CHEBI:69021 - berkeleydione

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ChEBI Name berkeleydione
ChEBI ID CHEBI:69021
Definition A meroterpenoid found in Penicillium rubrum. It has been shown to exhibit inhibitory activity against caspase-1.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C26H32O7
Net Charge 0
Average Mass 456.52810
Monoisotopic Mass 456.21480
InChI InChI=1S/C26H32O7/c1-13-15-11-18(27)33-22(3,4)16(15)9-10-24(6)17(13)12-23(5)14(2)26(24,21(30)32-8)20(29)25(7,31)19(23)28/h9,17,31H,2,10-12H2,1,3-8H3/t17-,23+,24-,25-,26-/m0/s1
InChIKey RBGYOLFHIDJTOX-VMXKAMJHSA-N
SMILES COC(=O)[C@@]12C(=C)[C@@](C)(C[C@H]3C(C)=C4CC(=O)OC(C)(C)C4=CC[C@]13C)C(=O)[C@](C)(O)C2=O
Metabolite of Species Details
Penicillium rubrum (NCBI:txid1266769) Chloroform extract See: PubMed
Roles Classification
Biological Role(s): cysteine protease inhibitor
Any protease inhibitor that restricts the action of a cysteine protease.
Penicillium metabolite
Any fungal metabolite produced during a metabolic reaction in Penicillium.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via meroterpenoid )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing berkeleydione (CHEBI:69021) has role Penicillium metabolite (CHEBI:76964)
berkeleydione (CHEBI:69021) has role antineoplastic agent (CHEBI:35610)
berkeleydione (CHEBI:69021) has role cysteine protease inhibitor (CHEBI:64152)
berkeleydione (CHEBI:69021) is a β-diketone (CHEBI:67265)
berkeleydione (CHEBI:69021) is a cyclic terpene ketone (CHEBI:36130)
berkeleydione (CHEBI:69021) is a meroterpenoid (CHEBI:64419)
berkeleydione (CHEBI:69021) is a methyl ester (CHEBI:25248)
berkeleydione (CHEBI:69021) is a organic heterotetracyclic compound (CHEBI:38163)
berkeleydione (CHEBI:69021) is a terpene lactone (CHEBI:37668)
berkeleydione (CHEBI:69021) is a tertiary α-hydroxy ketone (CHEBI:139592)
berkeleydione (CHEBI:69021) is a tertiary alcohol (CHEBI:26878)
IUPAC Name
methyl (5aS,7R,9S,11R,11aS)-9-hydroxy-1,1,5,7,9,11a-hexamethyl-14-methylidene-3,8,10-trioxo-3,4,5a,6,7,8,9,10,11a,12-decahydro-7,11-methanocycloocta[4,5]cyclohepta[1,2-c]pyran-11(1H)-carboxylate
Synonym Source
berkeleydione UniProt
Registry Number Type Source
9740878 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15012097 PubMed citation Europe PMC
17970594 PubMed citation Europe PMC
18237180 PubMed citation Europe PMC
21916432 PubMed citation Europe PMC
Last Modified
18 August 2020