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211110-63-3 | Acetic acid, 2-[4-[[4-hydroxy-3-(1-methylethyl)phenyl]methyl]-3,5-dimethylphenoxy]-
CAS No: 211110-63-3 Catalog No: AG002L62 MDL No:MFCD19443713
Product Description
Catalog Number:
AG002L62
Chemical Name:
Acetic acid, 2-[4-[[4-hydroxy-3-(1-methylethyl)phenyl]methyl]-3,5-dimethylphenoxy]-
CAS Number:
211110-63-3
Molecular Formula:
C20H24O4
Molecular Weight:
328.4022
MDL Number:
MFCD19443713
IUPAC Name:
2-[4-[(4-hydroxy-3-propan-2-ylphenyl)methyl]-3,5-dimethylphenoxy]acetic acid
InChI:
InChI=1S/C20H24O4/c1-12(2)17-9-15(5-6-19(17)21)10-18-13(3)7-16(8-14(18)4)24-11-20(22)23/h5-9,12,21H,10-11H2,1-4H3,(H,22,23)
InChI Key:
QNAZTOHXCZPOSA-UHFFFAOYSA-N
SMILES:
OC(=O)COc1cc(C)c(c(c1)C)Cc1ccc(c(c1)C(C)C)O
UNII:
XQ31741E9Q
Properties
Complexity:
396
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
328.167g/mol
Formal Charge:
0
Heavy Atom Count:
24
Hydrogen Bond Acceptor Count:
4
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
328.408g/mol
Monoisotopic Mass:
328.167g/mol
Rotatable Bond Count:
6
Topological Polar Surface Area:
66.8A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
4.9
Literature
| Title | Journal |
|---|---|
| Identical gene regulation patterns of T3 and selective thyroid hormone receptor modulator GC-1. | Endocrinology 20120101 |
| The binding of synthetic triiodo l-thyronine analogs to human transthyretin: molecular basis of cooperative and non-cooperative ligand recognition. | Journal of structural biology 20110201 |
| Sobetirome: a selective thyromimetic for the treatment of dyslipidemia. | Recent patents on cardiovascular drug discovery 20110101 |
| Thyroid hormones, mitochondrial bioenergetics and lipid handling. | Current opinion in endocrinology, diabetes, and obesity 20101001 |
| TRbeta is the critical thyroid hormone receptor isoform in T3-induced proliferation of hepatocytes and pancreatic acinar cells. | Journal of hepatology 20101001 |
| The T3 receptor beta1 isoform regulates UCP1 and D2 deiodinase in rat brown adipocytes. | Endocrinology 20101001 |
| Human platelet aggregation and degranulation is induced in vitro by L-thyroxine, but not by 3,5,3'-triiodo-L-thyronine or diiodothyropropionic acid (DITPA). | Clinical and applied thrombosis/hemostasis : official journal of the International Academy of Clinical and Applied Thrombosis/Hemostasis 20100601 |
| The TRbeta-selective agonist, GC-1, stimulates mitochondrial oxidative processes to a lesser extent than triiodothyronine. | The Journal of endocrinology 20100601 |
| Sobetirome: a case history of bench-to-clinic drug discovery and development. | Heart failure reviews 20100301 |
| The resurgence of thyromimetics as lipid-modifying agents. | Current opinion in investigational drugs (London, England : 2000) 20090901 |
| Induction of the adrenoleukodystrophy-related gene (ABCD2) by thyromimetics. | The Journal of steroid biochemistry and molecular biology 20090801 |
| The thyroid hormone receptor (TR) beta-selective agonist GC-1 inhibits proliferation but induces differentiation and TR beta mRNA expression in mouse and rat osteoblast-like cells. | Calcified tissue international 20090401 |
| T3 and the thyroid hormone beta-receptor agonist GC-1 differentially affect metabolic capacity and oxidative damage in rat tissues. | The Journal of experimental biology 20090401 |
| Thyroid hormone receptor subtype specificity for hormone-dependent neurogenesis in Xenopus laevis. | Developmental biology 20090201 |
| Reduction of hepatic steatosis in rats and mice after treatment with a liver-targeted thyroid hormone receptor agonist. | Hepatology (Baltimore, Md.) 20090201 |
| Synthesis and biological evaluation of a series of liver-selective phosphonic acid thyroid hormone receptor agonists and their prodrugs. | Journal of medicinal chemistry 20081127 |
| [Thyroid hormone analogs: an important biological supply and new therapeutic possibilities]. | Annales d'endocrinologie 20080901 |
| Thyroid hormone (T3) and TRbeta agonist GC-1 inhibit/reverse nonalcoholic fatty liver in rats. | FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20080801 |
| Thyroid hormone analogues: useful biological probes and potential therapeutic agents. | Annales d'endocrinologie 20080401 |
