| Identification | Back Directory | [Name]
4H-1,4a-Propano-2H-phenanthro[1,2-c]pyran-7-carboxylic acid, 14-(acetyloxy)-8-[(1R)-1,2-dimethylpropyl]-15-(β-D-glucopyranosyloxy)-1,6,6a,7,8,9,10,10a,10b,11,12,12a-dodecahydro-4-hydroxy-1,6a,8,10a-tetramethyl-, (1S,4aR,6aS,7R,8R,10aR,10bR,12aS,14R,15R)- | [CAS]
260979-95-1 | [Synonyms]
4H-1,4a-Propano-2H-phenanthro[1,2-c]pyran-7-carboxylic acid, 14-(acetyloxy)-8-[(1R)-1,2-dimethylpropyl]-15-(β-D-glucopyranosyloxy)-1,6,6a,7,8,9,10,10a,10b,11,12,12a-dodecahydro-4-hydroxy-1,6a,8,10a-tetramethyl-, (1S,4aR,6aS,7R,8R,10aR,10bR,12aS,14R,15R)- | [Molecular Formula]
C38H60O12 | [MDL Number]
MFCD34167484 | [MOL File]
260979-95-1.mol | [Molecular Weight]
708.88 |
| Chemical Properties | Back Directory | [Boiling point ]
813.5±65.0 °C(Predicted) | [density ]
1.31±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
Chloroform: Slightly Soluble
DMSO: Soluble
Methanol: Slightly Soluble | [form ]
Solid | [pka]
4.67±0.70(Predicted) | [color ]
White to off-white | [InChIKey]
IAOFPTKYKOAKGZ-POFOAJDFNA-N |
| Questions And Answer | Back Directory | [Uses]
Infmufenamic acid is a triterpenoid compound with antifungal properties and can be used in pharmaceutical synthesis. Its semi-synthetic derivative, ibrexafungerp, has been approved by the U.S. Food and Drug Administration (FDA) as the first oral antifungal drug for the treatment of invasive vulvar candidiasis. |
| Hazard Information | Back Directory | [Description]
Enfumafungin is a natural product derived from fungi, belonging to the triterpene glycoside antibiotic class, and possesses significant antifungal activity[1]. Enfumafungin specifically inhibits 1,3-β-D-glucan synthase, an enzyme essential for fungal cell wall synthesis, thereby disrupting cell wall integrity and leading to fungal death [2]. Enfumafungin can be used to treat systemic infections caused by pathogenic fungi such as Candida and Aspergillus species[3]. Enfumafungin derivatives also demonstrate good activity against azole-resistant fungi, providing lead compounds for the development of new antifungal agents[4]. | [Definition]
ChEBI: Enfumafungin is a triterpene glycoside and hemiacetal isolated from a fermentation of Hormonema sp. and which specifically inhibits glucan synthesis in fungal cells. It has a role as an antifungal agent. It is a triterpenoid saponin, a monosaccharide derivative and a lactol. | [Biological Activity]
Enfumafungin, a triterpene glycoside, was isolated from extracts of the species Hormonema. It is an antifungal compound that acts on the fungal cell wall as a (1,3)-beta-D-glucan synthase inhibitor. | [in vitro]
Enfumafungin (24-48 h) has MICs of less than 0.5 μg/mL against the Candida and Aspergillus species tested and it is inactive against Cryptococcus , including the decapsulated form (MY2062). | [in vivo]
Enfumafungin (50-200 mg/kg; ip twice daily for 2 days) produces a significant decrease in the number of cfu in kidneys of mice challenged with C. albicans , with an ED 90 of 90 mg/kg. | [target]
(1,3)-beta-D-glucan synthase | [storage]
Store at -20°C | [Structure and conformation]
Enfumafungin is structurally characterized by four rings with the six-membered D-ring and glucose attached to 3′-OH. Based on its ring structures, enfumafungin was classified as a fernene-type triterpene. The enfumafungin synthase, efuA, is a member of this cryptic lineage of eukaryotic squalene-hopene cyclases (SHCs), and recognition of the linkage will guide recognition of other biosynthetic products of this widespread class of fungal terpenes. Enfumafungin is structurally characterized by four rings with the six-membered D-ring and glucose attached to 3′-OH. Based on its ring structures, enfumafungin was classified as a fernene-type triterpene. The enfumafungin synthase, efuA, is a member of this cryptic lineage of eukaryotic squalene-hopene cyclases (SHCs), and recognition of the linkage will guide recognition of other biosynthetic products of this widespread class of fungal terpenes[1]. | [References]
[1] Eric Kuhnert. “Enfumafungin synthase represents a novel lineage of fungal triterpene cyclases.” Environmental microbiology 20 9 (2018): 3325–3342. |
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