Structure Database (LMSD)

Common Name
Sterculic acid
Systematic Name
9,10-methylene-9-octadecenoic acid
Synonyms
  • omega-(2-n-octylcycloprop-1-enyl)octanoic acid
  • Stearculic acid
  • Stearculinic acid
  • Sterculinic acid
LM ID
LMFA01140018
Formula
C19H34O2
Exact Mass
Calculate m/z
294.25588
Sum Composition
FA 19:2
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]
Carbocyclic fatty acids [FA0114]
Unsaturated fatty acids [FA0103]
Branched fatty acids [FA0102]

Biological Context

Sterculic acid is a cyclopropene fatty acid that has been found in S. foetida.1 It is an inhibitor of Δ9-desaturase that decreases 9(Z)-myristoleic acid and increases oleic acid and 9(Z),11(E)-conjugated linoleic acid levels in the milk of lactating ewes when administered at a dose of 0.5 g per day.2 It also inhibits endoplasmic reticulum stress induced by 7-keto cholesterol in ARPE-19 cells when used at a concentration of 1 µM and prevents the formation of choroidal neovascularization when applied to eyes at concentrations of 0.1 to 10 mM in a rat model of macular degeneration induced by laser injury.1 Sterculic acid binds to a variety of kinases, including calcium/calmodulin-dependent protein kinase kinase 2 (CAMKK2), mammalian sterile20-related kinase 3 (MST3), and p90 ribosomal S5 kinase 4 (RSK4).3 [Matreya, LLC. Catalog No. 1235]

This information has been provided by Cayman Chemical

References

1. Huang, J.-D., Amaral, J., Lee, J.W., et al. Sterculic acid antagonizes 7-ketocholesterol-mediated inflammation and inhibits choroidal neovascularization. Biochim. Biophys. Acta 1821(4), 637-646 (2012).
2. Huang, J.-D., Amaral, J., Lee, J.W., et al. 7-Ketocholesterol-induced inflammation signals mostly through the TLR4 receptor both in vitro and in vivo. PLoS One 9(7), e100985 (2014).
3. Bichi, E., Toral, P.G., Hervás, G., et al. Inhibition of ∆9-desaturase activity with sterculic acid: Effect on the endogenous synthesis of cis-9 18:1 and cis-9, trans-11 18:2 in dairy sheep. J. Dairy Sci. 95(9), 5242-5252 (2012).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Sterculia foetida (#195802)
Magnoliopsida (#3398)
The Structure of Sterculic Acid.,
J. Chem. Soc., 1952

String Representations

InChiKey (Click to copy)
PQRKPYLNZGDCFH-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C19H34O2/c1-2-3-4-5-7-10-13-17-16-18(17)14-11-8-6-9-12-15-19(20)21/h2-16H2,1H3,(H,20,21)
SMILES (Click to copy)
C(CCCCCCC(=O)O)C1CC=1CCCCCCCC

Other Databases

Wikipedia
Sterculic_acid
KEGG ID
C08366
CHEBI ID
9261
PubChem CID
12921
PlantFA ID
10233
Cayman ID
26735

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 1
Aromatic Rings 0
Rotatable Bonds 15
Van der Waals Molecular Volume 337.20
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 6.25
Molar Refractivity 89.59

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Created at
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Updated at
16th Dec 2020