry Number 300-39-0
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 Key NYPYHUZRZVSYKL-ZETCQYMHSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha 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 Parent Alpha Amino Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility 0.617 mg/mL at 25 °C Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.52 g/L ALOGPS
LogP -0.70 ALOGPS
LogP 0.37 ChemAxon
LogS -2.92 ALOGPS
pKa (strongest acidic) 0.48 ChemAxon
pKa (strongest basic) 9.45 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 83.55 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 73.82 ChemAxon
Polarizability 28.94 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Tyrosine Metabolism SMP00006 map00350 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.0036 (0.0014-0.0099) uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.000049 +/- 0.000027 umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.0036 (0.0010-0.0134) uM Adult (>18 years old) Both Hyperthyroidism
Urine Detected and Quantified 0.00013 +/- 0.000098 umol/mmol creatinine Adult (>18 years old) Both Chronic renal disease
Associated Disorders and Diseases
Disease References
Hyperthyroidism
  • 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 Link_out
      Chronic kidney disease
      • 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 Link_out
          Associated OMIM IDs None
          DrugBank ID Not Available
          DrugBank Metabolite ID Not Available
          Phenol Explorer Compound ID Not Available
          Phenol Explorer Metabolite ID Not Available
          FoodDB ID FDB023181
          KNApSAcK ID Not Available
          Chemspider ID 8946 Link_out
          KEGG Compound ID C01060 Link_out
          BioCyc ID DIIODO-L-TYROSINE Link_out
          BiGG ID 36719 Link_out
          Wikipedia Link Not Available
          NuGOwiki Link HMDB03474 Link_out
          Metagene Link HMDB03474 Link_out
          METLIN ID 6940 Link_out
          PubChem Compound 9305 Link_out
          PDB ID TYI Link_out
          ChEBI ID 15768 Link_out
          References
          Synthesis Reference Savitskii, 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 Link_out
          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 Link_out
          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 Link_out

          Enzymes
          Name: Thyroid peroxidase
          Reactions:
          3,5-Diiodo-L-tyrosine + Hydrogen peroxide unknown Thyroxine + 2-Aminoacrylic acid + Water details
          Iodotyrosine + 3,5-Diiodo-L-tyrosine + Hydrogen peroxide unknown Liothyronine + 2-Aminoacrylic acid + Water details
          I(-) + 3,5-Diiodo-L-tyrosine unknown Iodotyrosine + Iodine details
          Gene Name: TPO
          Uniprot ID: P07202 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Iodotyrosine dehalogenase 1
          Reactions:
          L-Tyrosine + NADP + I(-) unknown 3,5-Diiodo-L-tyrosine + NADPH details
          Gene Name: IYD
          Uniprot ID: Q6PHW0 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA