Structure Database (LMSD)
Common Name
PE(P-16:0/20:4(5Z,8Z,10E,14Z)(12OH[S]))
Systematic Name
1-O-(1Z-hexadecenyl)-2-(12S-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine
Synonyms
- 16:0p/12-HETE-PE
- PE(P-38:4(OH))
- PE(P-16:0/20:4(OH))
LM ID
LMGP20020005
Status
Active
Exact Mass
Calculate m/z
739.515207
Formula
Abbrev
Abbrev Chains
PE P-16:0/20:4;O
Main
Classification
Category
Main Class
Sub Class
String Representations
InChiKey (Click to copy)
MOFSRTWFULYXNI-UWLBFGBLSA-N
InChi (Click to copy)
InChI=1S/C41H74NO8P/c1-3-5-7-9-11-12-13-14-15-16-19-22-26-30-35-47-37-40(38-49-51(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
SMILES (Click to copy)
[C@](COP(=O)(O)OCCN)([H])(OC(CCC/C=C\C/C=C\C=C\[C@@H](O)C/C=C\CCCCC)=O)CO/C=C\CCCCCCCCCCCCCC
References
Reference
Thomas, 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
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
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Homo sapiens
(#9606)
Mammalia
(#40674)
Phospholipid-esterified eicosanoids are generated in agonist-activated human platelets and enhance tissue factor-dependent thrombin generation.,
J Biol Chem, 2010
J Biol Chem, 2010
Pubmed ID:
20061396
Mus musculus
(#10090)
Mammalia
(#40674)
Phosphatidylethanolamine-esterified eicosanoids in the mouse: tissue localization and inflammation-dependent formation in Th-2 disease.,
J Biol Chem, 2009
J Biol Chem, 2009
Pubmed ID:
19531470
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
51
Rings
0
Aromatic Rings
0
Rotatable Bonds
38
Van der Waals Molecular Volume
803.17
Topological Polar Surface Area
137.54
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
8
logP
12.61
Molar Refractivity
214.09
Admin
Created at
-
Updated at
25th Apr 2022
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.
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.