Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP10010028
Common NamePA(18:0/18:0)
Systematic Name1,2-dioctadecanoyl-sn-glycero-3-phosphate
SynonymsDistearoyl phosphatidic acid; Octadecanoic acid, 1-[(phosphonooxy)methyl]-1,2-
ethanediyl ester, (R)-; β,γ-Distearoyl-L-α-phosphatidic acid; 1,2-Distearoyl-
L-phosphatidic acid; PA(36:0); PA(18:0_18:0)
Exact Mass
704.5356 (neutral)    Calculate m/z:
FormulaC39H77O8P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphates [GP10]
Sub ClassDiacylglycerophosphates [GP1001]
LIPIDAT ID8302
PubChem CID447938
SWISSLIPIDS IDSLM:000025492
InChIKeyYFWHNAWEOZTIPI-DIPNUNPCSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C39H77O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(40)45-35-37(36-46-48(42,43)44)47-39(41)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h37H,3-36H2,1-2H3,(H2,42,43,44)/t37-/m1/s1
Click to highlight InChI
SMILES
[C@](COP(=O)(O)O)([H])(OC(CCCCCCCCCCCCCCCCC)=O)COC(CCCCCCCCCCCCCCCCC)=O
Click to highlight SMILES
MS SpectraView MoNA MS spectra      Predict MS/MS spectrum (Neg. mode)
MS StandardView lipid standard
StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms48Rings0Aromatic Rings0Rotatable Bonds40
 van der Waals
Molecular Volume
768.13Topological Polar
Surface Area
119.36Hydrogen
Bond Donors
2Hydrogen
Bond Acceptors
8
 logP13.27Molar
Refractivity
199.14    
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.