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CHEBI:80024 - aureothin

ChEBI IDCHEBI:80024
ChEBI Nameaureothin
Stars
DefinitionA 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.
Last Modified18 November 2019
DownloadsMolfile
FormulaC22H23NO6
Net Charge0
Average Mass397.427
Monoisotopic Mass397.15254
SMILES[H][C@]1(c2oc(OC)c(C)c(=O)c2C)C/C(=C/C(C)=C/c2ccc([N+](=O)[O-])cc2)CO1
InChIInChI=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
InChIKeyGQKXCBCSVYJUMI-WACKOAQBSA-N
Species of MetaboliteComponentSourceComments
Streptomyces thioluteus (ncbitaxon:66431) cell suspension culture (BTO:0000221) Article (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 Roles:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of 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.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
antiparasitic agent  A substance used to treat or prevent parasitic infections.
ChEBI Ontology
Outgoing Relation(s)
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 C-nitro compound (CHEBI:35716)
aureothin (CHEBI:80024) is a 4-pyranones (CHEBI:131906)
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  Source
2-methoxy-3,5-dimethyl-6-[(2R,5Z)-5-[(E)-2-methyl-3-(4-nitrophenyl)prop-2-enylidene]oxolan-2-yl]pyran-4-oneChEBI
(+)-aureothinChEBI
UniProt Name  Source
aureothinUniProt
Manual XrefsDatabases
C15689KEGG COMPOUND
CPD-13144MetaCyc
Registry NumbersSources
CAS:2825-00-5KEGG COMPOUND
CAS:2825-00-5ChemIDplus
Citations