Structure Database (LMSD)
Common Name
PE(18:0/20:4(5Z,8Z,10E,14Z)(12Ke))
Systematic Name
1-octadecanoyl-2-(12-oxo-5Z,8Z,10E,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine
Synonyms
- 18:0/12-KETE-PE
LM ID
LMGP20020065
Formula
Exact Mass
Calculate m/z
781.525772
Sum Composition
Abbrev Chains
PE 18:0_20:5;O
Status
Active
3D model of PE(18:0/20:4(5Z,8Z,10E,14Z)(12Ke))
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)
VPCFQLHMLBMUIL-HEUKMSAXSA-N
InChi (Click to copy)
InChI=1S/C43H76NO9P/c1-3-5-7-9-11-12-13-14-15-16-17-18-22-26-30-34-42(46)50-38-41(39-52-54(48,49)51-37-36-44)53-43(47)35-31-27-23-20-19-21-25-29-33-40(45)32-28-24-10-8-6-4-2/h20-21,23-25,28-29,33,41H,3-19,22,26-27,30-32,34-39,44H2,1-2H3,(H,48,49)/b23-20-,25-21-,28-24-,33-29+/t41-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)(O)OCCN)([H])(OC(CCC/C=C\C/C=C\C=C\C(=O)C/C=C\CCCCC)=O)COC(CCCCCCCCCCCCCCCCC)=O
Calculated Physicochemical Properties
Heavy Atoms
54
Rings
Aromatic Rings
Rotatable Bonds
41
Van der Waals Molecular Volume
843.92
Topological Polar Surface Area
151.45
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
10
logP
12.72
Molar Refractivity
222.30
Admin
Created at
8th Nov 2024
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.