Structure Database (LMSD)

Common Name
PE(16:0/0:0)
Systematic Name
1-hexadecanoyl-sn-glycero-3-phosphoethanolamine
Synonyms
  • LPE(16:0/0:0)
  • 16:0 LYSO-PE
  • 1-palmitoyl-phosphatidylethenolamine
  • Hexadecanoic acid, 3-[[(2-aminoethoxy)hydroxyphosphinyl]oxy]-2-hydroxypropyl ester, (R)-
  • 1-Palmitoyl-sn-glycerol-3-L-alpha-phosphorylethanolamine
  • 1-Palmitoyl-sn-glycerophosphatidylethanolamine
  • LPE(16:0)
  • LPE(16:0)
LM ID
LMGP02050002
Formula
C21H44NO7P
Exact Mass
Calculate m/z
453.285542
Sum Composition
LPE 16:0
Abbrev Chains
LPE 16:0
Status
Curated
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Classification

Category
Main Class
Sub Class
Glycerophospholipids [GP]
Glycerophosphoethanolamines [GP02]
Monoacylglycerophosphoethanolamines [GP0205]

Biological Context

1-Palmitoyl-2-hydroxy-sn-glycero-3-PE is a naturally occurring lysophospholipid.1 It inhibits the growth of L. donovani promastigotes (GIC50 = 8 µM).2 1-Palmitoyl-2-hydroxy-sn-glycero-3-PE serum levels are decreased in a mouse model of alcohol-induced liver injury and in a hepatocellular carcinoma mouse xenograft model.3 Human serum levels are also decreased immediately after completing a three-day exercise regimen of 2.5 hours of running per day, as well as 14 hours after completing the regimen.1 1-Palmitoyl-2-hydroxy-sn-glycero-3-PE has been used as an internal standard for the quantification of saturated lysophosphoethanolamines.4

This information has been provided by Cayman Chemical

References

1. Nieman, D.C., Shanely, R.A., Gillitt, N.D., et al. Serum metabolic signatures induced by a three-day intensified exercise period persist after 14 h of recovery in runners. J. Proteome Res. 12(10), 4577-4584 (2013).
2. Achterberg, V., and Gercken, G. Cytotoxicity of ester and ether lysophospholipids on Leishmania donovani promastigotes. Mol. Biochem. Parasitol. 23(2), 117-122 (1987).
3. Li, S., Liu, H., Jin, Y., et al. Metabolomics study of alcohol-induced liver injury and hepatocellular carcinoma xenografts in mice. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 879(24), 2369-2375 (2011).
4. Avadhani, M., Geyer, R., White, D.C., et al. Lysophosphatidylethanolamine is a substrate for the short-chain alcohol dehydrogenase SocA from Myxococcus xanthus. J. Bacteriol. 188(24), 8543-8550 (2006).

Reactions

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String Representations

InChiKey (Click to copy)
YVYMBNSKXOXSKW-HXUWFJFHSA-N
InChi (Click to copy)
InChI=1S/C21H44NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-21(24)27-18-20(23)19-29-30(25,26)28-17-16-22/h20,23H,2-19,22H2,1H3,(H,25,26)/t20-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)(O)OCCN)([H])(O)COC(CCCCCCCCCCCCCCC)=O

Other Databases

LIPIDAT ID
7285
HMDB ID
HMDB0011503
CHEBI ID
73004
PubChem CID
9547069
SwissLipids ID
SLM:000000654
Cayman ID
26011

Calculated Physicochemical Properties

Heavy Atoms 30
Rings 0
Aromatic Rings 0
Rotatable Bonds 23
Van der Waals Molecular Volume 461.58
Topological Polar Surface Area 128.31
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 7
logP 6.06
Molar Refractivity 120.40

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.