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Showing Compound Eicosapentaenoic acid (FDB003102)

Record Information
Version1.0
Creation date2010-04-08 22:05:39 UTC
Update date2019-11-26 02:58:29 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
MOLSDFPDBSMILESInChI
Synonyms
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Description 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
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
SpectraNot Available
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
Food Biomarker OntologyNot Available
VMH IDNot Available
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
Processing...
Biological Effects and Interactions
Health Effects / Bioactivities
Enzymes
Pathways
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).