LIPID MAPS

1,2-Dipalmitoyl-sn-glycero-3-PC (1,2-DPPC) is a zwitterionic glycerophospholipid commonly used in the formation of lipid monolayers, bilayers, and liposomes for use in a variety of applications.^1,2,3,4 It has been used in the formation of proteoliposomes for implantation of γ-glutamyl transpeptidase into human erythrocyte membranes.³ Incorporation of glycosphingolipid antigens into 1,2-DPPC-containing liposomes increases the immunogenicity of the antigens in mice.⁴

This information has been provided by Cayman Chemical

References

1. Kalra, V.K., Sikka, S.C., and Sethi, G.S. Transport of amino acids in γ-glutamyl transpeptidase-implanted human erythrocytes. The Journal of Biological Chemisty 256(11), 5567-5571 (1981).

2. Uemura, A., Watarai, S., Iwasaki, T., et al. Induction of immune responses against glycosphingolipid antigens: Comparison of antibody responses in mice immunized with antigen associated with liposomes prepared from various phospholipids. J. Vet. Med. Sci. 67(12), 1197-1201 (2005).

3. Ege, C., and Lee, K.Y.C. Insertion of Alzheimer’s Aβ40 peptide into lipid monolayers. Biophys. J. 87(3), 1732-1740 (2004).

4. 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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String Representations

InChiKey (Click to copy)

KILNVBDSWZSGLL-KXQOOQHDSA-N

InChi (Click to copy)

InChI=1S/C40H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-39(42)46-36-38(37-48-50(44,45)47-35-34-41(3,4)5)49-40(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h38H,6-37H2,1-5H3/t38-/m1/s1

SMILES (Click to copy)

[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCCCCCCCCCCCCCC)=O)COC(CCCCCCCCCCCCCCC)=O

Other Databases

Wikipedia

Dipalmitoylphosphatidylcholine

LIPIDAT ID

9089

HMDB ID

CHEBI ID

PubChem CID

SwissLipids ID

Cayman ID

PDB ID

Calculated Physicochemical Properties

Heavy Atoms 50

Rings 0

Aromatic Rings 0

Rotatable Bonds 40

Van der Waals Molecular Volume 796.43

Topological Polar Surface Area 111.19

Hydrogen Bond Donors 0

Hydrogen Bond Acceptors 9

logP 12.04

Molar Refractivity 206.34

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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.

Structure Database (LMSD)

3D model of PC(16:0/16:0)

Classification

Biological Context