Record Information
Version1.0
Creation date2010-04-08 22:05:39 UTC
Update date2017-10-04 22:40:05 UTC
Primary IDFDB003102
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEicosapentaenoic acid
DescriptionPresent in fish oils as an acylglycerol and in animal phospholipids. Nutriceutical with antioxidation props. Eicosapentaenoic acid (EPA or also icosapentaenoic acid) is an omega-3 fatty acid. In physiological literature, it is given the name 20:5(n-3). It also has the trivial name timnodonic acid. In chemical structure, EPA is a carboxylic acid with a 20-carbon chain and five cis double bonds; the first double bond is located at the third carbon from the omega end. It is obtained in the human diet by eating oily fish or fish oil— e.g., cod liver, herring, mackerel, salmon, menhaden and sardine. It is also found in human breast milk. [Wikipedia]. EPA is a biomarker for the consumption of salt-water fish.
CAS Number10417-94-4
Structure
Thumb
Synonyms
SynonymSource
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-EicosapentaenoateGenerator
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Eicosapentaenoic acidbiospider
(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoatebiospider
(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoic acidbiospider
(5Z,8Z,11Z,14Z,17Z)-Icosa-5,8,11,14,17-pentaenoic acidbiospider
(5Z,8Z,11Z,14Z,17Z)-IcosapentaenoateGenerator
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoic acidbiospider
(all-cis)-5,8,11,14,17-Eicosapentaenoic acidbiospider
(all-Z)-5,8,11,14,17-EicosapentaenoateGenerator
(all-Z)-5,8,11,14,17-Eicosapentaenoic acidbiospider
(all-Z)-Delta5,8,11,14,17-Eicosapentaenoic acidbiospider
(Z,Z,Z,Z,Z)-5,8,11,14,17-Eicosapentaenoic acidbiospider
5,8,11,14,17-EICOSAPENTAENOateGenerator
5,8,11,14,17-EICOSAPENTAENOIC ACIDChEBI
5,8,11,14,17-Eicosapentaenoic acid, (5Z,8Z,11Z,14Z,17Z)-biospider
5,8,11,14,17-Eicosapentaenoic acid, (all-Z)- (8CI)biospider
5,8,11,14,17-IcosapentaenoateGenerator
5,8,11,14,17-Icosapentaenoic acidChEBI
5Z,8Z,11Z,14Z,17Z-Eicosapentaenoatebiospider
5Z,8Z,11Z,14Z,17Z-Eicosapentaenoic acidbiospider
all-cis-5,8,11,14,17-EicosapentaenoateGenerator
all-cis-5,8,11,14,17-Eicosapentaenoic acidChEBI
all-cis-Icosa-5,8,11,14,17-pentaenoateGenerator
all-cis-Icosa-5,8,11,14,17-pentaenoic acidbiospider
all-cis-Icosapentaenoatebiospider
all-cis-Icosapentaenoic acidbiospider
C20:5 omega-3biospider
cis-5,8,11,14,17-Eicosapentaenoatebiospider
cis-5,8,11,14,17-Eicosapentaenoic acidbiospider
cis-5,8,11,14,17-EPAChEBI
cis-delta(5,8,11,14,17)-EicosapentaenoateGenerator
cis-Delta(5,8,11,14,17)-Eicosapentaenoic acidbiospider
cis-δ(5,8,11,14,17)-eicosapentaenoateGenerator
cis-δ(5,8,11,14,17)-eicosapentaenoic acidGenerator
cis, cis, cis, cis, cis-Eicosa-5,8,11,14,17-pentaenoateGenerator
cis, cis, cis, cis, cis-Eicosa-5,8,11,14,17-pentaenoic acidChEBI
EicosapentaenoateGenerator
EPAbiospider
IcosapentChEBI
Icosapent, INNdb_source
Icosapentaenoatebiospider
Icosapentaenoic acidbiospider
IcosapentoChEBI
IcosapentumChEBI
Timnodonatebiospider
Timnodonic aciddb_source
Predicted Properties
PropertyValueSource
Water Solubility0.00029 g/LALOGPS
logP6.53ALOGPS
logP6.23ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity101.07 m³·mol⁻¹ChemAxon
Polarizability36.25 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H30O2
IUPAC name(5Z,8Z,11E,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
InChI IdentifierInChI=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-
InChI KeyJAZBEHYOTPTENJ-IKHGVYGUSA-N
Isomeric SMILESCC\C=C/C\C=C/C\C=C\C\C=C/C\C=C/CCCC(O)=O
Average Molecular Weight302.451
Monoisotopic Molecular Weight302.224580204
Classification
DescriptionThis compound belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 79.42%; H 10.00%; O 10.58%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
ChemSpider ID393682
ChEMBL IDCHEMBL460026
KEGG Compound IDC06428
Pubchem Compound ID446284
Pubchem Substance IDNot Available
ChEBI ID28364
Phenol-Explorer IDNot Available
DrugBank IDDB00159
HMDB IDHMDB01999
CRC / DFC (Dictionary of Food Compounds) IDHDJ50-Z:CQZ50-L
EAFUS IDNot Available
Dr. Duke IDEICOSAPENTAENOIC-ACID
BIGG ID2218016
KNApSAcK IDC00000408
HET IDEPA
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDEicosapentaenoic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
5-hydroxyeicosatetraenoic-acid inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti arthritic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti atherotic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti dermatitic50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti fibrosarcomicDUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti ischemic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti leukotriene-B435222 A substance that diminishes the rate of a chemical reaction.DUKE
anti melanomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti metastatic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti proliferantDUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
collagenase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
cyclooxygenase-2 inhibitor50629 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.DUKE
differentiatorDUKE
hypotensiveDUKE
nephroprotective76595 Any protective agent that is able to prevent damage to the kidney.DUKE
tyrosine-kinase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
VEGF inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
Enzymes
NameGene NameUniProt ID
Bile acid-CoA:amino acid N-acyltransferaseBAATQ14032
Peroxisome proliferator-activated receptor gammaPPARGP37231
Cytosolic acyl coenzyme A thioester hydrolaseACOT7O00154
Acyl-coenzyme A thioesterase 2, mitochondrialACOT2P49753
Acyl-coenzyme A thioesterase 4ACOT4Q8N9L9
Acyl-coenzyme A thioesterase 8ACOT8O14734
Acyl-coenzyme A thioesterase 1ACOT1Q86TX2
Peroxisome proliferator-activated receptor deltaPPARDQ03181
Pathways
NameSMPDB LinkKEGG Link
Alpha Linolenic Acid and Linoleic Acid MetabolismSMP00018 map00592
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).