Structure database (LMSD)

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LM IDLMGP00000059
Common NamePE(16:0/18:1(9Z))-15-isoLG pyrrole
Systematic Name-
SynonymsPE(34:1)-isoK pyrrole
Exact Mass
1033.7347 (neutral)    Calculate m/z:
FormulaC59H104NO11P
CategoryGlycerophospholipids [GP]
Main ClassOther Glycerophospholipids [GP00]
Sub Class-
PubChem CID52922110
InChIKeyJNADOARFVOZEIV-GZPZGTMLSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C59H104NO11P/c1-5-8-11-13-15-17-19-21-22-24-26-28-30-32-39-44-59(65)71-55(50-68-58(64)43-38-31-29-27-25-23-20-18-16-14-12-9-6-2)51-70-72(66,67)69-48-47-60-49-53(45-46-54(61)40-35-10-7-3)56(52(60)4)41-36-33-34-37-42-57(62)63/h21-22,33,36,45-46,49,54-55,61H,5-20,23-32,34-35,37-44,47-48,50-51H2,1-4H3,(H,62,63)(H,66,67)/b22-21-,36-33-,46-45+/t54?,55-/m1/s1
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SMILES
[C@](COP(=O)(O)OCCN1C=C(/C=C/C(O)CCCCC)C(=C1C)C/C=C\CCCC(O)=O)([H])(OC(CCCCCCC/C=C\CCCCCCCC)=O)COC(CCCCCCCCCCCCCCC)=O
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StatusActive
ReferencesIsoketals form cytotoxic phosphatidylethanolamine adducts in cells
C. Blake Sullivan, Elena Matafonova, L. Jackson Roberts II, Venkataraman Amarnath and Sean S. Davies
J. Lipid Res. 2010 51:(5) 999-1009
Calculated physicochemical properties (?):
 Heavy Atoms72Rings1Aromatic Rings1Rotatable Bonds53
 van der Waals
Molecular Volume
1112.40Topological Polar
Surface Area
170.82Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
12
 logP17.81Molar
Refractivity
297.37    
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.