(−)-rotiorin

CHEBI:68699 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

An azaphilone that is 9,9a-dihydro-2H-furo[3,2-g]isochromen-2-one substituted by an acetyl group at position 3, an oxo group at position 9, a 3,5-dimethylhepta-1,3-dien-1-yl group at position 6 and a methyl group at position 9a. It has been isolated from Chaetomium cupreum and exhibits antifungal activity. — 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:26979 CHEBI:26979
CHEBI:37581 CHEBI:37581
CHEBI:50941 CHEBI:50941
CHEBI:51689 CHEBI:51689
CHEBI:51867 CHEBI:51867

Chemical structure

Computed structure properties
Molecular formula	C23H24O5
Charge	0
Average mass	380.44 Da
Monoisotopic mass	380.16237 Da
Source	ChEBI
InChIKey	CJMOMVNHRUTOJX-SEAFAFSMSA-N

SMILES

CC[C@H](C)/C=C(C)/C=C/C1=CC2=CC3=C(C(C)=O)C(=O)O[C@@]3(C)C(=O)C2=CO1

InChI

InChI=1S/C23H24O5/c1-6-13(2)9-14(3)7-8-17-10-16-11-19-20(15(4)24)22(26)28-23(19,5)21(25)18(16)12-27-17/h7-13H,6H2,1-5H3/b8-7+,14-9+/t13-,23+/m0/s1

Also called

(9aR)-3-acetyl-6-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dien-1-yl]-9a-methyl-2H-furo[3,2-g]isochromene-2,9(9aH)-dione (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

chemspider:255838
reaxys:15840534

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:68699`	(−)-rotiorin	`antibioticmech:chebi-db69853751`	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.