Structure database (LMSD)

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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]
AbbrevPC 36:4;O3
PubChem CID134812344
InChIKeyCIZJGRKAYDGGIP-SVCIMYNVSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C44H80NO11P/c1-7-9-11-12-13-14-15-16-17-18-19-20-25-29-43(49)53-36-41(37-55-57(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)32-31-40(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
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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
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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.