Structure Database (LMSD)
Common Name
PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)
Systematic Name
1-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine
Synonyms
- PC(22:6/0:0)
- LPC(22:6)
LM ID
LMGP01050056
Formula
Exact Mass
Calculate m/z
567.332492
Sum Composition
Abbrev Chains
LPC 22:6
Status
Curated
3D model of PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)
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-Docosahexaenoyl-2-hydroxy-sn-glycero-3-PC is a lysophospholipid containing docosahexaenoic acid (DHA) at the sn-1 position that has been found in shark liver extract.1 1-Docosahexaenoyl-2-hydroxy-sn-glycero-3-PC decreases LPS-induced increases in TNF-α and IL-6 levels in RAW 264.7 cells in a concentration-dependent manner.2 It decreases LPS-induced production of nitric oxide (NO) in RAW 264.7 cells when used at concentrations ranging from 12 to 200 µM. 1-Docosahexaenoyl-2-hydroxy-sn-glycero-3-PC (15-500 µg/kg) inhibits plasma leakage into the peritoneum in a mouse model of peritonitis induced by zymosan A .
This information has been provided by Cayman Chemical
References
1. Chen, S., and Li, K.W. Mass spectrometric identification of molecular species of phosphatidylcholine and lysophosphatidylcholine extracted from shark liver. J. Agric. Food Chem. 55(23), 9670-9677 (2007).
Reactions
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String Representations
InChiKey (Click to copy)
LSOWKZULVQWMLY-APPDJCNMSA-N
InChi (Click to copy)
InChI=1S/C30H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-30(33)36-27-29(32)28-38-39(34,35)37-26-25-31(2,3)4/h6-7,9-10,12-13,15-16,18-19,21-22,29,32H,5,8,11,14,17,20,23-28H2,1-4H3/b7-6-,10-9-,13-12-,16-15-,19-18-,22-21-/t29-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(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
12343
HMDB ID
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID
Calculated Physicochemical Properties
Heavy Atoms
39
Rings
0
Aromatic Rings
0
Rotatable Bonds
24
Van der Waals Molecular Volume
601.44
Topological Polar Surface Area
105.12
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
8
logP
7.00
Molar Refractivity
159.30
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.