LIPID MAPS

1-Oleoyl-2-palmitoyl-sn-glycero-3-PC (1,2-OPPC) is a phospholipid containing oleic acid and palmitic acid at the sn-1 and sn-2 positions, respectively, that is found in biological membranes.¹ It can be used in the generation of liposomes and other artificial membranes.^2,3,4 Artificial membranes containing 1,2-OPPC have been used to study S. aureus α-toxin assembly and the effects of phytol on membranes, as well as for the characterization of phospholipase A2.

This information has been provided by Cayman Chemical

References

1. Picquart, M., and Lefèvre, T. Raman and Fourier transform infrared study of phytol effects on saturated and unsaturated lipid multibilayers. J. Raman Spectrosc. 34(1), 4–12 (2003).

2. Bayburt, T., Yu, B.-Z., Lin, H.-K., et al. Human nonpancreatic secreted phospholipase A2: Interfacial parameters, substrate specificities, and competitive inhibitors. Biochemistry 32(2), 573-582 (1993).

3. Tomita, T., Watanabe, M., and Yasuda, T. Influence of membrane fluidity on the assembly of Staphylococcus aureus α-toxin, a channel-forming protein, in liposome membrane. J. Biol. Chem. 267(19), 13391-13397 (1992).

4. Kuge, H., Akahori, K., Yagyu, K., et al. Functional compartmentalization of the plasma membrane of neurons by a unique acyl chain composition of phospholipids. J. Biol. Chem. 289(39), 26783-26793 (2014).

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String Representations

InChiKey (Click to copy)

RRVPPYNAZJRZFR-VYOBOKEXSA-N

InChi (Click to copy)

InChI=1S/C42H82NO8P/c1-6-8-10-12-14-16-18-20-21-23-24-26-28-30-32-34-41(44)48-38-40(39-50-52(46,47)49-37-36-43(3,4)5)51-42(45)35-33-31-29-27-25-22-19-17-15-13-11-9-7-2/h20-21,40H,6-19,22-39H2,1-5H3/b21-20-/t40-/m1/s1

SMILES (Click to copy)

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

Other Databases

LIPIDAT ID

9152

HMDB ID

CHEBI ID

PubChem CID

SwissLipids ID

Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 52

Rings 0

Aromatic Rings 0

Rotatable Bonds 41

Van der Waals Molecular Volume 828.39

Topological Polar Surface Area 111.19

Hydrogen Bond Donors 0

Hydrogen Bond Acceptors 9

logP 12.59

Molar Refractivity 215.48

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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(18:1(9Z)/16:0)

Classification

Biological Context