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CHEBI:69027 - berkeleyone C

ChEBI IDCHEBI:69027
ChEBI Nameberkeleyone C
Stars
DefinitionA meroterpenoid found in Penicillium rubrum and has been shown to exhibit inhibitory activity against caspase-1.
Last Modified7 February 2018
DownloadsMolfile
FormulaC26H34O7
Net Charge0
Average Mass458.551
Monoisotopic Mass458.23045
SMILES[H][C@@]12C[C@]3(C)C(=C)[C@@](C(=O)OC)(C(=O)[C@@](C)(O)C3=O)[C@@]1(C)CC=C(C(=C)C)[C@@]2(C)CCC(=O)O
InChIInChI=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
InChIKeyHBZLILHFZMWEGE-QFRJCEMRSA-N
Species of MetaboliteComponentSourceComments
Penicillium rubrum (ncbitaxon:1266769) - PubMed (21916432) Chloroform extract
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
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.
ChEBI Ontology
Outgoing Relation(s)
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 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 alcohol (CHEBI:26878)
berkeleyone C (CHEBI:69027) is a tertiary α-hydroxy ketone (CHEBI:139592)
berkeleyone C (CHEBI:69027) is a β-diketone (CHEBI:67265)
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 NumbersSources
Reaxys:21969352Reaxys
Citations