Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:24:24 UTC |
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Update date | 2019-11-26 03:21:07 UTC |
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Primary ID | FDB023082 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 8,11,14-Eicosatrienoic acid |
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Description | 8,11,14-Eicosatrienoic acid is a 20-carbon-chain omega-6 fatty acid, unsaturated at positions 8, 11, and 14. It differs from arachidonic acid (5,8,11,14-eicosatetraenoic acid) only at position 5. 8,11,14-Eicosatrienoic acid is also known as Dihomo-gamma-linolenic acid (DGLA). In physiological literature, it is given the name 20:3(n-6). DGLA is the elongation product of the 18 carbon gamma-linolenic acid (GLA). DGLA can be converted into prostaglandin E1 (PGE1). PGE1 inhibits platelet aggregation and also exerts a vasodilatory effect. DGLA competes with arachadonic acid for COX and lipoxygenase, inhibiting the production of arachadonic acid's eicosanoids [HMDB] |
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CAS Number | 1783-84-2 |
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Structure | |
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Synonyms | Synonym | Source |
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8,11,14-Eicosatrienoate | Generator | (8Z,11Z,14Z)-Icosatrienoate | hmdb | (8Z,11Z,14Z)-Icosatrienoic acid | hmdb | (Z,Z,Z)-8,11,14-Eicosatrienoate | hmdb | (Z,Z,Z)-8,11,14-Eicosatrienoic acid | hmdb | (Z,Z,Z)-8,11,14-Icosatrienoate | hmdb | (Z,Z,Z)-8,11,14-Icosatrienoic acid | hmdb | (Z,Z,Z)-icosatri-8,11,14-enoate | hmdb | (Z,Z,Z)-icosatri-8,11,14-enoic acid | hmdb | 20:3, N-6,9,12 all-cis | ChEBI | 8,11,14-all-cis-Eicosatrienoate | hmdb | 8,11,14-all-cis-Eicosatrienoic acid | hmdb | 8,11,14-Eicosatrienoic acid | hmdb | 8,11,14-Icosatrienoate | hmdb | 8,11,14-Icosatrienoic acid | hmdb | 8c,11c,14c-Eicosatrienoate | Generator | 8c,11c,14c-Eicosatrienoic acid | ChEBI | 8c,11c,14c-Eicosatriensaeure | ChEBI | 8Z,11Z,14Z-eicosatrienoate | hmdb | 8Z,11Z,14Z-eicosatrienoic acid | hmdb | all-cis-8,11,14-Eicosatrienoate | hmdb | all-cis-8,11,14-Eicosatrienoic acid | hmdb | all-cis-8,11,14-Icosatrienoate | Generator | all-cis-8,11,14-Icosatrienoic acid | ChEBI | all-cis-Eicosa-8,11,14-trienoate | Generator | all-cis-Eicosa-8,11,14-trienoic acid | ChEBI | all-cis-Eicosa-8,11,14-triensaeure | ChEBI | Bishomo-gamma-linolenate | hmdb | Bishomo-gamma-linolenic acid | hmdb | C20:3, N-6,9,12 all-cis | ChEBI | cis-8,11,14-Eicosatrienoate | hmdb | cis-8,11,14-Eicosatrienoic acid | hmdb | cis-8,cis-11,cis-14-Eicosatrienoate | hmdb | cis-8,cis-11,cis-14-Eicosatrienoic acid | hmdb | cis,cis,cis-8,11,14-Eicosatrienoate | hmdb | cis,cis,cis-8,11,14-Eicosatrienoic acid | hmdb | DGLA | hmdb | Dihomo-g-linolenate | Generator | Dihomo-g-linolenic acid | Generator | Dihomo-gamma-linolenate | hmdb | Dihomo-gamma-linolenic acid | hmdb | Dihomo-γ-linolenate | Generator | Dihomo-γ-linolenic acid | Generator | Eicosa-8Z,11Z,14Z-trienoate | Generator | Eicosa-8Z,11Z,14Z-trienoic acid | ChEBI | Eicosatrienoate | hmdb | Eicosatrienoic acid | hmdb | g-Homolinolenate | Generator | g-Homolinolenic acid | Generator | gamma-Homolinolenate | hmdb | gamma-Homolinolenic acid | hmdb | Homo-g-linolenate | Generator | Homo-g-linolenic acid | Generator | Homo-g-linolensaeure | Generator | Homo-gamma-linolenate | hmdb | Homo-gamma-linolenic acid | ChEBI | Homo-gamma-linolensaeure | ChEBI | Homo-γ-linolenate | Generator | Homo-γ-linolenic acid | Generator | Homo-γ-linolensaeure | Generator | γ-homolinolenate | Generator | γ-homolinolenic acid | Generator |
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Predicted Properties | |
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Chemical Formula | C20H34O2 |
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IUPAC name | icosa-8,11,14-trienoic acid |
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InChI Identifier | InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22) |
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InChI Key | HOBAELRKJCKHQD-UHFFFAOYSA-N |
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Isomeric SMILES | CCCCCC=CCC=CCC=CCCCCCCC(O)=O |
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Average Molecular Weight | 306.4828 |
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Monoisotopic Molecular Weight | 306.255880332 |
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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 - Experimental |
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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 | Not Available | |
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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 | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | 8,11,14-Eicosatrienoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0006-9570000000-cd036d3430a12b16dfb6 | Spectrum | Predicted GC-MS | 8,11,14-Eicosatrienoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 8,11,14-Eicosatrienoic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 8,11,14-Eicosatrienoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4r-4496000000-d2c86b500de1b25b89bd | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a5i-8920000000-c9e205f0c9bc159b6e85 | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05o4-9300000000-6f4b5c73d4ea8dd6ce7c | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0019000000-a547ddaba8c204ad4b7f | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4r-1069000000-b0557dab6092938359c2 | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9220000000-00dffbb43465bcaae37f | 2021-10-12 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 4444199 |
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ChEMBL ID | CHEMBL465183 |
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KEGG Compound ID | C03242 |
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Pubchem Compound ID | 5280581 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB00154 |
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HMDB ID | HMDB02925 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | 41475 |
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KNApSAcK ID | Not Available |
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HET ID | LAX |
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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 | DGLA |
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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 | Not Available |
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Enzymes | Name | Gene Name | UniProt ID |
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Bile acid-CoA:amino acid N-acyltransferase | BAAT | Q14032 | 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 |
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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 | show |
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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 | |
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