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1041-01-6 | 3,5-Diiodo-L-thyronine
CAS No: 1041-01-6 Catalog No: AG003INK MDL No:MFCD00064987
Product Description
Catalog Number:
AG003INK
Chemical Name:
3,5-Diiodo-L-thyronine
CAS Number:
1041-01-6
Molecular Formula:
C15H13I2NO4
Molecular Weight:
525.0770
MDL Number:
MFCD00064987
IUPAC Name:
(2S)-2-amino-3-[4-(4-hydroxyphenoxy)-3,5-diiodophenyl]propanoic acid
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)/t13-/m0/s1
InChI Key:
ZHSOTLOTTDYIIK-ZDUSSCGKSA-N
SMILES:
OC(=O)[C@H](Cc1cc(I)c(c(c1)I)Oc1ccc(cc1)O)N
EC Number:
213-867-7
UNII:
CAL3MRM51F
Properties
Complexity:
365
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
1
Defined Bond Stereocenter Count:
0
Exact Mass:
524.893g/mol
Formal Charge:
0
Heavy Atom Count:
22
Hydrogen Bond Acceptor Count:
5
Hydrogen Bond Donor Count:
3
Isotope Atom Count:
0
Molecular Weight:
525.081g/mol
Monoisotopic Mass:
524.893g/mol
Rotatable Bond Count:
5
Topological Polar Surface Area:
92.8A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.1
Literature
| Title | Journal |
|---|---|
| Thyroid hormone reduces cholesterol via a non-LDL receptor-mediated pathway. | Endocrinology 20121101 |
| Intracellular and plasma membrane-initiated pathways involved in the [Ca2+]i elevations induced by iodothyronines (T3 and T2) in pituitary GH3 cells. | American journal of physiology. Endocrinology and metabolism 20120601 |
| 3,5-Diiodo-L-thyronine modulates the expression of genes of lipid metabolism in a rat model of fatty liver. | The Journal of endocrinology 20120201 |
| Analysis of thyroid hormones in serum of Baikal seals and humans by liquid chromatography-tandem mass spectrometry (LC-MS/MS) and immunoassay methods: application of the LC-MS/MS method to wildlife tissues. | Environmental science & technology 20111201 |
| Nonthyrotoxic prevention of diet-induced insulin resistance by 3,5-diiodo-L-thyronine in rats. | Diabetes 20111101 |
| 3,5-Diiodo-L-thyronine prevents high-fat-diet-induced insulin resistance in rat skeletal muscle through metabolic and structural adaptations. | FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20111001 |
| Effect of 3,3',5-triiodothyronine and 3,5-diiodothyronine on progesterone production, cAMP synthesis, and mRNA expression of STAR, CYP11A1, and HSD3B genes in granulosa layer of chicken preovulatory follicles. | Domestic animal endocrinology 20111001 |
| 3,5-diiodo-L-thyronine increases FoF1-ATP synthase activity and cardiolipin level in liver mitochondria of hypothyroid rats. | Journal of bioenergetics and biomembranes 20110801 |
| Modulation of thyroid hormone concentrations in serum of rats coadministered with perchlorate and iodide-deficient diet. | Archives of environmental contamination and toxicology 20110701 |
| Direct effects of iodothyronines on excess fat storage in rat hepatocytes. | Journal of hepatology 20110601 |
| Determination of six thyroid hormones in the brain and thyroid gland using isotope-dilution liquid chromatography/tandem mass spectrometry. | Analytical chemistry 20110101 |
| The human serum metabolome. | PloS one 20110101 |
| TRC150094 attenuates progression of nontraditional cardiovascular risk factors associated with obesity and type 2 diabetes in obese ZSF1 rats. | Diabetes, metabolic syndrome and obesity : targets and therapy 20110101 |
| 3,5-diiodo-L-thyronine increases resting metabolic rate and reduces body weight without undesirable side effects. | Journal of biological regulators and homeostatic agents 20110101 |
| Pathways affected by 3,5-diiodo-l-thyronine in liver of high fat-fed rats: evidence from two-dimensional electrophoresis, blue-native PAGE, and mass spectrometry. | Molecular bioSystems 20101101 |
| Analysis of thyroid hormones in raw and treated waste water. | Journal of chromatography. A 20101015 |
| Thyroid hormones, mitochondrial bioenergetics and lipid handling. | Current opinion in endocrinology, diabetes, and obesity 20101001 |
| A method for the analysis of six thyroid hormones in thyroid gland by liquid chromatography-tandem mass spectrometry. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20100701 |
| 3,5-diiodo-L-thyronine upregulates rat-liver mitochondrial F(o)F(1)-ATP synthase by GA-binding protein/nuclear respiratory factor-2. | Biochimica et biophysica acta 20100201 |
| Short-term effects of thyroid hormones during development: Focus on signal transduction. | Steroids 20100101 |
| Disruption of insulin signalling preserves bioenergetic competence of mitochondria in ageing Caenorhabditis elegans. | BMC biology 20100101 |
| Thyroid hormone interactions with DMPC bilayers. A molecular dynamics study. | The journal of physical chemistry. B 20091008 |
| 3,5-diiodo-l-thyronine, by modulating mitochondrial functions, reverses hepatic fat accumulation in rats fed a high-fat diet. | Journal of hepatology 20090801 |
| 3,5-Diiodo-L-thyronine rapidly enhances mitochondrial fatty acid oxidation rate and thermogenesis in rat skeletal muscle: AMP-activated protein kinase involvement. | American journal of physiology. Endocrinology and metabolism 20090301 |
