5.38285
Glucosylceramide Synthase Inhibitor, Genz-123346
别名:
Glucosylceramide Synthase Inhibitor, Genz-123346, (1R,2R)-nonanoic acid[2-(2ʹ,3ʹ-dihydro-benzo [1, 4] dioxin-6ʹ-yl)-2-hydroxy-1-pyrrolidin-1-ylmethyl-ethyl]-amide, GL1 synthase Inhibitor, Genz-123346, Genz123346
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关于此项目
经验公式（希尔记法）:
C24H38N2O4
化学文摘社编号:
分子量:
418.57
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.77
Assay:
≥98% (HPLC)
Form:
solid
Storage condition:
OK to freeze, protect from light
assay
≥98% (HPLC)
Quality Segment
form
solid
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze, protect from light
color
white to off-white
solubility
DMSO: 50 mg/mL
storage temp.
−20°C
SMILES string
N3(CCCC3)C[C@@H](NC(=O)CCCCCCCC)[C@H](O)c1cc2c(cc1)OCCO2
InChI
1S/C24H38N2O4/c1-2-3-4-5-6-7-10-23(27)25-20(18-26-13-8-9-14-26)24(28)19-11-12-21-22(17-19)30-16-15-29-21/h11-12,17,20,24,28H,2-10,13-16,18H2,1H3,(H,25,27)/t20-,24-/m1/s1
InChI key
JMNXWOFCUJJYEO-HYBUGGRVSA-N
General description
A cell-permeable, orally bioavailable fatty acid amide derivative that acts as a highly potent and specific inhibitor of Glucosylceramide Synthase (GL1 synthase; IC50 = 14 nM for ganglioside GM1 inhibition). Does not affect the activities of other related glycosidase, such as 1-O-acylceramide synthase, a-glucosidase, and glucocerebrosidase in any significant manner. Shown to improve glucose tolerance, improve insulin sensitivity, and normalize hemoglobin A1C levels in Zucker diabetic fatty rats (75 mg/kg/day, p.o. for 6 weeks). Also acts as an inhibitor of GlcCer synthase and blocks the conversion of ceramide to GlcCer in murine models that are orthologous to human autosomal dominant polycystic kidney disease and nephronophthisis. Diminishes Akt-mTOR signaling by reducing phosphorylation of Akt and ribosomal S6 kinase in HEK293T cells without affecting their total levels.
Please note that the molecular weight for this compound is batch-specific due to variable water content. Please refer to the vial label or the certificate of analysis for the batch-specific molecular weight. The molecular weight provided represents the baseline molecular weight without water.
Please note that the molecular weight for this compound is batch-specific due to variable water content. Please refer to the vial label or the certificate of analysis for the batch-specific molecular weight. The molecular weight provided represents the baseline molecular weight without water.
Biochem/physiol Actions
Cell permeable: yes
Primary Target
glucosylceramide synthase
glucosylceramide synthase
Reversible: yes
Target IC50: 14 nM for ganglioside GM1 suppression
Packaging
Packaged under inert gas
Preparation Note
Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
Other Notes
Shen, W., et al. 2014. J. Neurochem.129, 884.
Natoli, T.A., et al. 2010. Nat. Med.16, 788.
Zhao, H., et al. 2007. Diabetes.56, 1210.
Natoli, T.A., et al. 2010. Nat. Med.16, 788.
Zhao, H., et al. 2007. Diabetes.56, 1210.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Disclaimer
Toxicity: Standard Handling (A)
存储类别
11 - Combustible Solids
闪点 (F)
Not applicable
闪点 (°C)
Not applicable
警示词
Warning
危险代码
Hazard Classifications
Acute Tox. 4 Oral - STOT RE 2