Showing metabocard for CE(18:3(6Z,9Z,12Z)) (BMDB0010369)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:05:15 UTC
Update Date2020-05-11 19:10:57 UTC
BMDB IDBMDB0010369
Secondary Accession Numbers
  • BMDB10369
Metabolite Identification
Common NameCE(18:3(6Z,9Z,12Z))
DescriptionCE(18:3(6Z,9Z,12Z)) 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(6Z,9Z,12Z)) may also accumulate in hereditary hypercholesterolemia, an inborn error of metabolism.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
cholesteryl 1-g-linolenoic acidLipid Annotator, HMDB
cholesterol 1-g-linolenoateLipid Annotator, HMDB
Cholesterol Ester(18:3/0:0)Lipid Annotator, HMDB
cholesterol 1-g-linolenoic acidLipid Annotator, HMDB
18:3(6Z,9Z,12Z) cholesterol esterLipid Annotator, HMDB
cholesterol 1-(6Z,9Z,12Z-octadecatrienoate)Lipid Annotator, HMDB
cholesteryl 1-(6Z,9Z,12Z-octadecatrienoate)Lipid Annotator, HMDB
cholesteryl 1-(6Z,9Z,12Z-octadecatrienoic acid)Lipid Annotator, HMDB
CE(18:3(6Z,9Z,12Z))Lipid Annotator
cholesteryl 1-g-linolenoateLipid Annotator, HMDB
CE(18:3/0:0)Lipid Annotator, HMDB
CE(18:3)Lipid Annotator, HMDB
1-g-linolenoyl-cholesterolLipid Annotator, HMDB
cholesterol 1-(6Z,9Z,12Z-octadecatrienoic acid)Lipid Annotator, HMDB
1-(6Z,9Z,12Z-octadecatrienoyl)-cholesterolLipid Annotator, HMDB
Cholesterol Ester(18:3)Lipid Annotator, HMDB
1-gamma-Linolenoyl-cholesterolHMDB
CE(18:3n6/0:0)HMDB
CE(18:3W6/0:0)HMDB
Cholesterol 1-(6Z,9Z,12Z-octadecatrienoateHMDB
Cholesterol 1-(6Z,9Z,12Z-octadecatrienoic acidHMDB
Cholesterol 1-gamma-linolenoateHMDB
Cholesterol 1-gamma-linolenoic acidHMDB
Cholesterol ester(18:3n6/0:0)HMDB
Cholesterol ester(18:3W6/0:0)HMDB
Cholesteryl 1-(6Z,9Z,12Z-octadecatrienoateHMDB
Cholesteryl 1-(6Z,9Z,12Z-octadecatrienoic acidHMDB
Cholesteryl 1-gamma-linolenoateHMDB
Cholesteryl 1-gamma-linolenoic 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 (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acidGenerator
Chemical FormulaC45H74O2
Average Molecular Weight647.0679
Monoisotopic Molecular Weight646.568881612
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 (6Z,9Z,12Z)-octadeca-6,9,12-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 (6Z,9Z,12Z)-octadeca-6,9,12-trienoate
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\C=C/C\C=C/CCCCC(=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/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/h11-12,14-15,17-18,26,35-36,38-42H,7-10,13,16,19-25,27-34H2,1-6H3/b12-11-,15-14-,18-17-/t36-,38+,39?,40?,41?,42?,44+,45-/m1/s1
InChI KeyGOHHVMNZYOLIPQ-BMVHEVBDSA-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 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
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
Polarizability83.27 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, Positivesplash10-02ai-3249037000-7258f8dae1da6a715d1cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0292-1155029000-6e5b06f7ae940132873bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02ti-5269041000-08f535575339d2c8acc6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ar0-5359020000-a9947635d38cff15eb25View 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0020009000-76957ac30c17037f6872View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0014009000-a8720f217de6ec358f6bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-9424445000-9bae75783e20ecc0d0d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-4129015000-5fca94bbe570d695ee21View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0api-9110000000-ebc8137871045f292bddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05po-9200000000-e8092e9a78d8e06ad85dView 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 IDHMDB0010369
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027521
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480458
PDB IDNot Available
ChEBI ID88756
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available