CHEBI:64397 - asperfuranone

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ChEBI Name asperfuranone
ChEBI ID CHEBI:64397
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C19H24O5
Net Charge 0
Average Mass 332.39090
Monoisotopic Mass 332.16237
InChI InChI=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
InChIKey ZNGSMORVYUMUDS-BYQFYWKXSA-N
SMILES CC[C@H](C)\C=C(C)\C=C\C(=O)c1occ2C(=O)[C@@](C)(O)[C@H](O)Cc12
Roles Classification
Biological Role(s): fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing 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 α-hydroxy ketone (CHEBI:139592)
asperfuranone (CHEBI:64397) is a tertiary alcohol (CHEBI:26878)
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
Registry Number Type Source
19447395 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
19199437 PubMed citation Europe PMC
20148857 PubMed citation Europe PMC
20952652 PubMed citation Europe PMC
Last Modified
05 June 2020