Record Information |
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Version | 2.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2020-11-24 22:22:43 UTC |
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NP-MRD ID | NP0001348 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Iodotyrosine |
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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 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. |
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Structure | N[C@@H](CC1=CC=C(O)C(I)=C1)C(O)=O 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 |
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Synonyms | Value | Source |
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(2S)-2-Amino-3-(4-hydroxy-3-iodophenyl)propanoic acid | ChEBI | 3-IODO-tyrosine | ChEBI | MIT | ChEBI | (2S)-2-Amino-3-(4-hydroxy-3-iodophenyl)propanoate | Generator | 3-Iodo-4-hydroxyphenylalanine | HMDB | 3-Iodo-L-tyrosine | HMDB | 3-Iodotyrosine | HMDB | 3-Monoiodo-L-tyrosine | HMDB | 4-Hydroxy-3-iodophenylalanine | HMDB | IYR | HMDB | L-Tyrosine-3-iodo | HMDB | Monoiodotyrosine | HMDB |
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Chemical Formula | C9H10INO3 |
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Average Mass | 307.0851 Da |
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Monoisotopic Mass | 306.97054 Da |
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IUPAC Name | (2S)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoic acid |
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Traditional Name | iodotyrosine |
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CAS Registry Number | 70-78-0 |
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SMILES | N[C@@H](CC1=CC=C(O)C(I)=C1)C(O)=O |
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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 |
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InChI Key | UQTZMGFTRHFAAM-ZETCQYMHSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Tyrosine and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 205 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 3 mg/mL | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - 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 ]
- 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 ]
- Ismail-Beigi F, Rahimifar M: A variant of iodotyrosine-dehalogenase deficiency. J Clin Endocrinol Metab. 1977 Mar;44(3):499-506. [PubMed:838849 ]
- 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 ]
- 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 ]
- 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 ]
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