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3,5-Diiodothyronine

3,5-Diiodothyronine (3,5-T2) is an active thyroid hormone within the class of iodothyronines. It has two iodine atoms at positions 3 and 5 of its inner ring.

Column 1Column 2
IUPAC name
2-Amino-3-[4-(4-hydroxyphenoxy)-3,5-diiodophenyl]propanoic acid
CAS Number.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}534-51-0 Y
3D model (JSmol)Interactive imageInteractive image
ChemSpider110252 Y
MeSH3,5-diiodothyronine
PubChem CID123675
UNIIU1Y9GN485M Y
CompTox Dashboard (EPA)DTXSID60862141
InChI
InChI=1S/C15H13I2NO4/c16-11-5-8(7-13(18)15(20)21)6-12(17)14(11)22-10-3-1-9(19)2-4-10/h1-6,13,19H,7,18H2,(H,20,21)Key: ZHSOTLOTTDYIIK-UHFFFAOYSA-N
SMILES
C1=CC(=CC=C1O)OC2=C(C=C(C=C2I)CC(C(=O)O)N)IC1=CC(=CC=C1O)OC2=C(C=C(C=C2I)CC(C(=O)O)N)I
Chemical formulaC15H13I2NO4
Molar mass525.081 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references | |

3,5-Diiodothyronine (3,5-T2) is an active thyroid hormone within the class of iodothyronines. It has two iodine atoms at positions 3 and 5 of its inner ring.

3,5-T2 is an active thyroid hormone. It stimulates the TR-beta receptor for thyroid hormones and thus increases energy expenditure. It has agonistic (thyromimetic) effects at myocardial tissue and pituitary, which results in 3,5-T2 suppressing TSH release. 3,5-T2 is an allosteric regulator of the cytochrome c oxidase, the complex IV of the electron transport chain. It increases its activity by preventing the interaction of adenosine triphosphate (ATP) as an allosteric inhibitor.

In nonthyroidal illness syndrome 3,5-T2 concentrations are increased. This could explain why patients with low T3 syndrome don't benefit from substitution therapy with thyroid hormones.

  • 3,5-diiodothyronine at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
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