Structure database (LMSD)

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LM IDLMGP20010002
Common NamePC(16:0/20:4(5Z,8Z,10E,14Z)(12OH[S]))
Systematic Name1-hexadecanoyl-2-(12S-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoyl)-sn-glycero-3-
phosphocholine
Synonyms16:0/12-HETE PC; PC(36:4(OH)); PC(16:0_20:4(OH))
Exact Mass
797.5571 (neutral)    Calculate m/z:
FormulaC44H80NO9P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphocholines [GP2001]
PubChem CID52929777
InChIKeyYQWFSBLEXGUMGO-GZXBEVTESA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C44H80NO9P/c1-6-8-10-12-14-15-16-17-18-19-23-27-31-35-43(47)51-39-42(40
-53-55(49,50)52-38-37-45(3,4)5)54-44(48)36-32-28-24-21-20-22-26-30-34-41(46)33-2
9-25-13-11-9-7-2/h21-22,24-26,29-30,34,41-42,46H,6-20,23,27-28,31-33,35-40H2,1-5
H3/b24-21-,26-22-,29-25-,34-30+/t41-,42+/m0/s1
SMILES[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCC/C=C\C/C=C\C=C\[C@@H](O)C/C=C\CCCCC
)=O)COC(CCCCCCCCCCCCCCC)=O
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 Atoms55Rings0Aromatic Rings0Rotatable Bonds40
 van der Waals
Molecular Volume
863.86Topological Polar
Surface Area
131.42Hydrogen
Bond Donors
1Hydrogen
Bond Acceptors
10
 logP11.96Molar
Refractivity
226.34    
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.