Structure Database (LMSD)
Common Name
PE(0:0/20:4;O)
Systematic Name
2-(15R-hydroxy-5Z,8Z,12E,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine
Synonyms
- 15R-HETE-LPE
LM ID
LMGP20020056
Formula
Exact Mass
Calculate m/z
517.280457
Sum Composition
Abbrev Chains
LPE 0:0/20:4;O
Status
Active
3D model of PE(0:0/20:4;O)
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
References
String Representations
InChiKey (Click to copy)
UNKGTCKGUVAXEP-QXBHDIFNSA-N
InChi (Click to copy)
InChI=1S/C25H44NO8P/c1-2-3-13-16-23(28)17-14-11-9-7-5-4-6-8-10-12-15-18-25(29)34-24(21-27)22-33-35(30,31)32-20-19-26/h4-5,8-11,14,17,23-24,27-28H,2-3,6-7,12-13,15-16,18-22,26H2,1H3,(H,30,31)/b5-4-,10-8-,11-9-,17-14+/t23-,24-/m1/s1
SMILES (Click to copy)
C(OP(OCCN)(O)=O)[C@]([H])(OC(=O)CCC/C=C\C/C=C\C/C=C\C=C\[C@H](O)CCCCC)CO
Calculated Physicochemical Properties
Heavy Atoms
35
Rings
0
Aromatic Rings
0
Rotatable Bonds
23
Van der Waals Molecular Volume
529.01
Topological Polar Surface Area
148.54
Hydrogen Bond Donors
4
Hydrogen Bond Acceptors
9
logP
5.98
Molar Refractivity
140.39
Admin
Created at
20th Aug 2020
Updated at
8th Nov 2024
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.