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Merck
CN

857360P

Avanti

VPC 23019

Avanti Research™ - A Croda Brand

Synonym(s):

(R)-phosphoric acid mono-[2-amino-2-(3-octyl-phenylcarbamoyl)-ethyl] ester

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About This Item

Empirical Formula (Hill Notation):
C17H29N2O5P
CAS Number:
449173-19-7
Molecular Weight:
372.40
UNSPSC Code:
12352211
NACRES:
NA.25

Key Documents

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Product Name

VPC 23019, Avanti Research™ - A Croda Brand 857360P, powder

SMILES string

CCCCCCCCC1=CC(NC([C@H]([NH3+])COP(O)([O-])=O)=O)=CC=C1

InChI

1S/C17H29N2O5P/c1-2-3-4-5-6-7-9-14-10-8-11-15(12-14)19-17(20)16(18)13-24-25(21,22)23/h8,10-12,16H,2-7,9,13,18H2,1H3,(H,19,20)(H2,21,22,23)/t16-/m1/s1

InChI key

MRUSUGVVWGNKFE-MRXNPFEDSA-N

assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 1 mg (857360P-1mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 857360P

lipid type

cardiolipins
sphingolipids

shipped in

dry ice

storage temp.

−20°C

General description

VPC 23019 is an aryl-amide compound. It is an analog of sphingosine-1-phosphate (S1P).

Application

VPC 23019 has been used:
  • for aequorin-based Ca2+ measurements
  • to analyse the modulation of sphingosine-1-phosphate (S1P) induced plasminogen activator inhibitor 1 (PAI-1) expression
  • to reverse the protective effects of the overexpression of apolipoprotein M in mice treated with lipopolysaccharide (LPS)

Biochem/physiol Actions

VPC 23019 acts as a competitive antagonist at the sphingosine-1-phosphate-1(S1P1) and S1P3 receptors.

Packaging

5 mL Amber Glass Screw Cap Vial (857360P-1mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Sphingosine 1-phosphate analogs as receptor antagonists
Davis MD, et al.
The Journal of biological chemistry, 280(11) (2005)
Vehicle-dependent effects of sphingosine 1-phosphate on plasminogen activator inhibitor-1 expression
Takahashi C, et al.
Journal of Atherosclerosis and Thrombosis, 37663-37663 (2017)
Apolipoprotein M protects lipopolysaccharide-treated mice from death and organ injury
Kurano M, et al.
Thrombosis and Haemostasis, 118(06) (2018)
A novel chimeric aequorin fused with caveolin-1 reveals a sphingosine kinase 1-regulated Ca2+ microdomain in the caveolar compartment
Pulli I, et al.
Biochimica et Biophysica Acta - Molecular Cell Research, 1853(9) (2015)
Eun-Young Kim et al.
Cells, 9(1) (2020-01-16)
The interleukin-22 (IL-22) signaling pathway is well known to be involved in the progression of various cancer types but its role in bone metastatic breast cancer remains unclear. We demonstrate using human GEO profiling that bone metastatic breast cancer displays
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