Showing metabocard for 22:5 Cholesteryl ester (BMDB0062604)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-08-29 17:08:37 UTC
Update Date2020-06-04 20:08:29 UTC
BMDB IDBMDB0062604
Secondary Accession Numbers
  • BMDB62604
Metabolite Identification
Common Name22:5 Cholesteryl ester
DescriptionCholest-5-en-3beta-yl (7Z,10Z,13Z,16Z,19Z-docosapentaenoate), also known as cholesterol 1-(7Z,10Z,13Z,16Z,19Z-docosapentaenoic acid) or 22:5(7Z,10Z,13Z,16Z,19Z) cholesterol ester, belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters are compounds containing an esterified cholestane moiety. Cholest-5-en-3beta-yl (7Z,10Z,13Z,16Z,19Z-docosapentaenoate) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
22:5(7Z,10Z,13Z,16Z,19Z) Cholesterol esterChEBI
CE 22:5(7Z,10Z,13Z,16Z,19Z)ChEBI
CE(22:5(7Z,10Z,13Z,16Z,19Z))ChEBI
Cholest-5-en-3beta-yl (7Z,10Z,13Z,16Z,19Z-docosapentaenoate)ChEBI
Cholesterol 1-(7Z,10Z,13Z,16Z,19Z-docosapentaenoate)ChEBI
Cholesteryl 1-(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
Cholesterol 1-(7Z,10Z,13Z,16Z,19Z-docosapentaenoic acid)Generator
Cholesteryl 1-(7Z,10Z,13Z,16Z,19Z-docosapentaenoic acid)Generator
Cholesteryl (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acidGenerator
22:5 Cholesteryl esterChEBI, HMDB
Chemical FormulaC49H78O2
Average Molecular Weight699.161
Monoisotopic Molecular Weight698.600181752
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 (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate
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 (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate
CAS Registry NumberNot Available
SMILES
[H]\C(CC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCCCCC(=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/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-DCDLNIKOSA-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 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
logP10.23ALOGPS
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
Polarizability90.21 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-1029005000-f8fa3229e6f96e0bd311View in MoNA
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-0009002000-77c8428eb99e82151378View 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, Negativesplash10-0002-0002009000-739c7d85e1a0aba4ad5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0107019000-2c151553abc5a117f431View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014s-9144007000-ca736ace18d0388cf174View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kk-1229017000-95d7573b299fa52bb0faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05u7-9210012000-1ec9841494b77fd4b5dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ku6-9310013000-400a5779d3b323f2f7f8View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected and Quantified23 +/- 2 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0062457
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound42608400
PDB IDNot Available
ChEBI ID73910
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.