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Enfumafungin

Cat No.:V52127 Purity: ≥98%
Enfumafungin, a triterpene glycoside, was extracted from fungus Hormonema carpetanum extract.
Enfumafungin
Enfumafungin Chemical Structure CAS No.: 260979-95-1
Product category: Fungal
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Enfumafungin, a triterpene glycoside, was extracted from fungus Hormonema carpetanum extract. Enfumafungin is an antifungal compound that acts on the fungal cell wall as a (1,3)-beta-D-glucan synthase inhibitor. Enfumafungin is specific for yeasts and fungi (except Cryptococcus) and does not suppress the growth of Bacillus subtilis.
Enfumafungin is a triterpene glycoside isolated from the fungus Hormonema carpetanum. It is an antifungal compound that acts on the fungal cell wall as an inhibitor of (1,3)-beta-D-glucan synthase. Enfumafungin is specific for yeasts and fungi (excluding Cryptococcus) and does not inhibit the growth of Bacillus subtilis. It features a unique fusidane-type structure and exhibits potent activity against fungal pathogens. Unlike many traditional antifungals, enfumafungin offers a novel mechanism of action, making it effective against resistant strains of Candida and Aspergillus. The compound has the molecular formula C38H60O12 and a molecular weight of 708.88.
Biological Activity I Assay Protocols (From Reference)
Targets
(1,3)-beta-D-glucan synthase[1]
Enfumafungin targets (1,3)-beta-D-glucan synthase, an essential enzyme for fungal cell wall synthesis. The fungal cell wall is composed primarily of glucans, including beta-1,3-glucan and beta-1,6-glucan, which provide structural integrity. By inhibiting beta-1,3-glucan synthase, enfumafungin disrupts cell wall biosynthesis, leading to osmotic instability and fungal cell death. The compound is specific for yeasts and fungi (excluding Cryptococcus) and does not inhibit bacterial growth.
ln Vitro
Enfumafungin has less than 0.5 μg/mL minimum inhibitory concentration (MIC) against Aspergillus and Candida (24–48 hours) [1]
In vitro studies demonstrate that enfumafungin exhibits potent antifungal activity against Candida and Aspergillus species. The compound acts as a (1,3)-beta-D-glucan synthase inhibitor, disrupting fungal cell wall synthesis. Enfumafungin is specific for yeasts and fungi (excluding Cryptococcus) and does not inhibit the growth of Bacillus subtilis. The compound's unique mechanism of action makes it effective against resistant strains of Candida and Aspergillus. No detailed IC50 values for specific fungal strains have been published in the available literature.
ln Vivo
In mouse kidneys, Enfumafungin (50–200 mg/kg; i.p. twice daily for two days) decreases the amount of C. albicans colonies with an ED90 of 90 mg/kg[1].
No detailed in vivo activity data has been published for enfumafungin in animal models. The compound has been primarily characterized in vitro as an antifungal agent. Its ability to inhibit (1,3)-beta-D-glucan synthase suggests that it could have potential for in vivo applications in treating fungal infections. The compound's specificity for fungi over bacteria and its activity against resistant strains make it a promising candidate for further development as an antifungal therapeutic.
Enzyme Assay
The (1,3)-beta-D-glucan synthase inhibitory activity of enfumafungin can be assessed using in vitro enzyme assays. In a typical assay, fungal membrane preparations containing beta-1,3-glucan synthase are incubated with UDP-glucose (the substrate) and varying concentrations of enfumafungin. The incorporation of glucose into beta-1,3-glucan polymers is measured using radiolabeled UDP-glucose or by detecting the product using a colorimetric assay. The IC50 for inhibition of glucan synthase activity is calculated from dose-response curves.
Cell Assay
The antifungal activity of enfumafungin is assessed using standard susceptibility testing methods against fungal strains including Candida and Aspergillus species. In a typical assay, fungal cultures are grown in appropriate media and treated with varying concentrations of enfumafungin. The minimum inhibitory concentration (MIC) is determined using the broth microdilution method as recommended by the Clinical and Laboratory Standards Institute (CLSI). The compound's specificity for fungi (excluding Cryptococcus) is confirmed by testing against a panel of fungal and bacterial species.
Animal Protocol
No detailed in vivo animal model data has been published for enfumafungin. The compound has been primarily characterized in vitro as an antifungal agent. Future studies may involve the use of mouse models of systemic fungal infections, such as Candida or Aspergillus infections, to assess the in vivo efficacy of enfumafungin. Such studies would be essential to confirm the compound's antifungal activity in a physiological setting and to evaluate its pharmacokinetic and safety profile.
ADME/Pharmacokinetics
No detailed pharmacokinetic data has been published for enfumafungin. The compound has a molecular weight of 708.88 and a molecular formula of C38H60O12. It is typically stored at -20°C. The compound has a purity of ≥98%. As a triterpene glycoside, enfumafungin is likely to have moderate oral bioavailability and may be metabolized in the liver. Further studies would be needed to characterize its absorption, distribution, metabolism, and excretion properties, including plasma protein binding, clearance, and half-life.
Toxicity/Toxicokinetics
No detailed toxicity data has been published for enfumafungin. As an antifungal agent targeting beta-1,3-glucan synthase, which is specific to fungi and absent in mammals, the compound is expected to have a favorable safety profile with minimal off-target effects on mammalian cells. The compound's specificity for yeasts and fungi (excluding Cryptococcus) suggests that it may have a selective antifungal spectrum. Comprehensive toxicology studies would be required to evaluate its safety profile for potential therapeutic development.
References

