Structure Database (LMSD)
Common Name
PC(O-16:0/9:0(COOH))
Systematic Name
1-hexadecyl-2-(9-carboxy-nonanoyl)-sn-glycero-3-phosphocholine
Synonyms
- Azelaoyl PAF
- 1-hexadecyl-2-azelaoyl-sn-glycero-3-phosphocholine
LM ID
LMGP01020279
Formula
Exact Mass
Calculate m/z
651.44752
Sum Composition
Status
Curated
3D model of PC(O-16:0/9:0(COOH))
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
Azelaoyl PAF is a potent PPARγ agonist which competes for the thiazolidinedione binding site. Azelaoyl PAF is more potent than 15-deoxy-Δ12,14-prostaglandin J2, and equipotent with rosiglitazone as a ligand for this receptor.1
This information has been provided by Cayman Chemical
References
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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References
String Representations
InChiKey (Click to copy)
ZDFOCDTXDPKJKA-WJOKGBTCSA-N
InChi (Click to copy)
InChI=1S/C33H66NO9P/c1-5-6-7-8-9-10-11-12-13-14-15-16-20-23-27-40-29-31(30-42-44(38,39)41-28-26-34(2,3)4)43-33(37)25-22-19-17-18-21-24-32(35)36/h31H,5-30H2,1-4H3,(H-,35,36,38,39)/t31-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCCCCCCC(O)=O)=O)COCCCCCCCCCCCCCCCC
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
44
Rings
0
Aromatic Rings
0
Rotatable Bonds
34
Van der Waals Molecular Volume
684.12
Topological Polar Surface Area
131.42
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
10
logP
9.13
Molar Refractivity
176.34
Admin
Created at
2nd Oct 2020
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.