Structure database (LMSD)

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LM IDLMGP20010008
Common NamePON-PC
Systematic Name1-hexadecanoyl-2-(9-oxo-nonanoyl)-sn-glycero-3-phosphocholine
Synonyms1-palmitoyl-2-(9-oxo-nonanoyl)-sn-glycero-3-phosphocholine
Exact Mass
649.4319 (neutral)    Calculate m/z:
FormulaC33H64NO9P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphocholines [GP2001]
AbbrevPC 25:1;O
PubChem CID46907874
CHEBI ID61042
SWISSLIPIDS IDSLM:000389546
InChIKeyPPTNNIINSOQWCE-WJOKGBTCSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C33H64NO9P/c1-5-6-7-8-9-10-11-12-13-14-15-18-21-24-32(36)40-29-31(30-42-44(38,39)41-28-26-34(2,3)4)43-33(37)25-22-19-16-17-20-23-27-35/h27,31H,5-26,28-30H2,1-4H3/t31-/m1/s1
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SMILES
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCCCCCCC([H])=O)=O)COC(CCCCCCCCCCCCCCC)=O
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StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms44Rings0Aromatic Rings0Rotatable Bonds34
 van der Waals
Molecular Volume
681.48Topological Polar
Surface Area
128.26Hydrogen
Bond Donors
0Hydrogen
Bond Acceptors
10
 logP8.49Molar
Refractivity
174.42    
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.