Structure database (LMSD)

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LM IDLMGP10010059
Common NamePA(12:0/20:3(8Z,11Z,14Z))
Systematic Name1-dodecanoyl-2-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphate
SynonymsPA(32:3); PA(12:0_20:3)
Exact Mass
642.4261 (neutral)    Calculate m/z:
FormulaC35H63O8P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphates [GP10]
Sub ClassDiacylglycerophosphates [GP1001]
AbbrevPA 32:3
Abbrev ChainsPA 12:0_20:3
PubChem CID52928652
SWISSLIPIDS IDSLM:000025863
InChIKeyWRKCZXKHSXKJFZ-UVXFUXOQSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C35H63O8P/c1-3-5-7-9-11-13-14-15-16-17-18-19-20-22-24-26-28-30-35(37)43-33(32-42-44(38,39)40)31-41-34(36)29-27-25-23-21-12-10-8-6-4-2/h11,13,15-16,18-19,33H,3-10,12,14,17,20-32H2,1-2H3,(H2,38,39,40)/b13-11-,16-15-,19-18-/t33-/m1/s1
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SMILES
[C@](COP(=O)(O)O)([H])(OC(CCCCCC/C=C\C/C=C\C/C=C\CCCCC)=O)COC(CCCCCCCCCCC)=O
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StatusActive (generated by computational methods)
Calculated physicochemical properties (?):
 Heavy Atoms44Rings0Aromatic Rings0Rotatable Bonds33
 van der Waals
Molecular Volume
691.01Topological Polar
Surface Area
119.36Hydrogen
Bond Donors
2Hydrogen
Bond Acceptors
8
 logP11.04Molar
Refractivity
180.39    
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.