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

in vivo

target

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.

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