Structure Database (LMSD)

Common Name
PC(16:0/0:0)
Systematic Name
1-hexadecanoyl-sn-glycero-3-phosphocholine
Synonyms
  • LPC(16:0/0:0)
  • LPC(16:0)
  • 16:0 LYSO-PC
  • 1-palmitoyl-phosphatidylcholine
LM ID
LMGP01050018
Formula
C24H50NO7P
Exact Mass
Calculate m/z
495.332492
Sum Composition
LPC 16:0
Abbrev Chains
LPC 16:0
Status
Curated
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Classification

Category
Main Class
Sub Class
Glycerophospholipids [GP]
Glycerophosphocholines [GP01]
Monoacylglycerophosphocholines [GP0105]

Biological Context

1-Palmitoyl-2-hydroxy-sn-glycero-3-PC is the ubiquitous lipid species generated following phospholipase A2 (PLA2) hydrolysis of phosphatidylcholine.1 It increases the production of reactive oxygen species (ROS) and decreases superoxide dismutase (SOD) and endothelial nitric oxide synthase (eNOS) protein levels and phosphorylation of ERK1/2 in human umbilical vein endothelial cells (HUVECs) when used at a concentration of 125 µM.2 1-Palmitoyl-2-hydroxy-sn-glycero-3-PC potentiates the secretion of IL-6, IL-1β, IL-12, and TNF-α in LPS-stimulated M1 macrophages, but has no effect on CD163, CD206, CD36, or IL-10 in LPS-stimulated M2 macrophages when used at concentrations of 0.3 and 1.0 µM.3 It increases TGF-β1 production and enhances Foxp3 protein levels in Treg cells in isolated human peripheral blood when used at a concentration of 10 µM.4 1-Palmitoyl-2-hydroxy-sn-glycero-3-PC enhances neutrophil function, bacterial clearance, and survival in mouse models of sepsis when administered at a dose of 10 mg/kg.5

This information has been provided by Cayman Chemical

References

1. Hasegawa, H., Lei, J., Matsumoto, T., et al. Lysophosphatidylcholine enhances the suppressive function of human naturally occurring regulatory T cells through TGF-β production. Biochem. Biophys. Res. Commun. 415(3), 526-531 (2011).
2. Qin, X., Qiu, C., and Zhao, L. Lysophosphatidylcholine perpetuates macrophage polarization toward classically activated phenotype in inflammation. Cell. Immunol. 289(1-2), 185-190 (2014).
3. Choi, S., Park, S., Liang, G.H., et al. Superoxide generated by lysophosphatidylcholine induces endothelial nitric oxide synthase downregulation in human endothelial cells. Cell Physiol. Biochem. 25(2-3), 233-240 (2010).
4. Yan, J.-J., Jung, J.-S., Lee, J.-E., et al. Therapeutic effects of lysophosphatidylcholine in experimental sepsis. Nat. Med. 10(2), 161-167 (2004).
5. Balsinde, J., Winstead, M.V., and Dennis, E.A. Phospholipase A2 regulation of arachidonic acid mobilization. FEBS Lett. 531(1), 2-6 (2002).

Reactions

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String Representations

InChiKey (Click to copy)
ASWBNKHCZGQVJV-HSZRJFAPSA-N
InChi (Click to copy)
InChI=1S/C24H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)30-21-23(26)22-32-33(28,29)31-20-19-25(2,3)4/h23,26H,5-22H2,1-4H3/t23-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(O)COC(CCCCCCCCCCCCCCC)=O

Other Databases

LIPIDAT ID
11815
HMDB ID
HMDB0010382
CHEBI ID
72998
PubChem CID
460602
SwissLipids ID
SLM:000000556
Cayman ID
10172

Calculated Physicochemical Properties

Heavy Atoms 33
Rings 0
Aromatic Rings 0
Rotatable Bonds 24
Van der Waals Molecular Volume 513.48
Topological Polar Surface Area 105.12
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 8
logP 6.01
Molar Refractivity 132.16

Admin

Created at
-
Updated at
9th Jun 2022
LIPID MAPS® abbreviations for glycerophospholipids (GP)

The LIPID MAPS® glycerophospholipid abbreviations (PC, PE, etc.) are used here to refer to species with one or two radyl side-chains where the structures of the side chains are indicated within parentheses in the 'Headgroup(sn1/sn2)' format (e.g. PC(16:0/18:1(9Z)). By default, R stereochemistry at the C-2 carbon of glycerol and attachment of the headgroup at the sn3 position is assumed. Also, acyl chains are assumed by default. The 'O-' prefix is used to indicate the presence of an alkyl ether substituent e.g. PC(O-16:0/18:1(9Z)), whereas the 'P-' prefix is used for the 1Z-alkenyl ether (Plasmalogen) substituent e.g. PC(P-16:0/18:1(9Z)).

For molecules with opposite (S) stereochemistry at C2 of the glycerol group and attachment of the headgroup at the sn1 position, the stereochemistry specification of [S] is appended to the abbreviation. The 'Headgroup(sn3/sn2)' abbreviation format is used.

For molecules with unknown stereochemistry at the C-2 carbon of the glycerol group, the stereochemistry specification of [U] is appended to the abbreviation and the structure is drawn with C-2 stereochemistry unspecified.