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Human Metabolome Database Version 3.5

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Showing metabocard for Erucic acid (HMDB02068)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:35 -0600
Update Date 2013-05-29 13:33:44 -0600
HMDB ID HMDB02068
Secondary Accession Numbers None
Metabolite Identification
Common Name Erucic acid
Description Erucic acid is a monounsaturated omega-9 fatty acid found mainly in the Brassica family of plants such as canola, rapeseed, wallflower seed, mustard seed as well as Brussels spouts and broccoli. Some Brassica cultivars can have up to 40 to 50 percent of their oil recovered as erucic acid. Erucic acid is also known as cis-13-docosenoic acid. The trans isomer is known as brassidic acid. Erucic acid occurs in nature only along with bitter-tasting compounds. Erucic acid has many of the same uses as mineral oils but with the advantage that it is more readily bio-degradable. Its high tolerance to temperature makes it suitable for transmission oil. Its ability to polymerize and dry means it can be - and is - used as a binder for oil paints. Increased levels of eicosenoic acid (20:ln9) and erucic acid (22:1n9) have been found in the red blood cell membranes of autistic subjects with developmental regression (PMID: 16581239 Link_out). Erucic acid is broken down long-chain acyl-coenzyme A (CoA) dehydrogenase, which is produced in the liver. This enzyme breaks this long chain fatty acid into shorter-chain fatty acids. human infants have relatively low amounts of this enzyme and because of this, babies should not be given foods high in erucic acid.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (13Z)-13-Docosenoate
  2. (13Z)-13-Docosenoic acid
  3. (13Z)-Docosenoate
  4. (13Z)-Docosenoic acid
  5. (Z)-13-Docosenoate
  6. (Z)-13-Docosenoic acid
  7. 13-Docosenoate
  8. 13-Docosenoic acid
  9. 13-Docosenoic acid (ACD/Name 4.0)
  10. cis-13-Docosenoate
  11. cis-13-Docosenoic acid
  12. cis-Erucic acid
  13. delta 13-cis-Docosenoate
  14. delta 13-cis-Docosenoic acid
  15. delta.13-cis-Docosenoate
  16. delta.13-cis-Docosenoic acid
  17. Prifrac 2990
Chemical Formula C22H42O2
Average Molecular Weight 338.5677
Monoisotopic Molecular Weight 338.318480588
IUPAC Name (13Z)-docos-13-enoic acid
Traditional IUPAC Name erucic acid
CAS Registry Number 112-86-7
SMILES CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O
InChI Identifier 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-
InChI Key DPUOLQHDNGRHBS-KTKRTIGZSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acids and Conjugates
Sub Class Unsaturated Fatty Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Monounsaturated fatty acids(KEGG)
  • Organic Compounds
  • Straight Chain Fatty Acids
  • Unsaturated fatty acids(KEGG)
  • Unsaturated fatty acids(Lipidmaps)
  • docosenoic acid(ChEBI)
Substituents
  • Acyclic Alkene
  • Carboxylic Acid
Direct Parent Unsaturated Fatty Acids
Ontology
Status Detected and Quantified
Origin
  • Food
  • Plant
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 33.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 2.270E-05 g/L ALOGPS
LogP 8.97 ALOGPS
LogP 8.56 ChemAxon
LogS -7.17 ALOGPS
pKa (strongest acidic) 4.95 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 A2 ChemAxon
Rotatable Bond Count 19 ChemAxon
Refractivity 105.81 ChemAxon
Polarizability 45.6 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Adrenal Gland
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
1.264 +/- 1.590 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
0.028 +/- 0.002 uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 150.0 (125.0-160.0) uM Adult (>18 years old) Both Adrenomyeloneuropathy
Associated Disorders and Diseases
Disease References
Adrenomyeloneuropathy
  • Aubourg P, Adamsbaum C, Lavallard-Rousseau MC, Rocchiccioli F, Cartier N, Jambaque I, Jakobezak C, Lemaitre A, Boureau F, Wolf C, et al.: A two-year trial of oleic and erucic acids ("Lorenzo's oil") as treatment for adrenomyeloneuropathy. N Engl J Med. 1993 Sep 9;329(11):745-52. Pubmed: 8350883 Link_out
    Associated OMIM IDs
    DrugBank ID Not Available
    DrugBank Metabolite ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB004287
    KNApSAcK ID C00001217 Link_out
    Chemspider ID 4444561 Link_out
    KEGG Compound ID C08316 Link_out
    BioCyc ID Not Available
    BiGG ID Not Available
    Wikipedia Link Erucic acid Link_out
    NuGOwiki Link HMDB02068 Link_out
    Metagene Link HMDB02068 Link_out
    METLIN ID 6470 Link_out
    PubChem Compound 5281116 Link_out
    PDB ID Not Available
    ChEBI ID 28792 Link_out
    References
    Synthesis Reference Not Available
    Material Safety Data Sheet (MSDS) Download (PDF)
    General References
    1. Rizzo WB, Leshner RT, Odone A, Dammann AL, Craft DA, Jensen ME, Jennings SS, Davis S, Jaitly R, Sgro JA: Dietary erucic acid therapy for X-linked adrenoleukodystrophy. Neurology. 1989 Nov;39(11):1415-22. Pubmed: 2682348 Link_out
    2. Bu B, Ashwood P, Harvey D, King IB, Water JV, Jin LW: Fatty acid compositions of red blood cell phospholipids in children with autism. Prostaglandins Leukot Essent Fatty Acids. 2006 Apr;74(4):215-21. Pubmed: 16581239 Link_out