Showing metabocard for CE(22:5(4Z,7Z,10Z,13Z,16Z)) (BMDB0010374)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:05:21 UTC
Update Date2020-05-11 19:11:01 UTC
BMDB IDBMDB0010374
Secondary Accession Numbers
  • BMDB10374
Metabolite Identification
Common NameCE(22:5(4Z,7Z,10Z,13Z,16Z))
DescriptionCE(22:5(4Z,7Z,10Z,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(22:5(4Z,7Z,10Z,13Z,16Z)) 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-osbondoateLipid Annotator, HMDB
CE(22:5(4Z,7Z,10Z,13Z,16Z))Lipid Annotator
cholesteryl 1-(4Z,7Z,10Z,13Z,16Z-docosapentaenoic acid)Lipid Annotator, HMDB
cholesteryl 1-osbondoic acidLipid Annotator, HMDB
cholesteryl 1-(4Z,7Z,10Z,13Z,16Z-docosapentaenoate)Lipid Annotator, HMDB
22:5(4Z,7Z,10Z,13Z,16Z) cholesterol esterLipid Annotator, HMDB
Cholesterol Ester(22:5)Lipid Annotator, HMDB
cholesterol 1-(4Z,7Z,10Z,13Z,16Z-docosapentaenoate)Lipid Annotator, HMDB
cholesterol 1-osbondoic acidLipid Annotator, HMDB
cholesterol 1-(4Z,7Z,10Z,13Z,16Z-docosapentaenoic acid)Lipid Annotator, HMDB
cholesteryl 1-osbondoateLipid Annotator, HMDB
Cholesterol Ester(22:5/0:0)Lipid Annotator, HMDB
1-osbondoyl-cholesterolLipid Annotator, HMDB
1-(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-cholesterolLipid Annotator, HMDB
CE(22:5)Lipid Annotator, HMDB
1-Docosapentaenoyl-cholesterolHMDB
CE(22:5n6/0:0)HMDB
CE(22:5W6/0:0)HMDB
Cholesterol 1-(4Z,7Z,10Z,13Z,16Z-docosapentaenoateHMDB
Cholesterol 1-(4Z,7Z,10Z,13Z,16Z-docosapentaenoic acidHMDB
Cholesterol 1-docosapentaenoateHMDB
Cholesterol 1-docosapentaenoic acidHMDB
Cholesterol ester(22:5n6/0:0)HMDB
Cholesterol ester(22:5W6/0:0)HMDB
Cholesteryl 1-(4Z,7Z,10Z,13Z,16Z-docosapentaenoateHMDB
Cholesteryl 1-(4Z,7Z,10Z,13Z,16Z-docosapentaenoic acidHMDB
Cholesteryl 1-docosapentaenoateHMDB
Cholesteryl 1-docosapentaenoic 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)-docosa-4,7,10,13,16-pentaenoic acidGenerator
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 (4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-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 (4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoate
CAS Registry NumberNot Available
SMILES
CCCCC\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/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/h11-12,14-15,17-18,20-21,23-24,30,39-40,42-46H,7-10,13,16,19,22,25-29,31-38H2,1-6H3/b12-11-,15-14-,18-17-,21-20-,24-23-/t40-,42+,43?,44?,45?,46?,48+,49-/m1/s1
InChI KeyOMHZQRFOHAXINE-QXYMPDJNSA-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
logP10.27ALOGPS
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
Polarizability90.1 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-f2d0b384ec26a32b8a81View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07ii-3139012000-44438ae06cb66d1acafcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0adi-4369003000-146d05e3f02ace963b64View 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-0009002000-77c8428eb99e82151378View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-2009000000-069abf8b27b5e9613049View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-1039006000-2cb78ef316ddd3390e1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aor-9241002000-d617a9b59dfe5aff22b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aou-9540003000-e97eae77e4260d37c164View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0002009000-50af9e59da196749b135View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0005019000-c370505d12a5ca159cb6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4s-5123219000-ad33c923f337ab05ff30View 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 IDHMDB0010374
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027526
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480462
PDB IDNot Available
ChEBI ID88754
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available