LIPID MAPS

Structure Database (LMSD)

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Common Name

FAHFA 16:0/5O(FA 18:0)

Systematic Name

5-hexadecanoyloxy-octadecanoic acid

Synonyms

5-PAHSA
5-(palmitoyloxy)octadecanoic acid

LM ID

LMFA07090001

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

5-PAHSA is a FAHFA in which palmitic acid is esterified at the 5th carbon of hydroxy stearic acid. PAHSA isoforms are the most abundant forms of FAHFA identified in the adipose tissue of glucose tolerant AG4OX mice.¹ PAHSAs are synthesized in vivo in both mice and humans and are regulated by fasting and high-fat feeding in mice.¹ PAHSA levels correlate highly with insulin sensitivity and are reduced in adipose tissue and serum of insulin-resistant humans. PAHSA administration lowers ambient glycemia, improves glucose tolerance, and stimulates GLP-1 and insulin secretion 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)

QBGKCWKQYJQHJX-UHFFFAOYSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

C(CCC(=O)O)C(OC(CCCCCCCCCCCCCCC)=O)CCCCCCCCCCCCC