Structure Database (LMSD)
Common Name
PE(P-18:1(9Z)/20:4(5Z,8Z,10E,14Z)(12Ke))
Systematic Name
1-O-(1Z,9Z-octadecadienyl)-2-(12-oxo-5Z,8Z,10E,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine
Synonyms
- 18:1p/12-KETE-PE
LM ID
LMGP20020064
Formula
Exact Mass
Calculate m/z
763.515207
Sum Composition
Abbrev Chains
PE P-18:1_20:5;O
Status
Active
3D model of PE(P-18:1(9Z)/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)
RATHUEVZDWFWRD-VPRSWRCCSA-N
InChi (Click to copy)
InChI=1S/C43H74NO8P/c1-3-5-7-9-11-12-13-14-15-16-17-18-21-24-28-32-37-49-39-42(40-51-53(47,48)50-38-36-44)52-43(46)35-31-27-23-20-19-22-26-30-34-41(45)33-29-25-10-8-6-4-2/h14-15,20,22-23,25-26,29-30,32,34,37,42H,3-13,16-19,21,24,27-28,31,33,35-36,38-40,44H2,1-2H3,(H,47,48)/b15-14-,23-20-,26-22-,29-25-,34-30+,37-32-/t42-/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)CO/C=C\CCCCCC/C=C\CCCCCCCC
Calculated Physicochemical Properties
Heavy Atoms
53
Rings
Aromatic Rings
Rotatable Bonds
39
Van der Waals Molecular Volume
832.49
Topological Polar Surface Area
134.38
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
9
logP
13.09
Molar Refractivity
221.72
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.