Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-21 13:39:07 UTC |
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Update Date | 2022-11-30 19:10:28 UTC |
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HMDB ID | HMDB0056381 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | DG(20:5n3/0:0/20:5n3) |
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Description | DG(20:5n3/0:0/20:5n3) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at the C-1 C-2, or C-3 positions. DG(20:5n3/0:0/20:5n3), in particular, consists of two chains of eicosapentaenoic acid at the C-1 and C-3 positions. The eicosapentaenoic acid moieties are derived from fish oils, liver and kidney. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol. Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-3 position. |
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Structure | [H]C(O)(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC InChI=1S/C43H64O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-42(45)47-39-41(44)40-48-43(46)38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h5-8,11-14,17-20,23-26,29-32,41,44H,3-4,9-10,15-16,21-22,27-28,33-40H2,1-2H3/b7-5-,8-6-,13-11-,14-12-,19-17-,20-18-,25-23-,26-24-,31-29-,32-30- |
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Synonyms | Value | Source |
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1-Eicosapentaenoyl-3-eicosapentaenoyl-sn-glycerol | HMDB | DAG(40:10) | HMDB | DAG(20:5N3/0:0/20:5N3) | HMDB | DAG(20:5W3/0:0/20:5W3) | HMDB | Diacylglycerol(40:10) | HMDB | Diglyceride | HMDB | Diacylglycerol(20:5/0:0/20:5) | HMDB | DAG(20:5/0:0/20:5) | HMDB | Diacylglycerol | HMDB | DG(40:10) | HMDB | Diacylglycerol(20:5W3/0:0/20:5W3) | HMDB | DG(20:5/0:0/20:5) | HMDB | Diacylglycerol(20:5n3/0:0/20:5n3) | HMDB | 1-(5Z,8Z,11Z,14Z,17Z-Eicosapentaenoyl)-3-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycerol | HMDB | DG(20:5W3/0:0/20:5W3) | HMDB | DG(20:5n3/0:0/20:5n3) | Lipid Annotator | 2-Hydroxy-3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propyl (5Z,8Z,11Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid | Generator |
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Chemical Formula | C43H64O5 |
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Average Molecular Weight | 660.9653 |
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Monoisotopic Molecular Weight | 660.475375158 |
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IUPAC Name | 2-hydroxy-3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate |
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Traditional Name | 2-hydroxy-3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate |
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CAS Registry Number | Not Available |
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SMILES | [H]C(O)(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC |
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InChI Identifier | InChI=1S/C43H64O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-42(45)47-39-41(44)40-48-43(46)38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h5-8,11-14,17-20,23-26,29-32,41,44H,3-4,9-10,15-16,21-22,27-28,33-40H2,1-2H3/b7-5-,8-6-,13-11-,14-12-,19-17-,20-18-,25-23-,26-24-,31-29-,32-30- |
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InChI Key | TXYVJIXIUGRAFF-LPEZNXMBSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as other hydroxyeicosapolyenoic acids. These are hydroxyeicosapolyenoic acids which do not belong to the Hydroxyeicosapentaenoic acids, the Hydroxyeicosatetraenoic acids, or the Hydroxyeicosatrienoic acids. |
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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 | Eicosanoids |
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Direct Parent | Other hydroxyeicosapolyenoic acids |
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Alternative Parents | |
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Substituents | - Hydroxyeicosapolyenoic acid
- 1,3-acyl-sn-glycerol
- Diacylglycerol
- Diradylglycerol
- Fatty acid ester
- Glycerolipid
- Dicarboxylic acid or derivatives
- Carboxylic acid ester
- Secondary alcohol
- Carboxylic acid derivative
- Hydrocarbon derivative
- Organooxygen compound
- Organic oxygen compound
- Organic oxide
- Carbonyl group
- Alcohol
- 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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Physiological effect | |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular 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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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
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