3,3'-Diiodothyronine

3,3'-Diiodothyronine

IUPAC name 2-Amino-3-[4-(4-hydroxy-3-iodo-phenoxy)-3-iodo-phenyl]propanoic acid
Other names O-(4-Hydroxy-3-iodophenyl)-3-iodotyrosine
Identifiers
CAS number	70-40-6
PubChem	65559
ChemSpider	59002^Y
MeSH	3,3'-diiodothyronine
ChEBI	CHEBI:35430
Jmol-3D images	Image 1 Image 2
SMILES NC(C(O)=O)CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C=C1 O=C(O)C(N)Cc2ccc(Oc1cc(I)c(O)cc1)c(I)c2
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)^Y Key: CPCJBZABTUOGNM-UHFFFAOYSA-N^Y InChI=1/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) Key: CPCJBZABTUOGNM-UHFFFAOYAW
Properties
Molecular formula	C₁₅H₁₃I₂NO₄
Molar mass	525.077
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

3,3'-Diiodothyronine is a metabolite of thyroid hormone.

It is formed from the breakdown of triiodothyronine. It 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 ATP as an allosteric inhibitor. ^[1]

Levels can be affected in certain disease states.^[2]

Reactions

^ Arnold S., Goglia F., Kadenbach B. (1998). [: http://www.ncbi.nlm.nih.gov/pubmed/9523704 "3,5-Diiodothyronine binds to subunit Va of cytochrome-c oxidase and abolishes the allosteric inhibition of respiration by ATP."]. Eur J Biochem. 252 (2): 325–330. PMID 9523704.

http://www.ncbi.nlm.nih.gov/pubmed/9523704.
^ Pinna G, Hiedra L, Meinhold H, et al (September 1998). "3,3'-Diiodothyronine concentrations in the sera of patients with nonthyroidal illnesses and brain tumors and of healthy subjects during acute stress". J. Clin. Endocrinol. Metab. 83 (9): 3071–7. doi:10.1210/jc.83.9.3071. PMID 9745405.

Tyrosine / iodotyrosine

Thyronine / iodothyronine

Thyronamine / iodothyronamine

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m(A16/C10),i(k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)

anat/phys/devp/horm

noco(d)/cong/tumr, sysi/epon

proc, drug (A10/H1/H2/H3/H5)