Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP01050139
Common NamePC(20:3(5Z,8Z,11Z)/0:0)
Systematic Name1-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycero-3-phosphocholine
SynonymsLPC(20:3)
Exact Mass
545.3481 (neutral)    Calculate m/z:
FormulaC28H52NO7P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphocholines [GP01]
Sub ClassMonoacylglycerophosphocholines [GP0105]
AbbrevLPC 20:3
Abbrev ChainsLPC 20:3
PubChem CID53480467
KEGG IDC04230
HMDB IDHMDB0010393
CHEBI ID74343
InChIKeyYHGXYYIGHBPDMX-BUTFDPNWSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C28H52NO7P/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/h12-13,15-16,18-19,27,30H,5-11,14,17,20-26H2,1-4H3/b13-12-,16-15-,19-18-/t27-/m1/s1
Click to highlight InChI
SMILES
C(OP(OCC[N+](C)(C)C)(=O)[O-])[C@@](O)([H])COC(=O)CCC/C=C\C/C=C\C/C=C\CCCCCCCC
Click to highlight SMILES
StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms37Rings0Aromatic Rings0Rotatable Bonds25
 van der Waals
Molecular Volume
574.76Topological Polar
Surface Area
105.12Hydrogen
Bond Donors
1Hydrogen
Bond Acceptors
8
 logP6.89Molar
Refractivity
150.35    
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.