Structure database (LMSD)

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LM IDLMGP20010001
Common NamePC(18:0/20:4(5Z,8Z,10E,14Z)(12OH[S]))
Systematic Name1-octadecanoyl-2-(12S-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoyl)-sn-glycero-3-
phosphocholine
Synonyms18:0/12-HETE PC; PC(38:4(OH)); PC(18:0_20:4(OH))
Exact Mass
825.5884 (neutral)    Calculate m/z:
FormulaC46H84NO9P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphocholines [GP2001]
AbbrevPC 38:4;O
Abbrev ChainsPC 18:0_20:4;O
PubChem CID52929775
InChIKeyYETXCLLSHIMTGE-KDCNQZJWSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C46H84NO9P/c1-6-8-10-12-14-15-16-17-18-19-20-21-25-29-33-37-45(49)53-41-44(42-55-57(51,52)54-40-39-47(3,4)5)56-46(50)38-34-30-26-23-22-24-28-32-36-43(48)35-31-27-13-11-9-7-2/h23-24,26-28,31-32,36,43-44,48H,6-22,25,29-30,33-35,37-42H2,1-5H3/b26-23-,28-24-,31-27-,36-32+/t43-,44+/m0/s1
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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(CCCCCCCCCCCCCCCCC)=O
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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 Atoms57Rings0Aromatic Rings0Rotatable Bonds42
 van der Waals
Molecular Volume
898.46Topological Polar
Surface Area
131.42Hydrogen
Bond Donors
1Hydrogen
Bond Acceptors
10
 logP12.74Molar
Refractivity
235.57    
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.