Structure Database (LMSD)
Common Name
PC(O-18:0/0:0)
Systematic Name
1-octadecyl-sn-glycero-3-phosphocholine
Synonyms
- 1-O-Octadecyl-sn-glycero-3-phosphocholine
- 1-O-Octadecylglycerol-3-phosphatidylcholine
- Lyso-platelet-activating factor
- Ro 14-8160
- LPC(O-18:0)
- LPC(O-18:0)
LM ID
LMGP01060014
Formula
Exact Mass
Calculate m/z
509.384527
Sum Composition
Abbrev Chains
LPC O-18:0
Status
Curated
3D model of PC(O-18:0/0:0)
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
Lyso-PAF C-18 can be formed by either the action of PAF-AH on PAF C-181 or by the action of a CoA-independent transacylase on 1-O-octadecyl-2-acyl-glycerophosphocholine.2,3 Lyso PAF C-18 is a substrate for either PAF C-18 formation by the remodeling pathway4 or selective acylation with arachidonic acid by a CoA-independent transacylase.5
This information has been provided by Cayman Chemical
References
1. Uemura, Y., Lee, T., and Snyder, F. A coenzyme A-independent transacylase is linked to the formation of platelet-activating factor (PAF) by generating the lyso-PAF intermediate in the remodeling pathway. The Journal of Biological Chemisty 266(13), 8268-8272 (1991).
2. Prescott, S.M., Zimmerman, G.A., and McIntyre, T.M. Platelet-activating factor. The Journal of Biological Chemisty 265(29), 17381-17384 (1990).
3. Venable, M.E., Nieto, M.L., Schmitt, J.D., et al. Conversion of 1-O-[3H]alkyl-2-arachidonoyl-sn-glycero-3-phosphorylcholine to lyso platelet-activating factor by the CoA-independent transacylase in membrane fractions of human neutrophils. The Journal of Biological Chemisty 266(28), 18691-18698 (1991).
4. Venable, M.E., Olson, S.C., Nieto, M.L., et al. Enzymatic studies of lyso platelet-activation factor acylation in human neutrophils and changes upon stimulation. The Journal of Biological Chemisty 268(11), 7965-7975 (1993).
5. Stafforini, D.M., Prescott, S.M., and McIntyre, T.M. Human plasma platelet-activating factor acetylhydrolase. The Journal of Biological Chemisty 262(9), 4223-4230 (1987).
Reactions
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String Representations
InChiKey (Click to copy)
XKBJVQHMEXMFDZ-AREMUKBSSA-N
InChi (Click to copy)
InChI=1S/C26H56NO6P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-22-31-24-26(28)25-33-34(29,30)32-23-21-27(2,3)4/h26,28H,5-25H2,1-4H3/t26-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(O)COCCCCCCCCCCCCCCCCCC
Other Databases
LIPIDAT ID
5799
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID
Calculated Physicochemical Properties
Heavy Atoms
34
Rings
0
Aromatic Rings
0
Rotatable Bonds
26
Van der Waals Molecular Volume
541.93
Topological Polar Surface Area
88.05
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
7
logP
7.54
Molar Refractivity
141.74
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.