Structure database (LMSD)

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LM IDLMGP10010023
Common NamePA(16:0/18:2(9Z,12Z))
Systematic Name1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphate
Synonyms9,12-Octadecadienoic acid (Z,Z)-, 1-[[(1-oxohexadecyl)oxy]methyl]-2-
(phosphonooxy)ethyl ester, (R)-; 1-Palmitoyl-2-linoleoyl-sn-glycero-3-
phosphate; PA(16:0/18:2); PA(34:2); PA(16:0_18:2)
Exact Mass
672.4730 (neutral)    Calculate m/z:
FormulaC37H69O8P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphates [GP10]
Sub ClassDiacylglycerophosphates [GP1001]
LIPIDAT ID7252
PubChem CID9547167
HMDB IDHMDB0007860
SWISSLIPIDS IDSLM:000000794
InChIKeyYQMUIZXKIKXZHD-UMKNCJEQSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C37H69O8P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-37(39)45-35(34-44-46(40,41)42)33-43-36(38)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h11,13,17-18,35H,3-10,12,14-16,19-34H2,1-2H3,(H2,40,41,42)/b13-11-,18-17-/t35-/m1/s1
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SMILES
[C@](COP(=O)(O)O)([H])(OC(CCCCCCC/C=C\C/C=C\CCCCC)=O)COC(CCCCCCCCCCCCCCC)=O
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MS SpectraView MoNA MS spectra      Predict MS/MS spectrum (Neg. mode)
MS StandardView lipid standard
StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms46Rings0Aromatic Rings0Rotatable Bonds36
 van der Waals
Molecular Volume
728.25Topological Polar
Surface Area
119.36Hydrogen
Bond Donors
2Hydrogen
Bond Acceptors
8
 logP12.04Molar
Refractivity
189.72    
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.