Structure Database (LMSD)

Common Name
FAHFA 16:1(9Z)/12O(FA 18:0)
Systematic Name
12-(9Z-hexadecenoyloxy)-octadecanoic acid
Synonyms
  • 12-POHSA
LM ID
LMFA07090023
Formula
Exact Mass
Calculate m/z
536.480461
Sum Composition
Abbrev Chains
FAHFA 16:1/18:0;O
Status
Curated

Classification

Biological Context

Branched fatty acid esters of hydroxy fatty acids (FAHFAs) are newly identified endogenous lipids regulated by fasting and high-fat feeding and associated with insulin sensitivity in mice.1 Structurally, these esters are comprised of a C-16 or C-18 fatty acid (e.g., palmitoleic, palmitic, oleic, or stearic acid) linked to either a C-16 or C-18 hydroxy substituent. 12-POHSA is a FAHFA consisting of palmitoleic acid esterified at the 12th carbon of stearic acid. The levels of POHSA are significantly elevated in 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, 12-POHSA may be a bioactive lipid with roles in metabolic syndrome and inflammation.1

This information has been provided by Cayman Chemical

References

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

String Representations

InChiKey (Click to copy)
XSYATLPMKFNWBI-QXMHVHEDSA-N
InChi (Click to copy)
InChI=1S/C34H64O4/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/h11-12,32H,3-10,13-31H2,1-2H3,(H,35,36)/b12-11-
SMILES (Click to copy)
C(CCCCCCCCCC(=O)O)C(OC(CCCCCCC/C=C\CCCCCC)=O)CCCCCC

Other Databases

HMDB ID
CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 38
Rings 0
Aromatic Rings 0
Rotatable Bonds 31
Van der Waals Molecular Volume 624.00
Topological Polar Surface Area 63.60
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 4
logP 11.40
Molar Refractivity 163.17

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Created at
-
Updated at
14th Jun 2023