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
Synonyms
SynonymSource
EicosapentaenoateGenerator
(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
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
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
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
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
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
5-hydroxyeicosatetraenoic-acid inhibitor35222 An agent that blocks the activity of 5-lipoxygenase, reducing leukotriene production and inflammation. Therapeutically, it's used to treat asthma, allergic rhinitis, and other inflammatory conditions, providing relief from symptoms such as congestion and bronchospasm.DUKE
Anti-arthritic52217 An agent that reduces joint inflammation and alleviates symptoms of arthritis, commonly used in managing rheumatoid arthritis, osteoarthritis, and other inflammatory joint disorders, to improve mobility and quality of life.DUKE
Anti-atherotic38070 An agent that prevents or slows the formation of atheromas (plaques) in arteries, reducing the risk of cardiovascular disease. It inhibits the accumulation of lipids and inflammatory cells, promoting healthy blood vessel function. Therapeutically, anti-atherotics are used to manage atherosclerosis, hyperlipidemia, and prevent cardiovascular events such as heart attacks and strokes.DUKE
Anti dermatitic50177 An agent that reduces skin inflammation and irritation, commonly used to treat dermatitis, eczema, and other skin disorders, providing relief from itching, redness, and swelling.DUKE
Anti fibrosarcomicAn agent that inhibits the growth of fibrosarcoma, a type of cancer characterized by malignant fibroblasts. It plays a biological role in regulating cell proliferation, and has therapeutic applications in oncology. Key medical uses include treating fibrosarcoma and other soft tissue sarcomas, reducing tumor growth and improving patient outcomes.DUKE
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti-ischemic52217 An agent that reduces or prevents tissue damage from inadequate blood flow, commonly used to manage angina, heart attacks, and strokes by improving oxygen delivery and reducing cardiac workload.DUKE
Anti leukemic35610 An agent that targets and inhibits the growth of leukemia cells, playing a crucial role in cancer treatment. Therapeutically, it is used to induce remission, manage symptoms, and improve survival rates in patients with leukemia. Key medical uses include treating acute and chronic leukemia, lymphoma, and other hematological malignancies.DUKE
Anti leukotriene-B435222 An agent that inhibits leukotriene B4, reducing inflammation and immune responses. It has therapeutic applications in managing inflammatory diseases, such as asthma and arthritis, by blocking leukotriene B4's role in attracting white blood cells to sites of inflammation. Key medical uses include treating respiratory and autoimmune disorders.DUKE
Anti-melanomic35610 An agent that inhibits melanin production, reducing melanoma cell growth. It has therapeutic applications in treating skin cancers, particularly melanoma, and key medical uses include preventing tumor progression and metastasis, as well as managing pigmentation disorders.DUKE
Anti metastatic35610 An agent that inhibits cancer cell spread, reducing tumor metastasis. It plays a biological role in blocking cell migration and invasion, and has therapeutic applications in cancer treatment. Key medical uses include preventing cancer recurrence and improving survival rates in patients with various types of cancer.DUKE
Anti proliferantAn agent that prevents or inhibits cell growth and division, used therapeutically to treat cancer, manage tumor growth, and prevent restenosis after angioplasty, reducing abnormal cell proliferation.DUKE
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.DUKE
Collagenase inhibitor23924 An agent that blocks the activity of collagenase, an enzyme that breaks down collagen. It reduces tissue damage and inflammation, commonly used in managing conditions such as osteoarthritis, tendonitis, and wound healing.DUKE
Cyclooxygenase-2 inhibitor50629 An agent that blocks the activity of cyclooxygenase-2 (COX-2), reducing inflammation and pain. Therapeutically, it is used to manage conditions such as arthritis, menstrual cramps, and other inflammatory disorders, providing relief from symptoms with reduced gastrointestinal side effects compared to non-selective NSAIDs.DUKE
DifferentiatorAn agent that induces cell differentiation, promoting mature cell formation. Its biological role involves regulating cell growth and development. Therapeutically, it has applications in cancer treatment, helping to mature cancer cells, making them more susceptible to chemotherapy. Key medical uses include leukemia and other malignancies, where differentiation therapy can improve treatment outcomes.DUKE
HypotensiveAn agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.DUKE
Nephroprotective76595 An agent that protects the kidneys from damage, reducing inflammation and oxidative stress. Therapeutically, it helps prevent or treat kidney diseases, such as nephropathy and acute kidney injury, and is used in managing conditions like diabetes and hypertension to preserve renal function.DUKE
Tyrosine-kinase inhibitor23924 An agent that blocks tyrosine kinase enzymes, reducing cell signaling and proliferation. Therapeutically, it's used to treat cancers, such as leukemia and breast cancer, by inhibiting tumor growth, and also has applications in managing certain autoimmune and inflammatory diseases.DUKE
VEGF inhibitor35222 An agent that blocks the activity of Vascular Endothelial Growth Factor (VEGF), reducing angiogenesis. Therapeutically, it's used to treat cancer, age-related macular degeneration, and diabetic retinopathy by inhibiting tumor growth and abnormal blood vessel formation.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).