Structure Database (LMSD)
Common Name
PE(16:0/16:0)
Systematic Name
1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine
Synonyms
- Dipalmitoyl phosphatidylethanolamine
- Hexadecanoic acid, 1-[[[(2-aminoethoxy)hydroxyphosphinyl]oxy]methyl]-1,2-ethanediyl ester, (R)-
- Palmitin, 1,2-di-, 2-aminoethyl hydrogen phosphate, L-
- 1,2-Dihexadecanoyl-sn-glycerol-3-phosphorylethanolamine
- 1,2-Dipalmitoyl-3-sn-phosphatidylethanolamine
- DPPE
- PE(32:0)
- PE(16:0_16:0)
LM ID
LMGP02010037
Formula
Exact Mass
Calculate m/z
691.515207
Sum Composition
Abbrev Chains
PE 16:0_16:0
Status
Curated
3D model of PE(16:0/16:0)
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
1,2-Dipalmitoyl-sn-glycero-3-PE (1,2-DPPE) is a naturally-occurring PE containing 16:0 fatty acids at the sn-1 and sn-2 positions. It belongs to a class of phospholipids that are the most abundant lipids in the inner leaflet of the plasma membrane.1 1,2-DPPE interacts with cholesterol to form a condensed lipid monolayer with tight hydrogen bonding of the 1,2-DPPE interheadgroups, resulting in a more fluid membrane that may aid in transport and signaling across the bilayer.2,3
This information has been provided by Cayman Chemical
References
3. Leekumjorn, S., and Sum, A.K. Molecular simulation study of structural and dynamic properties of mixed DPPC/DPPE bilayers. Biophys. J. 90(11), 3951-3965 (2006).
Reactions
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Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
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String Representations
InChiKey (Click to copy)
SLKDGVPOSSLUAI-PGUFJCEWSA-N
InChi (Click to copy)
InChI=1S/C37H74NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-36(39)43-33-35(34-45-47(41,42)44-32-31-38)46-37(40)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h35H,3-34,38H2,1-2H3,(H,41,42)/t35-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)(O)OCCN)([H])(OC(CCCCCCCCCCCCCCC)=O)COC(CCCCCCCCCCCCCCC)=O
Other Databases
LIPIDAT ID
1104
HMDB ID
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID
PDB ID
Calculated Physicochemical Properties
Heavy Atoms
47
Rings
0
Aromatic Rings
0
Rotatable Bonds
39
Van der Waals Molecular Volume
744.53
Topological Polar Surface Area
134.38
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
8
logP
12.09
Molar Refractivity
194.58
Admin
Created at
-
Updated at
25th Apr 2022
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.