Showing metabocard for 18:2 Cholesteryl ester (BMDB0062601)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-08-29 17:08:34 UTC
Update Date2020-06-04 20:20:23 UTC
BMDB IDBMDB0062601
Secondary Accession Numbers
  • BMDB62601
Metabolite Identification
Common Name18:2 Cholesteryl ester
DescriptionCholesteryl linoleate, also known as 18:2 cholesteryl ester or ce(18:2(9Z,12Z)), belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters are compounds containing an esterified cholestane moiety. Cholesteryl linoleate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3beta)-Cholest-5-en-3-ol, (9Z,12Z)-9,12-octadecadienoateChEBI
(3beta)-Cholest-5-en-3-ol, (Z,Z)-9,12-octadecadienoateChEBI
(Z,Z)-(3beta)-Cholest-5-en-3-ol 9,12-octadecadienoateChEBI
18:2 Cholesteryl esterChEBI
CE(18:2(9Z,12Z))ChEBI
CE(18:2)ChEBI
Cholest-5-en-3beta-yl (Z,Z)-octadeca-9,12-dienoateChEBI
Cholesteryl (9Z,12Z)-octadecadienoateChEBI
(3b)-Cholest-5-en-3-ol, (9Z,12Z)-9,12-octadecadienoateGenerator
(3b)-Cholest-5-en-3-ol, (9Z,12Z)-9,12-octadecadienoic acidGenerator
(3beta)-Cholest-5-en-3-ol, (9Z,12Z)-9,12-octadecadienoic acidGenerator
(3Β)-cholest-5-en-3-ol, (9Z,12Z)-9,12-octadecadienoateGenerator
(3Β)-cholest-5-en-3-ol, (9Z,12Z)-9,12-octadecadienoic acidGenerator
(3b)-Cholest-5-en-3-ol, (Z,Z)-9,12-octadecadienoateGenerator
(3b)-Cholest-5-en-3-ol, (Z,Z)-9,12-octadecadienoic acidGenerator
(3beta)-Cholest-5-en-3-ol, (Z,Z)-9,12-octadecadienoic acidGenerator
(3Β)-cholest-5-en-3-ol, (Z,Z)-9,12-octadecadienoateGenerator
(3Β)-cholest-5-en-3-ol, (Z,Z)-9,12-octadecadienoic acidGenerator
(Z,Z)-(3b)-Cholest-5-en-3-ol 9,12-octadecadienoateGenerator
(Z,Z)-(3b)-Cholest-5-en-3-ol 9,12-octadecadienoic acidGenerator
(Z,Z)-(3beta)-Cholest-5-en-3-ol 9,12-octadecadienoic acidGenerator
(Z,Z)-(3Β)-cholest-5-en-3-ol 9,12-octadecadienoateGenerator
(Z,Z)-(3Β)-cholest-5-en-3-ol 9,12-octadecadienoic acidGenerator
Cholest-5-en-3b-yl (Z,Z)-octadeca-9,12-dienoateGenerator
Cholest-5-en-3b-yl (Z,Z)-octadeca-9,12-dienoic acidGenerator
Cholest-5-en-3beta-yl (Z,Z)-octadeca-9,12-dienoic acidGenerator
Cholest-5-en-3β-yl (Z,Z)-octadeca-9,12-dienoateGenerator
Cholest-5-en-3β-yl (Z,Z)-octadeca-9,12-dienoic acidGenerator
Cholesteryl (9Z,12Z)-octadecadienoic acidGenerator
Cholesteryl linoleic acidGenerator
Cholesteryl linoleate, (e,e)-isomerMeSH
Cholesteryl trans-9-trans-12-octadecadienoateMeSH
CLOHMeSH
Cholesteryl linoleate, (Z,e)-isomerMeSH
Cholesteryl linolelaidateMeSH
Cholesteryl linoleate, (e,Z)-isomerMeSH
Cholesteryl (9Z,12Z-octadecadienoate)ChEBI
Cholesteryl (9Z,12Z-octadecadienoic acid)Generator
1-Linoleoyl-cholesterolHMDB
18:2(9Z,12Z) Cholesterol esterHMDB
CE(18:2/0:0)HMDB
CE(18:2n6/0:0)HMDB
CE(18:2W6/0:0)HMDB
Cholest-5-en-3beta-yl (9Z,12Z-octadecadienoateHMDB
Cholest-5-en-3beta-yl (9Z,12Z-octadecadienoate)HMDB
Cholest-5-en-3beta-yl (9Z,12Z-octadecadienoic acidHMDB
Cholesterol 1-(9Z,12Z-octadecadienoateHMDB
Cholesterol 1-(9Z,12Z-octadecadienoate)HMDB
Cholesterol 1-(9Z,12Z-octadecadienoic acidHMDB
Cholesterol 1-(9Z,12Z-octadecadienoic acid)HMDB
Cholesterol 1-linoleoateHMDB
Cholesterol 1-linoleoic acidHMDB
Cholesterol ester(18:2)HMDB
Cholesterol ester(18:2/0:0)HMDB
Cholesterol ester(18:2n6/0:0)HMDB
Cholesterol ester(18:2W6/0:0)HMDB
Cholesteryl 1-(9Z,12Z-octadecadienoateHMDB
Cholesteryl 1-(9Z,12Z-octadecadienoate)HMDB
Cholesteryl 1-(9Z,12Z-octadecadienoic acidHMDB
Cholesteryl 1-(9Z,12Z-octadecadienoic acid)HMDB
Cholesteryl 1-linoleoateHMDB
Cholesteryl 1-linoleoic acidHMDB
Cholesteryl linoleateMeSH
Chemical FormulaC45H76O2
Average Molecular Weight649.0837
Monoisotopic Molecular Weight648.584531676
IUPAC Name(1S,2R,5S,10S,11S,14R,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 (9Z,12Z)-octadeca-9,12-dienoate
Traditional Name(1S,2R,5S,10S,11S,14R,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 (9Z,12Z)-octadeca-9,12-dienoate
CAS Registry Number604-33-1
SMILES
[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])CCCCCCCC(=O)O[C@@]1([H])CC[C@@]2(C)C(C1)=CC[C@@]1([H])[C@]3([H])CC[C@]([H])([C@]([H])(C)CCCC(C)C)[C@@]3(C)CC[C@]21[H]
InChI Identifier
InChI=1S/C45H76O2/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/h11-12,14-15,26,35-36,38-42H,7-10,13,16-25,27-34H2,1-6H3/b12-11-,15-14-/t36-,38+,39+,40-,41+,42+,44+,45-/m1/s1
InChI KeyNAACPBBQTFFYQB-LJAITQKLSA-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
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP10.5ALOGPS
logP14.2ChemAxon
logS-8ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity205.64 m³·mol⁻¹ChemAxon
Polarizability85.39 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, Positivesplash10-02cu-2249036000-982a939d936e4145f409View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0000009000-be0d242fdc5dfce84520View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0002-0000009000-f746df3c4960ff441e25View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00kb-0380309000-9563a2875a28afc28571View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0024009000-b479bcbc8432f715aa1cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0059103000-cef9421654d1e2564a1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014u-2029000000-7145bc958a3ae9af06fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-1065029000-84e99b9271808ab4ffc4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02g9-5279041000-b6fa3a31ebc3ebc5d3ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0axr-5459020000-16fce5540582cb2804ffView in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected and Quantified55 +/- 3 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified102 +/- 8 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified110 +/- 5 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified20 +/- 1 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDNot Available
DrugBank IDDB02092
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC15441
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5287939
PDB IDNot Available
ChEBI ID41509
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.