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Bovine Rumen Metabolome Database



Showing metabocard for CE(16:1(9Z)) (RMDB00658)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:58:08
Accession Number RMDB00658
Common Name CE(16:1(9Z))
Description CE(16:1(9Z)) is an important plasma 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 palmitoleate is one of the two more prevalent esters that are a component of Dehydroepiandrosterone fatty acid esters (DHEA-FA). DHEA-FA is formed from DHEA by lecithin-cholesterol acyltransferase, localized on high density lipoprotein (HDL). Once DHEA-FA is formed, it is subsequently transferred to very low density lipoprotein (VLDL) and low density lipoprotein (LDL), like cholesteryl esters. Cholesteryl palmitoleate constitutes 20% of the total lipoidal pregnenolone (an important precursor steroid) in follicular fluid. The fatty acid components of the resulting lipoidal pregnenolone derivatives resemble those of cholesteryl esters formed in plasma by the enzymatic activity of lecithin: cholesterol acyltransferase. (PMID 2770299, 8943795)
Synonyms
  1. (Z)-Cholesterol 9-hexadecenoate
  2. Cholesterol palmitoleate
  3. Cholesteryl cis-hexadecenoate
  4. Cholesteryl palmitoleat
  5. Cholesteryl palmitoleate
  6. Cholesteryl palmitoleic acid
  7. cholesteryl 1-palmitoleoic acid
  8. cholesterol 1-palmitoleoate
  9. Cholesterol Ester(16:1)
  10. 16:1(9Z) cholesterol ester
  11. Cholesterol Ester(16:1w7/0:0)
  12. Cholesterol Ester(16:1n7/0:0)
  13. Cholesterol Ester(16:1/0:0)
  14. cholesterol 1-palmitoleoic acid
  15. cholesteryl 1-palmitoleoate
  16. cholesteryl 1-(9Z-hexadecenoic acid)
  17. cholesteryl 1-(9Z-hexadecenoate)
  18. cholesterol 1-(9Z-hexadecenoic acid)
  19. CE(16:1/0:0)
  20. CE(16:1)
  21. cholest-5-en-3beta-yl (9Z hexadecenoate)
  22. 1-palmitoleoyl-cholesterol
  23. cholesterol 1-(9Z-hexadecenoate)
  24. CE(16:1w7/0:0)
  25. CE(16:1n7/0:0)
  26. (Z)-Cholesterol 9-hexadecenoic acid
  27. Cholesteryl cis-hexadecenoic acid
  28. cholesteryl 1-(9Z-hexadecenoate
  29. cholesteryl 1-(9Z-hexadecenoic acid
  30. cholesterol 1-(9Z-hexadecenoate
  31. cholest-5-en-3beta-yl (9Z hexadecenoic acid
  32. cholesterol 1-(9Z-hexadecenoic acid
  33. cholest-5-en-3beta-yl (9Z hexadecenoate
Chemical IUPAC Name [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,
Chemical Formula C43H74O2
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 623.047
Monoisotopic Molecular Weight 622.568909
Isomeric SMILES CCCCCCC=C/CCCCCCCC(=O)OC1CC[C@]2(C)C3CC[C@]4(C)[C@H](CCC4C3CC=C2C1)[C@H](C)CCCC(C)C
Canonical SMILES CCCCCCC=CCCCCCCCC(=O)OC1CCC2(C)C3CCC4(C)C(CCC4C3CC=C2C1)C(C)CCCC(C)C
KEGG Compound ID C02530 Link Image
BioCyc ID Cholesterol-esters Link Image
BiGG ID Not Available
Wikipedia Link Not Available
METLIN ID 5629 Link Image
PubChem Compound 6449983 Link Image
PubChem Substance 11972016 Link Image
ChEBI ID Not Available
CAS Registry Number 16711-66-3
InChI Identifier InChI=1/C43H74O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-23-41(44)45-36-28-30-42(5)35(32-36)24-25-37-39-27-26-38(34(4)22-20-21-33(2)3)43(39,6)31-29-40(37)42/h12-13,24,33-34,36-40H,7-11,14-23,25-32H2,1-6H3/b13-12-/t34-,36?,37?,38-,39?,40?,42+,43-/m1/s1
Synthesis Reference Wang, Stephen T.; Peter, Frank. Gas-liquid chromatographic determination of fatty acid composition of cholesteryl esters in human serum using silica Sep-Pak cartridges. Journal of Chromatography (1983), 276(2), 249-56.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 5.78e-06 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 10.44 [Predicted by ALOGPS]; 14.594 [Predicted by PubChem via XLOGP] 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 Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
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Medium Energy
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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 1.7 +/- 1.21 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