Structure Database (LMSD)

Common Name
PC(16:0/18:2(9Z,12Z))
Systematic Name
1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine
Synonyms
  • 1-Palmitoyl-2-linoleoyl-sn-glycero-phosphatidylcholine
  • 1-Palmitoyl-2-linoleoyl-sn-glycero-3-phosphocholine
  • PC(16:0/18:2n6)
  • Phosphatidylcholine(16:0/18:2w6)
  • PC(34:2)
  • PC(16:0_18:2)
LM ID
LMGP01010594
Formula
Exact Mass
Calculate m/z
757.562157
Sum Composition
Abbrev Chains
PC 16:0_18:2
Status
Curated



Classification

Biological Context

1-Palmitoyl-2-Linoleoyl-sn-glycero-3-PC is a phospholipid containing palmitic (16:0) and linoleic (18:2) acids inserted at the sn-1 and sn-2 positions, respectively. It can be used in the generation of micelles, liposomes, and other types of artificial membranes and has been particularly useful in the study of lipid peroxidation.1,2,3

This information has been provided by Cayman Chemical

References

1. Milne, G.L., Seal, J.R., Havrilla, C.M., et al. Identification and analysis of products formed from phospholipids in the free radical oxidation of human low density lipoproteins. J. Lipid Res. 46(2), 307-319 (2005).
2. Høyrup, P., Mouritsen, O.G., and Jørgensen, K. Phospholipase A2 activity towards vesicles of DPPC and DMPC-DSPC containing small amounts of SMPC. Biochim. Biophys. Acta 1515(2), 133-143 (2001).

Reactions

Filter by species:
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.
Click on an edge to display the reaction(s).
Reactions graph legend

String Representations

InChiKey (Click to copy)
JLPULHDHAOZNQI-ZTIMHPMXSA-N
InChi (Click to copy)
InChI=1S/C42H80NO8P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h14,16,20-21,40H,6-13,15,17-19,22-39H2,1-5H3/b16-14-,21-20-/t40-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCCCCCC/C=C\C/C=C\CCCCC)=O)COC(CCCCCCCCCCCCCCC)=O

Other Databases

LIPIDAT ID
8638
HMDB ID
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID
PDB ID

Calculated Physicochemical Properties

Heavy Atoms 52
Rings 0
Aromatic Rings 0
Rotatable Bonds 40
Van der Waals Molecular Volume 825.75
Topological Polar Surface Area 111.19
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 9
logP 12.37
Molar Refractivity 215.39

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.