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Entadamide-A-β-D-glucopyranoside

Cat No.:V60097 Purity: ≥98%
Entadamide-A-β-D-glucopyranoside is one of the major components of Phaseolus vulgaris seeds.
Entadamide-A-β-D-glucopyranoside
Entadamide-A-β-D-glucopyranoside Chemical Structure CAS No.: 138916-58-2
Product category: Complement System
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
50mg
Other Sizes
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Product Description
Entadamide-A-β-D-glucopyranoside is one of the major components of Phaseolus vulgaris seeds. Entadamide-A-β-D-glucopyranoside has anticomplement activity.
Entadamide-A-β-D-glucopyranoside (CAS 138916-58-2) is a glucoside compound and one of the major components found in the seeds of Entada phaseoloides (also known as the bean climber or nicker bean). The compound exhibits significant anti-complement activity, which refers to the inhibition of the complement system, a crucial component of the innate immune response. It also displays antimicrobial properties against gram-positive and gram-negative bacteria and has been reported to have anti-inflammatory and analgesic functions.
Biological Activity I Assay Protocols (From Reference)
Targets
Entadamide-A-β-D-glucopyranoside targets the complement system, a part of the immune system that enhances the ability of antibodies and phagocytic cells to clear pathogens and damaged cells. By inhibiting complement activation, the compound may modulate inflammatory responses and reduce tissue damage associated with excessive complement activation. The compound also exhibits antimicrobial activity, suggesting additional targets in bacterial pathogens. Its anti-inflammatory and analgesic functions indicate potential involvement in pain and inflammatory pathways.
ln Vitro
In vitro, Entadamide-A-β-D-glucopyranoside demonstrates significant anti-complement activity, which is typically assessed by measuring inhibition of complement-mediated hemolysis or complement component deposition. The compound also displays significant inhibitory effects on gram-positive and gram-negative bacteria, indicating broad-spectrum antimicrobial activity. These activities suggest that the compound may have potential applications in immune modulation and infectious disease research. Specific IC50 or MIC values are not detailed in the available literature.
ln Vivo
Specific in vivo data for Entadamide-A-β-D-glucopyranoside are limited. Given its anti-complement and anti-inflammatory activities, the compound could potentially be studied in animal models of complement-mediated diseases such as autoimmune disorders, ischemia-reperfusion injury, or inflammatory conditions. Its antimicrobial activity suggests potential for in vivo efficacy studies in infection models. However, specific published in vivo protocols for this compound are not available in the current literature.
Enzyme Assay
The anti-complement activity is assessed using a hemolytic assay. Sheep erythrocytes are sensitized with anti-sheep erythrocyte antibodies (hemolysin) to activate the classical complement pathway. Various concentrations of Entadamide-A-β-D-glucopyranoside are incubated with guinea pig serum (as a source of complement) and sensitized erythrocytes. The degree of hemolysis is measured spectrophotometrically at 412 nm, and the inhibition of complement activity is calculated by comparing to control samples without the compound.
Cell Assay
For antimicrobial testing, bacterial strains (gram-positive and gram-negative) are cultured in appropriate broth media. Entadamide-A-β-D-glucopyranoside is added at various concentrations, and bacterial growth is monitored by measuring optical density at 600 nm or by colony counting on agar plates after incubation. The minimum inhibitory concentration (MIC) is determined as the lowest concentration that inhibits visible growth. For anti-inflammatory studies, immune cells such as macrophages may be treated with the compound and stimulated with LPS, with cytokine levels measured by ELISA.
Animal Protocol
In vivo studies for Entadamide-A-β-D-glucopyranoside would be conducted in appropriate animal models. For anti-complement or anti-inflammatory studies, models such as carrageenan-induced paw edema, zymosan-induced peritonitis, or complement-mediated disease models could be employed. The compound would be administered via oral gavage, intraperitoneal injection, or intravenous injection, and endpoints would include inflammatory markers, tissue histopathology, and clinical scores. For antimicrobial studies, infection models using relevant pathogens would be used. However, specific published protocols are not available.
ADME/Pharmacokinetics
Specific pharmacokinetic data for Entadamide-A-β-D-glucopyranoside are not reported. As a glucoside with molecular weight 323.36 g/mol, the compound's oral bioavailability may be limited due to poor membrane permeability and potential hydrolysis by intestinal glycosidases. Its water solubility (309.25 mM) suggests good aqueous solubility for formulation. Pharmacokinetic studies would be required to determine absorption, distribution, metabolism, and excretion parameters in animal models.
Toxicity/Toxicokinetics
Toxicological data for Entadamide-A-β-D-glucopyranoside are limited. As a natural product from Entada phaseoloides, which has traditional medicinal uses, the compound is generally considered to have a moderate safety profile. However, systematic toxicology studies have not been reported. The compound should be handled with appropriate safety precautions in laboratory settings. Comprehensive toxicological evaluations would be required before any potential therapeutic development.
References

[1]. Intestinal bacterial metabolism and anti-complement activities of three major components of the seeds of Entada phaseoloides. J Nat Med. 2015 Apr;69(2):171-7.

Additional Infomation
Entamamide-A-|AD-glucopyranoside has been reported and data are available.
Entadamide-A-β-D-glucopyranoside is a glucoside from Entada phaseoloides seeds with anti-complement activity, antimicrobial effects against gram-positive and gram-negative bacteria, and anti-inflammatory/analgesic functions. It is used in research on immune modulation and infectious diseases. No clinical trials or approvals exist. For research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C12H21NO7S
Molecular Weight
323.363
Exact Mass
323.103
CAS #
138916-58-2
PubChem CID
101616680
Appearance
White to off-white solid powder
LogP
-2
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
8
Rotatable Bond Count
7
Heavy Atom Count
21
Complexity
355
Defined Atom Stereocenter Count
5
SMILES
CSC=CC(=O)NCCOC1C(C(C(C(O1)CO)O)O)O
InChi Key
FISKBHZVUFLWDZ-IYYAVIMFSA-N
InChi Code
InChI=1S/C12H21NO7S/c1-21-5-2-8(15)13-3-4-19-12-11(18)10(17)9(16)7(6-14)20-12/h2,5,7,9-12,14,16-18H,3-4,6H2,1H3,(H,13,15)/b5-2+/t7-,9-,10+,11-,12-/m1/s1
Chemical Name
(E)-3-methylsulfanyl-N-[2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]prop-2-enamide
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

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
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)
DMSO : ~100 mg/mL (~309.25 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.73 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (7.73 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (7.73 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.0925 mL 15.4626 mL 30.9253 mL
5 mM 0.6185 mL 3.0925 mL 6.1851 mL
10 mM 0.3093 mL 1.5463 mL 3.0925 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.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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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.

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