EPA

5,8,11,14,17-EICOSAPENTAENOIC ACID

Created: 1999-07-08
Last modified:  2011-06-04

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Chemical Details

Formal Charge0
Atom Count52
Chiral Atom Count0
Bond Count51
Aromatic Bond Count0
2D diagram of EPA
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Chemical Component Summary

Name5,8,11,14,17-EICOSAPENTAENOIC ACID
Systematic Name (OpenEye OEToolkits)(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
FormulaC20 H30 O2
Molecular Weight302.451
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C(O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
SMILESCACTVS3.341CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O
SMILESOpenEye OEToolkits1.5.0CCC=CCC=CCC=CCC=CCC=CCCCC(=O)O
Canonical SMILESCACTVS3.341 CC\C=C/C/C=C\C\C=C/C/C=C\C\C=C/CCCC(O)=O
Canonical SMILESOpenEye OEToolkits1.5.0 CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)O
InChIInChI1.03 InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-
InChIKeyInChI1.03 JAZBEHYOTPTENJ-JLNKQSITSA-N

Drug Info: DrugBank

DrugBank IDDB00159 
NameIcosapent
Groups
  • nutraceutical
  • approved
DescriptionImportant polyunsaturated fatty acid found in fish oils. It serves as the precursor for the prostaglandin-3 and thromboxane-3 families. A diet rich in eicosapentaenoic acid lowers serum lipid concentration, reduces incidence of cardiovascular disorders, prevents platelet aggregation, and inhibits arachidonic acid conversion into the thromboxane-2 and prostaglandin-2 families.
Synonyms
  • all-cis-5,8,11,14,17-eicosapentaenoic acid
  • cis-5,8,11,14,17-EPA
  • (5Z,8Z,11Z,14Z,17Z)-Icosapentaenoic acid
  • 5,8,11,14,17-eicosapentaenoic acid
  • Icosapent sodium
Brand Names
  • VITAFOL Gummies
  • Pre-Tabs DHA Prenatal Multi-vitamin/Mineral Supplement with DHA/EPA
  • Virt-PN Plus
  • Tricare Prenatal 2-part Daily Prenatal Vitamin System
  • Vp-CH-pnv
IndicationEPA can be used for lowering elevated triglycerides in those who are hyperglyceridemic. In addition, EPA may play a therapeutic role in patients with cystic fibrosis by reducing disease severity and may play a similar role in type 2 diabetics in slowing the progression of diabetic nephropathy.
Categories
  • Agents causing hyperkalemia
  • Agents that produce hypertension
  • Anti-Inflammatory Agents
  • Anti-Inflammatory Agents, Non-Steroidal
  • Anti-Inflammatory Agents, Non-Steroidal (Non-Selective)
CAS number10417-94-4

Drug Targets

NameTarget SequencePharmacological ActionActions
Prostaglandin G/H synthase 2MLARALLLCAVLALSHTANPCCSHPCQNRGVCMSVGFDQYKCDCTRTGFY...unknowninhibitor
Prostaglandin G/H synthase 1MSRSLLLWFLLFLLLLPPLPVLLADPGAPTPVNPCCYYPCQHQGICVRFG...unknowninhibitor
Peroxisome proliferator-activated receptor gammaMGETLGDSPIDPESDSFTDTLSANISQEMTMVDTEMPFWPTNFGISSVDL...unknownagonist,regulator
Peroxisome proliferator-activated receptor deltaMEQPQEEAPEVREEEEKEEVAEAEGAPELNGGPQHALPSSSYTDLSRSSS...unknownagonist
Free fatty acid receptor 1MDLPPQLSFGLYVAAFALGFPLNVLAIRGATAHARLRLTPSLVYALNLGC...unknownagonist
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 446284
ChEMBL CHEMBL460026
ChEBI CHEBI:28364