Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA012126
PROPERTIES
| NPAID | NPA012126 |
|---|---|
| CLUSTER ID | 4598 |
| NODE ID | 433 |
| NAME | Berkeleyone A |
| FORMULA | C26H38O6 |
| MOLECULAR WEIGHT (Da) | 446.5840 |
| ACCURATE MASS (Da) | 446.2668 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Penicillium |
| ORIGIN SPECIES | rubrum |
| InChIKey | NNHHTFDBMMPBSL-JFPRQHOTSA-N |
| 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 |
| SMILES | C[C@@]12CC[C@H](C([C@H]1CC[C@]3([C@H]2C[C@@]4(C(=C)[C@]3(C(=O)[C@@](C4=O)(C)O)C(=O)OC)C)C)(C)C)O |
ORIGINAL ISOLATION REFERENCE
| CITATION | Stierle, Donald B.; Stierle, Andrea A.; Patacini, Brianna; McIntyre, Kyle; Girtsman, Teri; Bolstad, Erin Berkeleyones and related meroterpenes from a deep water acid mine waste fungus that inhibit the production of interleukin 1-β from induced inflammasomes Journal of Natural Products 2011 74 (10) 2273-2277. | ||
|---|---|---|---|
| DOI | 10.1021/np2003066 | PMID | 21916432 |
SYNTHESES
| CITATION 1 | Elkin M; Szewczyk SM; Scruse AC; Newhouse TR Total Synthesis of (±)-Berkeleyone A. Journal of the American Chemical Society 2017 139 (5) 1790-1793. DOI: 10.1021/jacs.6b12914 PMID: 28102673 | ||
|---|---|---|---|
| CITATION 2 | Ting CP; Xu G; Zeng X; Maimone TJ Annulative Methods Enable a Total Synthesis of the Complex Meroterpene Berkeleyone A. Journal of the American Chemical Society 2016 138 (45) 14868-14871. DOI: 10.1021/jacs.6b10397 PMID: 27809506 | ||
