General Information of MET (ID: META00588)
Name LysoPC(16:0/0:0)
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(2R)-2-Hydroxy-3-(hexadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate; (2R)-2-Hydroxy-3-(hexadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphoric acid; 1-16:0-LysoPC; 1-16:0-Lysophosphatidylcholine; 1-Hexadecanoyl-2-lysophosphatidylcholine; 1-Hexadecanoyl-3-glycerophosphorylcholine; 1-Hexadecanoyl-glycero-3-phosphocholine; 1-Hexadecanoyl-sn-glycero-3-phosphocholine; 1-Hexadecanoyl-sn-glycerol-3-phosphorylcholine; 1-Hexadecanoylglycerophosphocholine; 1-Hexadecanoyllysolecithin; 1-Hexadecyl-sn-glycero-3-phosphocholine; 1-O-Hexadecylpropanediol 3-phosphorylcholine; 1-O-Palmitoyl-2-lyso-sn-glycero-3-phosphocholine; 1-O-Palmitoyl-sn-glycero-3-phosphocholine; 1-O-Palmitoyl-sn-glyceryl-3-phosphorylcholine; 1-Palmitoyl-2-hydroxy-sn-glycero-3-phosphocholine; 1-Palmitoyl-2-lyso-sn-glycero-3-phosphocholine; 1-Palmitoyl-2-lysophosphatidylcholine; 1-Palmitoyl-3-glycerylphosphorylcholine; 1-Palmitoyl-GPC; 1-Palmitoyl-GPC (16:0); 1-Palmitoyl-glycero-3-phosphocholine; 1-Palmitoyl-lysophosphatidylcholine; 1-Palmitoyl-phosphatidylcholine; 1-Palmitoyl-sn-glycero-3-phosphocholine; 1-Palmitoyl-sn-glycero-3-phosphorylcholine; 1-Palmitoyl-sn-glycerol-3-phosphatidylcholine; 1-Palmitoyl-sn-glycerol-3-phosphocholine; 1-Palmitoyl-sn-glycerol-3-phosphorylcholine; 1-Palmitoylglycerol-3-phosphorylcholine; 1-Palmitoylglycerophosphocholine; 1-Palmitoyllecithin; 1-Palmitoyllysolecithin; 1-Palmitoyllysophosphatidylcholine; 1-Palmitoylphosphatidylcholine; 1-Pam-2-lysoptdcho; 16:0 LYSO-PC; C(16)-Lysophosphatidylcholine; GPC(16:0); GPC(16:0/0:0); GPCho 16:0/0:0; GPCho(16:0/0:0); Hydroxide inner salt(+-)-isomer OF we 201; Hydroxide inner salt(R)-isomer OF we 201; Hydroxide inner salt(S)-isomer OF we 201; L-Palmitoyllysolecithin; L-alpha-Lysopalmitoylphosphatidylcholine; LPC 16:0/0:0; LPC(16:0); LPC(16:0/0:0); LYSO-PC; LyPC(16:0); LyPC(16:0/0:0); LysoPC 16:0/0:0; LysoPC a C16:0; LysoPC(16:0); LysoPC(16:0/0:0); Lysophosphatidylcholine C16:0; Lysophosphatidylcholine(16:0); Lysophosphatidylcholine(16:0/0:0); MPPC; PC(16:0/0:0); Palmitoyl L-alpha-lysolecithin; Palmitoyl L-alpha-lysophosphatidylcholine; Palmitoyl lysophosphatidylcholine; Palmitoyllysolecithin; Palmitoyllysophosphatidyl choline
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
460602
HMDB ID
HMDB0010382
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
KEGG ID
C04230
ChEBI ID
72998
FooDB ID
FDB027533
ChemSpider ID
405287
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(16:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(16:0), in particular, consists of one chain of palmitic acid at the C-1 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. 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. In blood plasma significant amounts of lysophosphatidylcholine are formed by a specific enzyme system, lecithin:cholesterol acyltransferase (LCAT), which is secreted from the liver. The enzyme catalyzes the transfer of the fatty acids of position sn-2 of phosphatidylcholine to the free cholesterol in plasma, with formation of cholesterol esters and lysophosphatidylcholine. Lysophospholipids have a role in lipid signaling by acting on lysophospholipid receptors (LPL-R). LPL-R's are members of the G protein-coupled receptor family of integral membrane proteins.
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 LysoPC(16:0/0:0) concentration: decrease (FC = 0.63)
                      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 lysoPC(16:0/0:0) levels compared with control group.
      Pore-forming PNC peptide (PNC)
            Cellular tumor antigen p53 (TP53) 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 Knockout of TP53
                      Induced Change LysoPC(16:0/0:0) concentration: decrease (Log2 FC=0.42)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colon cancer [ICD-11: 2B90]
                      Details It is reported that knockout of TP53 leads to the decrease of lysoPC(16:0/0:0) 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.
2 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.

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