Structure Database (LMSD)

Common Name
13Z,16Z-docosadienoic acid
Systematic Name
13Z,16Z-docosadienoic acid
Synonyms
  • C22:2n-6,9
LM ID
LMFA01030405
Formula
C22H40O2
Exact Mass
Calculate m/z
336.30283
Sum Composition
FA 22:2
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]

Biological Context

13Z,16Z-Docosadienoic acid is a natural ω-6 polyunsaturated fatty acid (PUFA). It is an agonist of free fatty acid receptor 4 (FFAR4, also known as GPR120) and strongly inhibits the secretion of ghrelin by isolated mouse gastric cells.1 This 20:2 PUFA has been identified in mammals, fish, plants, and anaerobic fungi.2,3,4,5,6

This information has been provided by Cayman Chemical

References

1. de Oliveira, A.P., de Souza Franco, E., Barreto, R.R., et al. Effect of semisolid formulation of persea americana mill (avocado) oil on wound healing in rats. Evid. Based Complement. Altnernat. Med. 472382 (2013).
2. Gonzales, G.F., Gonzales, C., and Villegas, L. Exposure of fatty acids after a single oral administration of sacha inchi (Plukenetia volubilis L.) and sunflower oil in human adult subjects. Toxicol. Mech. Methods 24(1), 60-69 (2014).
3. Kim, S.-W., John, M., Kin, J.M., et al. Relationship between erythrocyte fatty acid composition and psychopathology in the vienna Omega-3 study. PLoS One 11(3), e0151417 (2016).
4. Koppová, I., Novotná, Z., Štrosová, L., et al. Analysis of fatty acid composition of anaerobic rumen fungi. Folia Microbiol. (Praha) 53(3), 217-220 (2008).
5. Lu, X., Zhao, X., Feng, J., et al. Postprandial inhibition of gastric ghrelin secretion by long-chain fatty acid through GPR120 in isolated gastric ghrelin cells and mice. Am. J. Physiol. Gastrointest. Liver Physiol. 303(3), G367-376 (2012).
6. Wågbø, A.M., Canigalosi, M.V., Ciero, N., et al. Perfluorooctane sulfonamide-mediated modulation of hepatocellular lipid homeostasis and oxidative stress responses in Atlantic salmon hepatocytes. Chem. Res. Toxicol. 25(6), 1253-1264 (2012).

Reactions

Filter by species:
ⓘ Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
Click on an edge to display the reaction(s).
Reactions graph legend

String Representations

InChiKey (Click to copy)
HVGRZDASOHMCSK-HZJYTTRNSA-N
InChi (Click to copy)
InChI=1S/C22H40O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h6-7,9-10H,2-5,8,11-21H2,1H3,(H,23,24)/b7-6-,10-9-
SMILES (Click to copy)
C(CCCCCCCCCCC/C=C\C/C=C\CCCCC)(=O)O

Other Databases

LIPIDAT ID
7621
KEGG ID
C16533
HMDB ID
HMDB0062219
CHEBI ID
75117
PubChem CID
5312554
PlantFA ID
10156
SwissLipids ID
SLM:000001120
Cayman ID
20749

Calculated Physicochemical Properties

Heavy Atoms 24
Rings 0
Aromatic Rings 0
Rotatable Bonds 18
Van der Waals Molecular Volume 398.82
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 7.44
Molar Refractivity 105.46

Admin

Created at
-
Updated at
25th Apr 2022