LIPID MAPS

Structure Database (LMSD)

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Common Name

FAHFA 18:1(9Z)/13O(FA 18:0)

Systematic Name

13-(9Z-octadecenoyloxy)-octadecanoic acid

Synonyms

13-OAHSA

LM ID

LMFA07090032

Formula

C₃₆H₆₈O₄

Exact Mass

Calculate m/z

564.51176

Sum Composition

FAHFA 36:1;O

Abbrev Chains

FAHFA 18:1/18:0;O

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

13-OAHSA is a form of FAHFA in which oleic acid is esterified to 13-hydroxy stearic acid. Among the FAHFA family members, OAHSAs are the most abundantly expressed in the serum 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, 13-OAHSA 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)

RCTXOTTXFKSGGU-SEYXRHQNSA-N

InChi (Click to copy)

InChI=1S/C36H68O4/c1-3-5-7-8-9-10-11-12-13-14-15-19-22-25-29-33-36(39)40-34(30-26-6-4-2)31-27-23-20-17-16-18-21-24-28-32-35(37)38/h12-13,34H,3-11,14-33H2,1-2H3,(H,37,38)/b13-12-

SMILES (Click to copy)

C(CCCCCCCCCCC(=O)O)C(OC(CCCCCCC/C=C\CCCCCCCC)=O)CCCCC