Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP01060042
Common Name1-O-(2-methoxyhexadecyl)-sn-glycerol-3-phosphocholine
Systematic Name1-O-(2-methoxyhexadecyl)-sn-glycerol-3-phosphocholine
Synonyms-
Exact Mass
511.3638 (neutral)    Calculate m/z:
FormulaC25H54NO7P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphocholines [GP01]
Sub ClassMonoalkylglycerophosphocholines [GP0106]
PubChem CID-
InChIKeyBRRAOCFWJYNWFK-IKOFQBKESA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C25H54NO7P/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-25(30-5)23-31-21-24(27
)22-33-34(28,29)32-20-19-26(2,3)4/h24-25,27H,6-23H2,1-5H3/t24-,25?/m1/s1
SMILES[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(O)COCC(OC)CCCCCCCCCCCCCC
StatusActive
ReferencesNew advances in the chemistry of methoxylated lipids. N.M.Carballeira. Progress in Lipid Research. Volume 41, Issue 6, November 2002, Pages 437-456.

https://www.sciencedirect.com/science/article/pii/S016378270200005X?via%3Dihub

Calculated physicochemical properties (?):
 Heavy Atoms34Rings0Aromatic Rings0Rotatable Bonds25
 van der Waals
Molecular Volume
533.42Topological Polar
Surface Area
97.28Hydrogen
Bond Donors
1Hydrogen
Bond Acceptors
8
 logP6.67Molar
Refractivity
139.20    
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.