Showing metabocard for CE(20:4(8Z,11Z,14Z,17Z)) (BMDB0010371)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:05:18 UTC
Update Date2020-05-11 19:10:59 UTC
BMDB IDBMDB0010371
Secondary Accession Numbers
  • BMDB10371
Metabolite Identification
Common NameCE(20:4(8Z,11Z,14Z,17Z))
DescriptionCE(20:4(8Z,11Z,14Z,17Z)) belongs to the family of cholesteryl esters, whose structure is characetized by a cholesterol esterified at the 3-position with a fatty acid. 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). CE(20:4(8Z,11Z,14Z,17Z)) may also accumulate in hereditary hypercholesterolemia, an inborn error of metabolism.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
cholesteryl 1-(8Z,11Z,14Z,17Z-eicosapentaenoate)Lipid Annotator, HMDB
cholesteryl 1-eicsoatetraenoic acidLipid Annotator, HMDB
cholesterol 1-(8Z,11Z,14Z,17Z-eicosapentaenoic acid)Lipid Annotator, HMDB
cholesterol 1-(8Z,11Z,14Z,17Z-eicosapentaenoate)Lipid Annotator, HMDB
CE(20:4/0:0)Lipid Annotator, HMDB
CE(20:4)Lipid Annotator, HMDB
Cholesterol Ester(20:4/0:0)Lipid Annotator, HMDB
1-eicsoatetraenoyl-cholesterolLipid Annotator, HMDB
cholesterol 1-eicsoatetraenoateLipid Annotator, HMDB
20:4(8Z,11Z,14Z,17Z) cholesterol esterLipid Annotator, HMDB
cholesteryl 1-(8Z,11Z,14Z,17Z-eicosapentaenoic acid)Lipid Annotator, HMDB
Cholesterol Ester(20:4)Lipid Annotator, HMDB
cholesterol 1-eicsoatetraenoic acidLipid Annotator, HMDB
CE(20:4(8Z,11Z,14Z,17Z))Lipid Annotator
1-(8Z,11Z,14Z,17Z-eicosapentaenoyl)-cholesterolLipid Annotator, HMDB
cholesteryl 1-eicsoatetraenoateLipid Annotator, HMDB
1-EicsoateHMDB
1-Eicsoic acidHMDB
CE(20:4n3/0:0)HMDB
CE(20:4W3/0:0)HMDB
Cholesterol 1-(8Z,11Z,14Z,17Z-eicosapentaenoateHMDB
Cholesterol 1-(8Z,11Z,14Z,17Z-eicosapentaenoic acidHMDB
Cholesterol 1-eicsoateHMDB
Cholesterol 1-eicsoic acidHMDB
Cholesterol ester(20:4n3/0:0)HMDB
Cholesterol ester(20:4W3/0:0)HMDB
Cholesteryl 1-(8Z,11Z,14Z,17Z-eicosapentaenoateHMDB
Cholesteryl 1-(8Z,11Z,14Z,17Z-eicosapentaenoic acidHMDB
Cholesteryl 1-eicsoateHMDB
Cholesteryl 1-eicsoic acidHMDB
(2R,5S,15R)-2,15-Dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoic acidGenerator
Chemical FormulaC47H76O2
Average Molecular Weight673.1051
Monoisotopic Molecular Weight672.584531676
IUPAC Name(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoate
Traditional Name(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoate
CAS Registry NumberNot Available
SMILES
CC\C=C/C\C=C/C\C=C/C\C=C/CCCCCCC(=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/C47H76O2/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/h8-9,11-12,14-15,17-18,28,37-38,40-44H,7,10,13,16,19-27,29-36H2,1-6H3/b9-8-,12-11-,15-14-,18-17-/t38-,40+,41?,42?,43?,44?,46+,47-/m1/s1
InChI KeyHZUAPDDXDDVFOX-FETKFLJASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters are compounds containing an esterified cholestane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentCholesteryl esters
Alternative Parents
Substituents
  • Cholesteryl ester
  • Cholesterol
  • Cholestane-skeleton
  • Delta-5-steroid
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP10.25ALOGPS
logP14.36ChemAxon
logS-8ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity217.08 m³·mol⁻¹ChemAxon
Polarizability86.37 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-2249018000-192bdfac71cf5c4a7310View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-1054019000-9c550044ea438e425f3dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-4169022000-f129db04919d37d4e6faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4069012000-d630d61bbbc58483f435View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dr-0015009000-637cc9bd3bafbdce9588View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0029002000-2f94d33c992a960491dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-2019000000-f76f34fa22154e621d36View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01e9-6229036000-9dcd9704257928f92517View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-069r-9101001000-4ba012345618f4d8b9ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05r3-9310000000-d2933ba78be1e1ecff2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0002009000-03ab7bed41cba80b0fddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0004019000-6fbd1ea580ac5da620d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-8333319000-56788a1fc579a651be67View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0010371
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027523
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480459
PDB IDNot Available
ChEBI ID88755
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available