Structure Database (LMSD)
Common Name
PC(O-16:0/20:4(5Z,8Z,11Z,14Z))
Systematic Name
1-hexadecyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine
Synonyms
- 1-O-Hexadecyl-2-arachidonoyl-sn-glycero-3-phosphocholine
- PC(O-16:0/20:4)
- PC(O-36:4)
- PC(O-16:0/20:4)
LM ID
LMGP01020056
Formula
Exact Mass
Calculate m/z
767.582891
Sum Composition
Abbrev Chains
PC O-16:0/20:4
Status
Curated
3D model of PC(O-16:0/20:4(5Z,8Z,11Z,14Z))
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
1-O-hexadecyl-2-Arachidonoyl-sn-glycero-3-PC is the product of acylation of lyso-PAF C-16 by a CoA-independent transacylase.1,2 It is the most common precursor for formation of PAF C-16 by the remodeling pathway.3
This information has been provided by Cayman Chemical
References
1. Kramer, R.M., Patton, G.M., Pritzker, C.R., et al. Metabolism of platelet-activating factor in human platelets. The Journal of Biological Chemisty 259, 13316-13320 (1984).
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., 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).
Reactions
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References
String Representations
InChiKey (Click to copy)
DUUSFCFZBREELS-WWBBCYQPSA-N
InChi (Click to copy)
InChI=1S/C44H82NO7P/c1-6-8-10-12-14-16-18-20-22-23-24-25-27-29-31-33-35-37-44(46)52-43(42-51-53(47,48)50-40-38-45(3,4)5)41-49-39-36-34-32-30-28-26-21-19-17-15-13-11-9-7-2/h14,16,20,22,24-25,29,31,43H,6-13,15,17-19,21,23,26-28,30,32-42H2,1-5H3/b16-14-,22-20-,25-24-,31-29-/t43-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)COCCCCCCCCCCCCCCCC
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
53
Rings
0
Aromatic Rings
0
Rotatable Bonds
40
Van der Waals Molecular Volume
848.92
Topological Polar Surface Area
94.12
Hydrogen Bond Donors
0
Hydrogen Bond Acceptors
8
logP
13.46
Molar Refractivity
224.79
Admin
Created at
-
Updated at
20th Dec 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.
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.