| Structural basis of GC-1 selectivity for thyroid hormone receptor isoforms. | BMC structural biology 20080101 |
| Influence of thyroid hormone and thyroid hormone receptors in the generation of cerebellar gamma-aminobutyric acid-ergic interneurons from precursor cells. | Endocrinology 20071201 |
| Thyroid hormone receptor beta-specific agonist GC-1 increases energy expenditure and prevents fat-mass accumulation in rats. | The Journal of endocrinology 20070401 |
| A phosphorimager-based filter binding thyroid hormone receptor competition assay for chemical screening. | Journal of pharmacological and toxicological methods 20070101 |
| The thyroid hormone receptor-beta agonist GC-1 induces cell proliferation in rat liver and pancreas. | Endocrinology 20060701 |
| Analysis of thyroid hormone receptor betaA mRNA expression in Xenopus laevis tadpoles as a means to detect agonism and antagonism of thyroid hormone action. | Toxicology and applied pharmacology 20060401 |
| Different configurations of specific thyroid hormone response elements mediate opposite effects of thyroid hormone and GC-1 on gene expression. | Endocrinology 20051101 |
| The proangiogenic action of thyroid hormone analogue GC-1 is initiated at an integrin. | Journal of cardiovascular pharmacology 20050901 |
| Mutant-selective thyromimetics for the chemical rescue of thyroid hormone receptor mutants associated with resistance to thyroid hormone. | Biochemistry 20050329 |
| The thyroid hormone receptor beta-specific agonist GC-1 selectively affects the bone development of hypothyroid rats. | Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20050201 |
| Thyroid hormone-dependent seasonality in American tree sparrows (Spizella arborea): effects of GC-1, a thyroid receptor beta-selective agonist, and of iopanoic acid, a deiodinase inhibitor. | Journal of comparative physiology. B, Biochemical, systemic, and environmental physiology 20040801 |
| Induction of larval tissue resorption in Xenopus laevis tadpoles by the thyroid hormone receptor agonist GC-1. | The Journal of biological chemistry 20040618 |
| Effects of the thyroid hormone receptor agonist GC-1 on metabolic rate and cholesterol in rats and primates: selective actions relative to 3,5,3'-triiodo-L-thyronine. | Endocrinology 20040401 |
| Selective activation of thyroid hormone signaling pathways by GC-1: a new approach to controlling cholesterol and body weight. | Trends in endocrinology and metabolism: TEM 20040101 |
| Differential effects of triiodothyronine and the thyroid hormone receptor beta-specific agonist GC-1 on thyroid hormone target genes in the b ain. | Endocrinology 20031201 |
| Structural determinants of selective thyromimetics. | Journal of medicinal chemistry 20030703 |
| Rational design and synthesis of a novel thyroid hormone antagonist that blocks coactivator recruitment. | Journal of medicinal chemistry 20020718 |
| Synthesis and biological activity of novel thyroid hormone analogues: 5'-aryl substituted GC-1 derivatives. | Bioorganic & medicinal chemistry 20020201 |
| A designed antagonist of the thyroid hormone receptor. | Bioorganic & medicinal chemistry letters 20011105 |
| Regulation of thyroid hormone receptor isoforms in physiological and pathological cardiac hypertrophy. | Circulation research 20010928 |
| Thyroid hormone--sympathetic interaction and adaptive thermogenesis are thyroid hormone receptor isoform--specific. | The Journal of clinical investigation 20010701 |
| Hormone selectivity in thyroid hormone receptors. | Molecular endocrinology (Baltimore, Md.) 20010301 |
| A high-affinity subtype-selective agonist ligand for the thyroid hormone receptor. | Chemistry & biology 19980601 |
| Binding of 3,5,3'-triiodothyronine (T3) and its analogs to the in vitro translational products of c-erbA protooncogenes: differences in the affinity of the alpha- and beta-forms for the acetic acid analog and failure of the human testis and kidney alpha-2 products to bind T3. | Molecular endocrinology (Baltimore, Md.) 19900201 |
| Opiate-dependent modulation of adenylate cyclase. | Proceedings of the National Academy of Sciences of the United States of America 19770801 |
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