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Bovine Rumen Metabolome Database



Showing metabocard for CE(22:1(13Z)) (RMDB10372)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2008-09-16 14:19:46
Update Date 2009-05-05 21:06:29
Accession Number RMDB10372
Common Name CE(22:1(13Z))
Description CE(22:1(13Z)) is a cholesterol fatty acid ester or simply a cholesterol ester (CE). Cholesterol esters are cholesterol molecules with long-chain fatty acids linked to the hydroxyl group. They are much less polar than free cholesterol and appear to be the preferred form for transport in plasma and for storage. Cholesterol esters do not contribute to membranes but are packed into intracellular lipid particles or lipoprotein particles. Because of the mechanism of synthesis, plasma cholesterol esters tend to contain relatively high proportions of C18 fatty acids. Cholesterol esters are major constituents of the adrenal glands and they also accumulate in the fatty lesions of atherosclerotic plaques. Cholesterol esters are also major constituents of the lipoprotein particles carried in blood (HDL, LDL, VLDL). The cholesterol esters in high-density lipoproteins (HDL) are synthesized largely by transfer of fatty acids to cholesterol from position sn-2 (or C-2) of phosphatidylcholine catalyzed by the enzyme lecithin cholesterol acyl transferase (LCAT). The enzyme also promotes the transfer of cholesterol from cells to HDL. As cholesterol esters accumulate in the lipoprotein core, cholesterol is removed from its surface thus promoting the flow of cholesterol from cell membranes into HDL. This in turn leads to morphological changes in HDL, which grow and become spherical. Subsequently, cholesterol esters are transferred to the other lipoprotein fractions LDL and VLDL, a reaction catalyzed by cholesteryl ester transfer protein. Another enzyme, acyl-CoA:cholesterol acyltransferase (ACAT) synthesizes cholesterol esters from CoA esters of fatty acids and cholesterol. Cholesterol ester hydrolases liberate cholesterol and free fatty acids when required for membrane and lipoprotein formation, and they also provide cholesterol for hormone synthesis in adrenal cells.
Synonyms
  1. 22:1(13Z) cholesterol ester
  2. Cholesterol Ester(22:1w9/0:0)
  3. cholesteryl 1-erucoate
  4. CE(22:1w9/0:0)
  5. Cholesterol Ester(22:1n9/0:0)
  6. cholesterol 1-(13Z-docosenoic acid)
  7. 1-erucoyl-cholesterol
  8. CE(22:1)
  9. CE(22:1/0:0)
  10. cholesterol 1-erucoate
  11. cholesterol 1-(13Z-docosenoate)
  12. CE(22:1n9/0:0)
  13. cholesteryl 1-erucoic acid
  14. Cholesterol Ester(22:1/0:0)
  15. cholesteryl 1-(13Z-docosenoic acid)
  16. cholesterol 1-erucoic acid
  17. cholesteryl 1-(13Z-docosenoate)
  18. Cholesterol Ester(22:1)
  19. cholesterol 1-(13Z-docosenoate
  20. cholesterol 1-(13Z-docosenoic acid
  21. cholesteryl 1-(13Z-docosenoate
  22. cholesteryl 1-(13Z-docosenoic acid
Chemical IUPAC Name 1-(13Z-docosenoyl)-cholesterol
Chemical Formula C49H86O2
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
  • Membrane component; Energy source; Cell signaling
Application
Source
  • Endogenous
Average Molecular Weight 707.206
Monoisotopic Molecular Weight 706.662781
Isomeric SMILES CCCCCCCCC=C/CCCCCCCCCCCC(=O)O[C@H]1CC[C@]2(C)C3CC[C@]4(C)C(CCC4C3CC=C2C1)[C@H](C)CCCC(C)C
Canonical SMILES CCCCCCCCC=CCCCCCCCCCCCC(=O)OC1CCC2(C)C3CCC4(C)C(CCC4C3CC=C2C1)C(C)CCCC(C)C
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
METLIN ID Not Available
PubChem Compound Not Available
PubChem Substance Not Available
ChEBI ID Not Available
CAS Registry Number Not Available
InChI Identifier InChI=1/C49H86O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-29-47(50)51-42-34-36-48(5)41(38-42)30-31-43-45-33-32-44(40(4)28-26-27-39(2)3)49(45,6)37-35-46(43)48/h14-15,30,39-40,42-46H,7-13,16-29,31-38H2,1-6H3/b15-14-/t40-,42+,43?,44?,45?,46?,48+,49-/m1/s1
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 7.18e-06 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 11.06 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
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 Not Available
Not Available
Predicted 13C NMR Spectrum Not Available
Not Available
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane
Biofluid Location
  • Rumen
Tissue Location
Concentrations (Normal)
Biofluid Rumen
Value 1.1 +/- 0.26 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