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GSK-J4 (Standard)

CAT: 0804-HY-15648BR-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-15648BR-01Size:5 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
GSK-J4 (Standard) is the analytical standard of GSK-J4. This product is intended for research and analytical applications. GSK-J4 is a potent dual inhibitor of H3K27me3/me2-demethylases JMJD3/KDM6B and UTX/KDM6A with IC50s of 8.6 and 6.6 μM, respectively. GSK-J4 inhibits LPS-induced TNF-α production in human primary macrophages with an IC50 of 9 μM. GSK J4 is a cell permeable proagent of GSK-J1[1][2][3]. GSK-J4 induces endoplasmic reticulum stress-related apoptosis[4].
CAS Number
1373423-53-0
UNSPSC
12352100
Target
Apoptosis; Histone Demethylase; Reference Standards
Related Pathways
Apoptosis; Epigenetics; Others
Field of Research
Cancer
Smiles
O=C(OCC)CCNC1=NC(C2=CC=CC=N2)=NC(N3CCC(C=CC=C4)=C4CC3)=C1
Molecular Formula
C24H27N5O2
Molecular Weight
417.50
References & Citations
[1]Kruidenier L, et al. A selective jumonji H3K27 demethylase inhibitor modulates the proinflammatory macrophage response. Nature. 2012 Aug 16;488 (7411) :404-8.|[2]Donas C, et al. The histone demethylase inhibitor GSK-J4 limits inflammation through the induction of a tolerogenic phenotype on DCs. J Autoimmun. 2016 Dec;75:105-117.|[3]Yapp C, et al. H3K27me3 demethylases regulate in vitro chondrogenesis and chondrocyte activity in osteoarthritis. Arthritis Res Ther. 2016 Jul 7;18 (1) :158|[4]Kamikawa YF, et al. Histone demethylation maintains Prdm14 and Tsix expression and represses xIst in embryonic stem cells. PLoS One. 2015 May 20;10 (5) :e0125626|[5]Heinemann B, et al. Inhibition of demethylases by GSK-J1/J4. Nature. 2014 Oct 2;514 (7520) :E1-2|[6]Majumder S, et al. Shifts in podocyte histone H3K27me3 regulate mouse and human glomerular disease. J Clin Invest. 2018 Jan 2;128 (1) :483-499.|[7]Xuan Chu, et al. GSK-J4 induces cell cycle arrest and apoptosis via ER stress and the synergism between GSK-J4 and decitabine in acute myeloid leukemia KG-1a cells. Cancer Cell International volume 20, Article number: 209 (2020) .
Shipping Conditions
Room temperature
Scientific Category
Reference Standards

Chemical Information

Gsk-J4

GSK-J4 is a member of the class of aminopyrimidines that is pyrimidine substituted by pyridin-2-yl, 3-ethoxy-3-oxopropylamino, and 1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl groups at positions 2, 4, and 6, respectively. It is an inhibitor of the histone demethylase JMJD3/UTX. It has a role as a ferroptosis inducer, an EC 1.14.11.68 ([histone H3]-trimethyl-L-lysine(27) demethylase) inhibitor, an antineoplastic agent and a prodrug. It is an ethyl ester, a member of pyridines, a benzazepine, an aminopyrimidine, a secondary amino compound and a tertiary amino compound. It is functionally related to a GSK-J1.

CAS Number1373423-53-0
PubChem CID71729975
IUPAC Nameethyl 3-[[2-pyridin-2-yl-6-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)pyrimidin-4-yl]amino]propanoate
Molecular FormulaC24H27N5O2
Molecular Weight417.5
XLogP4.3
Topological Polar Surface Area80.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count8
Heavy Atom Count31
Formal Charge0
Complexity546
SMILES
CCOC(=O)CCNC1=CC(=NC(=N1)C2=CC=CC=N2)N3CCC4=CC=CC=C4CC3
InChI
InChI=1S/C24H27N5O2/c1-2-31-23(30)10-14-26-21-17-22(28-24(27-21)20-9-5-6-13-25-20)29-15-11-18-7-3-4-8-19(18)12-16-29/h3-9,13,17H,2,10-12,14-16H2,1H3,(H,26,27,28)
InChIKey
WBKCKEHGXNWYMO-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Gsk-J4
CAS: 1373423-53-0
CID: 71729975
Formula: C24H27N5O2
MW: 417.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight417.5
XLogP34.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count8
Exact Mass417.21647512
Monoisotopic Mass417.21647512
Topological Polar Surface Area80.2 Ų
Heavy Atom Count31
Formal Charge0
Complexity546
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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