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
C30H50NO7P
Exact Mass
Calculate m/z
567.33249
Sum Composition
LPC 22:6
Abbrev Chains
LPC 22:6
Status
Curated
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Classification

Category
Main Class
Sub Class
Glycerophospholipids [GP]
Glycerophosphocholines [GP01]
Monoacylglycerophosphocholines [GP0105]

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).
2. Huang, L.S., Hung, N.D., Sok, D.-E., et al. Lysophosphatidylcholine containing docosahexaenoic acid at the sn-1 position is anti-inflammatory. Lipids 45(3), 225-236 (2010).

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
HMDB0010404
CHEBI ID
73873
PubChem CID
10415542
SwissLipids ID
SLM:000020735
Cayman ID
37340

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
11th Nov 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.