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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:01:06 UTC
Update Date2019-07-23 06:29:52 UTC
HMDB IDHMDB0039530
Secondary Accession Numbers
  • HMDB39530
Metabolite Identification
Common NameEthyl icosapentate
DescriptionEthyl icosapentate, also known as icosapent or epadel, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Ethyl icosapentate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563863392
Synonyms
ValueSource
(5Z,8Z,11Z,14Z,17Z)-Eicosapetaenoic acid ethyl esterChEBI
(all-Z)-5,8,11,14,17-Eicosapentaenoic acid ethyl esterChEBI
all-cis-Ethyl 5,8,11,14,17-icosapentaenoateChEBI
AMR 101ChEBI
AMR101ChEBI
cis-Eicosapentaenoic acid ethyl esterChEBI
e-EPAChEBI
Eicosapentaenoic acid ethyl esterChEBI
EpadelChEBI
Ethyl (5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoateChEBI
Ethyl (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoateChEBI
Ethyl (all cis)-5,8,11,14,17-icosapentaenoateChEBI
Ethyl all-cis-5,8,11,14,17-icosapentaenoateChEBI
Ethyl eicosapentaenoateChEBI
IcosapentChEBI
Icosapent ethylChEBI
Timnodonic acid ethyl esterChEBI
VascepaChEBI
EPA ethyl esterKegg
Epadel SKegg
(5Z,8Z,11Z,14Z,17Z)-Eicosapetaenoate ethyl esterGenerator
(all-Z)-5,8,11,14,17-Eicosapentaenoate ethyl esterGenerator
all-cis-Ethyl 5,8,11,14,17-icosapentaenoic acidGenerator
cis-Eicosapentaenoate ethyl esterGenerator
Eicosapentaenoate ethyl esterGenerator
Ethyl (5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoic acidGenerator
Ethyl (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoic acidGenerator
Ethyl (all cis)-5,8,11,14,17-icosapentaenoic acidGenerator
Ethyl all-cis-5,8,11,14,17-icosapentaenoic acidGenerator
Ethyl eicosapentaenoic acidGenerator
Timnodonate ethyl esterGenerator
Ethyl icosapentic acidGenerator
Eicosapentaenoic acid, ethyl esterHMDB
Epa-eHMDB
Ethyl epaHMDB
Ethyl ester(all-Z)-5,8,11,14,17-eicosapentaenoic acidHMDB
Ethyl icosapentaenoateHMDB
Ethyl icosapentate, janHMDB
MND 21HMDB
AMR-101MeSH
Ethyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoateMeSH
Ethyl icosapentateChEBI
Chemical FormulaC22H34O2
Average Molecular Weight330.5042
Monoisotopic Molecular Weight330.255880332
IUPAC Nameethyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
Traditional Nameethyl eicosapentaenoate
CAS Registry Number86227-47-6
SMILES
CCOC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C22H34O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24-4-2/h5-6,8-9,11-12,14-15,17-18H,3-4,7,10,13,16,19-21H2,1-2H3/b6-5-,9-8-,12-11-,15-14-,18-17-
InChI KeySSQPWTVBQMWLSZ-AAQCHOMXSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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
Water Solubility9.8e-05 g/LALOGPS
logP6.8ALOGPS
logP6.73ChemAxon
logS-6.5ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity110.59 m³·mol⁻¹ChemAxon
Polarizability40.32 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-4291000000-18f886cd2e21c8d674ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-1159000000-9886f5a2f77330b853eaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053g-5692000000-23e2063e5487c0d29421Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-8980000000-c25590507c531ab13ddbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-2059000000-829e86072be7ac6dfee2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003s-6095000000-5a3e6636c6ca7d2d3fc4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4m-9040000000-988f18172ee82d5feb36Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08887
Phenol Explorer Compound IDNot Available
FooDB IDFDB019145
KNApSAcK IDNot Available
Chemspider ID8007147
KEGG Compound IDC16184
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthyl_eicosapentaenoic_acid
METLIN IDNot Available
PubChem Compound9831415
PDB IDNot Available
ChEBI ID84883
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.