Details of Metabolite

General Information of MET (ID: META00490)
Name LysoPC(18:1(9Z))
Synonyms   Click to Show/Hide Synonyms of This Metabolite
1-(9Z)-Octadecenoyl-sn-glycero-3-phosphocholine; 1-(9Z-Octadecenoyl)-glycero-3-phosphocholine; 1-(9Z-Octadecenoyl)-sn-glycero-3-phosphocholine; 1-(cis-9-Octadecenoyl)-sn-glycero-3-phosphocholine; 1-O-Oleoyl-sn-glycero-3-phosphocholine; 1-OGPC; 1-Oleoyl lysophosphatidylcholine; 1-Oleoyl-2-hydroxy-sn-glycero-3-phosphocholine; 1-Oleoyl-2-hydroxy-sn-glycerol-3-phosphocholine; 1-Oleoyl-GPC; 1-Oleoyl-glycero-3-phosphocholine; 1-Oleoyl-lysopc; 1-Oleoyl-lysophosphatidylcholine; 1-Oleoyl-sn-glycero-3-phosphocholine; 1-Oleoyl-sn-glycero-3-phosphorylcholine; 1-Oleoyl-sn-glycerol-3-phosphatidylcholine; 1-Oleoyl-sn-glycerol-3-phosphorylcholine; 1-Oleoylglycerophosphocholine; 3-Oleoyl-rac-glycerol-1-phosphorylcholine; Choline phosphate (ester) 3-ester with 1-monoolein; Choline phosphate 3-ester with 1-monoolein; GPC(18:1(9Z)); GPC(18:1(9Z)/0:0); GPC(18:1); GPC(18:1W9); GPC(18:1W9/0:0); GPC(18:1n9); GPC(18:1n9/0:0); Gpcho(18:1(9Z)/0:0)[rac]; LPC 18:1; LPC 18:1(9Z)/0:0; LPC(18:1(9Z)); LPC(18:1(9Z)/0:0); LPC(18:1); LPC(18:1/0:0); LPC(18:1W9); LPC(18:1W9/0:0); LPC(18:1n9); LPC(18:1n9/0:0); LyPC(18:1); LyPC(18:1/0:0); LyPC(18:1W9/0:0); LysoPC 18:1(9Z)/0:0; LysoPC a C18:1; LysoPC(18:1(9Z)); LysoPC(18:1(9Z)/0:0); LysoPC(18:1); LysoPC(18:1/0:0); LysoPC(18:1W9); LysoPC(18:1W9/0:0); LysoPC(18:1n9); LysoPC(18:1n9/0:0); LysoPIC(18:1/0:0); Lysophosphatidylcholine 18:1; Lysophosphatidylcholine C18:1; Lysophosphatidylcholine(18:1(9Z)); Lysophosphatidylcholine(18:1(9Z)/0:0); Lysophosphatidylcholine(18:1); Lysophosphatidylcholine(18:1/0:0); Lysophosphatidylcholine(18:1W9); Lysophosphatidylcholine(18:1W9/0:0); Lysophosphatidylcholine(18:1n9); Lysophosphatidylcholine(18:1n9/0:0); Olein-1-mono-3-phosphate ester with choline; Oleoyl lysolecithin; Oleoyl lysophosphatidylcholine; PC 18:1(9Z)/0:0; PC(18:1(9Z)/0:0)
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
16081932
HMDB ID
HMDB0002815
Formula
C26H52NO7P
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
28610
FooDB ID
FDB005287
ChemSpider ID
17240641
Physicochemical Properties Molecular Weight 521.7 Topological Polar Surface Area 105
XlogP 5.7 Complexity 585
Heavy Atom Count 35 Rotatable Bond Count 25
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 7
Function
LysoPC(18:1(9Z)) 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(18:19Z)), in particular, consists of one chain of oleic acid at the C-1 position. The oleic acid moiety, an omega-9 fatty acid, is derived from various animal and vegetable sources such as olive oil, acai and grapeseed oil. 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(18:1(9Z)) concentration: increase (FC = 1.49)
                      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 lysoPC(18:1(9Z)) 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(18:1(9Z)) concentration: decrease (Log2 FC=0.49)
                      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(18:1(9Z)) levels compared with control group.
      Transcription factor (TF)
            R2R3-MYB (AN2) 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 [3]
                      Introduced Variation Overexpression of AN2
                      Induced Change LysoPC(18:1(9Z)) concentration: decrease (FC = 0.18)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of AN2 leads to the decrease of lysoPC(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.
2 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.
3 Comprehensive Influences of Overexpression of a MYB Transcriptor Regulating Anthocyanin Biosynthesis on Transcriptome and Metabolome of Tobacco Leaves. Int J Mol Sci. 2019 Oct 16;20(20):5123.

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