Structure Database (LMSD)
Common Name
PC(18:0/18:0)
Systematic Name
1,2-dioctadecanoyl-sn-glycero-3-phosphocholine
Synonyms
- Distearoyl phosphatidylcholine
- 1,2-distearoyl-sn-glycero-3-phosphocholine
- Di-stearoyl-phosphatidylcholine
- PC(36:0)
- PC(18:0/18:0)
LM ID
LMGP01010006
Formula
Exact Mass
Calculate m/z
789.624757
Sum Composition
Abbrev Chains
PC 18:0_18:0
Status
Curated
3D model of PC(18:0/18:0)
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-Distearoyl-sn-glycero-3-PC (1,2-DSPC) is a phospholipid containing the saturated long-chain (18:0) stearic 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 The transition temperature of 1,2-DSPC is approximately 55°C in a multilamellar aqueous solution.3
This information has been provided by Cayman Chemical
References
1. Heberle, F.A., and Feigenson, G.W. Phase separation in lipid membranes. Cold Spring Harb. Perspect. Biol. 3(4), 1-13 (2011).
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).
3. Mabrey, S., and Sturtevant, J.M. Investigation of phase transitions of lipids and lipid mixtures by sensitivity differential scanning calorimetry. Proc. Natl. Acad. Sci. USA 73(11), 3862-3866 (1976).
Reactions
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String Representations
InChiKey (Click to copy)
NRJAVPSFFCBXDT-HUESYALOSA-N
InChi (Click to copy)
InChI=1S/C44H88NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h42H,6-41H2,1-5H3/t42-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCCCCCCCCCCCCCCCC)=O)COC(CCCCCCCCCCCCCCCCC)=O
Other Databases
HMDB ID
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID
PDB ID
Calculated Physicochemical Properties
Heavy Atoms
54
Rings
0
Aromatic Rings
0
Rotatable Bonds
44
Van der Waals Molecular Volume
865.63
Topological Polar Surface Area
111.19
Hydrogen Bond Donors
0
Hydrogen Bond Acceptors
9
logP
13.60
Molar Refractivity
224.81
Admin
Created at
-
Updated at
14th Mar 2025
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.