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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

XCT790 is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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+
InChI Key HQFNFOOGGLSBBT-AWNIVKPZSA-N
References
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]