Structure Database (LMSD)
Common Name
PC(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
Systematic Name
1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine
Synonyms
- PC(18:0/22:6)
- PC(40:6)
- PC(18:0_22:6)
LM ID
LMGP01010821
Formula
Exact Mass
Calculate m/z
833.593457
Sum Composition
Abbrev Chains
PC 18:0_22:6
Status
Curated
3D model of PC(18:0/22:6(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-Stearoyl-2-docosahexaenoyl-sn-glycero-3-PC is a phospholipid containing stearic acid (Item No. 10011298) and docosahexaenoic acid (DHA; Item No. 90310) at the sn-1 and sn-2 positions, respectively. It has been used in the study of lipid membrane organization and dynamics.1 The levels of 1-stearoyl-2-docosahexaenoyl-sn-glycero-3-PC are decreased in the L5 anterior horn in a superoxide dismutase 1 mutant (SOD1G93A) transgenic mouse model of amyotrophic lateral sclerosis (ALS) at the terminal stage of disease.2
This information has been provided by Cayman Chemical
References
1. Arima, H., Omura, T., Hayasaka, T., et al. Reductions of docosahexaenoic acid-containing phosphatidylcholine levels in the anterior horn of an ALS mouse mode. Neuroscience 297, 127-136 (2015).
2. Leng, X., Kinnun, J.J., Cavazos, A.T., et al. All n-3 PUFA are not the same: MD simulations reveal differences in membrane organization for EPA, DHA and DPA. Biochim. Biophys. Acta Biomembr. 1860(5), 1125-1134 (2018).
Reactions
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String Representations
InChiKey (Click to copy)
FAUYAENFVCNTAL-PFFNLMTBSA-N
InChi (Click to copy)
InChI=1S/C48H84NO8P/c1-6-8-10-12-14-16-18-20-22-23-24-25-27-29-31-33-35-37-39-41-48(51)57-46(45-56-58(52,53)55-43-42-49(3,4)5)44-54-47(50)40-38-36-34-32-30-28-26-21-19-17-15-13-11-9-7-2/h8,10,14,16,20,22,24-25,29,31,35,37,46H,6-7,9,11-13,15,17-19,21,23,26-28,30,32-34,36,38-45H2,1-5H3/b10-8-,16-14-,22-20-,25-24-,31-29-,37-35-/t46-/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(CCCCCCCCCCCCCCCCC)=O
Other Databases
LIPIDAT ID
7230
HMDB ID
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID
Calculated Physicochemical Properties
Heavy Atoms
58
Rings
0
Aromatic Rings
0
Rotatable Bonds
42
Van der Waals Molecular Volume
918.99
Topological Polar Surface Area
111.19
Hydrogen Bond Donors
0
Hydrogen Bond Acceptors
9
logP
13.81
Molar Refractivity
242.72
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.