aureothin

CHEBI:80024 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A C-nitro compound that is (3Z)-3-[(2E)-2-methyl-3-(4-nitrophenyl)prop-2-en-1-ylidene]tetrahydrofuran which is substituted by a 6-methoxy-3,5-dimethyl-4-oxo-4H-pyran-2-yl group at position 5. It is isolated from the soil bacterium, Streptomyces thioluteus and exhibits antitumor, antifungal, and insecticidal activities. — 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:131906 CHEBI:131906
CHEBI:145408 CHEBI:145408
CHEBI:26912 CHEBI:26912
CHEBI:35716 CHEBI:35716
CHEBI:78840 CHEBI:78840

Chemical structure

Computed structure properties
Molecular formula	C22H23NO6
Charge	0
Average mass	397.427 Da
Monoisotopic mass	397.15254 Da
Source	ChEBI
InChIKey	GQKXCBCSVYJUMI-WACKOAQBSA-N

SMILES

[H][C@]1(c2oc(OC)c(C)c(=O)c2C)C/C(=C/C(C)=C/c2ccc([N+](=O)[O-])cc2)CO1

InChI

InChI=1S/C22H23NO6/c1-13(9-16-5-7-18(8-6-16)23(25)26)10-17-11-19(28-12-17)21-14(2)20(24)15(3)22(27-4)29-21/h5-10,19H,11-12H2,1-4H3/b13-9+,17-10-/t19-/m1/s1

Also called

2-methoxy-3,5-dimethyl-6-{(2R,4Z)-4-[(2E)-2-methyl-3-(4-nitrophenyl)prop-2-en-1-ylidene]tetrahydrofuran-2-yl}-4H-pyran-4-one (EXACT_SYNONYM)— chebi
(+)-aureothin (EXACT_SYNONYM)— chebi
2-methoxy-3,5-dimethyl-6-[(2R,5Z)-5-[(E)-2-methyl-3-(4-nitrophenyl)prop-2-enylidene]oxolan-2-yl]pyran-4-one (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:2825-00-5
kegg.compound:C15689
metacyc.compound:CPD-13144

Activity roles

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

CHEBI:33282 CHEBI:33282
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:80024`	aureothin	`antibioticmech:chebi-0ffaa02057`	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.