Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP20010045
Common NameP-IsoPGA2-PC
Systematic Name1-hexadecanoyl-2-(9-oxo-15-hydroxy-5Z,10,13E-prostatrienoyl)-sn-glycero-
phosphocholine
Synonyms 
Exact Mass
811.5363 (neutral)    Calculate m/z:
FormulaC44H78NO10P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphocholines [GP2001]
PubChem CID134812335
InChIKeyLZWBRRLOGAPWCI-VPEUXQEKSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C44H78NO10P/c1-6-8-10-11-12-13-14-15-16-17-18-19-24-28-43(48)52-36-40(37-54-56(50,51)53-35-34-45(3,4)5)55-44(49)29-25-21-20-23-27-41-38(31-33-42(41)47)30-32-39(46)26-22-9-7-2/h20,23,30-33,38-41,46H,6-19,21-22,24-29,34-37H2,1-5H3/b23-20-,32-30+/t38?,39?,40-,41?/m1/s1
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SMILES
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCC/C=C\CC1C(=O)C=CC1/C=C/C(O)CCCCC)=O)COC(CCCCCCCCCCCCCCC)=O
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StatusActive
ReferencesRole of oxidized phospholipids in cardiovascular pathology. David Allen, Devin Hasanally & Amir Ravandi. Clinical Lipidology. Volume 8. Issue 2, pp. 205-215. https://doi.org/10.2217/clp.13.13

https://www.tandfonline.com/doi/pdf/10.2217/clp.13.13
Calculated physicochemical properties (?):
 Heavy Atoms56Rings1Aromatic Rings0Rotatable Bonds38
 van der Waals
Molecular Volume
860.29Topological Polar
Surface Area
148.49Hydrogen
Bond Donors
1Hydrogen
Bond Acceptors
11
 logP10.83Molar
Refractivity
224.57    
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.