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CHEBI:64397 - asperfuranone

ChEBI IDCHEBI:64397
ChEBI Nameasperfuranone
Stars
DefinitionA member of the class of 2-benzofurans that is 6,7-dihydro-2-benzofuran-4(5H)-one that is substituted at positions 5 and 6 by hydroxy groups, at position 5 by a methyl group and at position 1 by a (2E,4E,6S)-4,6-dimethylocta-2,4-dienoyl group (the 5S,6R-diastereoisomer). A polyketide that was first obtained from the fungus Aspergillus nidulans by using a genomic mining approach.
Last Modified13 November 2024
SubmitterGareth Owen
DownloadsMolfile
FormulaC19H24O5
Net Charge0
Average Mass332.396
Monoisotopic Mass332.16237
SMILESCC[C@H](C)/C=C(C)/C=C/C(=O)c1occ2c1C[C@@H](O)[C@](C)(O)C2=O
InChIInChI=1S/C19H24O5/c1-5-11(2)8-12(3)6-7-15(20)17-13-9-16(21)19(4,23)18(22)14(13)10-24-17/h6-8,10-11,16,21,23H,5,9H2,1-4H3/b7-6+,12-8+/t11-,16+,19-/m0/s1
InChIKeyZNGSMORVYUMUDS-BYQFYWKXSA-N
Roles Classification
Biological Role:
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
asperfuranone (CHEBI:64397) has role antineoplastic agent (CHEBI:35610)
asperfuranone (CHEBI:64397) has role fungal metabolite (CHEBI:76946)
asperfuranone (CHEBI:64397) is a 2-benzofurans (CHEBI:38831)
asperfuranone (CHEBI:64397) is a cyclic ketone (CHEBI:3992)
asperfuranone (CHEBI:64397) is a diol (CHEBI:23824)
asperfuranone (CHEBI:64397) is a polyketide (CHEBI:26188)
asperfuranone (CHEBI:64397) is a secondary alcohol (CHEBI:35681)
asperfuranone (CHEBI:64397) is a tertiary alcohol (CHEBI:26878)
asperfuranone (CHEBI:64397) is a tertiary α-hydroxy ketone (CHEBI:139592)
IUPAC Name 
(5S,6R)-1-[(2E,4E,6S)-4,6-dimethylocta-2,4-dienoyl]-5,6-dihydroxy-5-methyl-6,7-dihydro-2-benzofuran-4(5H)-one
UniProt Name  Source
asperfuranoneUniProt
Registry NumbersSources
Reaxys:19447395Reaxys
Citations