SIS3, Smad3 inhibitor

Key facts

CAS number

521984-48-5

Purity

>98%

Form

Solid

form

Molecular weight

490 Da

Molecular formula

C₂₈H₂₈ClN₃O₃

PubChem

16079005

Nature

Synthetic

Solubility

Soluble in DMSO to >25 mM

Biochemical name

Sis3 HCl

Biological description

Potent and selective Smad3 inhibitor. Selectively inhibits TGF-beta 1/ALK5-induced Smad3 phosphorylation. Inhibits the TGF-beta 1 effect on type I procollagen expression at the transcriptional levels via the Smad3-binding site. Has no effect on Smad2, p38, MAPK, ERK or PI 3-kinase signaling.

Canonical smiles

CN1C(=C(C2=C1N=CC=C2)C=CC(=O)N3CCC4=CC(=C(C=C4C3)OC)OC)C5=CC=CC=C5.Cl

Isomeric smiles

CN1C(=C(C2=C1N=CC=C2)/C=C/C(=O)N3CCC4=CC(=C(C=C4C3)OC)OC)C5=CC=CC=C5.Cl

InChi

InChI=1S/C28H27N3O3.ClH/c1-30-27(19-8-5-4-6-9-19)22(23-10-7-14-29-28(23)30)11-12-26(32)31-15-13-20-16-24(33-2)25(34-3)17-21(20)18-31;/h4-12,14,16-17H,13,15,18H2,1-3H3;1H/b12-11+;

InChiKey

CDKIEBFIMCSCBB-CALJPSDSSA-N

IUPAC Name

(E)-1-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-3-(1-methyl-2-phenylpyrrolo[2,3-b]pyridin-3-yl)prop-2-en-1-one;hydrochloride