Structure database (LMSD)

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LM IDLMGP20010051
Common NamePC(0:0/PGE2)
Systematic Name2-(9-oxo-11R,15S-dihydroxy-5Z,13E-prostadienoyl)-sn-glycero-3-phosphocholine
SynonymsPGE2-LPC
Exact Mass
591.3172 (neutral)    Calculate m/z:
FormulaC28H50NO10P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphocholines [GP2001]
AbbrevLPC 20:4;O3
Abbrev ChainsLPC 0:0/20:4;O3
PubChem CID-
InChIKeyQFBMVHPGUOVSGP-QJRTVADPSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C28H50NO10P/c1-5-6-9-12-22(31)15-16-25-24(26(32)19-27(25)33)13-10-7-8-11-14-28(34)39-23(20-30)21-38-40(35,36)37-18-17-29(2,3)4/h7,10,15-16,22-25,27,30-31,33H,5-6,8-9,11-14,17-21H2,1-4H3/b10-7-,16-15+/t22-,23+,24+,25+,27+/m0/s1
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SMILES
C(OP(OCC[N+](C)(C)C)([O-])=O)[C@]([H])(OC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCCCC)CO
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StatusActive
ReferencesCyclooxygenase-2 Mediated Oxidation of 2-Arachidonoyl-Lysophospholipids Identifies Unknown Lipid Signaling Pathways
Cell Chem. Biol. 2016
DOI: 10.1016/j.chembiol.2016.08.009
PMID: 27642067
Calculated physicochemical properties (?):
 Heavy Atoms40Rings1Aromatic Rings0Rotatable Bonds22
 van der Waals
Molecular Volume
588.77Topological Polar
Surface Area
162.65Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
11
 logP4.28Molar
Refractivity
152.38    
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.