Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites MAYBE down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites MAYBE down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites MAYBE down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites MAYBE down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites MAYBE down
12/28 - 12/31
for maintenance.
twitter
MetaCyc Compound: 3,5,3'-triiodo-L-thyronine

Systematic Name: O-(4-hydroxy-3-iodo-phenyl)-3,5-diiodo-L-tyrosine

Synonyms: triiodothyronine, triothyrone, 4-(3-iodo-4-hydroxy-phenoxy)-3,5-diiodophenylalanine, L-3,5,3'-triiodothyronine, L-triiodothyronine, T3, T3, 3,5,3'-triiodothyronine

Superclasses: a hormone
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

Chemical Formula: C15H12NO4I3

Molecular Weight: 650.98 Daltons

Monoisotopic Molecular Weight: 650.7900368788 Daltons

SMILES: C1(C=C(O)C(I)=CC=1OC2(=C(I)C=C(C=C(I)2)CC([N+])C(=O)[O-]))

InChI: InChI=1S/C15H12I3NO4/c16-9-6-8(1-2-13(9)20)23-14-10(17)3-7(4-11(14)18)5-12(19)15(21)22/h1-4,6,12,20H,5,19H2,(H,21,22)/t12-/m0/s1

InChIKey: InChIKey=AUYYCJSJGJYCDS-LBPRGKRZSA-N

Unification Links: CAS:6893-02-3 , ChEBI:533015 , HMDB:HMDB00265 , KEGG:C02465 , MetaboLights:MTBLC533015 , PubChem:7048703

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 99.00345 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

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

thyroid hormone metabolism II (via conjugation and/or degradation) :
3,5,3'-triiodo-L-thyronine + UDP-α-D-glucuronate → 3,5,3'-triiodo-L-thyronine acyl β-D-glucuronide + UDP + H+
3,5,3'-triiodo-L-thyronine + 3'-phosphoadenylyl-sulfate → adenosine 3',5'-bisphosphate + triiodothyronine sulfate + H+
3,5,3'-triiodo-L-thyronine → thyronamine
3,5,3'-triiodo-L-thyronine → 3,3',5-triiodothyroacetate
3,5,3'-triiodo-L-thyronine + UDP-α-D-glucuronate → 3,5,3'-triiodo-L-thyronine phenolic β-D-glucuronide + UDP + H+

Reactions known to produce the compound:

thyroid hormone biosynthesis :
[thyroglobulin]-triiodothyronine + H2O → 3,5,3'-triiodo-L-thyronine + [unspecified degradation products]

thyroid hormone metabolism I (via deiodination) , thyroid hormone metabolism II (via conjugation and/or degradation) :
3,5,3'-triiodo-L-thyronine + iodide + an oxidized electron acceptor + H+ ← L-thyroxine + a reduced electron acceptor

Not in pathways:
a prohormone + H2O → a hormone

Reactions known to both consume and produce the compound:

Not in pathways:
3,5,3'-triiodo-L-thyronine + 2-oxoglutarate ↔ L-glutamate + 3,5,3'-triiodothyropyruvate

Enzymes inhibited by 3,5,3'-triiodo-L-thyronine, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: 3',5'-diiodothyronine 5'-deiodinase [Fekkes82]


References

Fekkes82: Fekkes D, Hennemann G, Visser TJ (1982). "Evidence for a single enzyme in rat liver catalysing the deiodination of the tyrosyl and the phenolic ring of iodothyronines." Biochem J 201(3);673-6. PMID: 7092818

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 18.5 on Sun Dec 28, 2014, biocyc12.