General Information of MET (ID: META00757)
Name LysoPC(0:0/16:0)
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(2R)-3-Hydroxy-2-(palmitoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate; (2R)-3-Hydroxy-2-(palmitoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphoric acid; 2-Hexadecanoyl-sn-glycero-3-phosphocholine; 2-Hexadecanoylglycerophosphocholine; 2-Palmitoyl-GPC; 2-Palmitoyl-lysophosphatidylcholine; 2-Palmitoyl-sn-glycero-3-phosphocholine; 2-Palmitoylglycerophosphocholine; 2-Palmitoyllysophosphatidylcholine; GPC(0:0/16:0); GPC(16:0); LPC(0:0/16:0); LPC(16:0); LysoPC(0:0/16:0); LysoPC(16:0); Lysophosphatidylcholine(0:0/16:0); Lysophosphatidylcholine(16:0); PC(0:0/16:0)
Source Aliphatic acyclic compounds
Structure Type   Glycerophosphocholines  (Click to Show/Hide the Complete Structure Type Hierarchy)
Lipids and lipid-like molecules
Glycerophospholipids
Glycerophosphocholines
PubChem CID
15061532
HMDB ID
HMDB0240262
Formula
C24H50NO7P
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
76078
ChemSpider ID
21403165
Physicochemical Properties Molecular Weight 495.6 Topological Polar Surface Area 105
XlogP 5.6 Complexity 517
Heavy Atom Count 33 Rotatable Bond Count 24
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 7
Function
LysoPC(0:0/16:0) is a lysophosphatidylcholine, which is a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2 as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. There is also a phospholipase A1, which is able to cleave the sn-1 ester bond. Lysophosphatidylcholine has pro-inflammatory properties in vitro and it is known to be a pathological component of oxidized lipoproteins (LDL) in plasma and of atherosclerotic lesions. Recently, it has been found to have some functions in cell signalling, and specific receptors (coupled to G proteins) have been identified. It activates the specific phospholipase C that releases diacylglycerols and inositol triphosphate with resultant increases in intracellular Ca2+ and activation of protein kinase C. It also activates the mitogen-activated protein kinase in certain cell types. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. LysoPC(0:0/16:0), in particular, consists of one chain of palmitic acid at the C-2 position.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Group 3 secretory phospholipase A2 (PLA2G3) 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 Pla2g3
                      Induced Change LysoPC(0:0/16:0) concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colorectal cancer [ICD-11: 2B91]
                      Details It is reported that knockout of Pla2g3 leads to the decrease of lysoPC(0:0/16:0) levels compared with control group.
            Sulfatase sulf-1 (SULF1) 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 [2]
                      Introduced Variation Knockdown (shRNA) of SULF1
                      Induced Change LysoPC(0:0/16:0) concentration: decrease (FC = 0.51)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Ovarian cancer [ICD-11: 2C73]
                      Details It is reported that knockdown of SULF1 leads to the decrease of lysoPC(0:0/16:0) levels compared with control group.
References
1 Group III phospholipase A 2 promotes colitis and colorectal cancer. Sci Rep. 2017 Sep 25;7(1):12261.
2 Erratum to: Loss of HSulf-1 promotes altered lipid metabolism in ovarian cancer. Cancer Metab. 2014 Nov 4;2:24.

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