Structure database (LMSD)

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LM IDLMGP20020005
Common NamePE(P-16:0/20:4(5Z,8Z,10E,14Z)(12OH[S]))
Systematic Name1-O-(1Z-hexadecenyl)-2-(12S-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoyl)-sn-glycero-
3-phosphoethanolamine
Synonyms16:0p/12-HETE-PE
Exact Mass
739.5152 (neutral)    Calculate m/z:
FormulaC41H74NO8P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoethanolamines [GP2002]
PubChem Compound ID (CID)52929787
InChIKeyMOFSRTWFULYXNI-UWLBFGBLSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C41H74NO8P/c1-3-5-7-9-11-12-13-14-15-16-19-22-26-30-35-47-37-40(38-49-5
1(45,46)48-36-34-42)50-41(44)33-29-25-21-18-17-20-24-28-32-39(43)31-27-23-10-8-6
-4-2/h18,20-21,23-24,27-28,30,32,35,39-40,43H,3-17,19,22,25-26,29,31,33-34,36-38
,42H2,1-2H3,(H,45,46)/b21-18-,24-20-,27-23-,32-28+,35-30-/t39-,40+/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)CO/C=C\CCCCCCCC
CCCCCC
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 Atoms51Rings0Aromatic Rings0Rotatable Bonds38
 van der Waals
Molecular Volume
803.17Topological Polar
Surface Area
137.54Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
8
 logP12.61Molar
Refractivity
214.09    
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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