Showing metabocard for CE(22:5(7Z,10Z,13Z,16Z,19Z)) (BMDB0010375)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:05:23 UTC
Update Date2020-05-11 19:11:02 UTC
BMDB IDBMDB0010375
Secondary Accession Numbers
  • BMDB10375
Metabolite Identification
Common NameCE(22:5(7Z,10Z,13Z,16Z,19Z))
DescriptionCE(22:5(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(22:5(7Z,10Z,13Z,16Z,19Z)) may also accumulate in hereditary hypercholesterolemia, an inborn error of metabolism.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
CE(22:5/0:0)Lipid Annotator, HMDB
cholesterol 1-(7Z,10Z,13Z,16Z,19Z-docosapentaenoate)Lipid Annotator, HMDB, ChEBI
cholesteryl 1-docosapentaenoic acidLipid Annotator, HMDB
22:5(7Z,10Z,13Z,16Z,19Z) cholesterol esterLipid Annotator, HMDB, ChEBI
1-docosapentaenoyl-cholesterolLipid Annotator, HMDB
cholesteryl 1-(7Z,10Z,13Z,16Z,19Z-docosapentaenoic acid)Lipid Annotator, HMDB, Generator
cholesteryl 1-docosapentaenoateLipid Annotator, HMDB
Cholesterol Ester(22:5)Lipid Annotator, HMDB
cholesterol 1-(7Z,10Z,13Z,16Z,19Z-docosapentaenoic acid)Lipid Annotator, HMDB, Generator
cholesterol 1-docosapentaenoic acidLipid Annotator, HMDB
cholesterol 1-docosapentaenoateLipid Annotator, HMDB
cholesteryl 1-(7Z,10Z,13Z,16Z,19Z-docosapentaenoate)Lipid Annotator, HMDB, ChEBI
Cholesterol Ester(22:5/0:0)Lipid Annotator, HMDB
CE(22:5(7Z,10Z,13Z,16Z,19Z))Lipid Annotator
1-(7Z,10Z,13Z,16Z,19Z-docosapentaenoyl)-cholesterolLipid Annotator, HMDB
CE(22:5)Lipid Annotator, HMDB
(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 (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoic acidGenerator
CE 22:5(7Z,10Z,13Z,16Z,19Z)ChEBI
Cholest-5-en-3beta-yl (7Z,10Z,13Z,16Z,19Z-docosapentaenoate)ChEBI
Cholesteryl ester(22:5(7Z,10Z,13Z,16Z,19Z))ChEBI
Cholest-5-en-3b-yl (7Z,10Z,13Z,16Z,19Z-docosapentaenoate)Generator
Cholest-5-en-3b-yl (7Z,10Z,13Z,16Z,19Z-docosapentaenoic acid)Generator
Cholest-5-en-3beta-yl (7Z,10Z,13Z,16Z,19Z-docosapentaenoic acid)Generator
Cholest-5-en-3β-yl (7Z,10Z,13Z,16Z,19Z-docosapentaenoate)Generator
Cholest-5-en-3β-yl (7Z,10Z,13Z,16Z,19Z-docosapentaenoic acid)Generator
Cholesteryl (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acidHMDB
22:5 Cholesteryl esterHMDB
Chemical FormulaC49H78O2
Average Molecular Weight699.1424
Monoisotopic Molecular Weight698.60018174
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 (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate
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 (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate
CAS Registry NumberNot Available
SMILES
CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(=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/C49H78O2/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/h8-9,11-12,14-15,17-18,20-21,30,39-40,42-46H,7,10,13,16,19,22-29,31-38H2,1-6H3/b9-8-,12-11-,15-14-,18-17-,21-20-/t40-,42+,43?,44?,45?,46?,48+,49-/m1/s1
InChI KeyXOLZNHXNFMEUGA-MCPSVCLNSA-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
logP10.23ALOGPS
logP14.89ChemAxon
logS-8ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity227.4 m³·mol⁻¹ChemAxon
Polarizability90.64 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, Positivesplash10-01ot-1017009000-e1e9f1c9499e2725e2c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07ii-3039002000-791702213937ad632950View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0adi-4059002000-07f7c365e96d4d69126dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0006009000-dcad2701b2db982ef75eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009002000-c4ee94a1e41c9fa54e2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-2009000000-f9ee4f41f3ac1abe98afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00l2-4229017000-f8119c76e17303fbe832View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05wf-9111011000-efe0794827520ffda7daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05po-9310011000-7fb54209d76d7c5125d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0002009000-f907010bee38cccec226View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0105019000-8c221da0a66c62a4ef88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4s-6123229000-67f9fee689a7700567dcView in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
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 IDHMDB0010375
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24850091
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480463
PDB IDNot Available
ChEBI ID73910
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available