857228P
Avanti
C18 LPA
1-O-octadecyl-2-hydroxy-sn-glycero-3-phosphate (ammonium salt), powder
Synonym(s):
1-octadecyl-sn-glycero-3-phosphate (ammonium salt); PA(18:0e/0:0)
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About This Item
Empirical Formula (Hill Notation):
C21H48NO6P
CAS Number:
Molecular Weight:
441.58
UNSPSC Code:
51191904
NACRES:
NA.25
Recommended Products
assay
>99% (LPA; may contain up to 10% of the 2-LPA isomer)
form
powder
packaging
pkg of 1 × 1 mg (857228P-1mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand 857228P
lipid type
phospholipids
cardiolipins
shipped in
dry ice
storage temp.
−20°C
SMILES string
O[C@](COP([O-])(O)=O)([H])COCCCCCCCCCCCCCCCCCC.[NH4+]
General description
Lysophosphatidic acid (LPA) is a class of phospholipids, which is water-soluble. It has a glycerol backbone attached via a phosphate group, an aliphatic chain and a hydroxyl group. The aliphatic chain is linked to either sn-1 or sn-2 position and the phosphate group is connected to the sn-3 position. The hydroxyl group is linked to the remaining sn-1 or sn-2 position.
Application
C18 LPA or 1-O-octadecyl-2-hydroxy-sn-glycero-3-phosphate may be used:
- to study its effects on Yes-associated protein (YAP) phosphorylation
- as a standard for the quantification of lysophosphatidic acid (LPA) compounds in proton samples using reversed-phase ultra-performance liquid chromatography-tandem mass spectrometer (UPLC-MS/MS)
- as a substrate to investigate the phosphatase activity of soluble epoxide hydrolase (sEH) towards LPA compounds
Biochem/physiol Actions
Lysophosphatidic acid (LPA) is a signaling molecule and alters various cellular responses through G protein-coupled receptors (GPCRs). It stimulates smooth muscle contraction, cytoskeleton rearrangement and chemotaxis. LPA is also involved in inducing neurotransmitter release, cell proliferation, platelet aggregation and Ca2+ mobilization. Increased levels of LPA in human plasma leads to ovarian cancer and atherosclerosis. LPA acts as a potential biomarker for ovarian cancer.
Packaging
5 mL Amber Glass Screw Cap Vial (857228P-1mg)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
Certificates of Analysis (COA)
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Ami Oguro et al.
Journal of lipid research, 53(3), 505-512 (2012-01-06)
Soluble epoxide hydrolase (sEH) is a bifunctional enzyme that has a C-terminus epoxide hydrolase domain and an N-terminus phosphatase domain. The endogenous substrates of epoxide hydrolase are known to be epoxyeicosatrienoic acids, but the endogenous substrates of the phosphatase activity
Selma Maric et al.
Applied microbiology and biotechnology, 99(1), 241-254 (2014-10-11)
Phosphatidylcholine (PC) is a major component of eukaryotic cell membranes and one of the most commonly used phospholipids for reconstitution of membrane proteins into carrier systems such as lipid vesicles, micelles and nanodiscs. Selectively deuterated versions of this lipid have
Lian Shan et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 864(1-2), 22-28 (2008-02-12)
Lysophosphatidic acid (LPA) is a class of lipids that play multiple biological functions. Several reports show that they are potential biomarkers for diagnosing ovarian cancer. Therefore, it is necessary to accurately quantify their levels in biological samples. Here we report
Han Han et al.
Molecular cell, 72(2), 328-340 (2018-10-09)
The Hippo pathway plays a crucial role in organ size control and tumor suppression, but its precise regulation is not fully understood. In this study, we discovered that phosphatidic acid (PA)-related lipid signaling is a key regulator of the Hippo
Jesica R Williams et al.
The Journal of biological chemistry, 284(25), 17304-17319 (2009-04-16)
Lysophosphatidic acid (LPA) is a ligand for LPA(1-3) of the endothelial differentiation gene family G-protein-coupled receptors, and LPA(4-8) is related to the purinergic family G-protein-coupled receptor. Because the structure-activity relationship (SAR) of GPR92/LPA(5) is limited and whether LPA is its
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