Structure Database (LMSD)
Common Name
PC(8:0/8:0)
Systematic Name
1,2-dioctanoyl-sn-glycero-3-phosphocholine
Synonyms
- 1,2-Dioctanoyl-sn-glycero-3-phosphocholine
- 1,2-Dioctanoyl-sn-glycerol-3-phosphocholine
- Dicapryloyl-L-alpha-lecithin
- Dioctanoyl-L-alpha-glycerophosphorylcholine
- Dioctanoyl-L-alpha-phosphatidylcholine
- PC(16:0)
- PC(8:0/8:0)
LM ID
LMGP01011251
Formula
Exact Mass
Calculate m/z
509.311757
Sum Composition
Abbrev Chains
PC 8:0_8:0
Status
Curated
3D model of PC(8:0/8:0)
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
Phosphatidylcholine (PC) species are a common class of phospholipids that comprise the mammalian cell membrane. 1,2-Dioctanoyl-sn-glycero-3-PC is a synthetic analog of natural phosphatidylcholine species containing saturated C8:O fatty acids in the sn-1 and sn-2 positions of the glycerol backbone. It exhibits a critical micelle concentration (CMC) value of 0.25 mM at 27°C.1 1,2-Dioctanoyl-sn-glycero-3-PC serves as an efficient substrate for phospholipase D (PLD) as well as sPLA2 isozymes from bovine pancreas and bee venom.2,3
This information has been provided by Cayman Chemical
References
2. Davis, L.L., Maglio, J.J., and Horwitz, J. Phospholipase D hydrolyzes short-chain analogs of phosphatidylcholine in the absence of detergent. Lipids 33, 223-227 (1998).
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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String Representations
InChiKey (Click to copy)
YHIXRNNWDBPKPW-JOCHJYFZSA-N
InChi (Click to copy)
InChI=1S/C24H48NO8P/c1-6-8-10-12-14-16-23(26)30-20-22(33-24(27)17-15-13-11-9-7-2)21-32-34(28,29)31-19-18-25(3,4)5/h22H,6-21H2,1-5H3/t22-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCCCCCC)=O)COC(CCCCCCC)=O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
34
Rings
0
Aromatic Rings
0
Rotatable Bonds
24
Van der Waals Molecular Volume
519.63
Topological Polar Surface Area
111.19
Hydrogen Bond Donors
0
Hydrogen Bond Acceptors
9
logP
5.80
Molar Refractivity
132.47
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.