Structure Database (LMSD)
Common Name
PA(18:1(9Z)/0:0)
Systematic Name
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate
Synonyms
- 9-Octadecenoic acid (Z)-, 2-hydroxy-3-(phosphonooxy)propyl ester, (R)-
- 1-Oleoyl-sn-glycero-3-phosphate
- 1-Oleoyl-sn-glycerol 3-phosphate
- PA(18:1/0:0)
- LPA(18:1)
- LPA(18:1)
3D model of PA(18:1(9Z)/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-Oleoyl-2-hydroxy-sn-glycero-3-PA (1-Oleoyl LPA) is a species of lysophosphatidic acid (LPA) containing oleic acid at the sn-1 position. Phosphatidic acid is produced either directly through the action of phospholipase D (PLD) or through a two step process involving liberation of diacylglycerol (DAG) by phospholipase C (PLC) followed by phosphorylation of DAG by diglycerol kinase.1 Hydrolysis of the fatty acid at the sn-2 position by phospholipase A2 (PLA2) yields bioactive LPA. LPA binds to one of five different G protein linked receptors to mediate a variety of biological responses including cell proliferation, smooth muscle contraction, platelet aggregation, neurite retraction, and cell motility.2,1 1-Oleoyl lysophosphatidic acid is the most potent of the LPA analogs for calcium mobilization in A431 cells and for growth stimulation of a variety of cell lines.3,4
This information has been provided by Cayman Chemical
References
1. Noguchi, K., Ishii, S., and Shimizu, T. Identification of p2y9/GPR23 as a novel G protein-coupled receptor for lysophosphatidic acid, structurally distant from the Edg family. J. Biol. Chem. 278(28), 25600-25606 (2003).
3. Jalink, K., Hengeveld, T., Mulder, S., et al. Lysophosphatidic acid-induced Ca2+ mobilization in human A4431 cells: Structure-activity analysis. Biochem. J. 307, 609-616 (1995).
4. Moolenaar, W.H. LPA: A novel lipid mediator with diverse biological actions. Trends Cell Biol. 4(6), 213-219 (1994).
Reactions
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String Representations
InChiKey (Click to copy)
WRGQSWVCFNIUNZ-GDCKJWNLSA-N
InChi (Click to copy)
InChI=1S/C21H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h9-10,20,22H,2-8,11-19H2,1H3,(H2,24,25,26)/b10-9-/t20-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)(O)O)([H])(O)COC(CCCCCCC/C=C\CCCCCCCC)=O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
29
Rings
0
Aromatic Rings
0
Rotatable Bonds
21
Van der Waals Molecular Volume
447.94
Topological Polar Surface Area
113.29
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
7
logP
6.23
Molar Refractivity
115.63
Admin
Created at
-
Updated at
1st Nov 2023
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.