Record Information |
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Version | 1.0 |
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Created at | 2022-09-02 06:19:08 UTC |
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Updated at | 2022-09-02 06:19:09 UTC |
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NP-MRD ID | NP0150274 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (2s)-1-hydroxy-3-(octadecanoyloxy)propan-2-yl (4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoate |
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Description | DG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0), Also known as diacylglycerol(18:0/22:6) Or DAG(18:0/22:6), Belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2. Thus, DG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) Is considered to be a diradylglycerol lipid molecule. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. DG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) Is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, DG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) Participates in a number of enzymatic reactions. In particular, CDP-ethanolamine and DG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) Can be converted into cytidine monophosphate and PE(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. In addition, CDP-choline and DG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) Can be converted into cytidine monophosphate and PC(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. In humans, DG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) Is involved in phosphatidylcholine biosynthesis. Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the DG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) Under the catalysis of DG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) Acyltransferase. It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. 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-2 position. Synthesis of DG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) 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). Phosphatidic acid is then de-phosphorylated to form diacylglycerol. DG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0), In particular, consists of one chain of stearic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. (2s)-1-hydroxy-3-(octadecanoyloxy)propan-2-yl (4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoate is found in Trypanosoma brucei. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. |
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Structure | [H][C@](CO)(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC InChI=1S/C43H72O5/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-43(46)48-41(39-44)40-47-42(45)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h5,7,11,13,17,19,21-22,26,28,32,34,41,44H,3-4,6,8-10,12,14-16,18,20,23-25,27,29-31,33,35-40H2,1-2H3/b7-5-,13-11-,19-17-,22-21-,28-26-,34-32-/t41-/m0/s1 |
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Synonyms | Value | Source |
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(2S)-1-Hydroxy-3-(stearoyloxy)propan-2-yl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate | HMDB | 1-Octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycerol | HMDB | 1-Stearoyl-2-docosahexaenoyl-sn-glycerol | HMDB | DAG 18:0/22:6(omega-3)/0:0 | HMDB | DAG(18:0/22:6) | HMDB | DAG(18:0/22:6N3) | HMDB | DAG(18:0/22:6OMEGA3) | HMDB | DAG(40:6) | HMDB | DG(18:0/22:6) | HMDB | DG(18:0/22:6/0:0) | HMDB | DG(18:0/22:6N3) | HMDB | DG(18:0/22:6OMEGA3) | HMDB | DG(40:6) | HMDB | Diacylglycerol(18:0/22:6) | HMDB | Diacylglycerol(18:0/22:6n3) | HMDB | Diacylglycerol(18:0/22:6omega3) | HMDB | Diacylglycerol(40:6) | HMDB | (2S)-1-Hydroxy-3-(stearoyloxy)propan-2-yl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid | HMDB | 1-Stearoyl-2-docosahexaenoylglycerol | HMDB | Diglyceride | HMDB | Diacylglycerol | HMDB | DG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) | Lipid Annotator, ChEBI |
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Chemical Formula | C43H72O5 |
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Average Mass | 669.0288 Da |
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Monoisotopic Mass | 668.53798 Da |
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IUPAC Name | (2S)-1-hydroxy-3-(octadecanoyloxy)propan-2-yl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate |
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Traditional Name | diacylglycerol |
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CAS Registry Number | Not Available |
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SMILES | [H][C@](CO)(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC |
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InChI Identifier | InChI=1S/C43H72O5/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-43(46)48-41(39-44)40-47-42(45)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h5,7,11,13,17,19,21-22,26,28,32,34,41,44H,3-4,6,8-10,12,14-16,18,20,23-25,27,29-31,33,35-40H2,1-2H3/b7-5-,13-11-,19-17-,22-21-,28-26-,34-32-/t41-/m0/s1 |
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InChI Key | LBDXVTOFXXDOGH-KXYFHQNYSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Glycerolipids |
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Sub Class | Diradylglycerols |
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Direct Parent | 1,2-diacylglycerols |
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Alternative Parents | |
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Substituents | - 1,2-acyl-sn-glycerol
- Fatty acid ester
- Fatty acyl
- Dicarboxylic acid or derivatives
- Carboxylic acid ester
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Carbonyl group
- Alcohol
- 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 | Not Available |
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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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