LIPID MAPS

1-Oleoyl-2-hydroxy-sn-glycero-3-PE is a naturally-occurring lysophospholipid and an analog of plasmalogen lysophosphatidylethanolamine.^1,2,3 It induces transient increases in intracellular calcium in PC12 rat neuronal cells in a concentration-dependent manner, an effect that can be blocked by the lysophosphatidic acid receptor 1 (LPA1) antagonist AM095 .² 1-Oleoyl-2-hydroxy-sn-glycero-3-PE (100 ng/ml) increases IL-2 production in CD1d-stimulated murine natural killer T (NKT) cell hybridoma 2H4 cells.³ It also induces production of IL-4, but not IFN-γ, in murine splenocytes when used at a concentration of 100 ng/ml and in mouse serum when administered at a dose of 1 μg per animal, indicating induction of the T helper 2 (Th2) response. 1-Oleoyl-2-hydroxy-sn-glycero-3-PE levels increase in interscapular brown adipose tissue (iBAT) in mice following three-day cold exposure.¹

This information has been provided by Cayman Chemical

References

1. Marcher, A.B., Loft, A., Nielsen, R., et al. RNA-Seq and mass-spectrometry-based lipidomics reveal extensive changes of glycerolipid pathways in brown adipose tissue in response to cold. Cell. Rep. 13(9), 2000-2013 (2015).

2. Lee, J.M., Park, S.J., and Im, D.S. Lysophosphatidylethanolamine increases intracellular Ca2+ through LPA1 in PC-12 neuronal cells. Biochem. Biophys. Res. Commun. 461(2), 378-382 (2015).

3. Ni, G., Li, Z., Liang, K., et al. Synthesis and evaluation of immunostimulant plasmalogen lysophosphatidylethanolamine and analogues for natural killer T cells. Bioorg. Med. Chem. 22(11), 2966-2973 (2014).

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String Representations

InChiKey (Click to copy)

PYVRVRFVLRNJLY-MZMPXXGTSA-N

InChi (Click to copy)

InChI=1S/C23H46NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(26)29-20-22(25)21-31-32(27,28)30-19-18-24/h9-10,22,25H,2-8,11-21,24H2,1H3,(H,27,28)/b10-9-/t22-/m1/s1

SMILES (Click to copy)

[C@](COP(=O)(O)OCCN)([H])(O)COC(CCCCCCC/C=C\CCCCCCCC)=O

Other Databases

LIPIDAT ID

7287

HMDB ID

CHEBI ID

PubChem CID

SwissLipids ID

Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 32

Rings 0

Aromatic Rings 0

Rotatable Bonds 24

Van der Waals Molecular Volume 493.54

Topological Polar Surface Area 128.31

Hydrogen Bond Donors 3

Hydrogen Bond Acceptors 7

logP 6.62

Molar Refractivity 129.54

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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.

Structure Database (LMSD)

3D model of PE(18:1(9Z)/0:0)

Classification

Biological Context