Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP02040015
Common Name-
Systematic Name1-tetradecanyl-2-(8-[3]-ladderane-octanyl)-sn-glycerophosphoethanolamine
Synonyms-
Exact Mass
683.5254 (neutral)    Calculate m/z:
FormulaC39H74NO6P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoethanolamines [GP02]
Sub ClassDialkylglycerophosphoethanolamines [GP0204]
PubChem CID42607459
InChIKeyBRDHQOGGOROTRW-MXFUHDRJSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C39H74NO6P/c1-2-3-4-5-6-7-8-9-10-12-15-18-26-43-30-33(31-46-47(41,42)45
-28-25-40)44-27-19-16-13-11-14-17-20-32-21-22-36-37(29-32)39-35-24-23-34(35)38(3
6)39/h32-39H,2-31,40H2,1H3,(H,41,42)/t32?,33-,34?,35?,36?,37?,38?,39?/m1/s1
SMILESO(P(=O)(O)OCCN)C[C@@](OCCCCCCCCC1CC2C3C4CCC4C3C2CC1)([H])COCCCCCCCCCCCCCC
StatusActive
CommentsSubmitted by Henry Boumann, Netherlands
ReferencesPubMed ID: 18385981
Calculated physicochemical properties (?):
 Heavy Atoms47Rings4Aromatic Rings0Rotatable Bonds31
 van der Waals
Molecular Volume
717.39Topological Polar
Surface Area
100.24Hydrogen
Bond Donors
2Hydrogen
Bond Acceptors
6
 logP12.40Molar
Refractivity
195.57    
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.