Structure database (LMSD)

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LM IDLMGP20040028
Common NameOHHdiA-PS
Systematic Name1-(9Z-octadecenoyl)-2-(4-hydroxy-6-carboxy-5E-hexenoyl)-sn-glycero-3-
phosphoserine
Synonyms-
Exact Mass
679.3333 (neutral)    Calculate m/z:
FormulaC31H54NO13P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoserines [GP2004]
AbbrevPS 25:3;O3
PubChem CID134812409
InChIKeyQIEJUDQZVLLPBX-FIGFAOPCSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
1S/C31H54NO13P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-29(36)42-22-26(23-43-46(40,41)44-24-27(32)31(38)39)45-30(37)21-19-25(33)18-20-28(34)35/h9-10,18,20,25-27,33H,2-8,11-17,19,21-24,32H2,1H3,(H,34,35)(H,38,39)(H,40,41)/b10-9-,20-18+/t25?,26-,27+/m1/s1
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SMILES
C(O)(=O)[C@@]([H])(N)COP(OC[C@]([H])(OC(CCC(O)/C=C/C(=O)O)=O)COC(CCCCCCC/C=C\CCCCCCCC)=O)(=O)O
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StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms46Rings0Aromatic Rings0Rotatable Bonds32
 van der Waals
Molecular Volume
674.12Topological Polar
Surface Area
229.21Hydrogen
Bond Donors
5Hydrogen
Bond Acceptors
14
 logP6.69Molar
Refractivity
172.52    
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.