General Information of MET (ID: META00700)
Name DG(18:3n3/0:0/18:3n3)
Synonyms   Click to Show/Hide Synonyms of This Metabolite
1,3-Di-(9Z,12Z,15Z)-octadecatrienoylglycerol; 1-(9Z,12Z,15Z-Octadeatrienoyl)-3-(9Z,12Z,15Z-octadeatrienoyl)-sn-glycerol; 1-a-Linolenoyl-3-a-linolenoyl-sn-glycerol; 1.3-Dilinolenin; DAG(18:3/0:0/18:3); DAG(18:3N3/0:0/18:3N3); DAG(18:3W3/0:0/18:3W3); DAG(36:6); DG(18:3/0:0/18:3); DG(18:3W3/0:0/18:3W3); DG(18:3n3/0:0/18:3n3); DG(36:6); DG[18:3(Omega-3)/0:0/18:3(omega-3)]; Diacylglycerol; Diacylglycerol(18:3/0:0/18:3); Diacylglycerol(18:3W3/0:0/18:3W3); Diacylglycerol(18:3n3/0:0/18:3n3); Diacylglycerol(36:6); Diglyceride; Glyceryl 1,3-dilinoleneate; Glyceryl 1,3-dilinoleneic acid
Source Aliphatic acyclic compounds
Structure Type   Lineolic acids and derivatives  (Click to Show/Hide the Complete Structure Type Hierarchy)
Lipids and lipid-like molecules
Fatty Acyls
Lineolic acids and derivatives
PubChem CID
45934043
HMDB ID
HMDB0056366
Formula
C39H64O5
Structure
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3D MOL is unavailable 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
ChEBI ID
75852
Physicochemical Properties Molecular Weight 612.9 Topological Polar Surface Area 72.8
XlogP 11.6 Complexity 766
Heavy Atom Count 44 Rotatable Bond Count 32
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Function
DG(18:3n3/0:0/18:3n3) 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(18:3n3/0:0/18:3n3), in particular, consists of two chains of a-linolenic acid at the C-1 and C-3 positions. The a-linolenic acid moieties are derived from seed oils, especially canola and soybean oil. 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.<br />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.<br />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.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Transcription factor (TF)
            Hypoxia-inducible factor 1-alpha (HIF1A) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Knockout of HIF1A
                      Induced Change DG(18:3n3/0:0/18:3n3) concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colorectal cancer [ICD-11: 2B91]
                      Details It is reported that knockout of HIF1A leads to the increase of DG(18:3n3/0:0/18:3n3) levels compared with control group.
References
1 Hypoxia induces a lipogenic cancer cell phenotype via HIF1-dependent and -independent pathways. Oncotarget. 2015 Feb 10;6(4):1920-41.

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