Structure Database (LMSD)
Common Name
PC(P-16:0/16:0)
Systematic Name
1-(1Z-hexadecenyl)-2-hexadecanoyl-glycero-3-phosphocholine
Synonyms
- PC(P-32:0)
- PC(P-16:0/16:0)
LM ID
LMGP01030025
Formula
Exact Mass
Calculate m/z
717.567241
Sum Composition
Abbrev Chains
PC P-16:0/16:0
Status
Curated
3D model of PC(P-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
1-1(Z)-Hexadecenyl-2-palmitoyl-sn-glycero-3-PC is a plasmalogen that has been found in various rat tissues, including the liver, heart, kidney, gluteus muscle, soleus muscle, and visceral and subcutaneous adipose tissue.1 It has been used in the synthesis of lipid bilayers to quantify the effects of amphiphilic compounds, such as lysophosphatidylcholine (1-palmitoyl-2-hydroxy-sn-glycero-3-PC; Item No. 10172) and lysoplasmenylcholine, on membrane dynamics.2
This information has been provided by Cayman Chemical
References
1. Pradas, I., Huynh, K., Cabré, R., et al. Lipidomics reveals a tissue-specific fingerprint. Front. Physiol. 9, 1165 (2018).
2. Han, X., and Gross, R.W. Alterations in membrane dynamics elicited by amphiphilic compounds are augmented in plasmenylcholine bilayers. Biochim. Biophys. Acta 1069(1), 37-45 (1991).
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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References
String Representations
InChiKey (Click to copy)
PEWXKAOBUSBJLD-MCBGMKGZSA-N
InChi (Click to copy)
InChI=1S/C40H80NO7P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-35-45-37-39(38-47-49(43,44)46-36-34-41(3,4)5)48-40(42)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h32,35,39H,6-31,33-34,36-38H2,1-5H3/b35-32-/t39-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCCCCCCCCCCCCCC)=O)CO/C=C\CCCCCCCCCCCCCC
Other Databases
HMDB ID
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID
Calculated Physicochemical Properties
Heavy Atoms
49
Rings
0
Aromatic Rings
0
Rotatable Bonds
39
Van der Waals Molecular Volume
787.64
Topological Polar Surface Area
94.12
Hydrogen Bond Donors
0
Hydrogen Bond Acceptors
8
logP
12.63
Molar Refractivity
205.86
Admin
Created at
-
Updated at
20th Dec 2024
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.