berkeleyone B (CHEBI:69025)

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CHEBI:69025 - berkeleyone B

ChEBI ID	CHEBI:69025
ChEBI Name	berkeleyone B
Stars
Definition	A meroterpenoid found in Penicillium rubrum and has been shown to exhibit inhibitory activity against caspase-1.
Last Modified	18 August 2020
Downloads	Molfile

Formula	C26H34O7
Net Charge	0
Average Mass	458.551
Monoisotopic Mass	458.23045
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)OC(=O)CC[C@]12C
InChI	InChI=1S/C26H34O7/c1-14-23(5)13-16-22(4)11-10-17(27)33-21(2,3)15(22)9-12-24(16,6)26(14,20(30)32-8)19(29)25(7,31)18(23)28/h9,16,31H,1,10-13H2,2-8H3/t16-,22+,23+,24-,25-,26-/m0/s1
InChIKey	IWYHWTWGKBGNTO-GSISZECUSA-N

Species of Metabolite	Component	Source	Comments
Penicillium rubrum (ncbitaxon:1266769)	-	PubMed (21916432)	Chloroform extract

Roles Classification

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 B (CHEBI:69025) has role Penicillium metabolite (CHEBI:76964)
	berkeleyone B (CHEBI:69025) has role cysteine protease inhibitor (CHEBI:64152)
	berkeleyone B (CHEBI:69025) is a cyclic terpene ketone (CHEBI:36130)
	berkeleyone B (CHEBI:69025) is a meroterpenoid (CHEBI:64419)
	berkeleyone B (CHEBI:69025) is a methyl ester (CHEBI:25248)
	berkeleyone B (CHEBI:69025) is a organic heterotetracyclic compound (CHEBI:38163)
	berkeleyone B (CHEBI:69025) is a terpene lactone (CHEBI:37668)
	berkeleyone B (CHEBI:69025) is a tertiary alcohol (CHEBI:26878)
	berkeleyone B (CHEBI:69025) is a tertiary α-hydroxy ketone (CHEBI:139592)
	berkeleyone B (CHEBI:69025) is a β-diketone (CHEBI:67265)
	berkeleyone B (CHEBI:69025) is a ε-lactone (CHEBI:50239)

IUPAC Name
rel-methyl (7aS,8R,10S,12R,13aS,13bS)-10-hydroxy-5,5,7a,10,12,13b-hexamethyl-14-methylidene-3,9,11-trioxo-1,2,3,7,7a,9,10,11,12,13,13a,13b-dodecahydro-8,12-methanocycloocta[3,4]benzo[1,2-c]oxepine-8(5H)-carboxylate

UniProt Name	Source
berkeleyone B	UniProt

Registry Numbers	Sources
Reaxys:21969349	Reaxys

Citations