Enfumafungin CAS 260979-95-1

Introduction：Basic information about Enfumafungin CAS 260979-95-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Enfumafungin Basic information

• Product Name: Enfumafungin
• 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)-;(1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aS)-3-acetoxy-13-hydroxy-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-2-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysene-7-carboxylic acid;enfumafungin;(1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aS)-3-Acetoxy-13-hydroxy-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-2-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-2H-1,4a-(methanooxymethano)chrysene-7-carboxylic acid;(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[13.3.3.01,1?.02,11.0?,1?]henicos-2-ene-6-carboxylic acid
• CAS: 260979-95-1
• MF: C38H60O12
• MW: 708.89
• Mol File: 260979-95-1.mol

Enfumafungin Chemical Properties

• 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
• pka: 4.67±0.70(Predicted)
• form: Solid
• color: White to off-white
• InChI: InChI=1/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+/s3
• InChIKey: IAOFPTKYKOAKGZ-POFOAJDFNA-N
• SMILES: OC1OC[C@]2([C@@H](O[C@@]3([H])[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)[C@H](OC(=O)C)C[C@@]31[C@@]2([H])CC[C@]1([H])[C@]2(CC[C@](C)([C@H](C)C(C)C)[C@@H](C(=O)O)[C@]2(C)CC=C31)C)C |&1:4,5,7,9,10,12,14,19,25,26,30,32,35,37,42,46,r|

Enfumafungin Usage And Synthesis

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.

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

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.
[2] J ONISHI. Discovery of novel antifungal (1,3)-beta-D-glucan synthase inhibitors.[J]. Antimicrobial Agents and Chemotherapy, 2000, 44 2: 368-377. DOI: 10.1128/aac.44.2.368-377.2000
[3] Jiménez-Ortigosa C, Paderu P, Motyl MR, et al. Enfumafungin derivative MK-3118 shows increased in vitro potency against clinical echinocandin-resistant Candida Species and Aspergillus species isolates. Antimicrob Agents Chemother. 2014;58(2):1248-51.
[4] Cheng Z, Wu W, Liu Y, et al. Natural Enfumafungin Analogues from Hormonema carpetanum and Their Antifungal Activities. J Nat Prod. 2023 Oct 27;86(10):2407-2413.