Showing metabocard for CE(22:2) (BMDB0006737)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:25:25 UTC
Update Date2020-05-21 16:28:48 UTC
BMDB IDBMDB0006737
Secondary Accession Numbers
  • BMDB06737
Metabolite Identification
Common NameCE(22:2)
DescriptionCE(22:2(13Z,16Z)) 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(22:2(13Z,16Z)) may also accumulate in hereditary hypercholesterolemia, an inborn error of metabolism.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
22:2 Cholesterol esterHMDB
Cholest-5-en-3beta-yl (13Z,16Z-docosadienoateHMDB
Cholest-5-en-3beta-yl (13Z,16Z-docosadienoate)HMDB
Cholest-5-en-3beta-yl (13Z,16Z-docosadienoic acidHMDB
Cholesteryl docosadienoateHMDB
Cholesteryl docosadienoic acidHMDB
Cholesteryl 1-(13Z,16Z-docosadienoic acid)HMDB
Cholesterol 1-docosadienoic acidHMDB
CE(22:2/0:0)HMDB
CE(22:2)HMDB
Cholesterol 1-(13Z,16Z-docosadienoate)HMDB
Cholesteryl 1-docosadienoic acidHMDB
Cholesterol 1-docosadienoateHMDB
1-Docosadienoyl-cholesterolHMDB
22:2(13Z,16Z) Cholesterol esterHMDB
Cholesterol ester(22:2)HMDB
Cholesteryl 1-docosadienoateHMDB
Cholesteryl 1-(13Z,16Z-docosadienoate)HMDB
Cholesterol ester(22:2/0:0)HMDB
1-(13Z,16Z-Docosadienoyl)-cholesterolHMDB
Cholesterol 1-(13Z,16Z-docosadienoic acid)HMDB
CE(22:2(13Z,16Z))Lipid Annotator
Chemical FormulaC49H84O2
Average Molecular Weight705.1901
Monoisotopic Molecular Weight704.647131932
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 (13Z,16Z)-docosa-13,16-dienoate
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 (13Z,16Z)-docosa-13,16-dienoate
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\C=C/CCCCCCCCCCCC(=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/C49H84O2/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/h11-12,14-15,30,39-40,42-46H,7-10,13,16-29,31-38H2,1-6H3/b12-11-,15-14-/t40-,42+,43?,44?,45?,46?,48+,49-/m1/s1
InChI KeyYSGVSTJGBYXXIM-OVUVNFMNSA-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
logP10.94ALOGPS
logP15.98ChemAxon
logS-8.1ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count25ChemAxon
Refractivity224.05 m³·mol⁻¹ChemAxon
Polarizability94.64 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ap0-1119003500-dddfae71c5d85b3f4eaaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-3129011000-eb2a33730aaa6c90d037View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-4259002000-29a3548c8f442a7ddfceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0007000900-05d122b7af61bcc0517fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0019000200-d9492ef0ba29fc8ba42dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014u-2019000000-a085efb38ed32c1e946cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0001000900-984496f3daadcff668adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0006000900-e32fda687ad1b2b95da3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbi-9108313200-003d8ee9201f753f124dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0670-7029023400-aa16ccde9f1decb394feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aou-9011010000-a72913163d900d9c9b1eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0693-9000000000-f92fc5bca7340d2a5172View in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006737
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024051
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC02530
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477893
PDB IDNot Available
ChEBI ID88774
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Gastric triacylglycerol lipase
General function:
Not Available
Specific function:
Not Available
Gene Name:
LIPF
Uniprot ID:
Q29458
Molecular weight:
45231.0
Reactions
CE(22:2) + Water → Cholesterol + Palmitic aciddetails