CHEBI:69027 - berkeleyone C

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ChEBI Name berkeleyone C
ChEBI ID CHEBI:69027
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 C26H34O7
Net Charge 0
Average Mass 458.54400
Monoisotopic Mass 458.23045
InChI InChI=1S/C26H34O7/c1-14(2)16-9-12-24(6)17(22(16,4)11-10-18(27)28)13-23(5)15(3)26(24,21(31)33-8)20(30)25(7,32)19(23)29/h9,17,32H,1,3,10-13H2,2,4-8H3,(H,27,28)/t17-,22+,23+,24-,25-,26-/m0/s1
InChIKey HBZLILHFZMWEGE-QFRJCEMRSA-N
SMILES COC(=O)[C@@]12C(=C)[C@@](C)(C[C@H]3[C@](C)(CCC(O)=O)C(=CC[C@]13C)C(C)=C)C(=O)[C@](C)(O)C2=O
Metabolite of Species Details
Penicillium rubrum (NCBI:txid1266769) Chloroform extract See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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 C (CHEBI:69027) has role Penicillium metabolite (CHEBI:76964)
berkeleyone C (CHEBI:69027) has role cysteine protease inhibitor (CHEBI:64152)
berkeleyone C (CHEBI:69027) is a β-diketone (CHEBI:67265)
berkeleyone C (CHEBI:69027) is a carbotricyclic compound (CHEBI:38032)
berkeleyone C (CHEBI:69027) is a cyclic terpene ketone (CHEBI:36130)
berkeleyone C (CHEBI:69027) is a dicarboxylic acid monoester (CHEBI:36244)
berkeleyone C (CHEBI:69027) is a meroterpenoid (CHEBI:64419)
berkeleyone C (CHEBI:69027) is a methyl ester (CHEBI:25248)
berkeleyone C (CHEBI:69027) is a tertiary α-hydroxy ketone (CHEBI:139592)
berkeleyone C (CHEBI:69027) is a tertiary alcohol (CHEBI:26878)
IUPAC Name
rel-3-[(1S,4aS,5R,7S,9R,10aS)-7-hydroxy-5-(methoxycarbonyl)-1,4a,7,9-tetramethyl-11-methylidene-6,8-dioxo-2-(prop-1-en-2-yl)-1,4,4a,5,6,7,8,9,10,10a-decahydro-5,9-methanobenzo[8]annulen-1-yl]propanoic acid
Registry Number Type Source
21969352 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
21916432 PubMed citation Europe PMC
Last Modified
07 February 2018