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Bovine Rumen Metabolome Database



Showing metabocard for Alpha-Linolenic acid (RMDB01388)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-07-31 19:11:39
Accession Number RMDB01388
Common Name Alpha-Linolenic acid
Description Alpha-linolenic acid (ALA) is a polyunsaturated fatty acid (PUFA). It is a member of the group of essential fatty acids called omega-3 fatty acids. Alpha-linolenic acid, in particular, is not synthesized by mammals and therefore is an essential dietary requirement for all mammals. Certain nuts (English walnuts) and vegetable oils (canola, soybean, flaxseed/linseed, olive) are particularly rich in alpha-linolenic acid (ALA). Omega-3 fatty acids get their name based on the location of one of their first double bond. In all omega-3 fatty acids, the first double bond is located between the third and fourth carbon atom counting from the methyl end of the fatty acid (n-3). Although humans and other mammals can synthesize saturated and some monounsaturated fatty acids from carbon groups in carbohydrates and proteins, they lack the enzymes necessary to insert a cis double bond at the n-6 or the n-3 position of a fatty acid. Omega-3 fatty acids like a-linolenic acid are important structural components of cell membranes. When incorporated into phospholipids, they affect cell membrane properties such as fluidity, flexibility, permeability and the activity of membrane bound enzymes. Omega-3 fatty acids can modulate the expression of a number of genes, including those involved with fatty acid metabolism and inflammation. Alpha linolenic acid and other omega 3 fatty acids may regulate gene expression by interacting with specific transcription factors, including peroxisome proliferator activated receptors (PPARs) and liver X receptors (LXRs).
Synonyms
  1. (9,12,15)-linolenate
  2. (9,12,15)-linolenic acid
  3. (9E,12E,15E)-9,12,15-Octadecatrienoate
  4. (9E,12E,15E)-9,12,15-Octadecatrienoic acid
  5. (9Z,12Z,15Z)-Octadecatrienoate
  6. (9Z,12Z,15Z)-Octadecatrienoic acid
  7. (Z,Z,Z)-9,12,15-Octadecatrienoate
  8. (Z,Z,Z)-9,12,15-Octadecatrienoic acid
  9. 9,12,15-Octadecatrienoate
  10. 9,12,15-Octadecatrienoic acid
  11. 9-cis,12-cis,15-cis-octadecatrienoate
  12. 9-cis,12-cis,15-cis-octadecatrienoic acid
  13. Industrene 120
  14. Linolenate
  15. Linolenic acid
  16. a-Linolenate
  17. all-cis-9,12,15-Octadecatrienoate
  18. all-cis-9,12,15-Octadecatrienoic acid
  19. alpha-Linolenate
  20. alpha-Linolenic acid
  21. cis,cis,cis-9,12,15-Octadecatrienoate
  22. cis,cis,cis-9,12,15-Octadecatrienoic acid
  23. cis-9,12,15-octadecatrienoate
  24. cis-9,12,15-octadecatrienoic acid
  25. a-Linolenic acid
Chemical IUPAC Name octadeca-9,12,15-trienoic acid
Chemical Formula C18H30O2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Organic acids
Class
  • Fatty Acids
Sub Class
  • Long chain fatty acids
Family
  • Mammalian_Metabolite
Species
  • carboxylic acid; alkene
Biofunction
  • Essential fatty acid
Application
Source
  • Exogenous
Average Molecular Weight 278.430
Monoisotopic Molecular Weight 278.224579
Isomeric SMILES CCC=CCC=CCC=CCCCCCCCC(O)=O
Canonical SMILES CCC=CCC=CCC=CCCCCCCCC(O)=O
KEGG Compound ID C06427 Link Image
BioCyc ID LINOLENIC_ACID Link Image
BiGG ID 48237 Link Image
Wikipedia Link Linolenic acid Link Image
METLIN ID 6208 Link Image
PubChem Compound 860 Link Image
PubChem Substance 11362510 Link Image
ChEBI ID 27432 Link Image
CAS Registry Number 463-40-1
InChI Identifier InChI=1/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3+,7-6+,10-9+
Synthesis Reference Li, Guihua; Qian, Xiangming; Jiang, Yanchao; Ma, Shushi. Preparation of a-linolenic acid from linseed oil. Zhengzhou Gongcheng Xueyuan Xuebao (2004), 25(3), 13-15.
Melting Point (Experimental) -16.5 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.000124 mg/mL [MEYLAN,WM et al. (1996)]; 2.66e-04 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Liquid
Experimental LogP/Hydrophobicity 6.46 [SANGSTER (1993)] Source: PhysProp
Predicted LogP/Hydrophobicity 6.62 [Predicted by ALOGPS]; 5.8 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
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High Energy
Download File
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane (Predicted from LogP)
  • Cytoplasm
  • Extracellular
Biofluid Location
  • Cow_Milk
  • Rumen
Tissue Location
Concentrations (Normal)
Biofluid Rumen
Value 0.5 +/- 0.4 uM
Age N/A
Sex Female
Condition Normal
Breed Not Available
Experimental Condition Not Available
Comments Not Available
References
  • The rumen metabolome (in preparation)
Concentrations (Abnormal) Not Available
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References
  1. Wikipedia Link Image