Structure Database (LMSD)
Common Name
PC(O-16:0/4:0)
Systematic Name
1-hexadecyl-2-butyryl-sn-glycero-3-phosphocholine
Synonyms
- PC(O-20:0)
- PC(O-16:0/4:0)
LM ID
LMGP01020072
Formula
Exact Mass
Calculate m/z
551.395092
Sum Composition
Abbrev Chains
PC O-16:0/4:0
Status
Curated
3D model of PC(O-16:0/4:0)
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
Oxidized low-density lipoprotein (oxLDL) particles contain low molecular weight species which promote the differentiation of monocytes and activate polymorphonuclear leukocytes.1 One of these substances was recently isolated and purified from oxLDL, and identified as azelaoyl PC.2 Butanoyl PAF is a closely related compound which retains at least 10% of the agonist potency of platelet-activating factor (PAF) itself.3 Further, butanoyl PAF is present in oxLDL in amounts more than 100 times greater than enzymatically generated PAF. Butanoyl PAF is therefore one of the important signalling molecules present in oxLDL.
This information has been provided by Cayman Chemical
References
2. Marathe, G.K., Davies, S.S., Harrison, K.A., et al. Inflammatory platelet-activating factor-like phospholipids in oxidized low density lipoproteins are fragmented alkyl phosphatidylcholines. The Journal of Biological Chemisty 274(40), 28395-28404 (1999).
3. Davies, S.S., Pontsler, A.V., Marathe, G.K., et al. Oxidized alkyl phospholipids are specific, high affinity peroxisome proliferator-activated receptor γ ligands and agonists. The Journal of Biological Chemisty 276(19), 16015-16023 (2001).
Reactions
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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.
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String Representations
InChiKey (Click to copy)
UVHUBDICYDPLIO-HHHXNRCGSA-N
InChi (Click to copy)
InChI=1S/C28H58NO7P/c1-6-8-9-10-11-12-13-14-15-16-17-18-19-20-23-33-25-27(36-28(30)21-7-2)26-35-37(31,32)34-24-22-29(3,4)5/h27H,6-26H2,1-5H3/t27-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCC)=O)COCCCCCCCCCCCCCCCC
Other Databases
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
-
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.