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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.
Biochem/physiol Actions
Cell permeable: yes
Primary Target
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.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Disclaimer
Toxicity: Standard Handling (A)
| assay | ≥98% (HPLC) |
| Quality Segment | 100 |
| 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 |
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¥ 1779.22
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¥ 9207.92
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¥ 3275.78
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¥ 4968.78
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¥ 2151.46
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¥ 1476.40
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¥ 4476.05
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