3,5-Diiodo-L-tyrosine (CHEM019913)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:37:29 UTC
Update Date2016-11-09 01:16:05 UTC
Accession NumberCHEM019913
Identification
Common Name3,5-Diiodo-L-tyrosine
ClassSmall Molecule
DescriptionA product from the iodination of MONOIODOTYROSINE. In the biosynthesis of thyroid hormones, 3,5-Diiodo-L-tyrosine residues are coupled with other monoiodotyrosine or 3,5-Diiodo-L-tyrosine residues to form T4 or T3 thyroid hormones (THYROXINE and TRIIODOTHYRONINE).
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
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 Mass432.982 g/mol
Monoisotopic Mass432.867 g/mol
CAS Registry Number300-39-0
IUPAC Name(2S)-2-amino-3-(4-hydroxy-3,5-diiodophenyl)propanoic acid
Traditional Name3,5-diiodotyrosine
SMILES[H][C@](N)(CC1=CC(I)=C(O)C(I)=C1)C(O)=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-014i-1890000000-abcce0f0eb05b9c55156Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-1890000000-abcce0f0eb05b9c55156Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052r-3009200000-5d38989f994f24e925d9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0avr-9302530000-665bd4d1e52bd2a50a9cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0000900000-ae6a8b173bc71991a4acSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-0200900000-0ba2bdb29d10e206243bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-0922200000-9937df05a2005a9dccdcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-0911000000-7b8269ff37ddf87ca91eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-0900000000-b8211c790d768a3d3ca4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-0000900000-22bf410c5cb442851336Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-001r-0017900000-b678ad76193892db31d6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-000i-0049100000-d8fdce763cb949d3c346Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-01p9-0197000000-70418018a4eb3733c732Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-03di-0191000000-83c286061170a2257b7cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03ei-2492000000-758324f5bb036f5e7439Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0000900000-ae6a8b173bc71991a4acSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0200900000-10d7f46230d75a69ca8aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0922200000-9937df05a2005a9dccdcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0911000000-7b8269ff37ddf87ca91eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-afdb17f670e1a6b9d237Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0000900000-22bf410c5cb442851336Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001r-0017900000-b678ad76193892db31d6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0049100000-d8fdce763cb949d3c346Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-0009600000-f51bf251094f35e469e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0009000000-68414bff61726c960b96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-0009000000-7623a376300575297b5fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0001900000-dce45ddc0efcbd787f4aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2006900000-6fb8e76ede4b97e18a40Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9036000000-4a8ca25b7e8f09067ce0Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB03374
HMDB IDHMDB0003474
FooDB IDFDB023181
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID36719
BioCyc IDNot Available
METLIN ID6940
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID8946
ChEBI ID15768
PubChem Compound ID9305
Kegg Compound IDC01060
YMDB IDNot Available
ECMDB IDECMDB24083
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Savitskii, A. Ya. The preparation and properties of 3,5-diiodo-l-tyrosine. Zhurnal Obshchei Khimii (1939), 9 1342-4.
2. Savitskii, A. Ya. The preparation and properties of 3,5-diiodo-l-tyrosine. Zhurnal Obshchei Khimii (1939), 9 1342-4.
3. Ismail-Beigi F, Rahimifar M: A variant of iodotyrosine-dehalogenase deficiency. J Clin Endocrinol Metab. 1977 Mar;44(3):499-506.
4. Bismuth J, Castay M, Lissitzky S: Binding of 3,5-diiodotyrosine to serum proteins. Clin Chim Acta. 1976 Jun 15;69(3):417-22.
5. Tompkins RK, Croke JC: Bile acids inhibit pepsin activity against a refined substrate. Am J Surg. 1980 Feb;139(2):237-9.
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=11344555
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=15206581
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=15589368