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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-08-12 21:39:17 UTC |
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Update Date | 2019-01-11 19:17:37 UTC |
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HMDB ID | HMDB0003474 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 3,5-Diiodo-L-tyrosine |
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Description | 3,5-Diiodo-L-tyrosine is a product from the iodination of monoiodotyrosine. In the biosynthesis of thyroid hormones, diiodotyrosine residues are coupled with other monoiodotyrosine or diiodotyrosine residues to form T4 or T3 thyroid hormones (thyroxine and triiodothyronine). |
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Structure | |
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Synonyms | Value | Source |
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(2S)-2-amino-3-(4-Hydroxy-3,5-diiodophenyl)propanoic acid | ChEBI | 3,5-Diiodotyrosine | ChEBI | Diiodotyrosine | ChEBI | DiIY | ChEBI | DIT | ChEBI | L-3,5-Diiodotyrosine | ChEBI | L-Diiodotyrosine | ChEBI | (2S)-2-amino-3-(4-Hydroxy-3,5-diiodophenyl)propanoate | Generator | 3,5-Diiodotyrocine | HMDB | 3,5-iodo-L-Tyrosine | HMDB | 3,5-L-Diiodotyrosine | HMDB | 4-Hydroxy-3,5-diiodophenylalanine | HMDB | Iodogorgoic acid | MeSH | Acid, iodogorgoic | MeSH |
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Chemical Formula | C9H9I2NO3 |
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Average Molecular Weight | 432.9816 |
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Monoisotopic Molecular Weight | 432.867179999 |
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IUPAC Name | (2S)-2-amino-3-(4-hydroxy-3,5-diiodophenyl)propanoic acid |
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Traditional Name | 3,5-diiodotyrosine |
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CAS Registry Number | 300-39-0 |
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SMILES | [H][C@](N)(CC1=CC(I)=C(O)C(I)=C1)C(O)=O |
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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 |
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InChI Key | NYPYHUZRZVSYKL-ZETCQYMHSA-N |
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Chemical Taxonomy |
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Description | This compound belongs to the class of organic compounds known as tyrosine and derivatives. These 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
- 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
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: |
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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 | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.62 mg/mL at 25 °C | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-MS (3 TMS) | splash10-014i-1890000000-abcce0f0eb05b9c55156 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-014i-1890000000-abcce0f0eb05b9c55156 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-052r-3009200000-5d38989f994f24e925d9 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-0avr-9302530000-665bd4d1e52bd2a50a9c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-001i-0000900000-ae6a8b173bc71991a4ac | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-001i-0200900000-0ba2bdb29d10e206243b | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-004i-0922200000-9937df05a2005a9dccdc | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-004i-0911000000-7b8269ff37ddf87ca91e | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-004i-0900000000-b8211c790d768a3d3ca4 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-001i-0000900000-22bf410c5cb442851336 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-001r-0017900000-b678ad76193892db31d6 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-000i-0049100000-d8fdce763cb949d3c346 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-01p9-0197000000-70418018a4eb3733c732 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-03di-0191000000-83c286061170a2257b7c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-03ei-2492000000-758324f5bb036f5e7439 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-001i-0000900000-ae6a8b173bc71991a4ac | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-001i-0200900000-10d7f46230d75a69ca8a | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-0922200000-9937df05a2005a9dccdc | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-0911000000-7b8269ff37ddf87ca91e | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-0900000000-afdb17f670e1a6b9d237 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-001i-0000900000-22bf410c5cb442851336 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-001r-0017900000-b678ad76193892db31d6 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-000i-0049100000-d8fdce763cb949d3c346 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0019-0009600000-f51bf251094f35e469e4 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0009000000-68414bff61726c960b96 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a6r-0009000000-7623a376300575297b5f | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0001900000-dce45ddc0efcbd787f4a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-2006900000-6fb8e76ede4b97e18a40 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00di-9036000000-4a8ca25b7e8f09067ce0 | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 0.0036 (0.0014-0.0099) uM | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.000049 +/- 0.000027 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 0.0036 (0.0010-0.0134) uM | Adult (>18 years old) | Both | Hyperthyroidism | | details | Urine | Detected and Quantified | 0.00013 +/- 0.000098 umol/mmol creatinine | Adult (>18 years old) | Both | Chronic renal disease | | details |
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Associated Disorders and Diseases |
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Disease References | Hyperthyroidism |
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- Nelson JC, Weiss RM, Lewis JE, Wilcox RB, Palmer FJ: A multiple ligand-binding radioimmunoassay of diiodotyrosine. J Clin Invest. 1974 Feb;53(2):416-22. [PubMed:11344555 ]
| Chronic kidney disease |
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- Ramsden DB, Farmer M, Mohammed MN, McGonigle RS, Sheppard MC: 3,5-Diiodotyrosine and thyronine in the urine of patients with chronic renal disease. Clin Endocrinol (Oxf). 1986 May;24(5):491-5. [PubMed:3098453 ]
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB03374 |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB023181 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 8946 |
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KEGG Compound ID | C01060 |
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BioCyc ID | DIIODO-L-TYROSINE |
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BiGG ID | 36719 |
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Wikipedia Link | Not Available |
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METLIN ID | 6940 |
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PubChem Compound | 9305 |
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PDB ID | TYI |
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ChEBI ID | 15768 |
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References |
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Synthesis Reference | Savitskii, A. Ya. The preparation and properties of 3,5-diiodo-l-tyrosine. Zhurnal Obshchei Khimii (1939), 9 1342-4. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Ismail-Beigi F, Rahimifar M: A variant of iodotyrosine-dehalogenase deficiency. J Clin Endocrinol Metab. 1977 Mar;44(3):499-506. [PubMed:838849 ]
- Bismuth J, Castay M, Lissitzky S: Binding of 3,5-diiodotyrosine to serum proteins. Clin Chim Acta. 1976 Jun 15;69(3):417-22. [PubMed:59643 ]
- Tompkins RK, Croke JC: Bile acids inhibit pepsin activity against a refined substrate. Am J Surg. 1980 Feb;139(2):237-9. [PubMed:6766680 ]
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