LIPID MAPS

Structure Database (LMSD)

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Common Name

FAHFA 16:0/10O(FA 18:0)

Systematic Name

10-hexadecanoyloxy-octadecanoic acid

Synonyms

10-PAHSA

LM ID

LMFA07090005

Formula

C₃₄H₆₆O₄

Exact Mass

Calculate m/z

538.496111

Sum Composition

FAHFA 34:0;O

Abbrev Chains

FAHFA 16:0/18:0;O

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

10-PAHSA is a newly identified endogenous lipid that belongs to a collection of branched fatty acid esters of hydroxy fatty acids (FAHFAs). It is a FAHFA in which palmitic acid is esterified to 10-hydroxy stearic acid. Among the FAHFA family members, PAHSAs are the most abundant in the adipose tissue of glucose tolerant AG4OX mice, which overexpress the Glut4 glucose transporter specifically in adipose tissue.¹ As other FAHFAs improve glucose tolerance, stimulate insulin secretion, and have anti-inflammatory effects, 10-PAHSA may be a bioactive lipid with roles in metabolic syndrome and inflammation.¹

This information has been provided by Cayman Chemical

References

1. Yore, M.M., Syed, I., Moraes-Vieira, P.M., et al. Discovery of a class of endogenous mammalian lipids with anti-diabetic and anti-inflammatory effects. Cell 159(2), 318-332 (2014).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Discovery of a class of endogenous mammalian lipids with anti-diabetic and anti-inflammatory effects,
Cell, 2014

Pubmed ID: 25303528

DOI: 10.1016/j.cell.2014.09.035

String Representations

InChiKey (Click to copy)

UVHRDGWHIDFWID-UHFFFAOYSA-N

InChi (Click to copy)

InChI=1S/C34H66O4/c1-3-5-7-9-11-12-13-14-15-16-17-23-27-31-34(37)38-32(28-24-20-10-8-6-4-2)29-25-21-18-19-22-26-30-33(35)36/h32H,3-31H2,1-2H3,(H,35,36)

SMILES (Click to copy)

C(CCCCCCCC(=O)O)C(OC(CCCCCCCCCCCCCCC)=O)CCCCCCCC