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)
ChEBI
ChEMBL
ChemSpider
  • 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
  • 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
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.

Notes

  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.


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