australifungin

CHEBI:65459 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A carbobicyclic compound that is 4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one substituted by hydroxy groups at positions 2, 5 and 8, a (2Z)-3-hydroxyprop-2-enoyl group at position 4, methyl groups at positions 4 and 7 and a 2R-octan-2-yl group at position 3 (the 4S,4aR,5S,7R,8R,8aS stereoisomer). It is isolated from the fermentation extracts of Sporormiella australis and exhibits antifungal activity by interfering with the fungal lipid metabolism. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:33823 CHEBI:33823
CHEBI:35681 CHEBI:35681
CHEBI:36785 CHEBI:36785
CHEBI:51689 CHEBI:51689

Chemical structure

Computed structure properties
Molecular formula	C23H36O6
Charge	0
Average mass	408.535 Da
Monoisotopic mass	408.25119 Da
Source	ChEBI
InChIKey	QURROFPXYUFYAZ-GFHGMWMXSA-N

SMILES

[H][C@@]12[C@@H](O)C[C@@H](C)[C@@H](O)[C@@]1([H])C(=O)C(O)=C([C@H](C)CCCCCC)[C@@]2(C)C(=O)/C=C\O

InChI

InChI=1S/C23H36O6/c1-5-6-7-8-9-13(2)18-22(29)21(28)17-19(15(25)12-14(3)20(17)27)23(18,4)16(26)10-11-24/h10-11,13-15,17,19-20,24-25,27,29H,5-9,12H2,1-4H3/b11-10-/t13-,14-,15+,17+,19-,20-,23-/m1/s1

Also called

(4S,4aR,5S,7R,8R,8aS)-2,5,8-trihydroxy-4-[(2Z)-3-hydroxyprop-2-enoyl]-4,7-dimethyl-3-[(2R)-octan-2-yl]-4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

reaxys:7226637

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:35718 CHEBI:35718
CHEBI:67268 CHEBI:67268

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:65459`	australifungin	`antibioticmech:chebi-b96e16ebbb`	2026-08-30

Mechanism summary

Mode of action: VIRAL_INTEGRASE_INHIBITION microbial target — Assigned from ChEBI role CHEBI:67268 (HIV-1 integrase inhibitor). ChEBI asserts the role on the compound, but this mechanism belongs to an anti-viral activity while the record is filed as ANTIFUNGAL. Either the compound has both activities, or the filing is wrong — the priority table has put azole antifungals under ANTIBACTERIAL before now. A curator should decide which. The role names a target specific to the microbe or virus — see mode_of_action_target_scope. Not a curator's mechanistic review.

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.