Structure Database (LMSD)

Common Name
FAHFA 16:1(9Z)/13O(FA 18:0)
Systematic Name
13-(9Z-hexadecenoyloxy)-octadecanoic acid
Synonyms
  • 13-POHSA
LM ID
LMFA07090024
Formula
C34H64O4
Exact Mass
Calculate m/z
536.480461
Sum Composition
FAHFA 34:1;O
Abbrev Chains
FAHFA 16:1/18:0;O
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty esters [FA07]
Fatty acid estolides [FA0709]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]

Biological Context

13-POHSA is a FAHFA consisting of palmitoleic acid esterified to 13-hydroxy 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, 13-POHSA 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).

String Representations

InChiKey (Click to copy)
FHXCZZFHUCAQAA-KHPPLWFESA-N
InChi (Click to copy)
InChI=1S/C34H64O4/c1-3-5-7-8-9-10-11-12-13-17-20-23-27-31-34(37)38-32(28-24-6-4-2)29-25-21-18-15-14-16-19-22-26-30-33(35)36/h10-11,32H,3-9,12-31H2,1-2H3,(H,35,36)/b11-10-
SMILES (Click to copy)
C(CCCCCCCCCCC(=O)O)C(OC(CCCCCCC/C=C\CCCCCC)=O)CCCCC

Other Databases

HMDB ID
HMDB0112139
CHEBI ID
137086
PubChem CID
126456519
Cayman ID
17111

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