Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP02060008
Common Name1-(2-methoxy-6Z-tetradecenyl)-sn-glycero-3-phosphoethanolamine
Systematic Name1-(2-methoxy-6Z-tetradecenyl)-sn-glycero-3-phosphoethanolamine
SynonymsPE(O-14:1/0:0)
Exact Mass
439.2699 (neutral)    Calculate m/z:
FormulaC20H42NO7P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoethanolamines [GP02]
Sub ClassMonoalkylglycerophosphoethanolamines [GP0206]
PubChem CID-
InChIKeyAKCHPDUNFXDCGC-IYVXGCKASA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C20H42NO7P/c1-3-4-5-6-7-8-9-10-11-12-13-20(25-2)18-26-16-19(22)17-28-29
(23,24)27-15-14-21/h9-10,19-20,22H,3-8,11-18,21H2,1-2H3,(H,23,24)/b10-9-/t19-,20
?/m1/s1
SMILES[C@](COP(=O)(O)OCCN)([H])(O)COCC(OC)CCC/C=C\CCCCCCC
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%3Dihub


Calculated physicochemical properties (?):
 Heavy Atoms29Rings0Aromatic Rings0Rotatable Bonds21
 van der Waals
Molecular Volume
444.28Topological Polar
Surface Area
120.47Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
8
 logP5.73Molar
Refractivity
118.11    
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.