Structure Database (LMSD)

Common Name
cis-erucic acid
Systematic Name
13Z-docosenoic acid
Synonyms
  • cis-13-docosenoic acid
  • C22:1n-9
LM ID
LMFA01030089
Formula
C22H42O2
Exact Mass
Calculate m/z
338.31848
Sum Composition
FA 22:1
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View MassBank spectra
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

13(Z)-Docosenoic acid is a 22-carbon monounsaturated fatty acid. It is found predominantly in canola oil.1 13(Z)-Docosenoic acid is metabolized to oleic acid in vivo. Diets rich in 13(Z)-docosenoic acid were shown to cause heart lipidosis in experimental animals.2,3 The C-1 amide of docosenoic acid has been identified as one of the anandamide-related neurotransmitters associated with sleep.4

This information has been provided by Cayman Chemical

References

1. Cravatt, B.F., Prospero-Garcia, O., Siuzdak, G., et al. Chemical characterization of a family of brain lipids that induce sleep. Science 268(5216), 1506-1509 (1995).
2. Hulan, H.W., Kramer, J.K.G., Mahadevan, S., et al. Relationship between erucic acid and myocardial changes in male rats. Lipids 11(1), 9-15 (1975).
3. Borg, K. Physiopathological effects of rapeseed oil: A review. Acta Med. Scand. Suppl. 585, 5-13 (1975).
4. Astorg, P.O. Heart lipidosis induced by short-term feeding of cis- or trans-docosenoic acids in weanling or 7-week-old rats. Ann. Nutr. Metab. 25(4), 201-207 (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
Homo sapiens (#9606)
Mammalia (#40674)
Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010
Pubmed ID: 20671299
Brassica napus (#3708)
Magnoliopsida (#3398)
Crismer values and erucic acid contents of rapeseed oils,
J Am Oil Chem Soc, 1977

String Representations

InChiKey (Click to copy)
DPUOLQHDNGRHBS-KTKRTIGZSA-N
InChi (Click to copy)
InChI=1S/C22H42O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h9-10H,2-8,11-21H2,1H3,(H,23,24)/b10-9-
SMILES (Click to copy)
C(=C/CCCCCCCCCCCC(=O)O)/CCCCCCCC

Other Databases

Wikipedia
erucic acid
KEGG ID
C08316
HMDB ID
HMDB0002068
CHEBI ID
28792
LIPIDBANK ID
DFA0128
PubChem CID
5281116
PlantFA ID
10152
SwissLipids ID
SLM:000001118
Cayman ID
90175
PDB ID
08O

Calculated Physicochemical Properties

Heavy Atoms 24
Rings 0
Aromatic Rings 0
Rotatable Bonds 19
Van der Waals Molecular Volume 401.46
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 7.67
Molar Refractivity 105.56

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Created at
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Updated at
25th Apr 2022