Structure Database (LMSD)

Common Name
PC(O-18:0/2:0)
Systematic Name
1-octadecyl-2-acetyl-sn-glycero-3-phosphocholine
Synonyms
  • PAF
  • Platelet-activating factor
  • 1-O-Octadecyl-2-acetyl-sn-glyceryl-3-phosphorylcholine
  • 1-O-Octadecyl-platelet-activating factor
  • 1-O-Stearoyl-2-acetyl-sn-glyceryl-3-phosphorylcholine
  • Blood platelet activating factor-acether
  • Blood platelet-activating factor
  • C18-PAF
  • C18-PAF-acether
  • PAF
  • PAF acether
  • Platelet activating factor-acether
  • Platelet-activating factor
  • Ro 14-8161
  • PC(O-20:0)
  • PC(O-18:0/2:0)
LM ID
LMGP01020094
Formula
C28H58NO7P
Exact Mass
Calculate m/z
551.395092
Sum Composition
PC O-20:0
Abbrev Chains
PC O-18:0/2:0
Status
Curated
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Classification

Category
Main Class
Sub Class
Glycerophospholipids [GP]
Glycerophosphocholines [GP01]
1-alkyl,2-acylglycerophosphocholines [GP0102]

Biological Context

PAF C-18 is a naturally occurring phospholipid produced upon stimulation through two distinct pathways known as the “remodeling” and 'de novo' pathways.1 It is less potent than PAF C-16 in the induction of platelet aggregation, but equipotent in activation of guinea pig macrophages.2 PAF C-18 induces the release of PGE2 and TXB2 from albumin-elicited guinea pig macrophages, and enhances the spreading of plated macrophages.3 Pathological processes involving PAF include necrotizing enterocolitis,4 inflammation, asthma, and allergy.5

This information has been provided by Cayman Chemical

References

1. Wang, H., Tan, X.D., Qu, X.W., et al. Platelet-activating factor (PAF) up-regulates plasma and tissue PAF-acetylhydrolase activity in the rat: Effect of cycloheximide. Pediatr. Res. 42(5), 597-603 (1997).
2. Stewart, A.G., and Grigoriadis, G. Structure-activity relationships for platelet-activating factor (PAF) and analogs reveal differences between PAF receptors on platelets and macrophages. J. Lipid Mediat. 4(3), 299-308 (1991).
3. Prescott, S.M., Zimmerman, G.A., and McIntyre, T.M. Platelet-activating factor. J. Biol. Chem. 265(29), 17381-17384 (1990).
4. Hartung, H.P. Acetyl glyceryl ether phosphorylcholine (platelet-activating factor) mediates heightened metabolic activity in macrophages. Studies on PGE, TXB2 and O2 production, spreading, and the influence of calmodulin-inhibitor W-7. FEBS Lett. 160, 209-212 (1983).
5. Sturk, A., Wouter Ten Cate, J., Hosford, D., et al. The synthesis, catabolism, and pathophysiological role of platelet-activating factor. Adv. Lipid. Res. 23, 219-276 (1989).

Reactions

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String Representations

InChiKey (Click to copy)
ZXCIEWBDUAPBJF-MUUNZHRXSA-N
InChi (Click to copy)
InChI=1S/C28H58NO7P/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-23-33-25-28(36-27(2)30)26-35-37(31,32)34-24-22-29(3,4)5/h28H,6-26H2,1-5H3/t28-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(C)=O)COCCCCCCCCCCCCCCCCCC

Other Databases

LIPIDAT ID
5800
CHEBI ID
52450
PubChem CID
2733535
SwissLipids ID
SLM:000000694
Cayman ID
60910

Calculated Physicochemical Properties

Heavy Atoms 37
Rings 0
Aromatic Rings 0
Rotatable Bonds 28
Van der Waals Molecular Volume 582.68
Topological Polar Surface Area 94.12
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 8
logP 8.11
Molar Refractivity 151.29

Admin

Created at
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Updated at
25th Apr 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.