Structure database (LMSD)

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LM IDLMGP00000056
Common NameCPA(18:1(9Z))
Systematic Name1-(9Z-octadecenoyl)-sn-glycero-2,3-cyclic phosphate
Synonyms1-oleoyl-cyclic phosphatidic acid; cLPA(18:1)
Exact Mass
418.2484 (neutral)    Calculate m/z:
CategoryGlycerophospholipids [GP]
Main ClassOther Glycerophospholipids [GP00]
Sub Class-
AbbrevCPA 18:1
Abbrev ChainsCPA 18:1
PubChem CID52922109
InChIKeyZUUIRLHAEZAVCP-GDCKJWNLSA-N  Show lipids differing only in stereochemistry/bond geometry
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ReferencesKobayashi T, Tanaka-Ishii R, Taguchi R, Ikezawa H, Murakami-Murofushi K.
Existence of a bioactive lipid, cyclic phosphatidic acid, bound to human serum albumin.
Life Sci. 1999;65:2185?91.
Calculated physicochemical properties (?):
 Heavy Atoms28Rings1Aromatic Rings0Rotatable Bonds18
 van der Waals
Molecular Volume
426.79Topological Polar
Surface Area
Bond Donors
Bond Acceptors
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.