Structure database (LMSD)

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LM IDLMGP20010046
Common NameP-IsoPGF2-PC
Systematic Name1-hexadecanoyl-2-(9,11,15-trihydroxy-5Z,13E-prostadienoyl)-sn-glycero-
phosphocholine
Synonyms1-palmitoyl-2-(9,11,15-trihydroxy-5Z,13E-prostadienoyl)-sn-glycero-
phosphocholine
Exact Mass
831.5626 (neutral)    Calculate m/z:
FormulaC44H82NO11P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphocholines [GP2001]
PubChem CID134812337
InChIKeyNJHGFFOICHJLQM-SMAMXKCCSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C44H82NO11P/c1-6-8-10-11-12-13-14-15-16-17-18-19-24-28-43(49)53-35-38(3
6-55-57(51,52)54-33-32-45(3,4)5)56-44(50)29-25-21-20-23-27-39-40(42(48)34-41(39)
47)31-30-37(46)26-22-9-7-2/h20,23,30-31,37-42,46-48H,6-19,21-22,24-29,32-36H2,1-
5H3/b23-20-,31-30+/t37?,38-,39?,40?,41?,42?/m1/s1
SMILES[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCC/C=C\CC1C(O)CC(O)C1/C=C/C(O)CCCCC)=
O)COC(CCCCCCCCCCCCCCC)=O
MS SpectraView MoNA MS spectra     
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 Atoms57Rings1Aromatic Rings0Rotatable Bonds38
 van der Waals
Molecular Volume
874.36Topological Polar
Surface Area
171.88Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
12
 logP10.39Molar
Refractivity
228.08    
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.