Structure Database (LMSD)
Common Name
PE(14:0/0:0)
Systematic Name
1-tetradecanoyl-sn-glycero-3-phosphoethanolamine
Synonyms
- Tetradecanoic acid, 3-[[(2-aminoethoxy)hydroxyphosphinyl]oxy]-2-hydroxypropyl ester, (R)-
- LPE(14:0)
- LPE(14:0)
LM ID
LMGP02050003
Formula
Exact Mass
Calculate m/z
425.254242
Sum Composition
Abbrev Chains
LPE 14:0
Status
Curated
3D model of PE(14:0/0:0)
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
1-Myristoyl-2-hydroxy-sn-glycero-3-PE is a naturally occurring lysophospholipid.1 It induces transient increases in intracellular calcium in PC12 cells.2 Serum levels of 1-myristoyl-2-hydroxy-sn-glycero-3-PE are elevated in patients with malignant breast cancer compared to healthy controls.1
This information has been provided by Cayman Chemical
References
1. 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).
2. More, T.H., Bagadi, M., RoyChoudhury, S., et al. Comprehensive quantitative lipidomic approach to investigate serum phospholipid alterations in breast cancer. Metabolomics 13:3, (2017).
Reactions
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Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
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String Representations
InChiKey (Click to copy)
RPXHXZNGZBHSMJ-GOSISDBHSA-N
InChi (Click to copy)
InChI=1S/C19H40NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-19(22)25-16-18(21)17-27-28(23,24)26-15-14-20/h18,21H,2-17,20H2,1H3,(H,23,24)/t18-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)(O)OCCN)([H])(O)COC(CCCCCCCCCCCCC)=O
Other Databases
LIPIDAT ID
7286
HMDB ID
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID
Calculated Physicochemical Properties
Heavy Atoms
28
Rings
0
Aromatic Rings
0
Rotatable Bonds
21
Van der Waals Molecular Volume
426.98
Topological Polar Surface Area
128.31
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
7
logP
5.28
Molar Refractivity
111.16
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.