berkeleyone A (CHEBI:69024)

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CHEBI:69024 - berkeleyone A

ChEBI ID	CHEBI:69024
ChEBI Name	berkeleyone A
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	C26H38O6
Net Charge	0
Average Mass	446.584
Monoisotopic Mass	446.26684
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@]1([H])C(C)(C)[C@H](O)CC[C@@]21C
InChI	InChI=1S/C26H38O6/c1-14-23(5)13-16-22(4)11-10-17(27)21(2,3)15(22)9-12-24(16,6)26(14,20(30)32-8)19(29)25(7,31)18(23)28/h15-17,27,31H,1,9-13H2,2-8H3/t15-,16+,17-,22-,23-,24+,25+,26+/m1/s1
InChIKey	NNHHTFDBMMPBSL-JFPRQHOTSA-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 A (CHEBI:69024) has role Penicillium metabolite (CHEBI:76964)
	berkeleyone A (CHEBI:69024) has role cysteine protease inhibitor (CHEBI:64152)
	berkeleyone A (CHEBI:69024) is a carbopolycyclic compound (CHEBI:35294)
	berkeleyone A (CHEBI:69024) is a cyclic terpene ketone (CHEBI:36130)
	berkeleyone A (CHEBI:69024) is a diol (CHEBI:23824)
	berkeleyone A (CHEBI:69024) is a meroterpenoid (CHEBI:64419)
	berkeleyone A (CHEBI:69024) is a methyl ester (CHEBI:25248)
	berkeleyone A (CHEBI:69024) is a tertiary α-hydroxy ketone (CHEBI:139592)
	berkeleyone A (CHEBI:69024) is a β-diketone (CHEBI:67265)

IUPAC Name
rel-methyl (3R,4aS,6aS,7R,9S,11R,12aS,12bS)-3,9-dihydroxy-4,4,6a,9,11,12b-hexamethyl-13-methylidene-8,10-dioxotetradecahydro-7,11-methanocycloocta[a]naphthalene-7(2H)-carboxylate

UniProt Name	Source
berkeleyone A	UniProt

Registry Numbers	Sources
Reaxys:23869569	Reaxys

Citations