Showing metabocard for CE(22:6) (BMDB0006733)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:25:22 UTC
Update Date2020-04-22 15:18:23 UTC
BMDB IDBMDB0006733
Secondary Accession Numbers
  • BMDB06733
Metabolite Identification
Common NameCE(22:6)
DescriptionCE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 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(22:6(4Z,7Z,10Z,13Z,16Z,19Z)) may also accumulate in hereditary hypercholesterolemia, an inborn error of metabolism.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
cholesterol 1-docosahexaenoateLipid Annotator, HMDB
Cholesterol Ester(22:6/0:0)Lipid Annotator, HMDB
1-docosahexaenoyl-cholesterolLipid Annotator, HMDB
cholesterol 1-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoic acid)Lipid Annotator, HMDB
Cholesterol Ester(22:6)Lipid Annotator, HMDB
cholesterol 1-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoate)Lipid Annotator, HMDB
22:6(4Z,7Z,10Z,13Z,16Z,19Z) cholesterol esterLipid Annotator, HMDB
CE(22:6(4Z,7Z,10Z,13Z,16Z,19Z))Lipid Annotator
cholesteryl 1-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoate)Lipid Annotator, HMDB
cholesteryl 1-docosahexaenoateLipid Annotator, HMDB
cholesteryl 1-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoic acid)Lipid Annotator, HMDB
CE(22:6/0:0)Lipid Annotator, HMDB
CE(22:6)Lipid Annotator, HMDB
cholesterol 1-docosahexaenoic acidLipid Annotator, HMDB
1-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-cholesterolLipid Annotator, HMDB
cholesteryl 1-docosahexaenoic acidLipid Annotator, HMDB
22:6 Cholesterol esterHMDB
Cholest-5-en-3beta-yl (4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoateHMDB
Cholest-5-en-3beta-yl (4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoate)HMDB
Cholest-5-en-3beta-yl (4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoic acidHMDB
Cholesteryl docosahexaenoateHMDB
Cholesteryl docosahexaenoic 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 (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acidGenerator
Chemical FormulaC49H76O2
Average Molecular Weight697.1265
Monoisotopic Molecular Weight696.584531676
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 (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate
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 (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate
CAS Registry Number70110-50-8
SMILES
CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=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/C49H76O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-29-47(50)51-42-34-36-48(5)41(38-42)30-31-43-45-33-32-44(40(4)28-26-27-39(2)3)49(45,6)37-35-46(43)48/h8-9,11-12,14-15,17-18,20-21,23-24,30,39-40,42-46H,7,10,13,16,19,22,25-29,31-38H2,1-6H3/b9-8-,12-11-,15-14-,18-17-,21-20-,24-23-/t40-,42+,43?,44?,45?,46?,48+,49-/m1/s1
InChI KeyVOEVEGPMRIYYKC-IWVSHIRDSA-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
logP10.03ALOGPS
logP14.53ChemAxon
logS-8ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity228.51 m³·mol⁻¹ChemAxon
Polarizability88.64 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-2129007000-98ed05d19dbec1fbcfcaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0292-1017009000-c25089f40d3051f51385View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02ti-3039003000-07691e811f212654c8c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ar0-4049002000-a699e4c8b5692c1ae391View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0006009000-04f0185c95916f16690cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009002000-3a7a89ce5def24d20412View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0673-2009000000-f50842a6b2a14d83e3ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-2129017000-e2b1f363b8a957e3636dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05a6-9132011000-f7a6af8d07c17e2cd9a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-015l-9651012000-01871da58996b21e96eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0002009000-4d7f43668f795ad2b831View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0105019000-87b924862b7226e4e6aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fs-3311059000-4095918426b2eb36860cView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006733
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024048
KNApSAcK IDNot Available
Chemspider ID29368174
KEGG Compound IDC02530
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477890
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available