General Information of MET (ID: META00580)
Name PI(18:1(9Z)/18:1(9Z))
Synonyms   Click to Show/Hide Synonyms of This Metabolite
1,2-Di(9Z-octadecenoyl)-rac-glycero-3-phospho-(1'-myo-inositol), '1,2-Dioleoyl-rac-glycero-3-phosphoinositol; 1,2-Di(9Z-octadecenoyl)-rac-glycero-3-phosphoinositol; PI(18:1(9Z)/18:1(9Z)); PI(18:1/18:1); PI(18:1W9/18:1W9); PI(18:1n9/18:1n9); PI(36:2); Phosphatidylinositol(18:1/18:1); Phosphatidylinositol(18:1W9/18:1W9); Phosphatidylinositol(18:1n9/18:1n9); Phosphatidylinositol(36:2); Pino(18:1/18:1); Pino(18:1W9/18:1W9); Pino(18:1n9/18:1n9); Pino(36:2)
Source Endogenous;Yeast Metabolite;Food;Microbial
Structure Type   Glycerophosphoinositols  (Click to Show/Hide the Complete Structure Type Hierarchy)
Lipids and lipid-like molecules
Glycerophospholipids
Glycerophosphoinositols
HMDB ID
HMDB0009837
Formula
C45H83O13P
Structure
2D MOL
KEGG ID
C00626
ChEBI ID
88612
FooDB ID
FDB027027
ChemSpider ID
24767722
Function
PI(18:1(9Z)/18:1(9Z)) is a phosphatidylinositol. Phosphatidylinositols are important lipids, both as a key membrane constituent and as a participant in essential metabolic processes, both directly and via a number of metabolites. Phosphatidylinositols are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to inositol (hexahydroxycyclohexane). Phosphatidylinositols 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 18 and 20 carbons are the most common. PI(18:1(9Z)/18:1(9Z)), in particular, consists of one chain of oleic acid at the C-1 position and one chain of oleic acid at the C-2 position. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. The inositol group that is part of every phosphatidylinositol lipid is covalently linked to the phosphate group that acts as a bridge to the lipid tail. In most organisms, the stereochemical form of this inositol is myo-D-inositol (with one axial hydroxyl in position 2 with the remainder equatorial), although other forms can be found in certain plant phosphatidylinositols. Phosphatidylinositol is especially abundant in brain tissue, where it can amount to 10% of the phospholipids, but it is present in all tissues and cell types. There is usually less of it than of phosphatidylcholine, phosphatidylethanolamine and phosphatidylserine. In animal tissues, phosphatidylinositol is the primary source of the arachidonic acid required for biosynthesis of eicosanoids, including prostaglandins, via the action of the enzyme phospholipase A2. Phosphatidylinositol can be phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated by a specific kinase. Seven different isomers are known, but the most important in both quantitative and biological terms are phosphatidylinositol 4-phosphate and phosphatidylinositol 4,5-bisphosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes.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. PIs contain almost exclusively stearic acid at carbon 1 and arachidonic acid at carbon 2. PIs composed exclusively of non-phosphorylated inositol exhibit a net charge of -1 at physiological pH. Molecules with phosphorylated inositol (such as PIP, PIP2, PIP3, etc.) are termed polyphosphoinositides. The polyphosphoinositides are important intracellular transducers of signals emanating from the plasma membrane. The synthesis of PI involves CDP-activated 1,2-diacylglycerol condensation with myo-inositol.
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 PI(18:1(9Z)/18:1(9Z)) concentration: decrease (FC = 0.19)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Lung cancer [ICD-11: 2C25]
                      Details It is reported that overexpression of KRAS leads to the decrease of PI(18:1(9Z)/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.

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