CHEBI:142841 - spectinabilin

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ChEBI Name spectinabilin
ChEBI ID CHEBI:142841
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
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Formula C28H31NO6
Net Charge 0
Average Mass 477.557
Monoisotopic Mass 477.21514
InChI InChI=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
InChIKey IZICQJAGBLBAMJ-QDYRYYKCSA-N
SMILES C1=CC(=CC=C1/C=C(\C)/C=C(\C)/C=C(\C)/C=C\2/C[C@@](OC2)(C3=C(C(C(=C(O3)OC)C)=O)C)[H])[N+]([O-])=O
Metabolite of Species Details
Streptomyces sp.ctabilis (NCBI:txid68270) See: Tetrahedron, 1976, 32(2), 217-222
Roles Classification
Biological Role(s): 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.
Application(s): 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).
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ChEBI Ontology
Outgoing 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 4-pyranones (CHEBI:131906)
spectinabilin (CHEBI:142841) is a C-nitro compound (CHEBI:35716)
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 Sources
(+)-neoaureothin ChEBI
(+)-spectinabilin ChEBI
neoaureothin MetaCyc
spectinabilin UniProt
Manual Xrefs Databases
CPD-21806 MetaCyc
Spectinabilin Wikipedia
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Registry Numbers Types Sources
28900-27-8 CAS Registry Number ChemIDplus
59795-94-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
15932226 PubMed citation Europe PMC
17763486 PubMed citation SUBMITTER
20094652 PubMed citation Europe PMC
23968564 PubMed citation Europe PMC
24402879 PubMed citation Europe PMC
25660274 PubMed citation Europe PMC
28490799 PubMed citation Europe PMC
30461185 PubMed citation Europe PMC
Last Modified
18 November 2019