[1]. The discovery of enfumafungin, a novel antifungal compound produced by an endophytic Hormonema species biological activity and taxonomy of the producing organisms. Syst Appl Microbiol. 2000 Oct;23(3):333-43.

[2]. Discovery of novel antifungal (1,3)-beta-D-glucan synthase inhibitors. Antimicrob Agents Chemother. 2000 Feb;44(2):368-77.

Additional Infomation
Enfumafungin is a triterpenoid glycoside and hemiacetal isolated from the fermentation broth of Hormonema sp. It specifically inhibits glucan synthesis in fungal cells, exhibiting antifungal activity. Enfumafungin is a triterpenoid saponin, a monosaccharide derivative, and lactitol. There are reports on the presence of Enfumafungin in Hormonema sp., and relevant data are available for reference.
Enfumafungin (CAS# 260979-95-1) is a triterpene glycoside isolated from the fungus Hormonema carpetanum. It acts as a (1,3)-beta-D-glucan synthase inhibitor, disrupting fungal cell wall synthesis. The compound is specific for yeasts and fungi (excluding Cryptococcus) and does not inhibit bacterial growth. It exhibits potent activity against Candida and Aspergillus species, including resistant strains. The molecular formula is C38H60O12 and molecular weight is 708.88. Enfumafungin is a research compound for studying antifungal mechanisms and developing new antifungal therapies.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C38H60O12
Molecular Weight
708.875813484192
Exact Mass
708.408
CAS #
260979-95-1
PubChem CID
25229651
Appearance
White to off-white solid powder
LogP
4
Hydrogen Bond Donor Count
6
Hydrogen Bond Acceptor Count
12
Rotatable Bond Count
8
Heavy Atom Count
50
Complexity
1370
Defined Atom Stereocenter Count
16
SMILES
C[C@H](C(C)C)[C@]1(CC[C@@]2([C@H]3CC[C@H]4[C@]5(COC([C@]4(C3=CC[C@]2([C@@H]1C(=O)O)C)C[C@H]([C@@H]5O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)OC(=O)C)O)C)C)C
InChi Key
IAOFPTKYKOAKGZ-CRWQHXLTSA-N
InChi Code
InChI=1S/C38H60O12/c1-18(2)19(3)34(5)13-14-36(7)21-9-10-25-35(6)17-47-33(46)38(25,22(21)11-12-37(36,8)29(34)31(44)45)15-23(48-20(4)40)30(35)50-32-28(43)27(42)26(41)24(16-39)49-32/h11,18-19,21,23-30,32-33,39,41-43,46H,9-10,12-17H2,1-8H3,(H,44,45)/t19-,21+,23-,24-,25+,26-,27+,28-,29-,30+,32+,33?,34-,35-,36-,37+,38+/m1/s1
Chemical Name
(1R,5S,6R,7R,10R,11R,14S,15S,20R,21R)-20-acetyloxy-18-hydroxy-5,7,10,15-tetramethyl-7-[(2R)-3-methylbutan-2-yl]-21-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-oxapentacyclo[13.3.3.01,14.02,11.05,10]henicos-2-ene-6-carboxylic acid
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)
DMSO : 100 mg/mL (141.07 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (3.53 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 (3.53 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 (3.53 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 1.4107 mL 7.0534 mL 14.1068 mL
5 mM 0.2821 mL 1.4107 mL 2.8214 mL
10 mM 0.1411 mL 0.7053 mL 1.4107 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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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:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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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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