Structure Database (LMSD)

Common Name
Sciadonic acid
Systematic Name
5Z,11Z,14Z-eicosatrienoic acid
Synonyms
  • C20:3n-6,9,15
  • Calthic acid
  • Sciadopinolenic acid
LM ID
LMFA01030380
Formula
C20H34O2
Exact Mass
Calculate m/z
306.25588
Sum Composition
FA 20:3
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

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

Biological Context

5(Z),11(Z),14(Z)-Eicosatrienoic acid is a polyunsaturated fatty acid found in various natural sources including maritime pine (Pinus pinaster) seed oil (MPSO), gymnospermae leaves and seeds, and freshwater gastropods.1,2,3 A diet containing MPSO lowered high-density lipoprotein and ApoA1 levels in transgenic mice expressing human ApoA1. MPSO was found to diminish cholesterol efflux in vitro.1 5(Z),11(Z),14(Z)-Eicosatrienoic acid methyl ester, when topically applied, reduces inflammatory processes, potentially by displacing arachidonic acid from phospholipid pools and reducing downstream inflammatory products such as prostaglandin E2 and leukotrienes.4

This information has been provided by Cayman Chemical

References

1. Go, J.V., Rezanka, T., Srebnik, M., et al. Variability of fatty acid components of murine and freshwater gastropod speices from the littoral zone of the Red Sea, Mediterranean Sea, and Sea of Galilee. Biochem. Syst. Ecol. 30, 819-835 (2002).
2. Berger, A., Monnard, I., Baur, M., et al. Epidermal anti-inflammatory properties of 5,11,14 20:3: Effects on mouse ear edema, PGE2 levels in cultured keratinocytes, and PPAR activation. Lipids Health Dis. 1(5), 1-12 (2002).
3. Mongrand, S., Badoc, A., Patouille, B., et al. Taxonomy of gymnospermae: Multivariate analyses of leaf fatty acid composition. Phytochemistry 58, 101-115 (2001).
4. Asset, G., Leroy, A., Bauge, E., et al. Effects of dietary maritime pine (Pinus pinaster)-seed oil on high-density lipoprotein levels and in vitro cholesterol efflux in mice expressing human apolipoprotein A-I. Br. J. Nutr. 84(3), 353-360 (2000).

Reactions

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References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Sciadopitys verticillata (#28979)
Pinopsida (#58019)
Positional distribution of Δ5‐olefinic acids in triacylglycerols from conifer seed oils: General and specific enrichment in the sn‐3 position,
J Am Oil Chem Soc, 1997
Mus musculus (#10090)
Mammalia (#40674)
Obesity resistance and deregulation of lipogenesis in Δ6-fatty acid desaturase (FADS2) deficiency.,
EMBO Rep, 2014
Pubmed ID: 24378641

String Representations

InChiKey (Click to copy)
PRHHYVQTPBEDFE-URZBRJKDSA-N
InChi (Click to copy)
InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,15-16H,2-5,8,11-14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,16-15-
SMILES (Click to copy)
C(CCC/C=C\CCCC/C=C\C/C=C\CCCCC)(=O)O

Other Databases

LIPIDAT ID
3508
CHEBI ID
82832
PubChem CID
445084
Cayman ID
10009999

Calculated Physicochemical Properties

Heavy Atoms 22
Rings 0
Aromatic Rings 0
Rotatable Bonds 15
Van der Waals Molecular Volume 361.58
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 6.44
Molar Refractivity 96.13

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Created at
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Updated at
25th Apr 2022