Showing metabocard for CE(20:3(5Z,8Z,11Z)) (BMDB0010373)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:05:20 UTC
Update Date2020-05-11 19:11:00 UTC
BMDB IDBMDB0010373
Secondary Accession Numbers
  • BMDB10373
Metabolite Identification
Common NameCE(20:3(5Z,8Z,11Z))
DescriptionCE(20:3(5Z,8Z,11Z)) 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(20:3(5Z,8Z,11Z)) may also accumulate in hereditary hypercholesterolemia, an inborn error of metabolism.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
20:3(5Z,8Z,11Z) cholesterol esterLipid Annotator, HMDB
CE(20:3)Lipid Annotator, HMDB
CE(20:3/0:0)Lipid Annotator, HMDB
Cholesterol Ester(20:3/0:0)Lipid Annotator, HMDB
cholesteryl 1-(5Z,8Z,11Z-eicosatrienoic acid)Lipid Annotator, HMDB
CE(20:3(5Z,8Z,11Z))Lipid Annotator
Cholesterol Ester(20:3)Lipid Annotator, HMDB
cholesteryl 1-(5Z,8Z,11Z-eicosatrienoate)Lipid Annotator, HMDB
cholesterol 1-(5Z,8Z,11Z-eicosatrienoate)Lipid Annotator, HMDB
cholesterol 1-meadoic acidLipid Annotator, HMDB
cholesterol 1-(5Z,8Z,11Z-eicosatrienoic acid)Lipid Annotator, HMDB
1-meadoyl-cholesterolLipid Annotator, HMDB
cholesteryl 1-meadoic acidLipid Annotator, HMDB
cholesterol 1-meadoateLipid Annotator, HMDB
1-(5Z,8Z,11Z-eicosatrienoyl)-cholesterolLipid Annotator, HMDB
cholesteryl 1-meadoateLipid Annotator, HMDB
CE(20:3n9/0:0)HMDB
CE(20:3W9/0:0)HMDB
Cholesterol 1-(5Z,8Z,11Z-eicosatrienoateHMDB
Cholesterol 1-(5Z,8Z,11Z-eicosatrienoic acidHMDB
Cholesterol ester(20:3n9/0:0)HMDB
Cholesterol ester(20:3W9/0:0)HMDB
Cholesteryl 1-(5Z,8Z,11Z-eicosatrienoateHMDB
Cholesteryl 1-(5Z,8Z,11Z-eicosatrienoic 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 (5Z,8Z,11Z)-icosa-5,8,11-trienoic acidGenerator
Chemical FormulaC47H78O2
Average Molecular Weight675.121
Monoisotopic Molecular Weight674.60018174
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 (5Z,8Z,11Z)-icosa-5,8,11-trienoate
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 (5Z,8Z,11Z)-icosa-5,8,11-trienoate
CAS Registry NumberNot Available
SMILES
CCCCCCCC\C=C/C\C=C/C\C=C/CCCC(=O)O[C@H]1CC[C@@]2(C)C(=CCC3C4CCC([C@H](C)CCCC(C)C)[C@@]4(C)CCC23)C1
InChI Identifier
InChI=1S/C47H78O2/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/h14-15,17-18,20-21,28,37-38,40-44H,7-13,16,19,22-27,29-36H2,1-6H3/b15-14-,18-17-,21-20-/t38-,40+,41?,42?,43?,44?,46+,47-/m1/s1
InChI KeyXQWTZYBOKFFMKJ-HXQMAXTDSA-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
logP10.56ALOGPS
logP14.73ChemAxon
logS-8.1ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity215.96 m³·mol⁻¹ChemAxon
Polarizability88.44 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, Positivesplash10-06tf-5168029000-ed09f4d07d58042120f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004r-1054019000-5de8cf64acb5aa969a0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-4189112000-1b54dad216d3c6584370View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0cdj-5289022000-7e6af171b3cf5496139eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dr-0015009000-f1056d88f463657c1679View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0029002000-38ebf00723c57b23d200View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-2029000000-df3e2b855bcd510118f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0001009000-dfc1f57d8c75edd87aedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0007009000-6b982272c517c992e0b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-9044618000-56045b3314dbd18b593bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00or-2129018000-1469af71fa047d458e11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0629-9230012000-1f4d83163086c6e6224eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0036-9410001000-9ed696d0ac03560c78dcView 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 IDHMDB0010373
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027525
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480461
PDB IDNot Available
ChEBI ID88752
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available