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Bovine Rumen Metabolome Database



Showing metabocard for CE(18:2(9Z,12Z)) (RMDB00610)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:58:06
Accession Number RMDB00610
Common Name CE(18:2(9Z,12Z))
Description Cholesteryl linoleic acid is a cholesteryl ester. A cholesteryl ester is an ester of cholesterol. Fatty acid esters of cholesterol constitute about two-thirds of the cholesterol in the plasma. Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. The accumulation of cholesterol esters in the arterial intima (the innermost layer of an artery, in direct contact with the flowing blood) is a characteristic feature of atherosclerosis. Atherosclerosis is a disease affecting arterial blood vessels. It is a chronic inflammatory response in the walls of arteries, in large part to the deposition of lipoproteins (plasma proteins that carry cholesterol and triglycerides). Cholesteryl linoleate is contained in low density lipoprotein and atherosclerotic lesions. The oxidation products of cholesteryl linoleate may cause chronic inflammatory processes. (PMID 9684755, 11950694)
Synonyms
  1. cholesterol 1-linoleoic acid
  2. Cholesterol Ester(18:2)
  3. cholesteryl 1-linoleoic acid
  4. Cholesterol Ester(18:2/0:0)
  5. cholesterol 1-(9Z,12Z-octadecadienoate)
  6. CE(18:2n6/0:0)
  7. cholesteryl 1-(9Z,12Z-octadecadienoate)
  8. Cholesterol Ester(18:2n6/0:0)
  9. 18:2(9Z,12Z) Cholesterol ester
  10. Cholesterol Ester(18:2w6/0:0)
  11. cholest-5-en-3beta-yl (9Z,12Z-octadecadienoate)
  12. cholesteryl 1-linoleoate
  13. 1-linoleoyl-cholesterol
  14. CE(18:2w6/0:0)
  15. cholesterol 1-(9Z,12Z-octadecadienoic acid)
  16. CE(18:2)
  17. CE(18:2/0:0)
  18. cholesterol 1-linoleoate
  19. cholesteryl 1-(9Z,12Z-octadecadienoic acid)
  20. cholesterol 1-(9Z,12Z-octadecadienoic acid
  21. cholesteryl 1-(9Z,12Z-octadecadienoic acid
  22. cholest-5-en-3beta-yl (9Z,12Z-octadecadienoic acid
  23. cholesterol 1-(9Z,12Z-octadecadienoate
  24. cholesteryl 1-(9Z,12Z-octadecadienoate
  25. cholest-5-en-3beta-yl (9Z,12Z-octadecadienoate
Chemical IUPAC Name [10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dode
Chemical Formula C45H76O2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Cholesterols and derivatives
Class
  • Steroids and Steroid Derivatives
Sub Class
  • Cholesterol esters
Family
  • Mammalian_Metabolite
Species
  • carboxylic acid ester; alkene
Biofunction
  • Hormones, Membrane component
Application
Source
  • Endogenous
Average Molecular Weight 649.084
Monoisotopic Molecular Weight 648.584534
Isomeric SMILES CCCCCC=C/CC=C/CCCCCCCC(=O)O[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)[C@H](CC[C@H]4[C@@H]3CC=C2C1)[C@H](C)CCCC(C)C
Canonical SMILES CCCCCC=CCC=CCCCCCCCC(=O)OC1CCC2(C)C3CCC4(C)C(CCC4C3CC=C2C1)C(C)CCCC(C)C
KEGG Compound ID C15441 Link Image
BioCyc ID Cholesterol-esters Link Image
BiGG ID Not Available
Wikipedia Link Not Available
METLIN ID 5584 Link Image
PubChem Compound 227041 Link Image
PubChem Substance 6080751 Link Image
ChEBI ID Not Available
CAS Registry Number 604-33-1
InChI Identifier InChI=1/C45H76O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25-43(46)47-38-30-32-44(5)37(34-38)26-27-39-41-29-28-40(36(4)24-22-23-35(2)3)45(41,6)33-31-42(39)44/h11-12,14-15,26,35-36,38-42H,7-10,13,16-25,27-34H2,1-6H3/b12-11-,15-14-/t36-,38+,39+,40-,41+,42+,44+,45-/m1/s1
Synthesis Reference Lundberg, Bo; Pellas, Lars. Preparation and characterization of cholesteryl linoleate. Acta Academiae Aboensis, Series B: Mathematica et Physica (1973), 33(4), 4 pp.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 5.79e-06 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 10.50 [Predicted by ALOGPS]; 15.2 [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 1CLE Link Image
Experimental PDB File Show
Experimental PDB Structure
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
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Medium Energy
Download File
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High Energy
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane (Predicted from LogP)
Biofluid Location
  • Rumen
Tissue Location Not Available
Concentrations (Normal)
Biofluid Rumen
Value 15.1 +/- 7.3 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 Not Available