General Information of MET (ID: META00595)
Name PG(16:0/18:1(9Z))
Synonyms   Click to Show/Hide Synonyms of This Metabolite
1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-sn-glycerol', 1-Palmitoyl-2-oleoyl-sn-glycero-3-phospho-(1'-sn-glycerol), '1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphoglycerol; 1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoglycerol; 16:0/18:1 PG; C16:0/18:1 PG; GPG(16:0/18:1(9Z)); GPG(16:0/18:1); GPG(16:0/18:1OMEGA9); GPG(16:0/18:1W9); GPG(34:1); PG(16:0/18:1(9Z)); PG(16:0/18:1); PG(16:0/18:1N9); PG(16:0/18:1OMEGA9); PG(16:0/18:1W9); PG(34:1); Phosphatidylglycerol(16:0/18:1(9Z)); Phosphatidylglycerol(16:0/18:1); Phosphatidylglycerol(16:0/18:1W9); Phosphatidylglycerol(16:0/18:1n9); Phosphatidylglycerol(16:0/18:1omega9); Phosphatidylglycerol(34:1)', 1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-glycerol), 'GPG(16:0/18:1N9)
Source Endogenous;Escherichia Coli Metabolite;Yeast Metabolite;Glycerophospholipids;Food
Structure Type   Glycerophosphoglycerols  (Click to Show/Hide the Complete Structure Type Hierarchy)
Lipids and lipid-like molecules
Glycerophospholipids
Glycerophosphoglycerols
PubChem CID
52941750
HMDB ID
HMDB0010574
Formula
C40H77O10P
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=52941750"></iframe>
3D MOL is unavailable 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
ChEBI ID
73234
FooDB ID
FDB027724
ChemSpider ID
24768073
Physicochemical Properties Molecular Weight 749 Topological Polar Surface Area 149
XlogP 12.3 Complexity 868
Heavy Atom Count 51 Rotatable Bond Count 41
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 10
Function
PG(16:0/18:1(9Z)) is a phosphatidylglycerol or glycerophospholipid (PG or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PG(16:0/18:1(9Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of oleic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidylglycerol is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of phosphatidylglycerol increases during fetal development. Phosphatidylglycerol may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PGs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PG also serves as a precursor for the synthesis of cardiolipin. PG is synthesized from CDP-diacylglycerol and glycerol-3-phosphate.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            GTPase KRas (KRAS) 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 Overexpression of KRAS
                      Induced Change PG(16:0/18:1(9Z)) concentration: increase (FC = 9.59)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Lung cancer [ICD-11: 2C25]
                      Details It is reported that overexpression of KRAS leads to the increase of PG(16:0/18:1(9Z)) levels compared with control group.
References
1 Capturing the metabolomic diversity of KRAS mutants in non-small-cell lung cancer cells. Oncotarget. 2014 Jul 15;5(13):4722-31.

If you find any error in data or bug in web service, please kindly report it to Dr. Zhang and Dr. Mou.