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857341P

Avanti

VPC 12249 (S)

(S)-phosphoric acid mono-[3-(4-benzyloxy-phenyl)-2-octadec-9-enoylamino-propyl] ester (ammonium salt), powder

Synonym(s):

[(2S)-2-[[(Z)-octadec-9-enoyl]amino]-3-(4-phenylmethoxyphenyl)propyl] hydrogen phosphate

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About This Item

Empirical Formula (Hill Notation):
C34H55N2O6P
CAS Number:
799268-73-8
Molecular Weight:
618.78
UNSPSC Code:
12352211
NACRES:
NA.25

assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 1 mg (857341P-1mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 857341P

lipid type

phospholipids
cardiolipins

shipped in

dry ice

storage temp.

−20°C

SMILES string

O=C(CCCCCCC/C=C\CCCCCCCC)N[C@H](COP(O)([O-])=O)CC1=CC=C(OCC2=CC=CC=C2)C=C1.[NH4+]

General description

VPC 12249 is an N-acyl (oleoyl) serine phosphate-based compound.[1]

Application

VPC 12249 has been used as lysophosphatidic acid (LPA)1/3 receptor antagonist in various experimental studies.[2][3]

Biochem/physiol Actions

Lysophosphatidic acids (LPAs) are bioactive lipid mediators.[1] It interacts with at least six specific LPA receptors (LPA1-6) to mediate extracellular signaling pathway.[4] LPA and its receptors (LPA1-3) are implicated in the pathogenesis of radiation pneumonitis (RP).[2] VPC 12249 (S) inhibits the binding ofLPA to LPA1 and LPA3 receptor.[5]

Packaging

5 mL Amber Glass Screw Cap Vial (857341P-1mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

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LPA receptor signaling: pharmacology, physiology, and pathophysiology
Yung, Y, et al.
Journal of Lipid Research, 55(7), 1192-1214 (2014)
Possible role of lysophosphatidic acid in rat model of hypoxic pulmonary vascular remodeling
Shlyonsky V, et al.
Pulmonary Circulation, 4(3), 471-481 (2014)
Identification of a phosphothionate analogue of lysophosphatidic acid (LPA) as a selective agonist of the LPA3 receptor
Hasegawa Y, et al.
The Journal of Biological Chemistry, 278(14), 11962-11969 (2003)
Effects of lysophosphatidic acid and its receptors LPA 1/3; on radiation pneumonitis
Xue J, et al.
Oncology Reports, 24(6), 1515-1520 (2010)
Lysophosphatidic acid inhibits insulin signaling in primary rat hepatocytes via the LPA3 receptor subtype and is increased in obesity
Fayyaz S, et al.
Cellular Physiology and Biochemistry, 43(2), 445-456 (2017)

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