Structure Database (LMSD)
Common Name
FAHFA 18:1(9Z)/5O(FA 18:0)
Systematic Name
5-(9Z-octadecenoyloxy)-octadecanoic acid
Synonyms
- 5-OAHSA
LM ID
LMFA07090025
Formula
Exact Mass
Calculate m/z
564.511761
Sum Composition
Abbrev Chains
FAHFA 18:1/18:0;O
Status
Curated
3D model of FAHFA 18:1(9Z)/5O(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. 5-OAHSA is a FAHFA in which oleic acid is esterified at the 5th carbon of hydroxy stearic acid. Among the FAHFA family members, OAHSAs are the most abundantly expressed in the serum of glucose tolerant AG4OX mice, which overexpress the Glut4 glucose transporter specifically in adipose tissue.1
This information has been provided by Cayman Chemical
References
String Representations
InChiKey (Click to copy)
FQZBGGYKEFIGPO-MSUUIHNZSA-N
InChi (Click to copy)
InChI=1S/C36H68O4/c1-3-5-7-9-11-13-15-16-17-18-20-22-24-26-28-33-36(39)40-34(31-29-32-35(37)38)30-27-25-23-21-19-14-12-10-8-6-4-2/h16-17,34H,3-15,18-33H2,1-2H3,(H,37,38)/b17-16-
SMILES (Click to copy)
C(CCC(=O)O)C(OC(CCCCCCC/C=C\CCCCCCCC)=O)CCCCCCCCCCCCC
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
40
Rings
0
Aromatic Rings
0
Rotatable Bonds
33
Van der Waals Molecular Volume
658.60
Topological Polar Surface Area
63.60
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
4
logP
12.18
Molar Refractivity
172.41
Admin
Created at
-
Updated at
14th Jun 2023