Structure Database (LMSD)

Common Name
cis-parinaric acid
Systematic Name
9Z,11E,13E,15Z-octadecatetraenoic acid
Synonyms
  • alpha-parinaric acid
  • C18:4n-3,5,7,9
LM ID
LMFA01030764
Formula
C18H28O2
Exact Mass
Calculate m/z
276.20893
Sum Composition
FA 18:4
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]
Octadecanoids [FA02]

Biological Context

cis-Parinaric acid is a naturally occurring polyunsaturated fatty acid containing an unusual conjugated (Z,E,E,Z) tetraene. This chromophore provides for a natural fluorescence at 432 nm with an excitation wavelength at 320 nm. cis-Parinaric acid occurs naturally in the seeds of the Makita tree, a tropical rainforest tree indigenous to Fiji. Makita seeds are inedible, and this toxicity may be due at least in part to the unstable conjugated fatty acids, including cis-parinaric acid, contained within the seed. cis-Parinaric acid has been used for the measurement of phospholipase activity, lipase activity, and as an indicator of lipid peroxidation.1,2,3,4

This information has been provided by Cayman Chemical

References

1. de Hingh, Y.C.M., Meyer, J., Fischer, J.C., et al. Direct measurement of lipid peroxidation in submitochondrial particles. Biochemistry 34, 12755-12760 (1995).
2. McGuire, S.O., James-Kracke, M.R., Sun, G.Y., et al. An esterification protocol for cis-parinaric acid-determined lipid peroxidation in immune cells. Lipids 32, 219-226 (1997).
3. Beisson, F., Ferté, N., Nari, J., et al. Use of naturally fluorescent triacylglycerols from Parinari glaberrimum to detect low lipase activities from Arabidopsis thaliana seedlings. J. Lipid Res. 40, 2313-2321 (1999).
4. Wolf, C., Sagaert, L., and Bereziat, G. A sensitive assay of phospholipase using the fluorescent probe 2-parinaroyllecithin. Biochem. Biophys. Res. Commun. 99, 275-283 (1981).

Reactions

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ⓘ 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.
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Reactions graph legend

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Parinari (#82156)
Magnoliopsida (#3398)
New tropical seed oils. Part I. conjugated trienoic and tetraenoic acids and their oxo derivatives in the seed oils of Chrysobalanus Icaco and Parinarium Laurinum,
Chem Phys Lipids, 1967

String Representations

InChiKey (Click to copy)
IJTNSXPMYKJZPR-ZSCYQOFPSA-N
InChi (Click to copy)
InChI=1S/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-10H,2,11-17H2,1H3,(H,19,20)/b4-3-,6-5+,8-7+,10-9-
SMILES (Click to copy)
C(CCCCCCC/C=C\C=C\C=C\C=C/CC)(=O)O

Other Databases

CHEBI ID
32409
PubChem CID
5460995
PlantFA ID
10373
Cayman ID
71430

Calculated Physicochemical Properties

Heavy Atoms 20
Rings 0
Aromatic Rings 0
Rotatable Bonds 12
Van der Waals Molecular Volume 324.34
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 5.44
Molar Refractivity 86.81

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Created at
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Updated at
25th Apr 2022