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Bovine Rumen Metabolome Database



Showing metabocard for Linoleic acid (RMDB00673)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-07-31 19:03:44
Accession Number RMDB00673
Common Name Linoleic acid
Description Linoleic acid is a doubly unsaturated fatty acid, also known as an omega-6 fatty acid, occurring widely in plant glycosides. In this particular polyunsaturated fatty acid (PUFA), the first double bond is located between the sixth and seventh carbon atom from the methyl end of the fatty acid (n-6). Linoleic acid is an essential fatty acid in human nutrition because it cannot be synthesized by humans. It is used in the biosynthesis of prostaglandins (via arachidonic acid) and cell membranes. (From Stedman, 26th ed)
Synonyms
  1. (9Z,12Z)-9,12-Octadecadienoate
  2. (9Z,12Z)-9,12-Octadecadienoic acid
  3. (Z,Z)-9,12-Octadecadienoate
  4. (Z,Z)-9,12-Octadecadienoic acid
  5. 9-cis,12-cis-Linoleate
  6. 9-cis,12-cis-Linoleic acid
  7. 9Z,12Z-Linoleate
  8. 9Z,12Z-Linoleic acid
  9. 9Z,12Z-Octadecadienoate
  10. 9Z,12Z-Octadecadienoic acid
  11. Emersol 315
  12. Extra Linoleic 90
  13. Linolate
  14. Linoleate
  15. Linoleic acid
  16. Linolic acid
  17. Polylin 515
  18. Unifac 6550
  19. all-cis-9,12-Octadecadienoate
  20. all-cis-9,12-Octadecadienoic acid
  21. cis,cis-Linoleate
  22. cis,cis-Linoleic acid
  23. cis-9,cis-12-Octadecadienoate
  24. cis-9,cis-12-Octadecadienoic acid
  25. cis-D9,12-Octadecadienoate
  26. cis-D9,12-Octadecadienoic acid
Chemical IUPAC Name 9,12-Octadecadienoic acid
Chemical Formula C18H32O2
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 280.445
Monoisotopic Molecular Weight 280.240234
Isomeric SMILES CCCCCC=C/CC=C/CCCCCCCC(O)=O
Canonical SMILES CCCCCC=CCC=CCCCCCCCC(O)=O
KEGG Compound ID C01595 Link Image
BioCyc ID Not Available
BiGG ID 37956 Link Image
Wikipedia Link Linoleic acid Link Image
METLIN ID 191 Link Image
PubChem Compound 3931 Link Image
PubChem Substance 11373233 Link Image
ChEBI ID 30245 Link Image
CAS Registry Number 60-33-3
InChI Identifier InChI=1/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-
Synthesis Reference Walborsky, Harry M.; Davis, Robert H.; Howton, David R. A total synthesis of linoleic acid. Journal of the American Chemical Society (1951), 73 2590-4.
Melting Point (Experimental) -8.5 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.000139 mg/mL [MEYLAN,WM et al. (1996)]; 1.54e-04 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Liquid
Experimental LogP/Hydrophobicity 7.05 [SANGSTER (1993)] Source: PhysProp
Predicted LogP/Hydrophobicity 7.06 [Predicted by ALOGPS]; 6.2 [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
Show Peaklist
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 3.5 +/- 2.6 uM
Age N/A
Sex N/A
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