XCT-790

XCT-790
Names

Preferred IUPAC name (2E)-3-(4-{[2,4-Bis(trifluoromethyl)phenyl]methoxy}-3-methoxyphenyl)-2-cyano-N-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]prop-2-enamide
Identifiers
CAS Number	796844-24-1^Y 725247-18-7 (non-specific)^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL189753^N
ChemSpider	5293979^N
ECHA InfoCard	100.163.130
IUPHAR/BPS	2832
PubChem CID	6918788
UNII	A4CE428LGJ^Y
CompTox Dashboard (EPA)	DTXSID40426088
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+^N Key: HQFNFOOGGLSBBT-AWNIVKPZSA-N^N InChI=1/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+ Key: HQFNFOOGGLSBBT-AWNIVKPZBQ
SMILES COC1=C(C=CC(=C1)/C=C(\C#N)/C(=O)NC2=NN=C(S2)C(F)(F)F)OCC3=C(C=C(C=C3)C(F)(F)F)C(F)(F)F
Properties
Chemical formula	C₂₃H₁₃F₉N₄O₃S
Molar mass	596.424949
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

XCT-790 is a potent and selective inverse agonist ligand of the estrogen-related receptor alpha (ERRα).^[1] Independent of its inhibition of ERRα, XCT-790 is a potent mitochondrial electron transport chain uncoupler.^[2]

Mitochondrial electron transport chain uncoupling effect

XCT-790 has been shown to uncouple oxygen consumption from ATP production in mitochondria at very low, nanomolar-range doses independently of ERRα expression. Its effects are similar to proton ionophores such as FCCP, which disrupt mitochondrial transmembrane electrochemical gradients. This uncoupling leads to a fast drop in ATP production and, consequently, a prompt activation of AMPK.^[2]

References

^ Busch BB, Stevens WC Jr, Martin R, Ordentlich P, Zhou S, Sapp DW, Horlick RA, Mohan R; Stevens (November 2004). "Identification of a selective inverse agonist for the orphan nuclear receptor estrogen-related receptor alpha". J. Med. Chem. 47 (23): 5593–6. doi:10.1021/jm049334f. PMID 15509154.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ ^a ^b Eskiocak B; Aktar Ali; White MA (July 7, 2014). "The estrogen-related receptor α inverse agonist XCT 790 is a nanomolar mitochondrial uncoupler". Biochemistry. 53 (29): 4839–4846. doi:10.1021/bi500737n. PMC 4116149. PMID 24999922.