Structure database (LMSD)

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LM IDLMGP01050048
Common NamePC(20:4(5Z,8Z,11Z,14Z)/0:0)
Systematic Name1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine
SynonymsPC(20:4/0:0)
Exact Mass
543.3325 (neutral)    Calculate m/z:
FormulaC28H50NO7P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphocholines [GP01]
Sub ClassMonoacylglycerophosphocholines [GP0105]
LIPIDAT ID12163
PubChem Compound ID (CID)24779476
HMDB IDHMDB10395
InChIKeyLAXQYRRMGGEGOH-JXRLJXCWSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C28H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-28(31)34
-25-27(30)26-36-37(32,33)35-24-23-29(2,3)4/h9-10,12-13,15-16,18-19,27,30H,5-8,11
,14,17,20-26H2,1-4H3/b10-9-,13-12-,16-15-,19-18-/t27-/m1/s1
SMILES[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(O)COC(CCC/C=CC/C=CC/C=CC/C=CCCCCC)=O
StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms37Rings0Aromatic Rings0Rotatable Bonds24
 van der Waals
Molecular Volume
572.12Topological Polar
Surface Area
105.12Hydrogen
Bond Donors
1Hydrogen
Bond Acceptors
8
 logP6.67Molar
Refractivity
150.25    
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.