GABAReceptorInhibitorgabareceptorinhibitor

Iodotyrosine

By rofalproject
Common Name

Iodotyrosine Description

Iodotyrosine 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 follicliar 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 moleclies of di-iodotyrosine combine to form T4, and one moleclie of mono-iodotyrosine combines with one moleclie of di-iodotyrosine to form T3. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (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 Formlia

C9H10INO3 Average Molecliar Weight

307.0851 Monoisotopic Molecliar Weight

306.970536611 IUPAC Name

(2S)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoic acid Traditional Name

iodotyrosine CAS Registry Number

70-78-0 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 Key

UQTZMGFTRHFAAM-ZETCQYMHSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as tyrosine and derivatives. These are compounds containing tyrosine or a derivative thereof resliting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Carboxylic acids and derivatives Direct Parent

Tyrosine and derivatives Alternative Parents

  • Phenylalanine and derivatives
  • Phenylpropanoic acids
  • Amphetamines and derivatives
  • L-alpha-amino acids
  • O-iodophenols
  • 1-hydroxy-2-unsubstituted benzenoids
  • Aralkylamines
  • Iodobenzenes
  • Aryl iodides
  • Amino acids
  • Monocarboxylic acids and derivatives
  • Carboxylic acids
  • Hydrocarbon derivatives
  • Carbonyl compounds
  • Organopnictogen compounds
  • Organic oxides
  • Organoiodides
  • Monoalkylamines

    • 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

    • Molecliar Framework

    Aromatic homomonocyclic compounds External Descriptors

  • non-proteinogenic L-alpha-amino acid (CHEBI:27847 )
  • L-tyrosine derivative (CHEBI:27847 )
  • monoiodotyrosine (CHEBI:27847 )
  • Other amino acids (C02515 )

    • Ontology Status

    Detected and Quantified Origin

  • Endogenous

    • Biofunction

  • Protein synthesis, amino acid biosynthesis

    • Application

    Not Available Cellliar locations

  • Cytoplasm

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point205 °CNot Available Boiling PointNot AvailableNot Available Water Solubility3 mg/mLNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.94 mg/mLALOGPS 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 Å2ChemAxon Rotatable Bond Count3ChemAxon Refractivity60.46 m3·mol-1ChemAxon Polarizability23.54 Å3ChemAxon Number of Rings1ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key GC-MS

    GC-MS Spectrum – GC-MS (2 TMS)splash10-0a4j-3913000000-be57e889200c60dc46d4View in MoNA GC-MS

    GC-MS Spectrum – GC-MS (3 TMS)splash10-014i-1790000000-785b6d6a13d0a8822946View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-08fu-0094000000-1cca0021f92a06ea8b50View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-01q9-1890000000-ff62addb3c23234d3cefView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-001i-2910000000-1938a4966cb53b4f5ed1View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4i-0009000000-29fdc92cbeae7ec37e5dView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-056r-0923000000-1f98738c0cc639f98dc7View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-1900000000-92c150757accb8a27fd9View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-2900000000-82ef54ff210098156f8cView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-2900000000-fffc0c2d97089650aadaView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0a4i-0329000000-39b160c87443d51e7611View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-03dl-0591000000-c54470130afba37dca28View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-03dr-1980000000-31e2dd7b1defc7cfb8c3View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-000i-1920000000-8e40ba504d905aa7a528View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-05n3-3900000000-368aad6dbdcc312ac3dfView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-01ox-0090000000-6e7318a85f3480d07477View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-03ka-0790000000-ed59bbe7e20256d8ad06View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-0900000000-6de0b405d60b85059abcView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0006-0090000000-9e84651efead6b6bfa2cView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-0900000000-972b9ebadf10c99787c4View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-014i-0900000000-6150f13b1005b3ec9effView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000b-0900000000-7b5ecd0f27a3ed9d67e2View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0a5i-0900000000-ec4129da39ac628164dcView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , negativesplash10-0a4i-0009000000-44efbf86abf86218185bView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , negativesplash10-056r-0923000000-f702b07a620f77aeef9fView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , negativesplash10-004i-1900000000-151c357f1c3d1af4b168View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , negativesplash10-004i-2900000000-3a76280be1a51177051dView in MoNA 1D NMR

    1H NMR SpectrumNot Available 2D NMR

    [1H,13C] 2D NMR SpectrumNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm

    • Biofluid Locations

  • Blood

    • Tissue Location

  • Thyroid Gland

    • Pathways

    Name SMPDB Link KEGG Link Thyroid hormone synthesisSMP00716Not Available Tyrosine MetabolismSMP00006map00350

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodDetected and Quantified0.00069 +/- 0.00020 uMAdlit (>18 years old)BothNormal

  • 2225717

    • details

    Abnormal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodDetected and Quantified0.00032 +/- 0.00008 uMAdlit (>18 years old)BothAthyroic patients

  • 2225717

    • 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 IDs

    None External Links DrugBank ID

    DB01758 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    FDB021875 KNApSAcK ID

    Not Available Chemspider ID

    388804 KEGG Compound ID

    C02515 BioCyc ID

    IODO-L-TYROSINE BiGG ID

    39998 Wikipedia Link

    Monoiodotyrosine NuGOwiki Link

    HMDB00021 Metagene Link

    HMDB00021 METLIN ID

    Not Available PubChem Compound

    439744 PDB ID

    IYR ChEBI ID

    27847

    Product: Neuropathiazol

    References Synthesis Reference Hillmann, Gunther; Hillmann-Elies, Anneliese. Synthesis of 3-iodo-L-tyrosine. Hoppe-Seylers 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-Tyrosine details Iodotyrosine + 3,5-Diiodo-L-tyrosine + Hydrogen peroxide → Liothyronine + 2-Aminoacrylic acid + Water details I(-) + 3,5-Diiodo-L-tyrosine → Iodotyrosine + Iodine details

    PMID: 24555641

    By rofalproject

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