| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:05:39 UTC |
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| Update date | 2019-11-26 02:58:29 UTC |
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| Primary ID | FDB003102 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Eicosapentaenoic acid |
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| Description | Present 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. |
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| CAS Number | 10417-94-4 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| Not Available | Not Available |
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| Predicted Properties | |
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| Chemical Formula | C20H30O2 |
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| IUPAC name | (5Z,8Z,11E,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid |
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| InChI Identifier | 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- |
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| InChI Key | JAZBEHYOTPTENJ-IKHGVYGUSA-N |
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| Isomeric SMILES | CC\C=C/C\C=C/C\C=C\C\C=C/C\C=C/CCCC(O)=O |
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| Average Molecular Weight | 302.451 |
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| Monoisotopic Molecular Weight | 302.224580204 |
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| Classification |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Fatty Acyls |
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| Sub Class | Fatty acids and conjugates |
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| Direct Parent | Long-chain fatty acids |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Ontology | No ontology term |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
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| Physical state | Solid | |
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| Physical Description | Not Available | |
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| Mass Composition | C 79.42%; H 10.00%; O 10.58% | DFC |
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| Melting Point | Not Available | |
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| Boiling Point | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Experimental logP | Not Available | |
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| Experimental pKa | Not Available | |
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| Isoelectric point | Not Available | |
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| Charge | Not Available | |
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| Optical Rotation | Not Available | |
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| Spectroscopic UV Data | Not Available | |
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| Density | Not Available | |
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| Refractive Index | Not Available | |
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| Spectra |
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| Spectra | Not Available |
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| External Links |
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| ChemSpider ID | 393682 |
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| ChEMBL ID | CHEMBL460026 |
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| KEGG Compound ID | C06428 |
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| Pubchem Compound ID | 446284 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | 28364 |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | DB00159 |
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| HMDB ID | HMDB01999 |
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| CRC / DFC (Dictionary of Food Compounds) ID | HDJ50-Z:CQZ50-L |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | EICOSAPENTAENOIC-ACID |
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| BIGG ID | 2218016 |
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| KNApSAcK ID | C00000408 |
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| HET ID | EPA |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Eicosapentaenoic acid |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | |
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| Enzymes | | Name | Gene Name | UniProt ID |
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| Bile acid-CoA:amino acid N-acyltransferase | BAAT | Q14032 | | Peroxisome proliferator-activated receptor gamma | PPARG | P37231 | | Cytosolic acyl coenzyme A thioester hydrolase | ACOT7 | O00154 | | Acyl-coenzyme A thioesterase 2, mitochondrial | ACOT2 | P49753 | | Acyl-coenzyme A thioesterase 4 | ACOT4 | Q8N9L9 | | Acyl-coenzyme A thioesterase 8 | ACOT8 | O14734 | | Acyl-coenzyme A thioesterase 1 | ACOT1 | Q86TX2 | | Peroxisome proliferator-activated receptor delta | PPARD | Q03181 |
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| Pathways | | Name | SMPDB Link | KEGG Link |
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| Alpha Linolenic Acid and Linoleic Acid Metabolism | SMP00018 | map00592 |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | Not Available |
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| Files |
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| MSDS | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| 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).
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