| Record Information |
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| Version | 1.0 |
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| Creation Date | 2018-09-23 03:10:41 UTC |
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| Update Date | 2020-06-04 19:33:23 UTC |
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| BMDB ID | BMDB0063598 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | DG(O-16:0/20:4(8E,11E,14E,17E)/0:0) |
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| Description | DG(O-16:0/20:4(8E,11E,14E,17E)/0:0), also referred to as DG(20:4), is a diglyceride which belongs to the family of Diacylglycerols (DAGs). These are glycerolipids containing a common glycerol backbone to which at least one fatty acyl group is esterified. 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. DAGs can have many different combinations of fatty acids attached at the C-1, C-2, or C-3 positions. DG(20:4), in particular, consists of one chain of hexadecyl acid at the C-1 position and one chain of arachidonic acid at the C-2 position. DG(20:4) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway. 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 | |
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| Synonyms | Not Available |
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| Chemical Formula | C39H70O4 |
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| Average Molecular Weight | 602.985 |
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| Monoisotopic Molecular Weight | 602.527410734 |
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| IUPAC Name | (2R)-1-(hexadecyloxy)-3-hydroxypropan-2-yl (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoate |
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| Traditional Name | (2R)-1-(hexadecyloxy)-3-hydroxypropan-2-yl (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoate |
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| CAS Registry Number | Not Available |
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| SMILES | [H][C@@](CO)(COCCCCCCCCCCCCCCCC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC |
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| InChI Identifier | InChI=1S/C39H70O4/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-39(41)43-38(36-40)37-42-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h5,7,11,13,17,19,21-22,38,40H,3-4,6,8-10,12,14-16,18,20,23-37H2,1-2H3/b7-5-,13-11-,19-17-,22-21-/t38-/m1/s1 |
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| InChI Key | ZOQPRIBCWWPWEH-SCBZKDMTSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as 1-alkyl,2-acylglycerols. These are glycerides consisting of two fatty acyl chains covalently bonded to a glycerol molecule at the 1- and 2-positions through an ether and an ester linkage, respectively. |
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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-alkyl,2-acylglycerols |
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| Alternative Parents | |
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| Substituents | - 1-alkyl,2-acylglycerol
- Glycerol ether
- Fatty acid ester
- Fatty acyl
- Carboxylic acid ester
- Monocarboxylic acid or derivatives
- Ether
- Dialkyl ether
- 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 | Not Available |
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| Ontology |
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| Status | Detected and Quantified |
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| Origin | Not Available |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | Not Available |
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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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| Spectra |
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| Spectra | |
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