InChI=1S/C34H66O4/c1-3-5-7-8-9-10-11-12-13-17-20-23-27-31-34(37)38-32(28-24-6-4-2)29-25-21-18-15-14-16-19-22-26-30-33(35)36/h32H,3-31H2,1-2H3,(H,35,36)/p-1 |
XCOROKUALFOQRK-UHFFFAOYSA-M |
CCCCCCCCCCCCCCCC(=O)OC(CCCCC)CCCCCCCCCCCC([O-])=O |
|
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
|
|
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
hypoglycemic agent
A drug which lowers the blood glucose level.
|
|
View more via ChEBI Ontology
13-(hexadecanoyloxy)octadecanoate
|
13-(palmitoyloxy)octadecanoate
|
IUPAC
|
13-(palmitoyloxy)stearate
|
ChEBI
|
hexadecanoyl-13-hydroxyoctadecanoate ester
|
UniProt
|
palmitoyl-13-hydroxystearate ester(1−)
|
SUBMITTER
|
Yore MM, Syed I, Moraes-Vieira PM, Zhang T, Herman MA, Homan EA, Patel RT, Lee J, Chen S, Peroni OD, Dhaneshwar AS, Hammarstedt A, Smith U, McGraw TE, Saghatelian A, Kahn BB (2014) Discovery of a class of endogenous mammalian lipids with anti-diabetic and anti-inflammatory effects. Cell 159, 318-332 (Source: SUBMITTER) [PubMed:25303528] [show Abstract] Increased adipose tissue lipogenesis is associated with enhanced insulin sensitivity. Mice overexpressing the Glut4 glucose transporter in adipocytes have elevated lipogenesis and increased glucose tolerance despite being obese with elevated circulating fatty acids. Lipidomic analysis of adipose tissue revealed the existence of branched fatty acid esters of hydroxy fatty acids (FAHFAs) that were elevated 16- to 18-fold in these mice. FAHFA isomers differ by the branched ester position on the hydroxy fatty acid (e.g., palmitic-acid-9-hydroxy-stearic-acid, 9-PAHSA). PAHSAs are synthesized in vivo and regulated by fasting and high-fat feeding. PAHSA levels correlate highly with insulin sensitivity and are reduced in adipose tissue and serum of insulin-resistant humans. PAHSA administration in mice lowers ambient glycemia and improves glucose tolerance while stimulating GLP-1 and insulin secretion. PAHSAs also reduce adipose tissue inflammation. In adipocytes, PAHSAs signal through GPR120 to enhance insulin-stimulated glucose uptake. Thus, FAHFAs are endogenous lipids with the potential to treat type 2 diabetes. |
|