Structure database (LMSD)

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LM IDLMGP03010041
Common NamePS-NAc(18:0/18:1(9Z)/16:0)
Systematic Name1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-N-hexadecanoyl-L-serine
SynonymsPS-NAc(18:0/18:1/16:0); PS-NAc(36:1)
Exact Mass
1027.7817 (neutral)    Calculate m/z:
FormulaC58H110NO11P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoserines [GP03]
Sub ClassDiacylglycerophosphoserines [GP0301]
PubChem CID24779547
CHEBI ID139397
InChIKeyDMBATYOPPCIICJ-YWPJBLNKSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C58H110NO11P/c1-4-7-10-13-16-19-22-25-27-30-33-36-39-42-45-48-56(61)67-50-53(70-57(62)49-46-43-40-37-34-31-28-26-23-20-17-14-11-8-5-2)51-68-71(65,66)69-52-54(58(63)64)59-55(60)47-44-41-38-35-32-29-24-21-18-15-12-9-6-3/h26,28,53-54H,4-25,27,29-52H2,1-3H3,(H,59,60)(H,63,64)(H,65,66)/b28-26-/t53-,54+/m1/s1
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SMILES
C(O)(=O)[C@@]([H])(NC(=O)CCCCCCCCCCCCCCC)COP(OC[C@]([H])(OC(CCCCCCC/C=C\CCCCCCCC)=O)COC(CCCCCCCCCCCCCCCCC)=O)(=O)O
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StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms71Rings0Aromatic Rings0Rotatable Bonds58
 van der Waals
Molecular Volume
1126.28Topological Polar
Surface Area
174.76Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
11
 logP18.52Molar
Refractivity
293.80    
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.