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Key Documents

SML1022

Sigma-Aldrich

AS1949490

≥98% (HPLC)

Synonym(s):

3-[(4-Chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]- 2-thiophenecarboxamide, AS 1949490

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About This Item

Empirical Formula (Hill Notation):
C20H18ClNO2S
CAS Number:
1203680-76-5
Molecular Weight:
371.88
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

InChI

1S/C20H18ClNO2S/c1-14(16-5-3-2-4-6-16)22-20(23)19-18(11-12-25-19)24-13-15-7-9-17(21)10-8-15/h2-12,14H,13H2,1H3,(H,22,23)/t14-/m0/s1

InChI key

RFZPGNRLOKVZJY-AWEZNQCLSA-N

Biochem/physiol Actions

AS1949490 is a potent, selective SHIP2 phosphatase inhibitor. AS1949490 activates insulin signaling pathways in liver and lowers glucose levels in diabetic mice.
AS1949490 is also known as (3-[(4-chlorobenzyl)oxy]-N-[(1S)-1-phenylethyl]-2-thiophenecarboxamide). It enhances the phosphorylation of Akt, glucose consumption and glucose uptake in L6 myotubes. AS1949490 has the ability to block gluconeogenesis in FAO (cell line) hepatocytes.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A Suwa et al.
British journal of pharmacology, 158(3), 879-887 (2009-08-22)
The lipid phosphatase known as SH2 domain-containing inositol 5'-phosphatase 2 (SHIP2) plays an important role in the regulation of the intracellular insulin signalling pathway. Recent studies have suggested that inhibition of SHIP2 could produce significant benefits in treatment of type
Akira Suwa et al.
European journal of pharmacology, 642(1-3), 177-182 (2010-06-19)
Lipid phosphatase SH2 domain-containing inositol 5'-phosphatase 2 (SHIP2) plays an important role in the regulation of insulin signaling. In this report, we identified AS1938909, a novel small-molecule SHIP2 inhibitor. AS1938909 showed potent inhibition of SHIP2 (Ki=0.44 microuM) and significant selectivity
Gilbert Salloum et al.
Journal of cell science, 132(16) (2019-08-15)
Macropinocytosis is an actin-dependent but clathrin-independent endocytic process by which cells nonselectively take up large aliquots of extracellular material. Macropinocytosis is used for immune surveillance by dendritic cells, as a route of infection by viruses and protozoa, and as a
Abdelhalim Azzi
FEBS open bio, 10(10), 2191-2205 (2020-09-04)
Phosphatidylinositol (3,4,5)-trisphosphate (PI(3,4,5)P3) is required for protein kinase B (AKT) activation. The level of PI(3,4,5)P3 is constantly regulated through balanced synthesis by phosphoinositide 3-kinase (PI3K) and degradation by phosphoinositide phosphatases phosphatase and tensin homologue (PTEN) and SH2-domain containing phosphatidylinositol-3,4,5-trisphosphate 5-phosphatase

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