Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA003891
PROPERTIES
| NPAID | NPA003891 |
|---|---|
| CLUSTER ID | 2095 |
| NODE ID | 1677 |
| NAME | Berkelic acid |
| FORMULA | C29H40O9 |
| MOLECULAR WEIGHT (Da) | 532.6300 |
| ACCURATE MASS (Da) | 532.2672 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Penicillium |
| ORIGIN SPECIES | sp. |
| InChIKey | KUPCHRRTAPZASB-FZIMWOAESA-N |
| InChI | InChI=1S/C29H40O9/c1-6-8-9-10-19-11-17-12-20(30)24(26(32)33)25-23(17)21(37-19)14-29(38-25)16(3)18(15-36-29)13-22(31)28(4,7-2)27(34)35-5/h12,16,18-19,21,30H,6-11,13-15H2,1-5H3,(H,32,33)/t16-,18+,19+,21-,28-,29-/m0/s1 |
| SMILES | CCCCC[C@@H]1CC2=CC(O)=C(C(=O)O)C3=C2[C@H](C[C@]2(OC[C@@H](CC(=O)[C@](C)(CC)C(=O)OC)[C@@H]2C)O3)O1 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Stierle, Andrea A.; Stierle, Donald B.; Kelly, Kal Berkelic Acid, A Novel Spiroketal with Selective Anticancer Activity from an Acid Mine Waste Fungal Extremophile Journal of Organic Chemistry 2006 71 (14) 5357-5360. | ||
|---|---|---|---|
| DOI | 10.1021/jo060018d | PMID | 16808526 |
SYNTHESES
| CITATION 1 | Bender CF; Yoshimoto FK; Paradise CL; De Brabander JK A concise synthesis of berkelic acid inspired by combining the natural products spicifernin and pulvilloric acid. Journal of the American Chemical Society 2009 131 (32) 11350-2. DOI: 10.1021/ja905387r PMID: 19722648 | ||
|---|---|---|---|
| CITATION 2 | Snaddon TN; Buchgraber P; Schulthoff S; Wirtz C; Mynott R; Fürstner A Total synthesis of berkelic acid. Chemistry - A European Journal 2010 16 (40) 12133-40. DOI: 10.1002/chem.201001133 PMID: 20853286 | ||
| CITATION 3 | Fañanás FJ; Mendoza A; Arto T; Temelli B; Rodríguez F Scalable total synthesis of (-)-berkelic acid by using a protecting-group-free strategy. Angewandte Chemie International Edition 2012 51 (20) 4930-3. DOI: 10.1002/anie.201109076 PMID: 22488814 | ||
| CITATION 4 | Bender CF; Paradise CL; Lynch VM; Yoshimoto FK; De Brabander JK A biosynthetically inspired synthesis of (-)-berkelic acid and analogs. Tetrahedron 2018 74 (9) 909-919. DOI: 10.1016/j.tet.2018.01.021 PMID: 29867257 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | CCCCC[C@@H]1CC2=CC(=C(C3=C2C(O1)C[C@]4(O3)[C@@H]([C@H](CO4)CC(=O)C(C)(CC)C(=O)OC)C)C(=O)O)O | Stierle, Andrea A.; Stierle, Donald B.; Kelly, Kal Berkelic Acid, A Novel Spiroketal with Selective Anticancer Activity from an Acid Mine Waste Fungal Extremophile Journal of Organic Chemistry 2006 71 (14) 5357-5360. DOI: 10.1021/jo060018d PMID: 16808526 | ||
| 2 | CCCCC[C@@H]1CC2=CC(O)=C(C(=O)O)C3=C2[C@H](C[C@]2(OC[C@@H](CC(=O)[C@](C)(CC)C(=O)OC)[C@@H]2C)O3)O1 | Wu, Xiaoxing; Zhou, Jingye; Snider, Barry B Introduction of the (-)-berkelic acid side chain and assignment of the C-22 stereochemistry. Journal of Organic Chemistry 2009 74 (16) 6245-52. DOI: 10.1021/jo901221a PMID: 19630376 | ||
