Structure database (LMSD)

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LM IDLMGP11010002
Common NamePPA(18:1(9Z)/18:1(9Z))
Systematic Name1,2-di-(9Z-octadecenoyl)-sn-glycero-3-pyrophosphate
Synonyms36:2 DAG PP; PPA(18:1/18:1); PPA(36:2); PPA(18:1/18:1)
Exact Mass
780.4706 (neutral)    Calculate m/z:
FormulaC39H74O11P2
CategoryGlycerophospholipids [GP]
Main ClassGlyceropyrophosphates [GP11]
Sub ClassDiacylglyceropyrophosphates [GP1101]
AbbrevPPA 36:2
Abbrev ChainsPPA 18:1/18:1
PubChem CID24779564
InChIKeySKWFYHADBYFCMH-DSSVUWSHSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C39H74O11P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(40)47-35-37(36-48-52(45,46)50-51(42,43)44)49-39(41)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,37H,3-16,21-36H2,1-2H3,(H,45,46)(H2,42,43,44)/b19-17-,20-18-/t37-/m1/s1
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SMILES
[C@](COP(=O)(O)OP(=O)(O)O)([H])(OC(CCCCCCC/C=C\CCCCCCCC)=O)COC(CCCCCCC/C=C\CCCCCCCC)=O
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MS StandardView lipid standard
StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms52Rings0Aromatic Rings0Rotatable Bonds40
 van der Waals
Molecular Volume
809.05Topological Polar
Surface Area
165.89Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
11
 logP13.11Molar
Refractivity
209.73    
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.