Showing Metabocard for 3-iodo-L-tyrosine (BASm0003873)
| Common Name | 3-iodo-l-tyrosine | ||||||
|---|---|---|---|---|---|---|---|
| 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. | ||||||
| Structure | |||||||
| Molecular Formula | C9H10INO3 | ||||||
| Average Mass | 307.08510 | ||||||
| Monoisotopic Mass | 306.97054 | ||||||
| IUPAC Name | (2S)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoic acid | ||||||
| Traditional Name | 3-iodo-tyrosine | ||||||
| CAS Registry Number | 70-78-0 | ||||||
| SMILES | [NH3+][C@@H](Cc1ccc(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 | ||||||
| CHEBI ID | CHEBI:59898 | ||||||
| HMDB ID | HMDB0000021 | ||||||
| Pathways |
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| State | Solid | ||||||
| Water Solubility | 9.37e-01 g/l | ||||||
| logP | -1.51 | ||||||
| logS | -2.52 | ||||||
| pKa (Strongest Acidic) | 0.99 | ||||||
| pKa (Strongest Basic) | 9.50 | ||||||
| Hydrogen Acceptor Count | 4 | ||||||
| Hydrogen Donor Count | 3 | ||||||
| Polar Surface Area | 83.55 Ų | ||||||
| Rotatable Bond Count | 3 | ||||||
| Physiological Charge | 0 | ||||||
| Formal Charge | 0 | ||||||
| Refractivity | 60.46 m³·mol⁻¹ | ||||||
| Polarizability | 23.48 |