Structure database (LMSD)

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LM IDLMGP20040015
Common NamePOV-PS
Systematic Name1-hexadecanoyl-2-(5-oxo-valeroyl)-sn-glycero-3-phosphoserine
Synonyms1-palmitoyl-2-(5-oxo-valeroyl)-sn-glycero-3-phosphoserine
Exact Mass
595.3122 (neutral)    Calculate m/z:
FormulaC27H50NO11P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoserines [GP2004]
AbbrevPS 21:1;O
PubChem CID134812396
CHEBI ID186953
InChIKeyWKTXKVFIBCEKJI-RPWUZVMVSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C27H50NO11P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17-25(30)36-20-23(39-26(31)18-15-16-19-29)21-37-40(34,35)38-22-24(28)27(32)33/h19,23-24H,2-18,20-22,28H2,1H3,(H,32,33)(H,34,35)/t23-,24+/m1/s1
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SMILES
C(O)(=O)[C@@]([H])(N)COP(OC[C@]([H])(OC(CCCC(=O)[H])=O)COC(CCCCCCCCCCCCCCC)=O)(=O)O
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StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms40Rings0Aromatic Rings0Rotatable Bonds30
 van der Waals
Molecular Volume
592.62Topological Polar
Surface Area
188.75Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
12
 logP6.44Molar
Refractivity
150.76    
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.