Structure Database (LMSD)

Common Name
PC(6:0/6:0)
Systematic Name
1,2-dihexanoyl-sn-glycero-3-phosphocholine
Synonyms
  • 1,2-Dihexanoyl-L-alpha-glycerophosphorylcholine
  • 1,2-Dihexanoyl-sn-3-glycerophosphocholine
  • 1,2-Dihexanoyl-sn-glycerol-3-phosphocholine
  • Dicaproyl-L-alpha-lecithin
  • Dihexanoyllecithin
  • L-alpha-Dihexanoyllecithin
  • L-alpha-Dihexanoylphosphatidylcholine
  • L-1,2-Dihexanoyllecithin
  • PC(12:0)
  • PC(6:0/6:0)
LM ID
LMGP01011229
Formula
C20H40NO8P
Exact Mass
Calculate m/z
453.249157
Sum Composition
PC 12:0
Abbrev Chains
PC 6:0_6:0
Status
Curated
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Classification

Category
Main Class
Sub Class
Glycerophospholipids [GP]
Glycerophosphocholines [GP01]
Diacylglycerophosphocholines [GP0101]

Biological Context

1,2-Dihexanoyl-sn-glycero-3-PC (DHPC-C6) is a synthetic phospholipid containing the short-chain (6:0) caproic acid inserted at the sn-1 and sn-2 positions. It is a substrate for phospholipase C isolated from B. cereus as well as phospholipase A2 isolated from A. halys blomhoffi and N. naja atra snake venom.1,2 DHPC is commonly used in the generation of micelles, liposomes, and other types of artificial membranes.3

This information has been provided by Cayman Chemical

References

1. Batenjany, M.M., O'Leary, T.J., Levin, I.W., et al. Packing characteristics of two-component bilayers composed of ester- and ether-linked phospholipids. Biophys. J. 72(4), 1695-1700 (1997).
2. Little, C. Phospholipase C from Bacillus cereus. Action on some artificial lecithins. Acta Chem. Scand. B 31(4), 267-272 (1977).
3. Teshima, K., Kitagawa, Y., Samejima, Y., et al. Role of Ca2+ in the substrate binding and catalytic functions of snake venom phospholipases A2. J. Biochem. 106(3), 518-527 (1989).

Reactions

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String Representations

InChiKey (Click to copy)
DVZARZBAWHITHR-GOSISDBHSA-N
InChi (Click to copy)
InChI=1S/C20H40NO8P/c1-6-8-10-12-19(22)26-16-18(29-20(23)13-11-9-7-2)17-28-30(24,25)27-15-14-21(3,4)5/h18H,6-17H2,1-5H3/t18-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCCCC)=O)COC(CCCCC)=O

Other Databases

LIPIDAT ID
8385
CHEBI ID
138194
PubChem CID
10072611
SwissLipids ID
SLM:000012486
Cayman ID
25585

Calculated Physicochemical Properties

Heavy Atoms 30
Rings 0
Aromatic Rings 0
Rotatable Bonds 20
Van der Waals Molecular Volume 450.43
Topological Polar Surface Area 111.19
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 9
logP 4.24
Molar Refractivity 114.00

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.