Structure Database (LMSD)

Common Name
FAHFA 16:0/9O(FA 16:0)
Systematic Name
9-hexadecanoyloxy-hexadecanoic acid
Synonyms
  • 9-PAHPA
LM ID
LMFA07090036
Formula
C32H62O4
Exact Mass
Calculate m/z
510.464811
Sum Composition
FAHFA 32:0;O
Abbrev Chains
FAHFA 16:0/16:0;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]

Biological Context

9-PAHPA is a FAHFA in which palmitic acid is esterified to 9-hydroxy palmitic 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 As other FAHFAs improve glucose tolerance, stimulate insulin secretion, and have anti-inflammatory effects, 9-PAHPA 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)
DPFVDUJFYPYAOO-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C32H62O4/c1-3-5-7-9-10-11-12-13-14-15-16-21-25-29-32(35)36-30(26-22-18-8-6-4-2)27-23-19-17-20-24-28-31(33)34/h30H,3-29H2,1-2H3,(H,33,34)
SMILES (Click to copy)
C(CCCCCCC(=O)O)C(OC(CCCCCCCCCCCCCCC)=O)CCCCCCC

Other Databases

HMDB ID
HMDB0112110
PubChem CID
126457340
Cayman ID
17038

Calculated Physicochemical Properties

Heavy Atoms 36
Rings 0
Aromatic Rings 0
Rotatable Bonds 30
Van der Waals Molecular Volume 592.04
Topological Polar Surface Area 63.60
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 4
logP 10.84
Molar Refractivity 154.03

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Created at
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Updated at
14th Jun 2023