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:
FormulaC21H39O6P
CategoryGlycerophospholipids [GP]
Main ClassOther Glycerophospholipids [GP00]
Sub Class-
AbbrevCPA 18:1
Abbrev ChainsCPA 18:1
PubChem CID52922109
CHEBI ID62838
InChIKeyZUUIRLHAEZAVCP-GDCKJWNLSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C21H39O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(22)25-18-20-19-26-28(23,24)27-20/h9-10,20H,2-8,11-19H2,1H3,(H,23,24)/b10-9-/t20-/m1/s1
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SMILES
[C@]1(COP(O1)(=O)O)([H])COC(CCCCCCC/C=C\CCCCCCCC)=O
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StatusActive
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
86.20Hydrogen
Bond Donors
1Hydrogen
Bond Acceptors
6
 logP7.11Molar
Refractivity
112.42    
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.