Showing metabocard for CE(20:4(5Z,8Z,11Z,14Z)) (BMDB0005195)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:15:35 UTC
Update Date2020-04-22 15:15:25 UTC
BMDB IDBMDB0005195
Secondary Accession Numbers
  • BMDB05195
Metabolite Identification
Common NameCE(20:4(5Z,8Z,11Z,14Z))
DescriptionCE(20:4(5Z,8Z,11Z,14Z)) 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(5Z,8Z,11Z,14Z)) may also accumulate in hereditary hypercholesterolemia, an inborn error of metabolism.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(5Z,8Z,11Z,14Z-EicosatetraenoateHMDB
(5Z,8Z,11Z,14Z-Eicosatetraenoate)HMDB
(5Z,8Z,11Z,14Z-Eicosatetraenoic acidHMDB
20:4 Cholesterol esterHMDB
Cholest-5-en-3-ol (3beta)- 5,8,11,14-eicosatetraenoateHMDB
Cholest-5-en-3-ol (3beta)- 5,8,11,14-eicosatetraenoic acidHMDB
Cholest-5-en-3beta-ylHMDB
Cholesterol arachidonateHMDB
Cholesteryl arachidonateHMDB
Cholesteryl arachidonic acidHMDB
Cholesteryl arachidonate eicosatetraenoateHMDB
Cholesteryl arachidonate, (3beta)-(all Z)-isomerHMDB
Cholesterol 1-(5Z,8Z,11Z,14Z-eicosatetraenoic acid)HMDB
Cholesteryl 1-(5Z,8Z,11Z,14Z-eicosatetraenoate)HMDB
Cholesteryl 1-arachidonoateHMDB
Cholesteryl 1-(5Z,8Z,11Z,14Z-eicosatetraenoic acid)HMDB
Cholesterol 1-arachidonoic acidHMDB
Cholesteryl 1-arachidonoic acidHMDB
CE(20:4/0:0)HMDB
CE(20:4)HMDB
Cholesterol ester(20:4/0:0)HMDB
20:4(5Z,8Z,11Z,14Z) Cholesterol esterHMDB
Cholesterol ester(20:4)HMDB
1-Arachidonoyl-cholesterolHMDB
Cholesterol 1-arachidonoateHMDB
1-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-cholesterolHMDB
Cholesterol 1-(5Z,8Z,11Z,14Z-eicosatetraenoate)HMDB
(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 (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acidHMDB
CE(20:4(5Z,8Z,11Z,14Z))Lipid Annotator
(2R,5S,15R)-2,15-Dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0,.0,]heptadec-7-en-5-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acidGenerator
Chemical FormulaC47H76O2
Average Molecular Weight673.123
Monoisotopic Molecular Weight672.584531687
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)-icosa-5,8,11,14-tetraenoate
Traditional 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)-icosa-5,8,11,14-tetraenoate
CAS Registry Number604-34-2
SMILES
CCCCC\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/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/h11-12,14-15,17-18,20-21,28,37-38,40-44H,7-10,13,16,19,22-27,29-36H2,1-6H3/b12-11-,15-14-,18-17-,21-20-/t38-,40+,41?,42?,43?,44?,46+,47-/m1/s1
InChI KeyIMXSFYNMSOULQS-SFCOZWKYSA-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
  • 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
logP10.27ALOGPS
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
Polarizability86.29 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, Positivesplash10-052o-2049017000-de026652b801d587805bView 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, Positivesplash10-00dr-1154019000-b11875970c0fb5adf992View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-5179022000-f79e7d8e7a946b312095View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-5379002000-9c3dca98011e0d7e3d8fView 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-0005019000-501e7316f1590589cb9aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0avr-8222329000-e0961ffd38bd726f521aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01b9-4139005000-4e74564816890983b7bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0cdi-9120001000-08eec88b1eebb254a151View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05po-9310001000-3c88899b0a4534583dc8View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006726
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB112234
KNApSAcK IDNot Available
Chemspider ID4980154
KEGG Compound IDC02530
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6479222
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available