Structure database (LMSD)

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LM IDLMGP20010007
Common NamePC(16:0/9:0(COOH))
Systematic Name1-hexadecanoyl-2-(9-carboxy-nonanoyl)-sn-glycero-3-phosphocholine
Synonyms1-palmitoyl-2-azelaoyl-sn-glycero-3-phosphocholine
Exact Mass
665.4268 (neutral)    Calculate m/z:
FormulaC33H64NO10P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphocholines [GP2001]
PubChem CID46907870
CAYMAN ID62924
InChIKeyGHQQYDSARXURNG-SSEXGKCCSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C33H64NO10P/c1-5-6-7-8-9-10-11-12-13-14-15-18-21-24-32(37)41-28-30(29-43-45(39,40)42-27-26-34(2,3)4)44-33(38)25-22-19-16-17-20-23-31(35)36/h30H,5-29H2,1-4H3,(H-,35,36,39,40)/t30-/m1/s1
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SMILES
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCCCCCCC(O)=O)=O)COC(CCCCCCCCCCCCCCC)=O
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StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms45Rings0Aromatic Rings0Rotatable Bonds34
 van der Waals
Molecular Volume
690.27Topological Polar
Surface Area
148.49Hydrogen
Bond Donors
1Hydrogen
Bond Acceptors
11
 logP8.37Molar
Refractivity
175.99    
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.