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Structure Database (LMSD)

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Common Name

FAHFA 16:0/12O(FA 18:0)

Systematic Name

12-hexadecanoyloxy-octadecanoic acid

Synonyms

12-PAHSA

LM ID

LMFA07090007

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

12-PAHSA is a FAHFA in which palmitic acid is esterified at the 12th carbon of 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 12-PAHSA is present at 2- to 3-fold higher levels in adipose tissue of AG4OX mice compared to wild type mice.¹ Levels of 12-PAHSA are also higher in fasted wild-type mice compared to fed mice and are reduced upon high-fat diet-induced obesity in insulin-resistant 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)

XXHBLSWAKHZVLN-UHFFFAOYSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

C(CCCCCCCCCC(=O)O)C(OC(CCCCCCCCCCCCCCC)=O)CCCCCC