Structure Database (LMSD)

Common Name
PE(P-18:1(9Z)/20:4(5Z,8Z,10E,14Z)(12OH[S]))
Systematic Name
1-O-(1Z,9Z-octadecadienyl)-2-(12S-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine
Synonyms
  • 18:1p/12-HETE-PE
  • PE(P-40:5(OH))
  • PE(P-18:1/20:4(OH))
LM ID
LMGP20020006
Status
Active
Exact Mass
Calculate m/z
765.530857
Formula
Abbrev
Abbrev Chains
PE P-18:1/20:4;O


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MDLMOL SDF CSV TSV
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Main

Classification

String Representations

InChiKey (Click to copy)
CCKPBQIDBAGJEM-YLQXPMJTSA-N
InChi (Click to copy)
InChI=1S/C43H76NO8P/c1-3-5-7-9-11-12-13-14-15-16-17-18-21-24-28-32-37-49-39-42(40-51-53(47,48)50-38-36-44)52-43(46)35-31-27-23-20-19-22-26-30-34-41(45)33-29-25-10-8-6-4-2/h14-15,20,22-23,25-26,29-30,32,34,37,41-42,45H,3-13,16-19,21,24,27-28,31,33,35-36,38-40,44H2,1-2H3,(H,47,48)/b15-14-,23-20-,26-22-,29-25-,34-30+,37-32-/t41-,42+/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\CCCCCC/C=C\CCCCCCCC

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

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
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
Pubmed ID: 19531470

Other Databases

CHEBI ID
PubChem CID

Calculated Physicochemical Properties

Heavy Atoms 53
Rings 0
Aromatic Rings 0
Rotatable Bonds 39
Van der Waals Molecular Volume 835.13
Topological Polar Surface Area 137.54
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 8
logP 13.17
Molar Refractivity 223.23

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Created at
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Updated at
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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.