Structure database (LMSD)

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LM IDLMGP10020013
Common NamePA(O-16:0/20:1(11Z))
Systematic Name1-hexadecyl-2-(11Z-eicosenoyl)-glycero-3-phosphate
SynonymsPA(O-36:1); PA(O-16:0/20:1)
Exact Mass
688.5407 (neutral)    Calculate m/z:
FormulaC39H77O7P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphates [GP10]
Sub Class1-alkyl,2-acylglycerophosphates [GP1002]
AbbrevPA O-36:1
Abbrev ChainsPA O-16:0/20:1
PubChem CID52929576
SWISSLIPIDS IDSLM:000045856
InChIKeyNYRJVTSYSYBQAL-NPBIGWJUSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C39H77O7P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-39(40)46-38(37-45-47(41,42)43)36-44-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h17,19,38H,3-16,18,20-37H2,1-2H3,(H2,41,42,43)/b19-17-/t38-/m1/s1
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SMILES
[C@](COP(=O)(O)O)([H])(OC(CCCCCCCCC/C=C\CCCCCCCC)=O)COCCCCCCCCCCCCCCCC
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StatusActive (generated by computational methods)
Calculated physicochemical properties (?):
 Heavy Atoms47Rings0Aromatic Rings0Rotatable Bonds39
 van der Waals
Molecular Volume
759.34Topological Polar
Surface Area
102.29Hydrogen
Bond Donors
2Hydrogen
Bond Acceptors
7
 logP13.80Molar
Refractivity
199.40    
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.