Structure Database (LMSD)
Common Name
PC(O-16:0/2:0)
Systematic Name
1-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine
Synonyms
- PAF
- Platelet-activating factor
- 1-O-Hexadecyl-2-acetyl-sn-glyceryl-3-phosphorylcholine
- 1-O-Hexadecyl-2-O-acetyl-sn-glycero-3-phosphocholine
- 1-O-Hexadecyl-2-O-acetyl-sn-glyceryl-3-phosphorylcholine
- 1-O-Hexadecyl-platelet-activating factor
- Blood platelet-activating factor
- Blood platelet-activating factor acether
- C16-PAF
- C16-PAF acether
- PAF
- PAF acether
- Platelet-activating factor
- Platelet-activating factor acether
- PC(O-18:0)
- PC(O-16:0/2:0)
LM ID
LMGP01020046
Formula
Exact Mass
Calculate m/z
523.363792
Sum Composition
Abbrev Chains
PC O-16:0/2:0
Status
Curated
3D model of PC(O-16:0/2:0)
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
PAF C-16 is a naturally occurring phospholipid produced upon stimulation through two distinct pathways known as the “remodeling” and 'de novo' pathways.1 It is a potent mediator of neutrophil migration,2 and the production of reactive oxygen species, and IL-6 in human macrophages.3,4 It is a more potent mediator of platelet aggregation than PAF C-18.5 Pathological processes involving PAF include necrotizing enterocolitis,6 inflammation, asthma, and allergy.7
This information has been provided by Cayman Chemical
References
2. Rouis, M., Nigon, F., and Chapman, M.J. Platelet activating factor is a potent stimulant of the production of active oxygen species by human monocyte-derived macrophages. Biochem. Biophys. Res. Commun. 156(3), 1293-1301 (1988).
3. Prescott, S.M., Zimmerman, G.A., and McIntyre, T.M. Platelet-activating factor. The Journal of Biological Chemisty 265(29), 17381-17384 (1990).
4. Carolan, E.J., and Casale, T.B. Degree of platelet activating factor-induced neutrophil migration is dependent upon the molecular species. J. Immunol. 145(8), 2561-2565 (1990).
5. Thivierge, M., and Rola-Pleszczynski, M. Platelet-activating factor enhances interleukin-6 production by alveolar macrophages. J. Allergy Clin. Immunol. 90(5), 796-802 (1992).
6. 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).
7. 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).
Reactions
Filter by species:
ⓘ
Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
Click on an edge to display the reaction(s).
String Representations
InChiKey (Click to copy)
HVAUUPRFYPCOCA-AREMUKBSSA-N
InChi (Click to copy)
InChI=1S/C26H54NO7P/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-21-31-23-26(34-25(2)28)24-33-35(29,30)32-22-20-27(3,4)5/h26H,6-24H2,1-5H3/t26-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(C)=O)COCCCCCCCCCCCCCCCC
Other Databases
LIPIDAT ID
7359
HMDB ID
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID
PDB ID
GuidePharm ID
Calculated Physicochemical Properties
Heavy Atoms
35
Rings
0
Aromatic Rings
0
Rotatable Bonds
26
Van der Waals Molecular Volume
548.08
Topological Polar Surface Area
94.12
Hydrogen Bond Donors
0
Hydrogen Bond Acceptors
8
logP
7.33
Molar Refractivity
142.06
Admin
Created at
-
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.
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.