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MetaCyc Compound: 3,3'-diiodothyronine

Synonyms: O-(4-hydroxy-3-iodophenyl)-3-iodotyrosine, 3,3'-T2, tyrosine, O-(4-hydroxy-3-iodophenyl)-3-iodo-, 2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3-iodophenyl]propanoic acid

Superclasses: an aromatic compound an iodoaromatic compound
an organohalogen compound a haloalkane an iodoalkane an iodoaromatic compound
an organohalogen compound an organoiodine compound an iodoalkane an iodoaromatic compound

Citations: [Bianco06]

Chemical Formula: C15H13NO4I2

Molecular Weight: 525.08 Daltons

Monoisotopic Molecular Weight: 524.8933939109 Daltons

3,3'-diiodothyronine compound structure

SMILES: C(C(CC1(=CC=C(C(=C1)I)OC2(=CC=C(C(I)=C2)O)))[N+])([O-])=O

InChI: InChI=1S/C15H13I2NO4/c16-10-7-9(2-3-13(10)19)22-14-4-1-8(5-11(14)17)6-12(18)15(20)21/h1-5,7,12,19H,6,18H2,(H,20,21)/t12-/m0/s1

InChIKey: InChIKey=CPCJBZABTUOGNM-LBPRGKRZSA-N

Unification Links: ChEBI:45698 , HMDB:HMDB05869 , MetaboLights:MTBLC45698 , PubChem:44237213

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 90.65457 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

thyroid hormone metabolism I (via deiodination) :
3,3'-diiodothyronine + an unknown reduced electron acceptor → 3'-monoiodothyronine + iodide + an unknown oxidized electron acceptor + H+
3,3'-diiodothyronine + an unknown reduced electron acceptor → 3-monoiodothyronine + iodide + an unknown oxidized electron acceptor + H+

Reactions known to produce the compound:

thyroid hormone metabolism I (via deiodination) :
3,3',5'-triiodo-L-thyronine + an unknown reduced electron acceptor → 3,3'-diiodothyronine + iodide + an unknown oxidized electron acceptor + H+
3,5,3'-triiodo-L-thyronine + an unknown reduced electron acceptor → 3,3'-diiodothyronine + iodide + an unknown oxidized electron acceptor + H+

This compound has been characterized as an alternative substrate of the following enzymes: 3,5,3'-triiodo-L-thyronine sulfotransferase

Credits:
Created 26-May-2009 by Fulcher CA , SRI International


References

Bianco06: Bianco AC, Kim BW (2006). "Deiodinases: implications of the local control of thyroid hormone action." J Clin Invest 116(10);2571-9. PMID: 17016550

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Tue Apr 21, 2015, biocyc13.