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CHEBI:69022 - berkeleytrione

Default Structure
ChEBI IDCHEBI:69022
ChEBI Nameberkeleytrione
Stars
DefinitionA meroterpenoid found in Penicillium rubrum and has been shown to exhibit inhibitory activity against caspase-1.
Last Modified20 August 2020
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=C1C(C)(C)C(=O)C[C@@H](O)[C@]12C
InChIInChI=1S/C26H34O7/c1-13-22(4)12-15-23(5,26(13,20(31)33-8)19(30)25(7,32)18(22)29)10-9-14-21(2,3)16(27)11-17(28)24(14,15)6/h9,15,17,28,32H,1,10-12H2,2-8H3/t15-,17-,22-,23+,24-,25+,26+/m1/s1
InChIKeyBNDPVNXDSQOTOY-OKCDOLPESA-N
Species of MetaboliteComponentSourceComments
Penicillium rubrum (ncbitaxon:1266769) - PubMed (21916432) Chloroform extract
Roles Classification
Biological Roles:
Penicillium metabolite  Any fungal metabolite produced during a metabolic reaction in Penicillium.
cysteine protease inhibitor  Any protease inhibitor that restricts the action of a cysteine protease.
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)
berkeleytrione (CHEBI:69022) has role Penicillium metabolite (CHEBI:76964)
berkeleytrione (CHEBI:69022) has role cysteine protease inhibitor (CHEBI:64152)
berkeleytrione (CHEBI:69022) is a carbopolycyclic compound (CHEBI:35294)
berkeleytrione (CHEBI:69022) is a cyclic terpene ketone (CHEBI:36130)
berkeleytrione (CHEBI:69022) is a meroterpenoid (CHEBI:64419)
berkeleytrione (CHEBI:69022) is a methyl ester (CHEBI:25248)
berkeleytrione (CHEBI:69022) is a tertiary alcohol (CHEBI:26878)
berkeleytrione (CHEBI:69022) is a tertiary α-hydroxy ketone (CHEBI:139592)
berkeleytrione (CHEBI:69022) is a β-diketone (CHEBI:67265)
IUPAC Name 
methyl (1R,6aS,7R,9S,11R,12aR,12bS)-1,9-dihydroxy-4,4,6a,9,11,12b-hexamethyl-13-methylidene-3,8,10-trioxo-1,3,4,6,6a,8,9,10,11,12,12a,12b-dodecahydro-7,11-methanocycloocta[a]naphthalene-7(2H)-carboxylate
UniProt Name  Source
berkeleytrioneUniProt
Registry NumbersSources
Reaxys:9741890Reaxys
Citations