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Record Information
Version1.0
Creation Date2016-09-30 22:18:33 UTC
Update Date2020-03-18 18:12:06 UTC
BMDB IDBMDB0000021
Secondary Accession Numbers
  • BMDB00021
Metabolite Identification
Common NameIodotyrosine
DescriptionIodotyrosine, also known as MIT or IYR, 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. Iodotyrosine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Iodotyrosine exists in all living organisms, ranging from bacteria to humans. In cattle, iodotyrosine is involved in the metabolic pathway called thyroid hormone synthesis pathway.
Structure
Thumb
Synonyms
ValueSource
(2S)-2-Amino-3-(4-hydroxy-3-iodophenyl)propanoic acidChEBI
3-IODO-tyrosineChEBI
MITChEBI
(2S)-2-Amino-3-(4-hydroxy-3-iodophenyl)propanoateGenerator
3-Iodo-4-hydroxyphenylalanineHMDB
3-Iodo-L-tyrosineHMDB
3-IodotyrosineHMDB
3-Monoiodo-L-tyrosineHMDB
4-Hydroxy-3-iodophenylalanineHMDB
IYRHMDB
L-Tyrosine-3-iodoHMDB
MonoiodotyrosineHMDB
Chemical FormulaC9H10INO3
Average Molecular Weight307.0851
Monoisotopic Molecular Weight306.970536611
IUPAC Name(2S)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoic acid
Traditional Nameiodotyrosine
CAS Registry Number70-78-0
SMILES
N[C@@H](CC1=CC=C(O)C(I)=C1)C(O)=O
InChI Identifier
InChI=1S/C9H10INO3/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14/h1-3,7,12H,4,11H2,(H,13,14)/t7-/m0/s1
InChI KeyUQTZMGFTRHFAAM-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
  • Alpha-amino acid
  • Amphetamine or derivatives
  • L-alpha-amino acid
  • 2-iodophenol
  • 2-halophenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Iodobenzene
  • Halobenzene
  • Phenol
  • Aralkylamine
  • Aryl iodide
  • Aryl halide
  • Benzenoid
  • Monocyclic benzene moiety
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organohalogen compound
  • Primary aliphatic amine
  • Organoiodide
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point205 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.5ALOGPS
logP-0.56ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)0.99ChemAxon
pKa (Strongest Basic)9.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity60.46 m³·mol⁻¹ChemAxon
Polarizability23.54 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0a4j-3913000000-be57e889200c60dc46d4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-014i-1790000000-785b6d6a13d0a8822946View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4j-3913000000-be57e889200c60dc46d4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-1790000000-785b6d6a13d0a8822946View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03e9-3090000000-2e5cb717605e800d4359View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00sr-9335100000-f5b1c103a54222cc59a3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-08fu-0094000000-1cca0021f92a06ea8b50View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01q9-1890000000-ff62addb3c23234d3cefView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-2910000000-1938a4966cb53b4f5ed1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4i-0009000000-29fdc92cbeae7ec37e5dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-056r-0923000000-1f98738c0cc639f98dc7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-1900000000-92c150757accb8a27fd9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-2900000000-82ef54ff210098156f8cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-2900000000-fffc0c2d97089650aadaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0a4i-0329000000-39b160c87443d51e7611View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-03dl-0591000000-c54470130afba37dca28View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-03dr-1980000000-31e2dd7b1defc7cfb8c3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-000i-1920000000-8e40ba504d905aa7a528View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-05n3-3900000000-368aad6dbdcc312ac3dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-01ox-0090000000-6e7318a85f3480d07477View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-03ka-0790000000-ed59bbe7e20256d8ad06View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-0900000000-6de0b405d60b85059abcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0006-0090000000-9e84651efead6b6bfa2cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-0900000000-972b9ebadf10c99787c4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-014i-0900000000-6150f13b1005b3ec9effView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000b-0900000000-7b5ecd0f27a3ed9d67e2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0a5i-0900000000-ec4129da39ac628164dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08fr-0093000000-003526fc59bf6620307fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0090000000-33a24ab6c37733eed168View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-1190000000-9bcf2d08fe940cf418a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0029000000-b815bb002ee417365e6fView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue Location
  • Thyroid Gland
Pathways
NameSMPDB LinkKEGG Link
Thyroid Hormone SynthesisSMP0087269Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01758
Phenol Explorer Compound IDNot Available
FooDB IDFDB021875
KNApSAcK IDNot Available
Chemspider ID388804
KEGG Compound IDC02515
BioCyc IDCPD-12288
BiGG ID39998
Wikipedia Link3-Iodotyrosine
METLIN IDNot Available
PubChem Compound439744
PDB IDNot Available
ChEBI ID27847
References
Synthesis ReferenceHillmann, Gunther; Hillmann-Elies, Anneliese. Synthesis of 3-iodo-L-tyrosine. Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie (1956), 305 177-81.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available