CHEBI:69024 - berkeleyone A

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ChEBI Name berkeleyone A
ChEBI ID CHEBI:69024
Definition A meroterpenoid found in Penicillium rubrum and 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 C26H38O6
Net Charge 0
Average Mass 446.57630
Monoisotopic Mass 446.26684
InChI InChI=1S/C26H38O6/c1-14-23(5)13-16-22(4)11-10-17(27)21(2,3)15(22)9-12-24(16,6)26(14,20(30)32-8)19(29)25(7,31)18(23)28/h15-17,27,31H,1,9-13H2,2-8H3/t15-,16+,17-,22-,23-,24+,25+,26+/m1/s1
InChIKey NNHHTFDBMMPBSL-JFPRQHOTSA-N
SMILES COC(=O)[C@@]12C(=C)[C@@](C)(C[C@H]3[C@]4(C)CC[C@@H](O)C(C)(C)[C@H]4CC[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 )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing berkeleyone A (CHEBI:69024) has role Penicillium metabolite (CHEBI:76964)
berkeleyone A (CHEBI:69024) has role cysteine protease inhibitor (CHEBI:64152)
berkeleyone A (CHEBI:69024) is a β-diketone (CHEBI:67265)
berkeleyone A (CHEBI:69024) is a carbopolycyclic compound (CHEBI:35294)
berkeleyone A (CHEBI:69024) is a cyclic terpene ketone (CHEBI:36130)
berkeleyone A (CHEBI:69024) is a diol (CHEBI:23824)
berkeleyone A (CHEBI:69024) is a meroterpenoid (CHEBI:64419)
berkeleyone A (CHEBI:69024) is a methyl ester (CHEBI:25248)
berkeleyone A (CHEBI:69024) is a tertiary α-hydroxy ketone (CHEBI:139592)
IUPAC Name
rel-methyl (3R,4aS,6aS,7R,9S,11R,12aS,12bS)-3,9-dihydroxy-4,4,6a,9,11,12b-hexamethyl-13-methylidene-8,10-dioxotetradecahydro-7,11-methanocycloocta[a]naphthalene-7(2H)-carboxylate
Synonym Source
berkeleyone A UniProt
Registry Number Type Source
23869569 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
21916432 PubMed citation Europe PMC
Last Modified
18 August 2020