Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP02010009
Common NamePE(16:0/18:1(9Z))
Systematic Name1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine
SynonymsPE(16:0/18:1)
Exact Mass
717.5309 (neutral)    Calculate m/z:
FormulaC39H76NO8P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoethanolamines [GP02]
Sub ClassDiacylglycerophosphoethanolamines [GP0201]
PubChem Compound ID (CID)5283496
HMDB IDHMDB08927
InChIKeyFHQVHHIBKUMWTI-OTMQOFQLSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C39H76NO8P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-39(42)48-37(3
6-47-49(43,44)46-34-33-40)35-45-38(41)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h
17-18,37H,3-16,19-36,40H2,1-2H3,(H,43,44)/b18-17-/t37-/m1/s1
SMILES[C@](COP(=O)(O)OCCN)([H])(OC(CCCCCCC/C=CCCCCCCCC)=O)COC(CCCCCCCCCCCCCCC)=O
MS StandardView lipid standard
StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms49Rings0Aromatic Rings0Rotatable Bonds40
 van der Waals
Molecular Volume
776.49Topological Polar
Surface Area
134.38Hydrogen
Bond Donors
2Hydrogen
Bond Acceptors
8
 logP12.65Molar
Refractivity
203.72    
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.