IWP 4 Chemical Properties

Density 

1.51±0.1 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

insoluble in H2O; insoluble in EtOH; insoluble in DMSO

pka

9.01±0.70(Predicted)

form 

powder

color 

white to light brown

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)

InChIKey

RHUJMHOIQBDFQR-UHFFFAOYSA-N

SMILES

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

Safety Information

WGK Germany 

3

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral

IWP 4 Usage And Synthesis

Uses

IWP 4 is a Porcn inhibitor.

Biological Activity

iwp 4 is an inhibitor of wnt production. iwp 4 impairs wnt pathway activity (ic50 = 25 nm) by inactivating porcupine, a membrane-bound acyltransferase responsible for attaching a palmitoyl group to wnt proteins, which is essential to wnt signaling and wnt secretion. the wnt family of signaling proteins is involved in most aspects of embryonic development and postembryonic tissue homeostasis. hyperactivation of the wnt/β-catenin pathway induces premature senescence of stem cells and age-related loss of stem cell function. in cancer, hyperactivation of the wnt/β-catenin pathway often exists along with mutations in other cell growth regulatory genes, which results in aberrant cell growth. thus, iwp 4 could serve a useful tool for researching tissue regeneration and wnt ligand-dependent tumors. iwp 4 has been used for inducing cardiomyocyte differentiation from human pluripotent stem cells.1. chen b, dodge me, tang w, et al. small molecule-mediated disruption of wnt-dependent signaling in tissue regeneration and cancer. nature chemical biology, 2009, 5(2): 100-107.2. lian x, hsiao c, wilson g, et al. robust cardiomyocyte differentiation from human pluripotent stem cells via temporal modulation of canonical wnt signaling. proceedings of the national academy of sciences of the united states of america, 2012, 109(27): e1848-1857.

Biochem/physiol Actions

IWP-4 blocks Wnt family member 5a. It blocks Wnt protein secretion and prevents the canonical and non-canonical signaling pathways.

storage

Store at +4°C