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CHEBI:142841 - spectinabilin

Default Structure
ChEBI IDCHEBI:142841
ChEBI Namespectinabilin
Stars
DefinitionA polyketide that is deoxyspectinabilin in which the tetramethyldeca-tetraen-1-yl chain attached to the 4-pyranone moiety has undergone oxidation at position 1 and at the methyl group at position 3 to afford the corresponding tetrahydrofuranyl moiety. Produced by Streptomyces spectabilis, it exhibits antiviral and antimalarial activity.
Last Modified18 November 2019
SubmitterKristian Axelsen
DownloadsMolfile
FormulaC28H31NO6
Net Charge0
Average Mass477.557
Monoisotopic Mass477.21514
SMILES[H][C@]1(c2oc(OC)c(C)c(=O)c2C)C/C(=C/C(C)=C/C(C)=C/C(C)=C/c2ccc([N+](=O)[O-])cc2)CO1
InChIInChI=1S/C28H31NO6/c1-17(11-18(2)13-22-7-9-24(10-8-22)29(31)32)12-19(3)14-23-15-25(34-16-23)27-20(4)26(30)21(5)28(33-6)35-27/h7-14,25H,15-16H2,1-6H3/b17-11+,18-13+,19-12+,23-14-/t25-/m1/s1
InChIKeyIZICQJAGBLBAMJ-QDYRYYKCSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Streptomyces spectabilis (ncbitaxon:68270) - Article (Tetrahedron, 1976, 32(2), 217-222)
Roles Classification
Biological Roles:
antiplasmodial drug  An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria.
antiviral agent  A substance that destroys or inhibits replication of viruses.
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
Applications:
antiplasmodial drug  An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria.
nematicide  A substance used to destroy pests of the phylum Nematoda (roundworms).
ChEBI Ontology
Outgoing Relation(s)
spectinabilin (CHEBI:142841) has functional parent deoxyspectinabilin (CHEBI:142843)
spectinabilin (CHEBI:142841) has role antiplasmodial drug (CHEBI:64915)
spectinabilin (CHEBI:142841) has role antiviral agent (CHEBI:22587)
spectinabilin (CHEBI:142841) has role bacterial metabolite (CHEBI:76969)
spectinabilin (CHEBI:142841) has role nematicide (CHEBI:25491)
spectinabilin (CHEBI:142841) is a C-nitro compound (CHEBI:35716)
spectinabilin (CHEBI:142841) is a 4-pyranones (CHEBI:131906)
spectinabilin (CHEBI:142841) is a ketene acetal (CHEBI:145408)
spectinabilin (CHEBI:142841) is a oxolanes (CHEBI:26912)
spectinabilin (CHEBI:142841) is a polyketide (CHEBI:26188)
IUPAC Name 
2-methoxy-3,5-dimethyl-6-{(2R,4Z)-4-[(2E,4E,6E)-2,4,6-trimethyl-7-(4-nitrophenyl)hepta-2,4,6-trien-1-ylidene]tetrahydrofuran-2-yl}-4H-pyran-4-one
Synonyms  Source
(+)-neoaureothinChEBI
neoaureothinMetaCyc
(+)-spectinabilinChEBI
UniProt Name  Source
spectinabilinUniProt
Manual XrefsDatabases
CPD-21806MetaCyc
SpectinabilinWikipedia
Registry NumbersSources
CAS:28900-27-8ChemIDplus
CAS:59795-94-7ChemIDplus
Citations