Structure Database (LMSD)

Common Name
PE(18:0/18:0)
Systematic Name
1,2-dioctadecanoyl-sn-glycero-3-phosphoethanolamine
Synonyms
  • Distearoyl phosphatidylethanolamine
  • Octadecanoic acid, 1-[[[(2-aminoethoxy)hydroxyphosphinyl]oxy]methyl]-1,2-ethanediyl ester, (R)-
  • Stearin, 1,2-di-, 2-aminoethyl hydrogen phosphate, L-
  • 1,2-Distearoyl-sn-glycero-3-phosphoethanolamine
  • L-alpha-Distearoylphosphatidylethanolamine
  • L-beta,gamm
  • PE(36:0)
  • PE(18:0_18:0)
LM ID
LMGP02010097
Formula
C41H82NO8P
Exact Mass
Calculate m/z
747.577807
Sum Composition
PE 36:0
Abbrev Chains
PE 18:0_18:0
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
Predict MS/MS spectrum (Neg. Mode)
View ion mobility data

Classification

Category
Main Class
Sub Class
Glycerophospholipids [GP]
Glycerophosphoethanolamines [GP02]
Diacylglycerophosphoethanolamines [GP0201]

Biological Context

Phosphatidylethanolamines (PEs) are phospholipids found in biological membranes that serve both structural and functional roles.1,2 Different types of PEs are commonly used in the generation of micelles, liposomes, and other types of artificial membranes.3,4 1,2-Distearoyl-sn-glycero-3-PE (DSPE) is a phospholipid containing the saturated long-chain (18:0) stearic acid inserted at the sn-1 and sn-2 positions.

This information has been provided by Cayman Chemical

References

1. Fattal, E., Couvreur, P., and Dubernet, C. "Smart" delivery of antisense oligonucleotides by anionic pH-sensitive liposomes. Adv. Drug Deliv. Rev. 56(7), 931-946 (2004).
2. Simões, S., Moreira, J.N., Fonseca, C., et al. On the formulation of pH-sensitive liposomes with long circulation times. Adv. Drug Deliv. Rev. 56(7), 947-965 (2004).
3. Vance, J.E., and Tasseva, G. Formation and function of phosphatidylserine and phosphatidylethanolamine in mammalian cells. Biochim. Biophys. Acta 1831(3), 543-554 (2013).
4. Wellner, N., Diep, T.A., Janfelt, C., et al. N-acylation of phosphatidylethanolamine and its biological functions in mammals. Biochim. Biophys. Acta 1831(3), 652-662 (2013).

Reactions

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String Representations

InChiKey (Click to copy)
LVNGJLRDBYCPGB-LDLOPFEMSA-N
InChi (Click to copy)
InChI=1S/C41H82NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(43)47-37-39(38-49-51(45,46)48-36-35-42)50-41(44)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h39H,3-38,42H2,1-2H3,(H,45,46)/t39-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)(O)OCCN)([H])(OC(CCCCCCCCCCCCCCCCC)=O)COC(CCCCCCCCCCCCCCCCC)=O

Other Databases

LIPIDAT ID
8303
HMDB ID
HMDB0008991
CHEBI ID
39934
PubChem CID
447078
SwissLipids ID
SLM:000034913
Cayman ID
15095
PDB ID
3PE

Calculated Physicochemical Properties

Heavy Atoms 51
Rings 0
Aromatic Rings 0
Rotatable Bonds 43
Van der Waals Molecular Volume 813.73
Topological Polar Surface Area 134.38
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 8
logP 13.65
Molar Refractivity 213.05

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.