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Showing metabocard for 3,5-Diiodo-L-tyrosine (HMDB0003474)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-12 21:39:17 UTC
Update Date2019-07-23 05:45:48 UTC
HMDB IDHMDB0003474
Secondary Accession Numbers
  • HMDB03474
Metabolite Identification
Common Name3,5-Diiodo-L-tyrosine
Description3,5-Diiodo-L-tyrosine, also known as diiy or DIT, belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. 3,5-Diiodo-L-tyrosine is a drug. 3,5-Diiodo-L-tyrosine is a product from the iodination of monoiodotyrosine. 3,5-Diiodo-L-tyrosine is a very strong basic compound (based on its pKa). 3,5-Diiodo-L-tyrosine exists in all living organisms, ranging from bacteria to humans. In humans, 3,5-diiodo-L-tyrosine is involved in thyroid hormone synthesis. A product from the iodination of monoiodotyrosine.
Structure
Data?1563860748
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S)-2-Amino-3-(4-hydroxy-3,5-diiodophenyl)propanoic acidChEBI
3,5-DiiodotyrosineChEBI
DiiodotyrosineChEBI
DiIYChEBI
DITChEBI
L-3,5-DiiodotyrosineChEBI
L-DiiodotyrosineChEBI
(2S)-2-Amino-3-(4-hydroxy-3,5-diiodophenyl)propanoateGenerator
3,5-DiiodotyrocineHMDB
3,5-Iodo-L-tyrosineHMDB
3,5-L-DiiodotyrosineHMDB
4-Hydroxy-3,5-diiodophenylalanineHMDB
Iodogorgoic acidHMDB
Acid, iodogorgoicHMDB
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
[H][C@](N)(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
Description belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine 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 ParentTyrosine and derivatives
Alternative Parents
Substituents
  • Tyrosine or derivatives
  • Phenylalanine or derivatives
  • 3-phenylpropanoic-acid
  • Amphetamine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • 2-iodophenol
  • 2-halophenol
  • Aralkylamine
  • Halobenzene
  • Phenol
  • Iodobenzene
  • Aryl iodide
  • Monocyclic benzene moiety
  • Benzenoid
  • Aryl halide
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organoiodide
  • Organohalogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.62 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 Area83.55 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity73.82 m³·mol⁻¹ChemAxon
Polarizability29.1 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-014i-1890000000-abcce0f0eb05b9c55156JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-1890000000-abcce0f0eb05b9c55156JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052r-3009200000-5d38989f994f24e925d9JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0avr-9302530000-665bd4d1e52bd2a50a9cJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0000900000-ae6a8b173bc71991a4acJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-0200900000-0ba2bdb29d10e206243bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-0922200000-9937df05a2005a9dccdcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-0911000000-7b8269ff37ddf87ca91eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-0900000000-b8211c790d768a3d3ca4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-0000900000-22bf410c5cb442851336JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-001r-0017900000-b678ad76193892db31d6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-000i-0049100000-d8fdce763cb949d3c346JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-01p9-0197000000-70418018a4eb3733c732JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-03di-0191000000-83c286061170a2257b7cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03ei-2492000000-758324f5bb036f5e7439JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0000900000-ae6a8b173bc71991a4acJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0200900000-10d7f46230d75a69ca8aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0922200000-9937df05a2005a9dccdcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0911000000-7b8269ff37ddf87ca91eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-afdb17f670e1a6b9d237JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0000900000-22bf410c5cb442851336JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001r-0017900000-b678ad76193892db31d6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0049100000-d8fdce763cb949d3c346JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-0009600000-f51bf251094f35e469e4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0009000000-68414bff61726c960b96JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-0009000000-7623a376300575297b5fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0001900000-dce45ddc0efcbd787f4aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2006900000-6fb8e76ede4b97e18a40JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9036000000-4a8ca25b7e8f09067ce0JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
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 ]
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 ]
Associated OMIM IDsNone
DrugBank IDDB03374
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023181
KNApSAcK IDNot Available
Chemspider ID8946
KEGG Compound IDC01060
BioCyc IDNot Available
BiGG ID36719
Wikipedia LinkNot Available
METLIN ID6940
PubChem Compound9305
PDB IDNot Available
ChEBI ID15768
Food Biomarker OntologyNot Available
VMH IDNot Available
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

Enzyme Details
1. Thyroid peroxidase
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
Enzyme Details
2. Iodotyrosine dehalogenase 1
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