Structure database (LMSD)

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LM IDLMGP20020001
Common NamePE(18:0/20:4(5Z,8Z,10E,14Z)(12OH[S]))
Systematic Name1-octadecanoyl-2-(12S-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoyl)-sn-glycero-3-
phosphoethanolamine
Synonyms18:0/12-HETE-PE
Exact Mass
783.5414 (neutral)    Calculate m/z:
FormulaC43H78NO9P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoethanolamines [GP2002]
PubChem Compound ID (CID)52929783
InChIKeyQFAWNLPDAMJEPH-ABBGXWPISA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C43H78NO9P/c1-3-5-7-9-11-12-13-14-15-16-17-18-22-26-30-34-42(46)50-38-4
1(39-52-54(48,49)51-37-36-44)53-43(47)35-31-27-23-20-19-21-25-29-33-40(45)32-28-
24-10-8-6-4-2/h20-21,23-25,28-29,33,40-41,45H,3-19,22,26-27,30-32,34-39,44H2,1-2
H3,(H,48,49)/b23-20-,25-21-,28-24-,33-29+/t40-,41+/m0/s1
SMILESCCCCC/C=C\C[C@@H](O)/C=C/C=C\C/C=C\CCCC(=O)O[C@H](COP(O)(=O)OCCN)COC(=O)CCCCCCCC
CCCCCCCCC
StatusActive
ReferencesThomas, CP., Morgan, L, Maskery, BH, Murphy, RC, Kuhn, H, Hazen, SL, Goodall, AH, Hamali,
HA, Collins, PW, and O'Donnell, VB (2010)
Phospholipid-esterified eicosanoids are generated in response in agonist-activated human platelets,
and enhance tissue factor dependent thrombin generation
J Biol Chem 285, 6891-03.

Morgan, AH, Dioszeghy, V., Maskrey, BH, Thomas, CP, Clark, SR, Mathie, SA, Lloyd, CM, Kuhn,
H., Topley, N., Coles, B., Taylor, PR, Jones, SA. and O'Donnell, VB
Phosphatidylethanolamine-esterified eicosanoids in the mouse: tissue localisation and
inflammation-dependent formation in Th-2 disease
(2009) J Biol Chem 284, 21185-21191
Calculated physicochemical properties (?):
 Heavy Atoms54Rings0Aromatic Rings0Rotatable Bonds41
 van der Waals
Molecular Volume
846.56Topological Polar
Surface Area
154.61Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
9
 logP12.79Molar
Refractivity
223.81    
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.

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