Structure Database (LMSD)

Common Name
PE P-18:1(9Z)/20:4(5Z,8Z,11Z,13E)(15Ke)
Systematic Name
1-O-(1Z,9Z-octadecadienyl)-2-(15-oxo-5Z,8Z,11Z,13E-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine
Synonyms
  • 18:1p/15-KETE-PE
LM ID
LMGP20020061
Formula
C43H74NO8P
Exact Mass
Calculate m/z
763.515206
Sum Composition
PE O-38:7;O
Abbrev Chains
PE P-18:1/20:5;O
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
Predict MS/MS spectrum (Neg. Mode)

Classification

Category
Main Class
Sub Class
Glycerophospholipids [GP]
Oxidized glycerophospholipids [GP20]
Oxidized glycerophosphoethanolamines [GP2002]
Glycerophosphoethanolamines [GP02]
1Z-alkenylglycerophosphoethanolamines [GP0207]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Novel keto-phospholipids are generated by monocytes and macrophages, detected in cystic fibrosis, and activate peroxisome proliferator-activated receptor-γ.,
J Biol Chem, 2012
Pubmed ID: 23060450

String Representations

InChiKey (Click to copy)
HSQMMOJMWPPIHU-DNFORWTRSA-N
InChi (Click to copy)
InChI=1S/C43H74NO8P/c1-3-5-7-8-9-10-11-12-13-14-15-19-22-25-28-32-37-49-39-42(40-51-53(47,48)50-38-36-44)52-43(46)35-31-27-24-21-18-16-17-20-23-26-30-34-41(45)33-29-6-4-2/h12-13,16-17,21,23-24,26,30,32,34,37,42H,3-11,14-15,18-20,22,25,27-29,31,33,35-36,38-40,44H2,1-2H3,(H,47,48)/b13-12-,17-16-,24-21-,26-23-,34-30+,37-32-/t42-/m1/s1
SMILES (Click to copy)
C(/OC[C@@](COP(=O)(O)OCCN)([H])OC(CCC/C=C\C/C=C\C/C=C\C=C\C(=O)CCCCC)=O)=C/CCCCCC/C=C\CCCCCCCC

Other Databases

PubChem CID
178330822

Calculated Physicochemical Properties

Heavy Atoms 53
Rings
Aromatic Rings
Rotatable Bonds 39
Van der Waals Molecular Volume 832.49
Topological Polar Surface Area 134.38
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 9
logP 13.09
Molar Refractivity 221.72

Admin

Created at
8th Nov 2024
Updated at
11th Nov 2025
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.