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
3D model of FAHFA 16:1(9Z)/12O(FA 18:0)
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
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
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
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
Admin
Created at
-
Updated at
14th Jun 2023