Structure Database (LMSD)
Common Name
PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
Systematic Name
1,2-di-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine
Synonyms
- PC(22:6/22:6)
- PC(44:12)
- PC(22:6/22:6)
LM ID
LMGP01011119
Formula
Exact Mass
Calculate m/z
877.562157
Sum Composition
Abbrev Chains
PC 22:6_22:6
Status
Curated
3D model of PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
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-Didocosahexaenoyl-sn-glycero-3-PC is a phospholipid that contains docosahexaenoic acid at the sn-1 and sn-2 positions. It has been used in the formation of polyunsaturated endoplasmic reticulum-targeting liposomes (PERLs) that reduce cellular cholesterol levels in human peripheral blood mononuclear cells (PBMCs) and decrease the secretion of HIV-1 particles in PBMCs infected with HIV-1LAI.1 It has been used as a component of lipid monolayers and small unilamellar vesicles to study the effect of phospholipid composition on membrane fluidity.2
This information has been provided by Cayman Chemical
References
1. Pollock, S., Nichita, N.B., Böhmer, A., et al. Polyunsaturated liposomes are antiviral against hepatitis B and C viruses and HIV by decreasing cholesterol levels in infected cells. Proc. Natl. Acad. Sci. USA 107(40), 17176-17181 (2010).
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)
XLKQWAMTMYIQMG-SVUPRYTISA-N
InChi (Click to copy)
InChI=1S/C52H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-42-44-51(54)58-48-50(49-60-62(56,57)59-47-46-53(3,4)5)61-52(55)45-43-41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h8-11,14-17,20-23,26-29,32-35,38-41,50H,6-7,12-13,18-19,24-25,30-31,36-37,42-49H2,1-5H3/b10-8-,11-9-,16-14-,17-15-,22-20-,23-21-,28-26-,29-27-,34-32-,35-33-,40-38-,41-39-/t50-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)=O)COC(CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)=O
Other Databases
LIPIDAT ID
7269
HMDB ID
PubChem CID
SwissLipids ID
Cayman ID
Calculated Physicochemical Properties
Heavy Atoms
62
Rings
0
Aromatic Rings
0
Rotatable Bonds
40
Van der Waals Molecular Volume
972.35
Topological Polar Surface Area
111.19
Hydrogen Bond Donors
0
Hydrogen Bond Acceptors
9
logP
14.03
Molar Refractivity
260.62
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.