Structure database (LMSD)

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LM IDLMGP20010052
Common NamePC(0:0/20:4;O)
Systematic Name2-(11R-hydroxy-5Z,8Z,12E,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine
Synonyms11R-HETE-LPC
Exact Mass
559.3274 (neutral)    Calculate m/z:
FormulaC28H50NO8P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphocholines [GP2001]
AbbrevLPC 20:4;O
Abbrev ChainsLPC 0:0/20:4;O
PubChem CID-
InChIKeyLVIIPAXNGUJAAT-YLLKXINESA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C28H50NO8P/c1-5-6-7-8-10-13-16-19-26(31)20-17-14-11-9-12-15-18-21-28(32)37-27(24-30)25-36-38(33,34)35-23-22-29(2,3)4/h9-10,12-14,16-17,19,26-27,30-31H,5-8,11,15,18,20-25H2,1-4H3/b12-9-,13-10-,17-14-,19-16+/t26-,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=C\C[C@@H](O)/C=C/C=C\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 Atoms38Rings0Aromatic Rings0Rotatable Bonds24
 van der Waals
Molecular Volume
580.91Topological Polar
Surface Area
125.35Hydrogen
Bond Donors
2Hydrogen
Bond Acceptors
9
 logP5.93Molar
Refractivity
152.15    
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.