Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:45:25 UTC |
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Update date | 2015-07-21 06:58:07 UTC |
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Primary ID | FDB024521 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | DG(18:4(6Z,9Z,12Z,15Z)/14:1(9Z)/0:0) |
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Description | DG(18:4(6Z,9Z,12Z,15Z)/14:1(9Z)/0:0) 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 both the C-1 and C-2 positions. DG(18:4(6Z,9Z,12Z,15Z)/14:1(9Z)/0:0), in particular, consists of one chain of stearidonic acid at the C-1 position and one chain of myristoleic acid at the C-2 position. The stearidonic acid moiety is derived from seed oils, while the myristoleic acid moiety is derived from milk fats. 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-2 position. [HMDB] |
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CAS Number | Not Available |
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Structure | |
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Synonyms | Synonym | Source |
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1-stearidonoyl-2-myristoleoyl-sn-glycerol | hmdb | DAG(18:4/14:1) | hmdb | DAG(18:4n3/14:1n5) | hmdb | DAG(18:4w3/14:1w5) | hmdb | DG(18:4/14:1) | hmdb | DG(18:4n3/14:1n5) | hmdb | DG(18:4w3/14:1w5) | hmdb | Diacylglycerol(18:4/14:1) | hmdb | Diacylglycerol(18:4n3/14:1n5) | hmdb | Diacylglycerol(18:4w3/14:1w5) | hmdb |
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Predicted Properties | |
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Chemical Formula | C35H58O5 |
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IUPAC name | (2S)-3-hydroxy-2-(tetradec-9-enoyloxy)propyl octadeca-6,9,12,15-tetraenoate |
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InChI Identifier | InChI=1S/C35H58O5/c1-3-5-7-9-11-13-15-16-17-18-20-21-23-25-27-29-34(37)39-32-33(31-36)40-35(38)30-28-26-24-22-19-14-12-10-8-6-4-2/h5,7,10-13,16-17,20-21,33,36H,3-4,6,8-9,14-15,18-19,22-32H2,1-2H3/t33-/m0/s1 |
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InChI Key | DJPSDNJBZWPDDE-XIFFEERXSA-N |
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Isomeric SMILES | [H][C@](CO)(COC(=O)CCCCC=CCC=CCC=CCC=CCC)OC(=O)CCCCCCCC=CCCCC |
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Average Molecular Weight | 558.832 |
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Monoisotopic Molecular Weight | 558.428424966 |
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Classification |
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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
- 1,2-acyl-sn-glycerol
- Diacylglycerol
- Diradylglycerol
- Fatty acid ester
- Glycerolipid
- Dicarboxylic acid or derivatives
- Carboxylic acid ester
- Carboxylic acid derivative
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxygen compound
- Organic oxide
- Carbonyl group
- Primary alcohol
- 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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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 | Not Available |
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External Links |
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ChemSpider ID | 24766065 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 53478157 |
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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 | Not Available |
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HMDB ID | HMDB07328 |
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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 | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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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 | Not Available |
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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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Pancreatic triacylglycerol lipase | PNLIP | P16233 | Hepatic triacylglycerol lipase | LIPC | P11150 | Inactive pancreatic lipase-related protein 1 | PNLIPRP1 | P54315 | Patatin-like phospholipase domain-containing protein 3 | PNPLA3 | Q9NST1 | Gastric triacylglycerol lipase | LIPF | P07098 | Endothelial lipase | LIPG | Q9Y5X9 | Diacylglycerol O-acyltransferase 1 | DGAT1 | O75907 | Pancreatic lipase-related protein 2 | PNLIPRP2 | P54317 | Lipoprotein lipase | LPL | P06858 | 2-acylglycerol O-acyltransferase 2 | MOGAT2 | Q3SYC2 | Patatin-like phospholipase domain-containing protein 4 | PNPLA4 | P41247 | Diacylglycerol O-acyltransferase 2 | DGAT2 | Q96PD7 | 2-acylglycerol O-acyltransferase 1 | MOGAT1 | Q96PD6 | 2-acylglycerol O-acyltransferase 3 | MOGAT3 | Q86VF5 | Patatin-like phospholipase domain-containing protein 2 | PNPLA2 | Q96AD5 | Pancreatic lipase-related protein 3 | PNLIPRP3 | Q17RR3 | Choline-phosphate cytidylyltransferase A | PCYT1A | P49585 | Acyl-CoA wax alcohol acyltransferase 2 | AWAT2 | Q6E213 | Acyl-CoA wax alcohol acyltransferase 1 | AWAT1 | Q58HT5 | Galactosylceramide sulfotransferase | GAL3ST1 | Q99999 | Phosphatidate cytidylyltransferase 2 | CDS2 | O95674 | Phosphatidylcholine:ceramide cholinephosphotransferase 2 | SGMS2 | Q8NHU3 | Phosphatidylcholine:ceramide cholinephosphotransferase 1 | SGMS1 | Q86VZ5 | Diacylglycerol O-acyltransferase 2-like protein 6 | DGAT2L6 | Q6ZPD8 | Putative diacylglycerol O-acyltransferase 2-like protein 7 | DGAT2L7 | Q6IED9 | CDC42 binding protein kinase beta (DMPK-like) | CDC42BPB | A9JR72 | Kinase suppressor of Ras 2 | KSR2 | Q6VAB6 | Tensin-like C1 domain-containing phosphatase | TENC1 | Q63HR2 | Kinase suppressor of Ras 1 | KSR1 | Q8IVT5 | CDC42-binding protein kinase beta | CDC42BPA | Q8IWQ7 |
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Pathways | Not Available |
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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 | Not Available |
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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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