Ethyl icosapentate (CHEM032856)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:45:01 UTC
Update Date2016-11-09 01:20:48 UTC
Accession NumberCHEM032856
Identification
Common NameEthyl icosapentate
ClassSmall Molecule
DescriptionA long-chain fatty acid ethyl ester resulting from the formal condensation of the carboxy group of (5Z,8Z,11Z,14Z,17Z)-icosapentaenoic acid with the hydroxy group of ethanol.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoic 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
EPA 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
Epadel SKegg
(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoate 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
(5Z,8Z,11Z,14Z,17Z)-Eicosapetaenoic acid ethyl esterChEBI
(5Z,8Z,11Z,14Z,17Z)-Eicosapetaenoate ethyl esterGenerator
Eicosapentaenoic acid, ethyl esterHMDB
Epa-eHMDB, MeSH
Ethyl epaHMDB
Ethyl ester(all-Z)-5,8,11,14,17-eicosapentaenoic acidHMDB
Ethyl icosapentaenoateHMDB, MeSH
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 Mass330.504 g/mol
Monoisotopic Mass330.256 g/mol
CAS Registry Number86227-47-6
IUPAC Nameethyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
Traditional Nameethyl eicosapentaenoate
SMILESCCOC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-4291000000-18f886cd2e21c8d674ebSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-3259000000-fe24128a1e2918a071daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0540-7971000000-1e744aeb98753f57cb46Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lr-6910000000-60e082cfeb16521a6d49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0019000000-f5738e4a74132a2c3d43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1092000000-692b4d72693803b6fee4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052r-9380000000-3139bc0db38ab21fa593Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB08887
HMDB IDHMDB0039530
FooDB IDFDB019145
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEthyl_eicosapentaenoic_acid
Chemspider ID8007147
ChEBI ID84883
PubChem Compound ID9831415
Kegg Compound IDC16184
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22819432
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22894624
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23312052
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23325450
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23701295
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23835245
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23992935
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24075771
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24259598
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=24516343
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=24760401
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=24973042
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=24977343
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=25028554
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=25428605
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=25471740
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=25515964
18. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
19. 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.
20. 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.
21. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
22. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
23. The lipid handbook with CD-ROM