Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP20040009
Common NamePHOHA-PS
Systematic Name1-hexadecanoyl-2-(4-hydroxy-7-oxo-5E-heptenoyl)-sn-glycero-3-phosphoserine
Synonyms1-palmitoyl-2-(4-hydroxy-7-oxo-5E-heptenoyl)-sn-glycero-3-phosphoserine
Exact Mass
637.3227 (neutral)    Calculate m/z:
FormulaC29H52NO12P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoserines [GP2004]
AbbrevPS 23:2;O2
PubChem CID134812390
CHEBI ID185418
InChIKeyVIJFPBAJWYVKSQ-WQVBGXLGSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C29H52NO12P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17-27(33)39-21-25(42-28(34)19-18-24(32)16-15-20-31)22-40-43(37,38)41-23-26(30)29(35)36/h15-16,20,24-26,32H,2-14,17-19,21-23,30H2,1H3,(H,35,36)(H,37,38)/b16-15+/t24?,25-,26+/m1/s1
Click to highlight InChI
SMILES
C(O)(=O)[C@@]([H])(N)COP(OC[C@]([H])(OC(CCC(O)/C=C/C(=O)[H])=O)COC(CCCCCCCCCCCCCCC)=O)(=O)O
Click to highlight SMILES
StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms43Rings0Aromatic Rings0Rotatable Bonds31
 van der Waals
Molecular Volume
633.37Topological Polar
Surface Area
208.98Hydrogen
Bond Donors
4Hydrogen
Bond Acceptors
13
 logP6.25Molar
Refractivity
161.80    
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.