CHEBI:64435 - arugosin A (lactol form)

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ChEBI Name arugosin A (lactol form)
ChEBI ID CHEBI:64435
Definition A dibenzooxepine that is dibenzo[b,e]oxepin-11(6H)-one which is substituted by hydroxy groups at positions 1, 6, and 10, a 3,3-dimethylallyl group at position 2, a 3,3-dimethylallyloxy group at position 7, and a methyl group at position 8.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C25H28O6
Net Charge 0
Average Mass 424.48620
Monoisotopic Mass 424.18859
InChI InChI=1S/C25H28O6/c1-13(2)6-7-16-8-9-18-20(22(16)27)23(28)19-17(26)12-15(5)24(21(19)25(29)31-18)30-11-10-14(3)4/h6,8-10,12,25-27,29H,7,11H2,1-5H3
InChIKey WFHNNILBVLUOKP-UHFFFAOYSA-N
SMILES CC(C)=CCOc1c(C)cc(O)c2C(=O)c3c(OC(O)c12)ccc(CC=C(C)C)c3O
Metabolite of Species Details
Aspergillus nidulans (NCBI:txid162425) See: PubMed
Emericella rugulosa (NCBI:txid41736) See: PubMed
Aspergillus (NCBI:txid5052) See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via arugosin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing arugosin A (lactol form) (CHEBI:64435) is a arugosin A (CHEBI:64440)
arugosin A (lactol form) (CHEBI:64435) is a cyclic ketone (CHEBI:3992)
arugosin A (lactol form) (CHEBI:64435) is a dibenzooxepine (CHEBI:38926)
arugosin A (lactol form) (CHEBI:64435) is a lactol (CHEBI:38131)
arugosin A (lactol form) (CHEBI:64435) is a polyphenol (CHEBI:26195)
arugosin A (lactol form) (CHEBI:64435) is tautomer of arugosin A (hydroxy-aldehyde form) (CHEBI:64439)
Incoming arugosin A (hydroxy-aldehyde form) (CHEBI:64439) is tautomer of arugosin A (lactol form) (CHEBI:64435)
IUPAC Name
1,6,10-trihydroxy-8-methyl-2-(3-methylbut-2-en-1-yl)-7-[(3-methylbut-2-en-1-yl)oxy]dibenzo[b,e]oxepin-11(6H)-one
Synonym Source
arugosin A (hemiacetal form) ChEBI
Registry Number Type Source
2025563 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
21658102 PubMed citation Europe PMC
Last Modified
22 July 2013
General Comment
2012-04-30 NMR data show that in methanol, arugosin A exists in equilibrium between the ring-opened and lactol forms, whereas in dimethyl sulfoxide, the equilibrium is shifted completely to the ring-opened (hydroxy-aldehyde) form.