XCT790   Click here for help

GtoPdb Ligand ID: 2832

Synonyms: XCT 790 | XCT-790
Compound class: Synthetic organic
Comment: XCT790 is a selective estrogen-related receptor α (ERRα) antagonist/inverse agonist [1-2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 11
Topological polar surface area 125.37
Molecular weight 596.06
XLogP 6.24
No. Lipinski's rules broken 1
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Canonical SMILES N#CC(=Cc1ccc(c(c1)OC)OCc1ccc(cc1C(F)(F)F)C(F)(F)F)C(=O)Nc1nnc(s1)C(F)(F)F
Isomeric SMILES N#C/C(=C\c1ccc(c(c1)OC)OCc1ccc(cc1C(F)(F)F)C(F)(F)F)/C(=O)Nc1nnc(s1)C(F)(F)F
InChI InChI=1S/C23H13F9N4O3S/c1-38-17-7-11(6-13(9-33)18(37)34-20-36-35-19(40-20)23(30,31)32)2-5-16(17)39-10-12-3-4-14(21(24,25)26)8-15(12)22(27,28)29/h2-8H,10H2,1H3,(H,34,36,37)/b13-6+
1. Kong X, Fan H, Liu X, Wang R, Liang J, Gupta N, Chen Y, Fang F, Chang Y. (2009)
Peroxisome proliferator-activated receptor gamma coactivator-1alpha enhances antiproliferative activity of 5'-deoxy-5-fluorouridine in cancer cells through induction of uridine phosphorylase.
Mol Pharmacol, 76 (4): 854-60. [PMID:19602572]
2. Lanvin O, Bianco S, Kersual N, Chalbos D, Vanacker JM. (2007)
Potentiation of ICI182,780 (Fulvestrant)-induced estrogen receptor-alpha degradation by the estrogen receptor-related receptor-alpha inverse agonist XCT790.
J Biol Chem, 282 (39): 28328-34. [PMID:17631492]
3. Suetsugi M, Su L, Karlsberg K, Yuan YC, Chen S. (2003)
Flavone and isoflavone phytoestrogens are agonists of estrogen-related receptors.
Mol Cancer Res, 1 (13): 981-91. [PMID:14638870]
4. Willy PJ, Murray IR, Qian J, Busch BB, Stevens WC, Martin R, Mohan R, Zhou S, Ordentlich P, Wei P, Sapp DW, Horlick RA, Heyman RA, Schulman IG. (2004)
Regulation of PPARgamma coactivator 1alpha (PGC-1alpha) signaling by an estrogen-related receptor alpha (ERRalpha) ligand.
Proc Natl Acad Sci USA, 101 (24): 8912-7. [PMID:15184675]
5. Zuercher WJ, Gaillard S, Orband-Miller LA, Chao EY, Shearer BG, Jones DG, Miller AB, Collins JL, McDonnell DP, Willson TM. (2005)
Identification and structure-activity relationship of phenolic acyl hydrazones as selective agonists for the estrogen-related orphan nuclear receptors ERRbeta and ERRgamma.
J Med Chem, 48 (9): 3107-9. [PMID:15857113]