aureothin
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.
Also appears inslm
Exact Synonyms
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
aureothin
Related Synonyms
(+)-aureothin
2-methoxy-3,5-dimethyl-6-[(2R,5Z)-5-[(E)-2-methyl-3-(4-nitrophenyl)prop-2-enylidene]oxolan-2-yl]pyran-4-one
class Information
charge
0
formula
C22H23NO6
has_dbxref
has_obo_namespace
chebi_ontology
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
in_subset
mass
397.427
monoisotopicmass
397.15254
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
class Relations
Subclass of
- 4-pyranones
- ketene acetal
- oxolanes
- C-nitro compound
- olefinic compound
- has rolerosomeantibacterial agent
- has rolerosomeantiparasitic agent
- has rolerosomeantineoplastic agent
- has rolerosomeantifungal agent
- has rolerosomeEC 1.6.5.3 [NADH:ubiquinone reductase (H(+)-translocating)] inhibitor
- has rolerosomebacterial metabolite
- has functional parentsomedeoxyaureothin