berkeleydione (CHEBI:69021)

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CHEBI:69021 - berkeleydione

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ChEBI ID	CHEBI:69021
ChEBI Name	berkeleydione
Stars
Definition	A meroterpenoid found in Penicillium rubrum. It has been shown to exhibit inhibitory activity against caspase-1.
Last Modified	18 August 2020
Downloads	Molfile

Formula	C26H32O7
Net Charge	0
Average Mass	456.535
Monoisotopic Mass	456.21480
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(=C2C)CC(=O)OC1(C)C
InChI	InChI=1S/C26H32O7/c1-13-15-11-18(27)33-22(3,4)16(15)9-10-24(6)17(13)12-23(5)14(2)26(24,21(30)32-8)20(29)25(7,31)19(23)28/h9,17,31H,2,10-12H2,1,3-8H3/t17-,23+,24-,25-,26-/m0/s1
InChIKey	RBGYOLFHIDJTOX-VMXKAMJHSA-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.
Application:	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology

Outgoing Relation(s)
	berkeleydione (CHEBI:69021) has role Penicillium metabolite (CHEBI:76964)
	berkeleydione (CHEBI:69021) has role antineoplastic agent (CHEBI:35610)
	berkeleydione (CHEBI:69021) has role cysteine protease inhibitor (CHEBI:64152)
	berkeleydione (CHEBI:69021) is a cyclic terpene ketone (CHEBI:36130)
	berkeleydione (CHEBI:69021) is a meroterpenoid (CHEBI:64419)
	berkeleydione (CHEBI:69021) is a methyl ester (CHEBI:25248)
	berkeleydione (CHEBI:69021) is a organic heterotetracyclic compound (CHEBI:38163)
	berkeleydione (CHEBI:69021) is a terpene lactone (CHEBI:37668)
	berkeleydione (CHEBI:69021) is a tertiary alcohol (CHEBI:26878)
	berkeleydione (CHEBI:69021) is a tertiary α-hydroxy ketone (CHEBI:139592)
	berkeleydione (CHEBI:69021) is a β-diketone (CHEBI:67265)

IUPAC Name
methyl (5aS,7R,9S,11R,11aS)-9-hydroxy-1,1,5,7,9,11a-hexamethyl-14-methylidene-3,8,10-trioxo-3,4,5a,6,7,8,9,10,11a,12-decahydro-7,11-methanocycloocta[4,5]cyclohepta[1,2-c]pyran-11(1H)-carboxylate

UniProt Name	Source
berkeleydione	UniProt

Registry Numbers	Sources
Reaxys:9740878	Reaxys

Citations