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
InChIInChI=1S/C44H78NO10P/c1-6-8-10-11-12-13-14-15-16-17-18-19-24-28-43(48)52-36-40(3
7-54-56(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/b2
3-20-,32-30+/t38?,39?,40-,41?/m1/s1
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
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.