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Merck
CN

SML3549

Sigma-Aldrich

KIRA9

≥98% (HPLC)

Synonym(s):

(S)-3,3,3-trifluoro-N-(4-((3-(2-(piperidin-3-ylamino)pyrimidin-4-yl)pyridin-2-yl)oxy)naphthalen-1-yl)propane-1-sulfonamide

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About This Item

Empirical Formula (Hill Notation):
C27H27F3N6O3S
Molecular Weight:
572.60
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=S(NC(C=C1)=C2C(C=CC=C2)=C1OC3=NC=CC=C3C4=CC=NC(N[C@@H]5CNCCC5)=N4)(CCC(F)(F)F)=O

InChI

1S/C27H27F3N6O3S/c28-27(29,30)12-16-40(37,38)36-23-9-10-24(20-7-2-1-6-19(20)23)39-25-21(8-4-14-32-25)22-11-15-33-26(35-22)34-18-5-3-13-31-17-18/h1-2,4,6-11,14-15,18,31,36H,3,5,12-13,16-17H2,(H,33,34,35)/t18-/m0/s1

InChI key

HLEZGQAFDDCWDE-SFHVURJKSA-N

Biochem/physiol Actions

Cell penetrant, potent and selective ATP-competitive antagonist of both the kinase and RNase activities of IRE1α
KIRA9 is a cell penetrant, potent and selective ATP-competitive antagonist of both the kinase and RNase activities of IRE1α (endoplasmic reticulum to nucleus signaling 1). KIRA9 suppresses destructive ER mRNA endonucleolytic decay and apoptosis.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000223285
0000223287
0000210406
0000223287
0000223285

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Hannah C Feldman et al.
Nature chemical biology, 17(11), 1148-1156 (2021-09-25)
The unfolded protein response (UPR) homeostatically matches endoplasmic reticulum (ER) protein-folding capacity to cellular secretory needs. However, under high or chronic ER stress, the UPR triggers apoptosis. This cell fate dichotomy is promoted by differential activation of the ER transmembrane

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