| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 23:23:13 UTC |
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| Update Date | 2020-06-04 20:30:58 UTC |
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| MCDB ID | BMDB0006547 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Stearidonic acid |
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| Description | Stearidonic acid, also known as stearidonate, belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Stearidonic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Stearidonic acid participates in a number of enzymatic reactions, within cattle. In particular, Stearidonic acid can be biosynthesized from alpha-linolenic acid through its interaction with the enzyme fatty acid desaturase 2. In addition, Stearidonic acid can be converted into cis-8,11,14,17-eicosatetraenoic acid through the action of the enzyme elongation OF very long chain fatty acids protein 5. In cattle, stearidonic acid is involved in the metabolic pathway called the Alpha linolenic Acid and linoleic Acid metabolism pathway. |
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| Structure | |
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| Synonyms | | Value | Source |
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| Stearidonate | Generator | | 6,9,12,15-Octadecatetraenoate | Generator |
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| Chemical Formula | C18H28O2 |
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| Average Molecular Weight | 276.42 |
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| Monoisotopic Molecular Weight | 276.208930142 |
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| IUPAC Name | (6E,9E,12E,15E)-octadeca-6,9,12,15-tetraenoic acid |
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| Traditional Name | (6E,9E,12E,15E)-octadeca-6,9,12,15-tetraenoic acid |
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| CAS Registry Number | Not Available |
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| SMILES | [H]\C(CC)=C(\[H])C\C([H])=C(/[H])C\C([H])=C(/[H])C\C([H])=C(/[H])CCCCC(O)=O |
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| InChI Identifier | InChI=1S/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10,12-13H,2,5,8,11,14-17H2,1H3,(H,19,20)/b4-3+,7-6+,10-9+,13-12+ |
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| InChI Key | JIWBIWFOSCKQMA-GFRMADBLSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. |
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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 | Lineolic acids and derivatives |
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| Direct Parent | Lineolic acids and derivatives |
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| Alternative Parents | |
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| Substituents | - Octadecanoid
- Long-chain fatty acid
- 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 | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| | Spectrum Type | Description | Splash Key | Deposition Date | View |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0090000000-e75e59d4b3d4e9edbd18 | 2019-02-23 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0arr-4790000000-9b7041bf3a990ff65378 | 2019-02-23 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05n3-8930000000-1753d6e5ddbcf668e67e | 2019-02-23 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0090000000-80834337f5bd3aad0e3e | 2019-02-23 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-057i-0090000000-154995698a43b955e2bf | 2019-02-23 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9230000000-6dcdc9428d851f16051e | 2019-02-23 | View Spectrum |
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| Concentrations |
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| Detected and Quantified | 1230 +/- 507 uM | Total fatty acid | | details | | Detected and Quantified | 1049 +/- 362 uM | Total fatty acid | | details |
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| External Links |
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| HMDB ID | Not Available |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FoodDB ID | Not Available |
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| KNApSAcK ID | Not Available |
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| Chemspider ID | Not Available |
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| KEGG Compound ID | Not Available |
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| BioCyc ID | Not Available |
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| BiGG ID | Not Available |
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| Wikipedia Link | Stearidonic acid |
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| METLIN ID | Not Available |
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| PubChem Compound | 5282837 |
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| PDB ID | Not Available |
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| ChEBI ID | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - M. Ferrand, B. Huquet. S. Barbey, F. Barillet, F. Faucon, H. Larroque, O. Leray, J.M. Trommenschlager, M. Brochard (2011). M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189. Chemometrics and Intelligent Laboratory Systems.
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