Structure Database (LMSD)
Common Name
PKODiA-PC
Systematic Name
1-hexadecanoyl-2-(5-oxo-7-carboxy-6E-heptenoyl)-sn-glycero-3-phosphocholine
Synonyms
- 1-palmitoyl-2-(5-oxo-7-carboxy-6E-heptenoyl)-sn-glycero-3-phosphocholine
LM ID
LMGP20010013
Formula
Exact Mass
Calculate m/z
663.374752
Sum Composition
Status
Curated
3D model of PKODiA-PC
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
1-(Palmitoyl)-2-(5-keto-6-octene-dioyl) phosphatidylcholine, or KOdiA-PC, is one of the most potent CD36 ligands among the oxLDL species.1 KOdiA-PC confers CD36 scavenger receptor binding affinity to LDL at a frequency of only 2 to 3 KOdiA-PC molecules/LDL particle, and may be one of the more important structural determinants of oxLDL.
This information has been provided by Cayman Chemical
References
1. Podrez, E.A., Poliakov, E., Shen, Z., et al. Identification of a novel family of oxidized phospholipids that serve as ligands for the macrophage scavenger receptor CD36. The Journal of Biological Chemisty 277(41), 38503-38516 (2002).
References
String Representations
InChiKey (Click to copy)
PEZXEQJZQAVYCZ-NLMPBQEBSA-N
InChi (Click to copy)
InChI=1S/C32H58NO11P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-20-31(37)41-26-29(27-43-45(39,40)42-25-24-33(2,3)4)44-32(38)21-18-19-28(34)22-23-30(35)36/h22-23,29H,5-21,24-27H2,1-4H3,(H-,35,36,39,40)/b23-22+/t29-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCCC(=O)/C=C/C(=O)O)=O)COC(CCCCCCCCCCCCCCC)=O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
45
Rings
0
Aromatic Rings
0
Rotatable Bonds
32
Van der Waals Molecular Volume
676.48
Topological Polar Surface Area
165.56
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
12
logP
6.94
Molar Refractivity
171.67
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.