Structure Database (LMSD)
Common Name
PE(P-16:0/20:4(5Z,8Z,10E,14Z)(12Ke))
Systematic Name
1-O-(1Z-hexadecenyl)-2-(12-oxo-5Z,8Z,10E,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine
Synonyms
- 16:0p/12-KETE-PE
LM ID
LMGP20020062
Formula
Exact Mass
Calculate m/z
737.499557
Sum Composition
Abbrev Chains
PE P-16:0_20:5;O
Status
Active
3D model of PE(P-16:0/20:4(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)
LEUCHPDWNXLOMS-MCTVNBDBSA-N
InChi (Click to copy)
InChI=1S/C41H72NO8P/c1-3-5-7-9-11-12-13-14-15-16-19-22-26-30-35-47-37-40(38-49-51(45,46)48-36-34-42)50-41(44)33-29-25-21-18-17-20-24-28-32-39(43)31-27-23-10-8-6-4-2/h18,20-21,23-24,27-28,30,32,35,40H,3-17,19,22,25-26,29,31,33-34,36-38,42H2,1-2H3,(H,45,46)/b21-18-,24-20-,27-23-,32-28+,35-30-/t40-/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\CCCCCCCCCCCCCC
Calculated Physicochemical Properties
Heavy Atoms
51
Rings
Aromatic Rings
Rotatable Bonds
38
Van der Waals Molecular Volume
800.53
Topological Polar Surface Area
134.38
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
9
logP
12.53
Molar Refractivity
212.58
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.