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SML1114

Sigma-Aldrich

IWP-4

≥95% (HPLC)

Synonym(s):

N-(6-Methyl-2-benzothiazolyl)-2-[[3,4,6,7-tetrahydro-3-(2-methoxyphenyl)-4-oxothieno[3,2-d]pyrimidin-2-yl]thio]-acetamide

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About This Item

Empirical Formula (Hill Notation):
C23H20N4O3S3
CAS Number:
686772-17-8
Molecular Weight:
496.62
UNSPSC Code:
12352200
PubChem Substance ID:
329825655
NACRES:
NA.77

Assay

≥95% (HPLC)

form

powder

color

white to light brown

solubility

DMSO: 0.5 mg/mL, clear (warmed)

storage temp.

−20°C

SMILES string

O=C1C2=C(CCS2)N=C(SCC(NC3=NC(C=CC(C)=C4)=C4S3)=O)N1C5=C(OC)C=CC=C5

InChI

1S/C23H20N4O3S3/c1-13-7-8-14-18(11-13)33-22(24-14)26-19(28)12-32-23-25-15-9-10-31-20(15)21(29)27(23)16-5-3-4-6-17(16)30-2/h3-8,11H,9-10,12H2,1-2H3,(H,24,26,28)

InChI key

RHUJMHOIQBDFQR-UHFFFAOYSA-N

Biochem/physiol Actions

IWP-4 blocks Wnt family member 5a. It blocks Wnt protein secretion and prevents the canonical and non-canonical signaling pathways.
IWP-4 is a potent inhbitor of the Wnt pathway regulatory protein porupine (Porcn). IWP-4 blocks palmitylation, and subsquent secretion and activity of Wnt. IWP-4 induces the differentiation of human pluripotent stem cells into cardiomyocytes.

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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Microbioreactor Array Screening of Wnt Modulators and Microenvironmental Factors in Osteogenic Differentiation of Mesenchymal Progenitor Cells
Frith JE, et al.
PLoS ONE, 8(12), e82931-e82931 (2013)
Alla Narytnyk et al.
Stem cell reviews, 10(2), 316-326 (2014-01-09)
Here we provide a protocol for the directed differentiation of hEPI-NCSC into midbrain dopaminergic neurons, which degenerate in Parkinson's disease. hEPI-NCSC are neural crest-derived multipotent stem cells that persist into adulthood in the bulge of hair follicles. The experimental design
Qinghua Wang et al.
Communications biology, 5(1), 1018-1018 (2022-09-28)
The formation of wound epithelium initiates regeneration of amputated tail in Gekko japonicus. Energy metabolism is indispensable for the growth of living creatures and typically influenced by temperature. In this study, we reveal that low temperature lowers energy metabolism level
Oliver Schneider et al.
Materials today. Bio, 15, 100280-100280 (2022-05-24)
Over the last decade, Organ-on-Chip (OoC) emerged as a promising technology for advanced in vitro models, recapitulating key physiological cues. OoC approaches tailored for cardiac tissue engineering resulted in a variety of platforms, some of which integrate stimulation or probing

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