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Bovine Rumen Metabolome Database



Showing metabocard for CE(18:1(9Z)) (RMDB00918)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-08-20 15:40:18
Accession Number RMDB00918
Common Name CE(18:1(9Z))
Description Cholesteryl oleate 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 esters, formed by the esterification of cholesterol with long-chain fatty acids, on one hand, are the means by which cholesterol is transported through the blood by lipoproteins, on the other, the way cholesterol itself can be accumulated in the cells. (PMID: 15939411)
Synonyms
  1. 3beta-Hydroxy-5-cholestene 3-oleate
  2. 5-Cholesten-3b-ol 3-oleate
  3. Cholest-5-en-3-beta-yl oleate
  4. Cholesterol 3beta-oleate
  5. Cholesteroyl-oleate
  6. Cholesteryl [9,10-3H]oleate
  7. Cholesteryl cis-9-octadecenoate
  8. Cholesteryl oleate-9,10-3H
  9. Cholesteryl oleate-9,10-t2
  10. Cholesteryl oleic ester
  11. Cholesteryl-beta-D-glucoside
  12. Oleic acid cholesteryl ester
  13. Oleoylcholesterol
  14. cholest-5-en-3b-yl
  15. Cholesteryl-beta-delta-glucoside
  16. Cholesteryl oleate
  17. cholesteryl 1-oleoate
  18. cholesterol 1-(9Z-octadecenoate)
  19. 1-oleoyl-cholesterol
  20. CE(18:1n9/0:0)
  21. CE(18:1w9/0:0)
  22. 18:1(9Z) Cholesterol ester
  23. Cholesterol Ester(18:1/0:0)
  24. CE(18:1/0:0)
  25. CE(18:1)
  26. Cholesterol Ester(18:1n9/0:0)
  27. Cholesterol Ester(18:1)
  28. Cholesterol Ester(18:1w9/0:0)
  29. cholesterol 1-(9Z-octadecenoic acid)
  30. Cholest-5-en-3-ol (3b)-(Z)-9-octadecenoate
  31. Cholesteryl cis-9-octadecenoic acid
  32. cholesteryl 1-oleoic acid
  33. cholesterol 1-(9Z-octadecenoic acid
  34. cholesterol 1-(9Z-octadecenoate
  35. Cholest-5-en-3-ol (3b)-(Z)-9-octadecenoic acid
Chemical IUPAC Name [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] (Z)-octadec-9-enoate
Chemical Formula C45H78O2
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 651.100
Monoisotopic Molecular Weight 650.600159
Isomeric SMILES CCCCCCCCC=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 CCCCCCCCC=CCCCCCCCC(=O)OC1CCC2(C)C3CCC4(C)C(CCC4C3CC=C2C1)C(C)CCCC(C)C
KEGG Compound ID C14641 Link Image
BioCyc ID Cholesterol-esters Link Image
BiGG ID Not Available
Wikipedia Link Not Available
METLIN ID 5872 Link Image
PubChem Compound 5283632 Link Image
PubChem Substance 11039045 Link Image
ChEBI ID 46898 Link Image
CAS Registry Number 303-43-5
InChI Identifier InChI=1/C45H78O2/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/h14-15,26,35-36,38-42H,7-13,16-25,27-34H2,1-6H3/b15-14-/t36-,38+,39+,40-,41+,42+,44+,45-/m1/s1
Synthesis Reference Sripada P K Synthesis of single- and double-13C-labeled cholesterol oleate. Chemistry and physics of lipids (1988), 48(1-2), 147-51.
Melting Point (Experimental) 94 oC
Experimental Water Solubility 3 mg/mL [HMP experimental] Source: PhysProp
Predicted Water Solubility 6.33e-06 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 15.5 [Predicted by PubChem via XLOGP]; 10.68 [Predicted by ALOGPS] 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)
Biofluid Location
  • Rumen
Tissue Location
Concentrations (Normal)
Biofluid Rumen
Value 23.5 +/- 15.68 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