Structure Database (LMSD)
Common Name
PON-PC
Systematic Name
1-hexadecanoyl-2-(9-oxo-nonanoyl)-sn-glycero-3-phosphocholine
Synonyms
- 1-palmitoyl-2-(9-oxo-nonanoyl)-sn-glycero-3-phosphocholine
LM ID
LMGP20010008
Formula
Exact Mass
Calculate m/z
649.431872
Sum Composition
Status
Curated
3D model of PON-PC
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
PON-PC is an oxidized phospholipid containing a truncated 9-carbon fatty acyl chain terminating in an aldehyde at the sn-2 position.1,2 It is a component of oxidized LDL formed by oxidation of palmitoyl oleoyl phosphatidylcholine (POPC) and can also be formed via a reaction with ozone in pulmonary surfactant.1,2,3 PON-PC decreases the production of TNF-α, nitric oxide (NO), and NADP+ in primary mouse alveolar macrophages, as well as reduces the bactericidal activity of RAW 264.7 cells, when used at a concentration of 40 µM.1 Bronchoalveolar lavage fluid (BALF) levels of PON-PC are elevated in mice exposed to cigarette smoke and in aged mice.2,4
This information has been provided by Cayman Chemical
References
1. Ke, Y., Karki, P., Kim, J., et al. Elevated truncated oxidized phospholipids as a factor exacerbating ALI in the aging lungs. FASEB J. 33(3), 3887-3900 (2019).
String Representations
InChiKey (Click to copy)
PPTNNIINSOQWCE-WJOKGBTCSA-N
InChi (Click to copy)
InChI=1S/C33H64NO9P/c1-5-6-7-8-9-10-11-12-13-14-15-18-21-24-32(36)40-29-31(30-42-44(38,39)41-28-26-34(2,3)4)43-33(37)25-22-19-16-17-20-23-27-35/h27,31H,5-26,28-30H2,1-4H3/t31-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCCCCCCC([H])=O)=O)COC(CCCCCCCCCCCCCCC)=O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
44
Rings
0
Aromatic Rings
0
Rotatable Bonds
34
Van der Waals Molecular Volume
681.48
Topological Polar Surface Area
128.26
Hydrogen Bond Donors
0
Hydrogen Bond Acceptors
10
logP
8.49
Molar Refractivity
174.42
Admin
Created at
-
Updated at
8th Nov 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.