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Fagomine

Alias: Fagomine D-Fagomine 1,2,5-Trideoxy-1,5-imino-D-arabino-hexitol
Cat No.:V6958 Purity: ≥98%
Fagomine is a mild glycosidase inhibitor.
Fagomine
Fagomine Chemical Structure CAS No.: 53185-12-9
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
10mg
Other Sizes
Official Supplier of:
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Product Description
Fagomine is a mild glycosidase inhibitor. Fagomine works on Amyloglucosidase (A.niger), β-Glucosidase (bovine) and Isomaltase (yeast), with Ki of 4.8 μM, 39 μM and 70 μM respectively.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Fagomine (D-fagomine) is a metastable sugar that coagulates enterotoxins locally and selectively. Fagomine has the ability to specifically coagulate fibriated enterotoxins, such as Escherichia coli, and prevents them from adhering to the intestinal mucosa. This may be because lectins and binding sugars, such mannose, have structural similarities. The effects of a high-fat, high-sugar diet (HFHS) on intestinal E. coli and E. coli can be altered by fagomine [2].
ln Vivo
Natural dietary subsaccharide gomovine (D-fagomine) regulates body weight, fasting blood glucose levels, and putrefactive Enterobacteriaceae in response to high-energy-density diets in the short term [3]. The percentage of animals fed a high-fat and high-sugar diet (HFHS) and Fagomine (D-fagomine) increased at a much slower rate than that of animals fed HFHS (20.9%) as compared to the standard group [2].
References

[1]. Inhibitor versus chaperone behaviour of d-fagomine, DAB and LAB sp2-iminosugar conjugates againstglycosidases: A structure-activity relationship study in Gaucher fibroblasts. Eur J Med Chem. 2015 Aug 31. pii: S0223-5234(15)30222-1.

[2]. Effect of (D)-fagomine on excreted Enterobacteria and weight gain in rats fed a high-fat high-sucrose diet. Obesity (Silver Spring). 2014 Apr;22(4):976-9.

[3]. D-Fagomine attenuates metabolic alterations induced by a high-energy-dense diet in rats. Food Funct. 2015 Aug;6(8):2614-9.

Additional Infomation
Fagomine is a member of piperidines.
Fagomine has been reported in Bombyx mori, Lycium chinense, and other organisms with data available.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C6H13NO3
Molecular Weight
147.174
Exact Mass
147.089
CAS #
53185-12-9
Related CAS #
53185-12-9;53185-13-0 (HCl);1337470-51-5 (tartrate);
PubChem CID
72259
Appearance
White to khaki solid powder
Density
1.3±0.1 g/cm3
Boiling Point
315.4±42.0 °C at 760 mmHg
Melting Point
186 - 188 °C
Flash Point
170.5±18.5 °C
Vapour Pressure
0.0±1.5 mmHg at 25°C
Index of Refraction
1.535
LogP
-1.63
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
1
Heavy Atom Count
10
Complexity
109
Defined Atom Stereocenter Count
3
SMILES
C1CN[C@@H]([C@H]([C@@H]1O)O)CO
InChi Key
YZNNBIPIQWYLDM-HSUXUTPPSA-N
InChi Code
InChI=1S/C6H13NO3/c8-3-4-6(10)5(9)1-2-7-4/h4-10H,1-3H2/t4-,5-,6-/m1/s1
Chemical Name
(2R,3R,4R)-2-(hydroxymethyl)piperidine-3,4-diol
Synonyms
Fagomine D-Fagomine 1,2,5-Trideoxy-1,5-imino-D-arabino-hexitol
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
H2O : ≥ 36 mg/mL (~244.62 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 100 mg/mL (679.49 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 6.7949 mL 33.9743 mL 67.9486 mL
5 mM 1.3590 mL 6.7949 mL 13.5897 mL
10 mM 0.6795 mL 3.3974 mL 6.7949 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT01528631 COMPLETED Other: D-Fagomine
Other: D-Fagomine
Glycaemic Response
Insulinemic Response
Bioglane 2012-02 Not Applicable
NCT01811303 COMPLETEDWITH RESULTS Other: D-fagomine Reduction of Post-prandial Glycaemic Response Bioglane 2012-09 Not Applicable
NCT06490263 RECRUITING Drug: Experimental: Mulberry Twig Alkaloids
Tablets 126 mg single dose in healthy subjects
Drug: Mulberry Twig Alkaloids Tablets with single dose in healthy subjects
Drug: Mulberry Twig Alkaloids Tablets with multiple dose in healthy subjects
Drug: Mulberry Twig Alkaloids Tablets with multiple dose in overweight or obese subjects
Healthy
Overweight and Obesity
Beijing Wehand-Bio Pharmaceutical Co., Ltd 2024-05-13 Phase 1
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