Structure Database (LMSD)
Common Name
PE(0:0/20:4;O2)
Systematic Name
2-(12S-hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine
Synonyms
- 12S-HpETE-LPE
LM ID
LMGP20020057
Formula
Exact Mass
Calculate m/z
533.275372
Sum Composition
Abbrev Chains
LPE 0:0/20:4;O2
Status
Active
3D model of PE(0:0/20:4;O2)
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)
ZGEKQEOYROFIFO-CNZMPJCYSA-N
InChi (Click to copy)
InChI=1S/C25H44NO9P/c1-2-3-4-5-10-13-16-23(35-29)17-14-11-8-6-7-9-12-15-18-25(28)34-24(21-27)22-33-36(30,31)32-20-19-26/h7-11,13-14,17,23-24,27,29H,2-6,12,15-16,18-22,26H2,1H3,(H,30,31)/b9-7-,11-8-,13-10-,17-14+/t23-,24+/m0/s1
SMILES (Click to copy)
C(O[C@@]([H])(COP(O)(=O)OCCN)CO)(CCC/C=C\C/C=C\C=C\[C@@H](OO)C/C=C\CCCCC)=O
Other Databases
PubChem CID
Calculated Physicochemical Properties
Heavy Atoms
36
Rings
0
Aromatic Rings
0
Rotatable Bonds
24
Van der Waals Molecular Volume
537.80
Topological Polar Surface Area
157.77
Hydrogen Bond Donors
4
Hydrogen Bond Acceptors
10
logP
6.65
Molar Refractivity
141.75
Admin
Created at
27th 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.