CHEBI:80024 - aureothin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name aureothin
ChEBI ID CHEBI:80024
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
more structures >>
Formula C22H23NO6
Net Charge 0
Average Mass 397.427
Monoisotopic Mass 397.15254
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
InChIKey GQKXCBCSVYJUMI-WACKOAQBSA-N
SMILES C1=C(C=CC(=C1)/C=C(/C=C/2\CO[C@](C2)(C3=C(C(C(=C(O3)OC)C)=O)C)[H])\C)[N+]([O-])=O
Metabolite of Species Details
Streptomyces thioluteus (NCBI:txid66431) Found in cell suspension culture (BTO:0000221). See: Hirata, Y., Nakata, H., Yamada, K., Okuhara, K. and Naito, T. (1961) The structure of aureothin, a nitro compound obtained from Streptomyces thioluteus. Tetrahedron, 14(3), 252-274.
Roles Classification
Biological Role(s): antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
EC 1.6.5.3 [NADH:ubiquinone reductase (H(+)-translocating)] inhibitor
A respiratory-chain inhibitor that interferes with the action of the the enzyme NADH:ubiquinone reductase (H+-translocating), EC 1.6.5.3.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
antiparasitic agent
A substance used to treat or prevent parasitic infections.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing aureothin (CHEBI:80024) has functional parent deoxyaureothin (CHEBI:142840)
aureothin (CHEBI:80024) has role antibacterial agent (CHEBI:33282)
aureothin (CHEBI:80024) has role antifungal agent (CHEBI:35718)
aureothin (CHEBI:80024) has role antineoplastic agent (CHEBI:35610)
aureothin (CHEBI:80024) has role antiparasitic agent (CHEBI:35442)
aureothin (CHEBI:80024) has role bacterial metabolite (CHEBI:76969)
aureothin (CHEBI:80024) has role EC 1.6.5.3 [NADH:ubiquinone reductase (H+-translocating)] inhibitor (CHEBI:38503)
aureothin (CHEBI:80024) is a 4-pyranones (CHEBI:131906)
aureothin (CHEBI:80024) is a C-nitro compound (CHEBI:35716)
aureothin (CHEBI:80024) is a ketene acetal (CHEBI:145408)
aureothin (CHEBI:80024) is a olefinic compound (CHEBI:78840)
aureothin (CHEBI:80024) is a oxolanes (CHEBI:26912)
IUPAC Name
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
Synonyms Sources
(+)-aureothin 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 ChEBI
aureothin UniProt
Manual Xrefs Databases
C15689 KEGG COMPOUND
CPD-13144 MetaCyc
View more database links
Registry Numbers Types Sources
2825-00-5 CAS Registry Number KEGG COMPOUND
2825-00-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11079808 PubMed citation Europe PMC
13174453 PubMed citation Europe PMC
14700630 PubMed citation Europe PMC
15038705 PubMed citation Europe PMC
15612710 PubMed citation Europe PMC
17551211 PubMed citation Europe PMC
17763486 PubMed citation Europe PMC
18667785 PubMed citation Europe PMC
18690656 PubMed citation Europe PMC
27213834 PubMed citation Europe PMC
27559404 PubMed citation Europe PMC
770405 PubMed citation Europe PMC
8307034 PubMed citation Europe PMC
Last Modified
18 November 2019