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Human Metabolome Database Version 3.5

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Showing metabocard for CE(20:5(5Z,8Z,11Z,14Z,17Z) (HMDB06731)

Record Information
Version 3.5
Creation Date 2007-09-06 03:24:53 -0600
Update Date 2013-02-08 17:15:13 -0700
HMDB ID HMDB06731
Secondary Accession Numbers None
Metabolite Identification
Common Name CE(20:5(5Z,8Z,11Z,14Z,17Z)
Description Cholesteryl eicosapentaenoic 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). In patients with triglyceride levels above 500 mg/dl, approximately 4 g/day of eicosapentaenoic acid reduces triglyceride levels 45% and very low-density lipoprotein cholesterol levels by more than 50%. Physical exercise and fish oil (a rich source of eicosapentaenoic acid) suppress the activity of endothelial lipase (EL) and this, in turn, enhances the plasma concentrations of HDL cholesterol. EL has been shown to have a significant role in modulating the concentrations of plasma HDL. (PMID: 17461707 Link_out, 15664301 Link_out, 15524182 Link_out, 15485592 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (3b)-Cholest-5-en-3-ol (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-eicosapentaenoate
  2. (3b)-Cholest-5-en-3-ol (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-eicosapentaenoic acid
  3. (3b)-Cholest-5-en-3-ol (all-Z)-5,8,11,14,17-eicosapentaenoate
  4. (3b)-Cholest-5-en-3-ol (all-Z)-5,8,11,14,17-eicosapentaenoic acid
  5. 20:5 Cholesterol ester
  6. Cholest-5-en-3beta-yl (5Z,8Z,11Z,14Z,17Z-eicosapentaenoate
  7. Cholest-5-en-3beta-yl (5Z,8Z,11Z,14Z,17Z-eicosapentaenoate)
  8. Cholest-5-en-3beta-yl (5Z,8Z,11Z,14Z,17Z-eicosapentaenoic acid
  9. Cholesteryl 5,8,11,14,17-eicosapentaenoate
  10. Cholesteryl 5,8,11,14,17-eicosapentaenoic acid
  11. Cholesteryl eicosapentaenoate
  12. Cholesteryl eicosapentaenoic acid
Chemical Formula C47H74O2
Average Molecular Weight 671.0893
Monoisotopic Molecular Weight 670.568881612
IUPAC Name (2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
Traditional IUPAC Name (2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
CAS Registry Number 74892-97-0
SMILES CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)O[C@H]1CC[C@]2(C)C3CC[C@]4(C)C(CCC4C3CC=C2C1)[C@H](C)CCCC(C)C
InChI Identifier InChI=1S/C47H74O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-27-45(48)49-40-32-34-46(5)39(36-40)28-29-41-43-31-30-42(38(4)26-24-25-37(2)3)47(43,6)35-33-44(41)46/h8-9,11-12,14-15,17-18,20-21,28,37-38,40-44H,7,10,13,16,19,22-27,29-36H2,1-6H3/b9-8-,12-11-,15-14-,18-17-,21-20-/t38-,40+,41?,42?,43?,44?,46+,47-/m1/s1
InChI Key XZFUGMCJZFRBKF-JIKDAPOUSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Steroid Esters
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Branched Fatty Acids
  • Carbocyclic Fatty Acids
  • Organic Compounds
  • Triterpenes
  • Unsaturated Fatty Acids
Substituents
  • Bicyclohexane
  • Carboxylic Acid Ester
  • Cyclohexane
  • Cyclohexene
Direct Parent Cholesteryl Esters
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
LogP 10.03 ALOGPS
LogP 14 ChemAxon
LogS -7.97 ALOGPS
pKa (strongest basic) -7 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 26.3 A2 ChemAxon
Rotatable Bond Count 20 ChemAxon
Refractivity 218.19 ChemAxon
Polarizability 85.65 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
39.07 +/- 11.07 uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB024047
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID C02530 Link_out
BioCyc ID Cholesterol-esters Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB06731 Link_out
Metagene Link HMDB06731 Link_out
METLIN ID Not Available
PubChem Compound 53477889 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Shimada, Yuji; Hirota, Yoshinori; Baba, Takashi; Sugihara, Akio; Moriyama, Shigeru; Tominaga, Yoshio; Terai, Tadamasa. Enzymatic synthesis of steryl esters of polyunsaturated fatty acids. Journal of the American Oil Chemists' Society (1999), 76(6), 713-716.
Material Safety Data Sheet (MSDS) Not Available
General References Not Available
Enzymes
Name: Phosphatidylcholine-sterol acyltransferase
Reactions:
  • phosphatidylcholine + a sterol = 1-acylglycerophosphocholine + a sterol ester [RN:R02114]
Gene Name: LCAT
Uniprot ID: P04180 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysosomal acid lipase/cholesteryl ester hydrolase
Reactions:
  • a steryl ester + H2O = a sterol + a fatty acid [RN:R02115]
Gene Name: LIPA
Uniprot ID: P38571 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Bile salt-activated lipase
Reactions:
  • a steryl ester + H2O = a sterol + a fatty acid [RN:R02115]
Gene Name: CEL
Uniprot ID: P19835 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Liver carboxylesterase 1
Reactions:
  • a carboxylic ester + H2O = an alcohol + a carboxylate [RN:R00630]
Gene Name: CES1
Uniprot ID: P23141 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sterol O-acyltransferase 2
Reactions:
  • acyl-CoA + cholesterol = CoA + cholesterol ester [RN:R01461]
Gene Name: SOAT2
Uniprot ID: O75908 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sterol O-acyltransferase 1
Reactions:
  • acyl-CoA + cholesterol = CoA + cholesterol ester [RN:R01461]
Gene Name: SOAT1
Uniprot ID: P35610 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Scavenger receptor class B member 1
Reactions:
    Gene Name: SCARB1
    Uniprot ID: Q8WTV0 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Neutral cholesterol ester hydrolase 1
    Reactions:
      Gene Name: NCEH1
      Uniprot ID: Q6PIU2 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA