yanuthone K

CHEBI:133035 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A class I yanuthone that is 5,6-epoxy-cyclohex-2-en-1-one which is substituted at positions 3, 4, and 6 by methyl, acetoxy, and trans,trans-farnesyl groups, respectively (the R,R,R stereoisomer). Isolated from the filamentous fungus Aspergillus niger, it shows antifungal activity towards the pathogenic yeast Candida albicans (IC50 = 17.5 ±3.9 μM). — 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:133075 CHEBI:133075
CHEBI:47622 CHEBI:47622

Chemical structure

Computed structure properties
Molecular formula	C24H34O4
Charge	0
Average mass	386.532 Da
Monoisotopic mass	386.24571 Da
Source	ChEBI
InChIKey	DOKAHTTXUSOTHL-YVCJEVKHSA-N

SMILES

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

InChI

InChI=1S/C24H34O4/c1-16(2)9-7-10-17(3)11-8-12-18(4)13-14-24-21(26)15-19(5)22(23(24)28-24)27-20(6)25/h9,11,13,15,22-23H,7-8,10,12,14H2,1-6H3/b17-11+,18-13+/t22-,23-,24+/m1/s1

Also called

(1R,2R,6R)-3-methyl-5-oxo-6-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-7-oxabicyclo[4.1.0]hept-3-en-2-yl acetate (EXACT_SYNONYM)— chebi
yanuthone-K (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

reaxys:27991879

Activity roles

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

CHEBI:35718 CHEBI:35718

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:133035`	yanuthone K	`antibioticmech:chebi-bf4abb2ea5`	2026-08-30

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

Provenance

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