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CHEBI:142841 - spectinabilin

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:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
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.
Applications:
nematicide  A substance used to destroy pests of the phylum Nematoda (roundworms).
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.
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
neoaureothinMetaCyc
(+)-spectinabilinChEBI
(+)-neoaureothinChEBI
UniProt Name  Source
spectinabilinUniProt
Manual XrefsDatabases
CPD-21806MetaCyc
SpectinabilinWikipedia
Registry NumbersSources
CAS:59795-94-7ChemIDplus
CAS:28900-27-8ChemIDplus
Citations