Structure Database (LMSD)

Common Name
PC(16:0/5:0(COOH))
Systematic Name
1-hexadecanoyl-2-glutaroyl-sn-glycero-3-phosphocholine
Synonyms
  • 1-Palmitoyl-2-glutaroyl-sn-glycero-3-phosphorylcholine
  • PGPC
LM ID
LMGP20010006
Formula
C29H56NO10P
Exact Mass
Calculate m/z
609.364187
Sum Composition
PC 21:1;O2
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Glycerophospholipids [GP]
Oxidized glycerophospholipids [GP20]
Oxidized glycerophosphocholines [GP2001]
Glycerophosphocholines [GP01]
Diacylglycerophosphocholines [GP0101]

Biological Context

PGPC is an oxidized phospholipid that can be formed under conditions of oxidative stress.1 It is found as a component in mildly oxidized LDL (MM-LDL) and in products formed from the oxidation of 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine (Ox-PAPC).2 PGPC activates peroxisome proliferator-activated receptor (PPARα) in a concentration-dependent manner in a cell-based ligand-binding assay.3 It increases VCAM1 and E-selectin expression in human aortic endothelial cells (HAECs), as well as HAEC binding by monocytes and polymorphonuclear neutrophils (PMNs), in a concentration-dependent manner.4 PGPC (37.5 μM) also increases total 5-lipoxygenase metabolites in murine resident peritoneal macrophages (RPMs) and induces apoptosis in A7r5 rat aortic smooth muscle cells in vitro when used at a concentration of 50 μM.5,6 PGPC levels are increased in the serum, LDL, and peripheral blood mononuclear cells (PBMCs) of patients with coronary artery disease.7 UVA irradiation increases PGPC levels in cultured human skin fibroblasts.8

This information has been provided by Cayman Chemical

References

1. Watson, A.D., Leitinger, N., Navab, M., et al. Structural identification by mass spectrometry of oxidized phospholipids in minimally oxidized low density lipoprotein that induce monocyte/endothelial interactions and evidence for their presence in vivo. The Journal of Biological Chemisty 272(21), 13597-13607 (1997).
2. Leitinger, N., Tyner, T.R., Oslund, L., et al. Structurally similar oxidized phospholipids differentially regulate endothelial binding of monocytes and neutrophils. Proc. Natl. Acad. Sci. USA 96(21), 12010-12015 (1999).
3. Fruhwirth, G.O., Loidl, A., and Hermetter, A. Oxidized phospholipids: From molecular properties to disease. Biochim. Biophys. Acta 1772, 718-736 (2007).
4. Zemski Berry, K.A., and Murphy, R.C. Phospholipid ozonation products activate the 5-lipoxygenase pathway in macrophages. Chem. Res. Toxicol. 29(8), 1355-1364 (2016).
5. Fruhwirth, G.O., Moumtzi, A., Loidl, A., et al. The oxidized phospholipids POVPC and PGPC inhibit growth and induce apoptosis in vascular smooth muscle cells. Biochim. Biophys. Acta 1761(9), 1060-1069 (2006).
6. Mozzini, C., Frata Pasini, A., Garbin, U., et al. Increased endoplasmic reticulum stress and Nrf2 repression in peripheral blood mononuclear cells of patients with stable coronary artery disease. Free Radic. Biol. Med. 68, 178-185 (2014).
7. Gruber, F., Bicker, W., Oskolkova, O.V., et al. A simplified procedure for semi-targeted lipidomic analysis of oxidized phosphatidylcholines induced by UVA irradiation. J. Lipid. Res. 53(6), 1232-1242 (2012).
8. Lee, H., Shi, W., Tontonoz, P., et al. Role for peroxisome proliferator-activated receptor α in oxidized phospholipid-induced synthesis of monocyte chemotactic protein-1 and interleukin-8 by endothelial cells. Circ. Res. 87(6), 516-521 (2000).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Oryctolagus cuniculus (#9986)
Mammalia (#40674)
Structural identification by mass spectrometry of oxidized phospholipids in minimally oxidized low density lipoprotein that induce monocyte/endothelial interactions and evidence for their presence in vivo.,
J Biol Chem, 1997
Pubmed ID: 9153208

String Representations

InChiKey (Click to copy)
CDZVJFRXJAUXPP-AREMUKBSSA-N
InChi (Click to copy)
InChI=1S/C29H56NO10P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-20-28(33)37-24-26(40-29(34)21-18-19-27(31)32)25-39-41(35,36)38-23-22-30(2,3)4/h26H,5-25H2,1-4H3,(H-,31,32,35,36)/t26-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCCC(O)=O)=O)COC(CCCCCCCCCCCCCCC)=O

Other Databases

CHEBI ID
61822
PubChem CID
46907872
SwissLipids ID
SLM:000389543
Cayman ID
10044

Calculated Physicochemical Properties

Heavy Atoms 41
Rings 0
Aromatic Rings 0
Rotatable Bonds 30
Van der Waals Molecular Volume 621.07
Topological Polar Surface Area 148.49
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 11
logP 6.81
Molar Refractivity 157.52

Admin

Created at
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Updated at
8th Nov 2024
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.