Showing metabocard for CE(18:3(9Z,12Z,15Z)) (BMDB0010370)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:05:16 UTC
Update Date2020-05-11 19:10:58 UTC
BMDB IDBMDB0010370
Secondary Accession Numbers
  • BMDB10370
Metabolite Identification
Common NameCE(18:3(9Z,12Z,15Z))
DescriptionCE(18:3(9Z,12Z,15Z)) 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(18:3(9Z,12Z,15Z)) may also accumulate in hereditary hypercholesterolemia, an inborn error of metabolism.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
18:3 Cholesteryl esterChEBI
CE(18:3)ChEBI
Cholesteryl (9Z,12Z,15Z)-octadeca-9,12,15-trienoateChEBI
Cholesteryl (9Z,12Z,15Z)-octadecatrienoateChEBI
Cholesteryl (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acidGenerator
Cholesteryl (9Z,12Z,15Z)-octadecatrienoic acidGenerator
Cholesteryl (9Z,12Z,15Z-octadecatrienoate)ChEBI
Cholesteryl (9Z,12Z,15Z-octadecatrienoic acid)Generator
(3b) Cholest 5 en 3 ol (Z,Z,Z) octadecatrienoateHMDB
(3b) Cholest 5 en 3 ol (Z,Z,Z) octadecatrienoic acidHMDB
1-a-Linolenoyl-cholesterolHMDB
1-alpha-Linolenoyl-cholesterolHMDB
18:3(9Z,12Z,15Z) Cholesterol esterHMDB
CE(18:3/0:0)HMDB
CE(18:3n3/0:0)HMDB
CE(18:3W3/0:0HMDB
Cholest 5 en 3beta yl (Z,Z,Z) octadeca 9,12,15 trien 1 OateHMDB
Cholest 5 en 3beta yl (Z,Z,Z) octadeca 9,12,15 trien 1 Oic acidHMDB
Cholesterol 1-(9Z,12Z,15Z-octadeatrienoateHMDB
Cholesterol 1-(9Z,12Z,15Z-octadeatrienoate)HMDB
Cholesterol 1-(9Z,12Z,15Z-octadeatrienoic acidHMDB
Cholesterol 1-(9Z,12Z,15Z-octadeatrienoic acid)HMDB
Cholesterol 1-a-linolenoateHMDB
Cholesterol 1-a-linolenoic acidHMDB
Cholesterol 1-alpha-linolenoateHMDB
Cholesterol 1-alpha-linolenoic acidHMDB
Cholesterol a linolenateHMDB
Cholesterol alpha linolenateHMDB
Cholesterol ester(18:3)HMDB
Cholesterol ester(18:3/0:0)HMDB
Cholesterol ester(18:3n3/0:0)HMDB
Cholesterol ester(18:3W3/0:0)HMDB
Cholesterol linolenateHMDB
Cholesterol octadecatrienoateHMDB
Cholesterol octadecatrienoic acidHMDB
Cholesteryl 1-(9Z,12Z,15Z-octadeatrienoateHMDB
Cholesteryl 1-(9Z,12Z,15Z-octadeatrienoate)HMDB
Cholesteryl 1-(9Z,12Z,15Z-octadeatrienoic acidHMDB
Cholesteryl 1-(9Z,12Z,15Z-octadeatrienoic acid)HMDB
Cholesteryl 1-a-linolenoateHMDB
Cholesteryl 1-a-linolenoic acidHMDB
Cholesteryl 1-alpha-linolenoateHMDB
Cholesteryl 1-alpha-linolenoic acidHMDB
Cholesteryl linolenateHMDB, MeSH
Cholesteryl linolenic acidHMDB, Generator
Cholesteryl octadecatrienoateHMDB
Cholesteryl octadecatrienoic acidHMDB
Linolenic acid cholesteryl esterHMDB
CLL-9,12,15MeSH
CE(18:3(9Z,12Z,15Z))ChEBI
Chemical FormulaC45H74O2
Average Molecular Weight647.0679
Monoisotopic Molecular Weight646.568881612
IUPAC Name(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
Traditional Name18:3 cholesteryl ester
CAS Registry Number2545-22-4
SMILES
CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@@]3([H])[C@]4([H])CC[C@]([H])([C@H](C)CCCC(C)C)[C@@]4(C)CC[C@]23[H])C1
InChI Identifier
InChI=1S/C45H74O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25-43(46)47-38-30-32-44(5)37(34-38)26-27-39-41-29-28-40(36(4)24-22-23-35(2)3)45(41,6)33-31-42(39)44/h8-9,11-12,14-15,26,35-36,38-42H,7,10,13,16-25,27-34H2,1-6H3/b9-8-,12-11-,15-14-/t36-,38+,39+,40-,41+,42+,44+,45-/m1/s1
InChI KeyFYMCIBHUFSIWCE-WVXFKAQASA-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
  • Octadecanoid
  • 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 Descriptors
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
logP10.24ALOGPS
logP13.84ChemAxon
logS-8ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity206.76 m³·mol⁻¹ChemAxon
Polarizability85.34 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, Positivesplash10-00lu-1239016000-7566d44e90aebe06d4e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0292-1055029000-6923f5c26c734f51d0b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02ti-4069031000-700a85d4dfa851151e72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ar0-4259020000-6ba3a596720fc2ed8da3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0024009000-ed4c858ea523e29ed695View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0049003000-03af1dd8b7259cd08ae8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0673-2029000000-43715a67bb63b0d40732View 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 IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6436907
PDB IDNot Available
ChEBI ID84341
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available