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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:43:50 UTC
HMDB IDHMDB0000021
Secondary Accession Numbers
  • HMDB00021
Metabolite Identification
Common NameIodotyrosine
DescriptionIodotyrosine is an iodated derivative of L-tyrosine. This is an early precursor to L-thyroxine, one of the primary thyroid hormones. In the thyroid gland, iodide is trapped, transported, and concentrated in the follicular lumen for thyroid hormone synthesis. Before trapped iodide can react with tyrosine residues, it must be oxidized by thyroid peroxidase. Iodotyrosine is made from tyrosine via thyroid peroxidase and then further iodinated by this enzyme to make the di-iodo and tri-iodo variants. Two molecules of di-iodotyrosine combine to form T4, and one molecule of mono-iodotyrosine combines with one molecule of di-iodotyrosine to form T3.
Structure
Data?1563860630
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
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Role

Industrial application:

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
Water Solubility0.94 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0a4j-3913000000-be57e889200c60dc46d4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-014i-1790000000-785b6d6a13d0a8822946JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4j-3913000000-be57e889200c60dc46d4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-1790000000-785b6d6a13d0a8822946JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03e9-3090000000-2e5cb717605e800d4359JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00sr-9335100000-f5b1c103a54222cc59a3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-08fu-0094000000-1cca0021f92a06ea8b50JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01q9-1890000000-ff62addb3c23234d3cefJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-2910000000-1938a4966cb53b4f5ed1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4i-0009000000-29fdc92cbeae7ec37e5dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-056r-0923000000-1f98738c0cc639f98dc7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-1900000000-92c150757accb8a27fd9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-2900000000-82ef54ff210098156f8cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-2900000000-fffc0c2d97089650aadaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0a4i-0329000000-39b160c87443d51e7611JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-03dl-0591000000-c54470130afba37dca28JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-03dr-1980000000-31e2dd7b1defc7cfb8c3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-000i-1920000000-8e40ba504d905aa7a528JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-05n3-3900000000-368aad6dbdcc312ac3dfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-01ox-0090000000-6e7318a85f3480d07477JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-03ka-0790000000-ed59bbe7e20256d8ad06JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-0900000000-6de0b405d60b85059abcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0006-0090000000-9e84651efead6b6bfa2cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-0900000000-972b9ebadf10c99787c4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-014i-0900000000-6150f13b1005b3ec9effJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000b-0900000000-7b5ecd0f27a3ed9d67e2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0a5i-0900000000-ec4129da39ac628164dcJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08fr-0093000000-003526fc59bf6620307fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0090000000-33a24ab6c37733eed168JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-1190000000-9bcf2d08fe940cf418a1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0029000000-b815bb002ee417365e6fJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
Tissue Locations
  • Thyroid Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00069 +/- 0.00020 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00032 +/- 0.00008 uMAdult (>18 years old)BothAthyroic patients details
Associated Disorders and Diseases
Disease References
Athyreosis
  1. Tan SA, Lewis JE, Berk LS, Wilcox RB: Extrathyroidal physiology of monoiodotyrosine in humans. Clin Physiol Biochem. 1990;8(3):109-15. [PubMed:2225717 ]
Associated OMIM IDsNone
DrugBank IDDB01758
Phenol Explorer Compound IDNot Available
FoodDB 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)Download (PDF)
General References
  1. Sakamoto K, Hayashi A, Sakamoto A, Kiga D, Nakayama H, Soma A, Kobayashi T, Kitabatake M, Takio K, Saito K, Shirouzu M, Hirao I, Yokoyama S: Site-specific incorporation of an unnatural amino acid into proteins in mammalian cells. Nucleic Acids Res. 2002 Nov 1;30(21):4692-9. [PubMed:12409460 ]
  2. Painter K, Vader CR: Interference of iodine-125 ligands in radioimmunoassay: evidence implicating thyroxine-binding globulin. Clin Chem. 1979 May;25(5):797-9. [PubMed:108034 ]
  3. Ismail-Beigi F, Rahimifar M: A variant of iodotyrosine-dehalogenase deficiency. J Clin Endocrinol Metab. 1977 Mar;44(3):499-506. [PubMed:838849 ]
  4. Smythe GA, Compton PJ, Lazarus L: The stimulation of human prolactin secretion by 3-Iodo-L-tyrosine. J Clin Endocrinol Metab. 1975 Apr;40(4):714-6. [PubMed:1127080 ]
  5. Muller EE, Locatelli V, Cella S, Penalva A, Novelli A, Cocchi D: Prolactin-lowering and -releasing drugs. Mechanisms of action and therapeutic applications. Drugs. 1983 Apr;25(4):399-432. [PubMed:6133737 ]
  6. Kucerova Z, Ticha M: Aromatic amino acids and their derivatives as ligands for the isolation of aspartic proteinases. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Apr 25;770(1-2):121-8. [PubMed:12013218 ]

Enzymes

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
I(-) + Iodotyrosine → Iodine + L-Tyrosinedetails
Iodotyrosine + 3,5-Diiodo-L-tyrosine + Hydrogen peroxide → Liothyronine + 2-Aminoacrylic acid + Waterdetails
I(-) + 3,5-Diiodo-L-tyrosine → Iodotyrosine + Iodinedetails