Structure Database (LMSD)
Common Name
PC(12:0/12:0)
Systematic Name
1,2-didodecanoyl-sn-glycero-3-phosphocholine
Synonyms
- Dilauroyl phosphatidylcholine
- 1,2-dilauroyl-sn-glycero-3-phosphocholine
- 1,2-didodecanoyl-sn-phosphatidylcholine
- 1,2-Didodecanoyl-sn-glycero-3-phosphocholine
- 1,2-Dilauroyl-L-phosphatidylcholine
- 1,2-Dilauroyl-sn-3-phosphatidylcholine
- PC(24:0)
- PC(12:0_12:0)
LM ID
LMGP01010429
Formula
Exact Mass
Calculate m/z
621.436957
Sum Composition
Abbrev Chains
PC 12:0_12:0
Status
Curated
3D model of PC(12:0/12:0)
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
1,2-Dilauroyl-sn-glycero-3-PC (1,2-DLPC) is a phospholipid containing the medium-chain (12:0) lauric acid inserted at the sn-1 and sn-2 positions. It is commonly used in the generation of micelles, liposomes, and other types of artificial membranes.1,2,3 Experimentally, 1,2-DLPC is used to form thinner membranes than those produced with PC containing the more common long-chain or very long-chain fatty acids, or to simply vary membrane formulation.3,4
This information has been provided by Cayman Chemical
References
1. Mazari, A., Iwamoto, S., and Yamauchi, R. Effects of linoleic acid position in phosphatidylcholines and cholesterol addition on their rates of peroxidation in unilamellar liposomes. Biosci. Biotechnol. Biochem. 74(5), 1013-1017 (2010).
2. Muhle-Goll, C., Hoffmann, S., Afonin, S., et al. Hydrophobic matching controls the tilt and stability of the dimeric platelet-derived growth factor receptor (PDGFR) β transmembrane segment. The Journal of Biological Chemisty 287(31), 26178-26186 (2012).
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).
String Representations
InChiKey (Click to copy)
IJFVSSZAOYLHEE-SSEXGKCCSA-N
InChi (Click to copy)
InChI=1S/C32H64NO8P/c1-6-8-10-12-14-16-18-20-22-24-31(34)38-28-30(29-40-42(36,37)39-27-26-33(3,4)5)41-32(35)25-23-21-19-17-15-13-11-9-7-2/h30H,6-29H2,1-5H3/t30-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCCCCCCCCCC)=O)COC(CCCCCCCCCCC)=O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
42
Rings
0
Aromatic Rings
0
Rotatable Bonds
32
Van der Waals Molecular Volume
658.03
Topological Polar Surface Area
111.19
Hydrogen Bond Donors
0
Hydrogen Bond Acceptors
9
logP
8.92
Molar Refractivity
169.41
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.
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.