Structure database (LMSD)

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LM IDLMGP11010001
Common NamePPA(16:0/18:1(9Z))
Systematic Name1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-pyrophosphate
SynonymsPPA(16:0/18:1); PPA(34:1); PPA(16:0_18:1)
Exact Mass
754.4550 (neutral)    Calculate m/z:
FormulaC37H72O11P2
CategoryGlycerophospholipids [GP]
Main ClassGlyceropyrophosphates [GP11]
Sub ClassDiacylglyceropyrophosphates [GP1101]
PubChem CID5283538
InChIKeyKGPOTEGAEDLRDC-QEJMHMKOSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C37H72O11P2/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-37(39)47-35(
34-46-50(43,44)48-49(40,41)42)33-45-36(38)31-29-27-25-23-21-19-16-14-12-10-8-6-4
-2/h17-18,35H,3-16,19-34H2,1-2H3,(H,43,44)(H2,40,41,42)/b18-17-/t35-/m1/s1
SMILES[C@](COP(=O)(O)OP(O)(=O)O)([H])(OC(CCCCCCC/C=C\CCCCCCCC)=O)COC(CCCCCCCCCCCCCCC)=
O
StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms50Rings0Aromatic Rings0Rotatable Bonds39
 van der Waals
Molecular Volume
777.09Topological Polar
Surface Area
165.89Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
11
 logP12.55Molar
Refractivity
200.59    
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.