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Merck
CN

SML2702

ST045849

≥98% (HPLC)

Synonym(s):

2-[(4-Chlorophenyl)imino]tetrahydro-4-oxo-3-(2-tricyclo[3.3.1.13,7]dec-1-ylethyl)-2H-1,3-thiazine-6-carboxylic acid, 3-(2-Adamantanylethyl)-2-[(4-chlorophenyl)azamethylene]-4-oxo-l,3-thiazaperhyd roine-6-carboxylic acid, TT04

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About This Item

Empirical Formula (Hill Notation):
C23H27ClN2O3S
CAS Number:
442665-87-4
Molecular Weight:
446.99
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.

−20°C

SMILES string

O=C(N/1CCC23C[C@H](C4)C[C@H](C[C@H]4C3)C2)CC(SC1=N/C5=CC=C(C=C5)Cl)C(O)=O

InChI

1S/C23H27ClN2O3S/c24-17-1-3-18(4-2-17)25-22-26(20(27)10-19(30-22)21(28)29)6-5-23-11-14-7-15(12-23)9-16(8-14)13-23/h1-4,14-16,19H,5-13H2,(H,28,29)/b25-22-/t14-,15+,16-,19?,23?

InChI key

HLPZEZRNGAXCJH-QLAUEMIBSA-N

Related Categories

Biochem/physiol Actions

O-GlcNAc transferase (OGT) inhibitor with in vitro and in vivo efficay.
ST045849 (TT04) is an O-GlcNAc transferase (OGT) Inhibitor (IC50/human splice variant = 30 μM/sOGT & 53 μM/ncOGT; 6.25 μM UDP-GlcNAc, 500 μM peptide substrate KKKYPGGSTPVSSANMM). ST045849 is typically employed in the 1-100 μM range for probing O-GlcNAcylation-dependent cellular processes in cultures, although low 10-50 nM and high 1-20 mM dosing ranges have also been reported. Daily oral administration is reported to prevent embryos neural tube defects at E10.5 among diabetic pregnant mice (20 mg/kg/day p.o. from E6.5 to E9.5).

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
0000095685
0000095685
0000169322
0000169322
0000095686

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Shimeng Cheng et al.
Biochemical and biophysical research communications, 478(4), 1497-1502 (2016-08-18)
GNB2L1 is an intercellular scaffold protein of the Trp-Asp (WD) repeat protein family, and has been reported to play suppressive roles in the progression of gastric cancer. However, the regulatory mechanisms of GNB2L1 in gastric cancer still remain largely elusive.
Arim Min et al.
Microbes and infection, 20(6), 376-384 (2018-06-04)
Trichomonas vaginalis is a sexually-transmitted protozoan parasite that causes vaginitis and cervicitis. Although mast cell activation is important for provoking tissue inflammation during infection with parasites, information regarding the signaling mechanisms in mast cell activation and T. vaginalis infection is
Joshua A Moore et al.
Cellular signalling, 28(5), 384-390 (2016-02-09)
Resistance to insulin action is a key cause of diabetic complications, yet much remains unknown about the molecular mechanisms that contribute to the defect. Glucose-induced insulin resistance in peripheral tissues such as the retina is mediated in part by the
Teresa Vanessa Fiorentino et al.
Cardiovascular research, 107(2), 295-306 (2015-06-04)
We hypothesized that a disproportionate activation of the glucosamine (GlcN) pathway, caused by a prolonged exposure to hyperglycaemia, could impair endothelial integrity promoting endoplasmic reticulum (ER) stress. We also tested the possibility that SRT1720 may be able to counteract GlcN-induced
Benjamin J Gross et al.
Journal of the American Chemical Society, 127(42), 14588-14589 (2005-10-20)
O-GlcNAcylation of serine and threonine residues is a dynamic and essential post-translational modification involved in signaling pathways in eukaryotes. Studies of O-GlcNAcylation would be aided by small-molecule inhibitors of O-GlcNAc transferase (OGT), the sole enzyme know to mediate this modification
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