Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP20010050
Common NameP-LGD2-PC
Systematic Name1-hexadecanoyl-2-(9,10-seco-9,11-dioxo-15-hydroxy-5Z,13E-prostadienoyl)-sn-
glycero-phosphocholine
Synonyms-
Exact Mass
829.5469 (neutral)    Calculate m/z:
FormulaC44H80NO11P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphocholines [GP2001]
PubChem CID134812344
InChIKeyCIZJGRKAYDGGIP-SVCIMYNVSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C44H80NO11P/c1-7-9-11-12-13-14-15-16-17-18-19-20-25-29-43(49)53-36-41(3
7-55-57(51,52)54-34-33-45(4,5)6)56-44(50)30-26-22-21-24-27-39(35-46)42(38(3)47)3
2-31-40(48)28-23-10-8-2/h21,24,31-32,35,39-42,48H,7-20,22-23,25-30,33-34,36-37H2
,1-6H3/b24-21-,32-31+/t39?,40?,41-,42?/m1/s1
SMILES[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCC/C=C\CC(C=O)C(/C=C/C(O)CCCCC)C(C)=O
)=O)COC(CCCCCCCCCCCCCCC)=O
StatusActive
ReferencesOxidized phospholipids: From molecular properties to disease.Gilbert O. Fruhwirth, Alexandra Loidl and Albin Hermetter.Biochimica et Biophysica Acta (BBA) - Molecular Basis of Disease. Volume 1772, Issue 7, July 2007, Pages 718-736. doi.org/10.1016/j.bbadis.2007.04.009

https://www.sciencedirect.com/science/article/pii/S0925443907001032?via%3Dihub
Calculated physicochemical properties (?):
 Heavy Atoms57Rings0Aromatic Rings0Rotatable Bonds41
 van der Waals
Molecular Volume
881.44Topological Polar
Surface Area
165.56Hydrogen
Bond Donors
1Hydrogen
Bond Acceptors
12
 logP10.48Molar
Refractivity
227.17    
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.