Showing metabocard for 3,5-Diiodo-L-tyrosine (BMDB0003474)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:04:53 UTC
Update Date2020-04-22 15:12:22 UTC
BMDB IDBMDB0003474
Secondary Accession Numbers
  • BMDB03474
Metabolite Identification
Common Name3,5-Diiodo-L-tyrosine
Description3,5-Diiodo-L-tyrosine, also known as 3,5-diiodo-l-tyrosine 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 possibly soluble (in water) and 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 cattle, 3,5-diiodo-L-tyrosine is involved in the metabolic pathway called thyroid hormone synthesis pathway.
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 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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-014i-1890000000-abcce0f0eb05b9c55156View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-1890000000-abcce0f0eb05b9c55156View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052r-3009200000-5d38989f994f24e925d9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0avr-9302530000-665bd4d1e52bd2a50a9cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0000900000-ae6a8b173bc71991a4acView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-0200900000-0ba2bdb29d10e206243bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-0922200000-9937df05a2005a9dccdcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-0911000000-7b8269ff37ddf87ca91eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-0900000000-b8211c790d768a3d3ca4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-0000900000-22bf410c5cb442851336View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-001r-0017900000-b678ad76193892db31d6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-000i-0049100000-d8fdce763cb949d3c346View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-01p9-0197000000-70418018a4eb3733c732View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-03di-0191000000-83c286061170a2257b7cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03ei-2492000000-758324f5bb036f5e7439View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0000900000-ae6a8b173bc71991a4acView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0200900000-10d7f46230d75a69ca8aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0922200000-9937df05a2005a9dccdcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0911000000-7b8269ff37ddf87ca91eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-afdb17f670e1a6b9d237View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0000900000-22bf410c5cb442851336View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001r-0017900000-b678ad76193892db31d6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0049100000-d8fdce763cb949d3c346View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-0009600000-f51bf251094f35e469e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0009000000-68414bff61726c960b96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-0009000000-7623a376300575297b5fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0001900000-dce45ddc0efcbd787f4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2006900000-6fb8e76ede4b97e18a40View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9036000000-4a8ca25b7e8f09067ce0View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0003474
DrugBank IDDB03374
Phenol Explorer Compound IDNot Available
FooDB 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
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)Not Available
General ReferencesNot Available