Showing metabocard for CE(20:5) (BMDB0006731)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:25:19 UTC
Update Date2020-04-22 15:18:23 UTC
BMDB IDBMDB0006731
Secondary Accession Numbers
  • BMDB06731
Metabolite Identification
Common NameCE(20:5)
DescriptionCE(20:5(5Z,8Z,11Z,14Z,17Z), also known as 20:5 cholesterol ester or cholesteryl eicosapentaenoate, belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters are compounds containing an esterified cholestane moiety. CE(20:5(5Z,8Z,11Z,14Z,17Z) is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3b)-Cholest-5-en-3-ol (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-eicosapentaenoateHMDB
(3b)-Cholest-5-en-3-ol (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-eicosapentaenoic acidHMDB
(3b)-Cholest-5-en-3-ol (all-Z)-5,8,11,14,17-eicosapentaenoateHMDB
(3b)-Cholest-5-en-3-ol (all-Z)-5,8,11,14,17-eicosapentaenoic acidHMDB
20:5 Cholesterol esterHMDB
Cholest-5-en-3beta-yl (5Z,8Z,11Z,14Z,17Z-eicosapentaenoateHMDB
Cholest-5-en-3beta-yl (5Z,8Z,11Z,14Z,17Z-eicosapentaenoate)HMDB
Cholest-5-en-3beta-yl (5Z,8Z,11Z,14Z,17Z-eicosapentaenoic acidHMDB
Cholesteryl 5,8,11,14,17-eicosapentaenoateHMDB
Cholesteryl 5,8,11,14,17-eicosapentaenoic acidHMDB
Cholesteryl eicosapentaenoateHMDB
Cholesteryl eicosapentaenoic 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 (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acidGenerator
Chemical FormulaC47H74O2
Average Molecular Weight671.0893
Monoisotopic Molecular Weight670.568881612
IUPAC Name(2R,5S,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 (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
Traditional Name(2R,5S,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 (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
CAS Registry Number74892-97-0
SMILES
CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(=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/C47H74O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-27-45(48)49-40-32-34-46(5)39(36-40)28-29-41-43-31-30-42(38(4)26-24-25-37(2)3)47(43,6)35-33-44(41)46/h8-9,11-12,14-15,17-18,20-21,28,37-38,40-44H,7,10,13,16,19,22-27,29-36H2,1-6H3/b9-8-,12-11-,15-14-,18-17-,21-20-/t38-,40+,41?,42?,43?,44?,46+,47-/m1/s1
InChI KeyXZFUGMCJZFRBKF-JIKDAPOUSA-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
logP14ChemAxon
logS-8ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity218.19 m³·mol⁻¹ChemAxon
Polarizability86.27 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, Positivesplash10-0a6u-3059027000-760dac5dc7c59015750dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-1054019000-3b4ee664ddb50e8d1e90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-4169021000-f77f2a0e40387c86e104View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4059021000-90a6428c189f7ca1a041View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0015009000-a0a6ddddf91e7a54c1ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0029002000-1c3937081231757409b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-015l-2019000000-f91dd41525aec38fdd3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01di-4229026000-109f7ec7f9e49cbf53c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-067l-9111011000-92e5a9cf6fa82a82b8adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05po-9310010000-1f0728d808e2e181019bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0002009000-ebdeac35b674337ec18bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0004019000-2aa9d1c58e9b8fa5841bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-9322348000-47cf9b3117ef9a4ca5f2View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006731
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024047
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC02530
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477889
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceShimada, Yuji; Hirota, Yoshinori; Baba, Takashi; Sugihara, Akio; Moriyama, Shigeru; Tominaga, Yoshio; Terai, Tadamasa. Enzymatic synthesis of steryl esters of polyunsaturated fatty acids. Journal of the American Oil Chemists' Society (1999), 76(6), 713-716.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available