Eicosapentaenoic acidEPA

PUFA20:5Ω-3

  Overview

Stats

PUFA
Type
20
Carbons
5
Double bonds
4
Bis-allylic sites
302.5
Weight · g/mol
—
Melting point
C20H30O2
Formula

Also known as

IUPAC (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
Traditional Timnodonic acid

  At a Glance

Key Points

An omega-3 fatty acid, also called timnodonic acid; a major fish-oil fatty acid and eicosanoid precursor.

Source

Conditionally essential. Primarily from fish & seafood. Also made by the body.

Type

Long-chain polyunsaturated fatty acid with 20 carbons and five cis double bonds, an omega-3 fatty acid. Its multiple bis-allylic sites make it prone to oxidation.

Identification

  Synonyms

Common Name Eicosapentaenoic acid
IUPAC Name (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
Traditional Name Timnodonic acid
Other Synonyms No other synonyms recorded.

  External IDs

General References
Lipids
Lipid Maps LMFA01030759
Lipid Bank —
Swiss Lipids 000000409
PlantFA ID —
Food & Nutrition
FooDB FDB030126
INFOODS —
Chemistry / Compounds
PubChem CID 446284
CAS 10417-94-4
ChEBI 28364
ChEMBL CHEMBL460026
ChemSpider 393682
InChIKey —
ZINC ID ZINC000004474603
NIKKAJI ID J343.473G
PDBe EPA
UCI (UniChem) 72568
SureChEMBL 20469
CCDC —
NMRShiftDB —
Metabolites & Pathways
HMDB HMDB0001999
METLIN 6423
RefMet ID —
RefMet Name —
MetaboLights ID —
BioCyc/MetaCyc EICOSAPENTAENOATE
MetaNetX ID MNXM2801
BiGG ID 2218016
KEGG C06428
KNApSAcK C00001215
Reactome ID —
Drugs & Pharmacology
DrugBank DB00159
DrugCentral 3174
BindingDB 50242349
Guide to Pharm 3362
Probes & Drugs PD010195
Clinical & Medical
SNOMED-CT —
MeSH D015118
NCIt Code C68434
Regulatory
NIH UNII (USA) AAN7QOV9EA
FDA SRS (USA) AAN7QOV9EA
NHPID (Canada) —
DTXSID (USA) DTXSID9041023
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-003-933-180
eMolecules —
Mcule —
ChemicalBook —
MedChemExpress —

Isomers of 20:5 (3)

Other fatty acids sharing the 20:5 notation — differing by double-bond position, geometry (cis/trans), or conjugation.

Name Geometry Trans Structure PubChem
Current Fatty Acid
Eicosapentaenoic acid
(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
 5Z,8Z,11Z,14Z,17Z —
446284
Category —
Conjugation Type Isolated
SMILES CC/C=C\C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
Description —
Origin Details

No origin information recorded.
Geometric (1)
all-trans-Eicosapentaenoic Acid
(5E,8E,11E,14E,17E)-icosa-5,8,11,14,17-pentaenoic acid
 5E,8E,11E,14E,17E Trans
Category Isolated all-trans Omega-3 Polyunsaturated Fatty Acid
Conjugation Type Isolated
SMILES CC/C=C/C/C=C/C/C=C/C/C=C/C/C=C/CCCC(=O)O
Description The all-trans geometric isomer of EPA, generated as a trace byproduct during high-temperature deodorization and refining of fish oils.
Origin Details
Origin Source Type Details
Industrial Deodorization Industrial Formed at trace levels during high-temperature deodorization, refining, or thermal stress of EPA-rich marine oils through free-radical-mediated geometric isomerization.
Positional (1)
Bosseopentaenoic Acid
(5Z,8Z,10E,12E,14Z)-icosa-5,8,10,12,14-pentaenoic acid
 5Z,8Z,10E,12E,14Z Trans
21773816
Category Conjugated Tetraene-Containing Omega-6 Polyunsaturated Fatty Acid
Conjugation Type Conjugated
SMILES CCCCC\C=C/C=C/C=C/C=C\C\C=C/CCCC(=O)O
Description A conjugated tetraene-containing C20 pentaenoic fatty acid isolated from the marine red coralline alga Bossiella orbigniana, biosynthesized from arachidonic acid.
Origin Details
Origin Source Type Details
Bossiella orbigniana Natural First isolated from the marine red coralline alga Bossiella orbigniana (Corallinaceae); biosynthesized in vivo from arachidonic acid through coupled lipoxygenase and isomerase reactions.

Chemical Properties

Name(s):
Common Name Eicosapentaenoic acid
Abbreviation EPA
Simple Notation 20:5
Notation 20:5(n-3)
IUPAC Name (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
Traditional Name Timnodonic acid
Semi-systematic Eicosapentaenoic acid
Structure:
Molecular C20H30O2
SMILES CC/C=C\C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
Cis / Trans cis
E-Z 5Z,8Z,11Z,14Z,17Z
Physical:
Weight 302.5 g/mol
Reactivity
Double Bonds 5
Bis-Allylic Carbons 4 (High Reactivity)
Beta-Oxidation
Beta Oxidation Cycles 9
ATP Yield (Net) 126.5 ATP