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Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP03020031
Common NamePS(O-18:0/18:4(6Z,9Z,12Z,15Z))
Systematic Name1-octadecyl-2-(6Z,9Z,12Z,15Z-octadecatetraenoyl)-glycero-3-phosphoserine
SynonymsPS(O-36:4); PS(O-18:0/18:4)
Exact Mass
769.5258 (neutral)    Calculate m/z:
FormulaC42H76NO9P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoserines [GP03]
Sub Class1-alkyl,2-acylglycerophosphoserines [GP0302]
AbbrevPS O-36:4
Abbrev ChainsPS O-18:0/18:4
PubChem CID52926120
SWISSLIPIDS IDSLM:000044421
InChIKeyMNRFNPBWEUNTNM-DCBFBIAFSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C42H76NO9P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-49-36-39(37-50-53(47,48)51-38-40(43)42(45)46)52-41(44)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h6,8,12,14,18,20,24,26,39-40H,3-5,7,9-11,13,15-17,19,21-23,25,27-38,43H2,1-2H3,(H,45,46)(H,47,48)/b8-6-,14-12-,20-18-,26-24-/t39-,40+/m1/s1
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SMILES
C(O)(=O)[C@@]([H])(N)COP(OC[C@]([H])(OC(CCCC/C=C\C/C=C\C/C=C\C/C=C\CC)=O)COCCCCCCCCCCCCCCCCCC)(=O)O
Click to highlight SMILES
StatusActive (generated by computational methods)
Calculated physicochemical properties (?):
 Heavy Atoms53Rings0Aromatic Rings0Rotatable Bonds40
 van der Waals
Molecular Volume
829.26Topological Polar
Surface Area
154.61Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
9
 logP12.97Molar
Refractivity
219.60    
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.