LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG SVG

Common Name

FAHFA 16:0/9O(FA 18:0)

Systematic Name

9-hexadecanoyloxy-octadecanoic acid

Synonyms

9-PAHSA

LM ID

LMFA07090004

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

9-PAHSA is a FAHFA in which palmitic acid is esterified to 9-hydroxy stearic acid. PAHSAs are the most abundant forms of FAHFA in serum as well as white and brown adipose tissues of glucose tolerant AG4OX mice, which overexpress Glut4 specifically in adipose tissue.¹ 9-PAHSA is the predominant isomer of PAHSA in wild type and AG4OX mice.¹ It is found in humans and is reduced in the serum and adipose tissues of insulin-resistant humans.¹ 9-PAHSA improves glucose tolerance, stimulates insulin secretion, and has anti-inflammatory effects in mice.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)

MHQWHZLXDBVXML-UHFFFAOYSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

C(CCCCCCC(=O)O)C(OC(CCCCCCCCCCCCCCC)=O)CCCCCCCCC