// Workers AI · dad joke modeWhat did Berkeleydione say? "I'm a dione to meet you.

Berkeleydione
Names
	Preferred 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
Identifiers
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:69021;
ChEMBL	ChEMBL400514;
ChemSpider	10193089;
PubChem CID	21580417;
CompTox Dashboard (EPA)	DTXSID001045475 ;
	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 Key: RBGYOLFHIDJTOX-VMXKAMJHSA-N; InChI=1/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 Key: RBGYOLFHIDJTOX-VMXKAMJHBZ;
	SMILES CC1=C2CC(=O)OC(C2=CC[C@]3([C@H]1C[C@@]4(C(=C)[C@]3(C(=O)[C@@](C4=O)(C)O)C(=O)OC)C)C)(C)C;
Properties
Chemical formula	C26H32O7
Molar mass	456.535 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Berkeleydione is a chemical compound isolated from a Penicillium species that has in vitro activity in a cancer cell line.^[1] It was first discovered in fungal species which evolved to live in an acidic lake at Berkeley Pit. It is a precursor to several other fungal meroterpenoids, such as paraherquonin [wd] and the berkeleyacetals, miniolutelides, and dhilirolides.^[2]

Notes

↑ Stierle, DB; Stierle, AA; Hobbs, JD; Stokken, J; Clardy, J (2004). "Berkeleydione and berkeleytrione, new bioactive metabolites from an acid mine organism". Organic Letters. 6 (6): 1049–52. doi:10.1021/ol049852k. PMID 15012097.
↑ Matsuda, Yudai; Abe, Ikuro (2016). "Biosynthesis of fungal meroterpenoids". Natural Product Reports. 33 (1): 26–53. doi:10.1039/C5NP00090D.

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[1] Stierle, DB; Stierle, AA; Hobbs, JD; Stokken, J; Clardy, J (2004). "Berkeleydione and berkeleytrione, new bioactive metabolites from an acid mine organism". Organic Letters. 6 (6): 1049–52. doi:10.1021/ol049852k. PMID 15012097.

[Matsuda2016-2] Matsuda, Yudai; Abe, Ikuro (2016). "Biosynthesis of fungal meroterpenoids". Natural Product Reports. 33 (1): 26–53. doi:10.1039/C5NP00090D.

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