| Short-term effects of thyroid hormones on Na+-K+-ATPase activity of chick embryo hepatocytes during development: focus on signal transduction. | American journal of physiology. Cell physiology 20090101 |
| Thyroid hormone-induced angiogenesis. | Current cardiology reviews 20090101 |
| Effects of 3,5-diiodo-L-thyronine administration on the liver of high fat diet-fed rats. | Experimental biology and medicine (Maywood, N.J.) 20080501 |
| Metabolic effects of thyroid hormone derivatives. | Thyroid : official journal of the American Thyroid Association 20080201 |
| Molecular evolution of the cytochrome c oxidase subunit 5A gene in primates. | BMC evolutionary biology 20080101 |
| Relating circulating thyroid hormone concentrations to serum interleukins-6 and -10 in association with non-thyroidal illnesses including chronic renal insufficiency. | BMC endocrine disorders 20080101 |
| Acute administration of 3,5-diiodo-L-thyronine to hypothyroid rats affects bioenergetic parameters in rat skeletal muscle mitochondria. | FEBS letters 20071222 |
| 3,5-Diiodothyronine in vivo maintains euthyroidal expression of type 2 iodothyronine deiodinase, growth hormone, and thyroid hormone receptor beta1 in the killifish. | American journal of physiology. Regulatory, integrative and comparative physiology 20070801 |
| T-screen to quantify functional potentiating, antagonistic and thyroid hormone-like activities of poly halogenated aromatic hydrocarbons (PHAHs). | Toxicology in vitro : an international journal published in association with BIBRA 20060601 |
| Role of thyrotropin in metabolism of thyroid hormones in nonthyroidal tissues. | Metabolism: clinical and experimental 20060601 |
| Identification and quantitation of iodotyrosines and iodothyronines in hydrolysate of iodinated casein by capillary electrophoresis. | Talanta 20060315 |
| Differentiation of diiodothyronines using electrospray ionization tandem mass spectrometry. | Journal of mass spectrometry : JMS 20060201 |
| Short-term stimulation of lipogenesis by 3,5-L-diiodothyronine in cultured rat hepatocytes. | Endocrinology 20050901 |
| 3,5-diiodo-L-thyronine powerfully reduces adiposity in rats by increasing the burning of fats. | FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20050901 |
| Biological effects of 3,5-diiodothyronine (T(2)). | Biochemistry. Biokhimiia 20050201 |
| Development of a validated HPLC method for the determination of iodotyrosines and iodothyronines in pharmaceuticals and biological samples using solid phase extraction. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20050105 |
| Short-term effects of thyroid hormone in prenatal development and cell differentiation. | Steroids 20050101 |
| 3,5-diiodothyronine mimics the effect of triiodothyronine on insulin-like growth factor binding protein-4 expression in cultured rat hepatocytes. | Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme 20041001 |
| The possible role of cytochrome c oxidase in stress-induced apoptosis and degenerative diseases. | Biochimica et biophysica acta 20040412 |
| Inhibition of the activity of the native gamma-aminobutyric acid A receptor by metabolites of thyroid hormones: correlations with molecular modeling studies. | Brain research 20040409 |
| Effects of iodothyronines on the hepatic outer-ring deiodinating pathway in killifish. | General and comparative endocrinology 20040115 |
| Thyroid hormones in the rat amygdala as common targets for antidepressant drugs, mood stabilizers, and sleep deprivation. | Biological psychiatry 20031115 |
| Identification of 3,5-diiodo-L-thyronine-binding proteins in rat liver cytosol by photoaffinity labeling. | Endocrinology 20030601 |
| Thyroid hormones affect the membrane dipolar organization. Is it a general event in their non-genomic action? | The Journal of membrane biology 20030201 |
| Identification of a novel human organic anion transporting polypeptide as a high affinity thyroxine transporter. | Molecular endocrinology (Baltimore, Md.) 20021001 |
| Short-term effects of thyroid hormones and 3,5-diiodothyronine on membrane transport systems in chick embryo hepatocytes. | Endocrinology 20020501 |
| Concentrations of seven iodothyronine metabolites in brain regions and the liver of the adult rat. | Endocrinology 20020501 |
| Are the effects of T3 on resting metabolic rate in euthyroid rats entirely caused by T3 itself? | Endocrinology 20020201 |
| Thyroid hormones and mitochondria. | Bioscience reports 20020201 |
| Control of energy metabolism by iodothyronines. | Journal of endocrinological investigation 20011201 |
| Cytochrome C oxidase and the regulation of oxidative phosphorylation. | Chembiochem : a European journal of chemical biology 20010601 |
| Short-term effects of thyroid hormones on lipogenic enzymes and 14C-acetate incorporation into various lipid classes: in vivo and in vitro studies. | Indian journal of experimental biology 20010501 |
| Effects of thyroid hormones on inner mitochondrial membrane fluidity. | Bollettino della Societa italiana di biologia sperimentale 20010101 |
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