Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA005593
PROPERTIES
| NPAID | NPA005593 |
|---|---|
| CLUSTER ID | 2725 |
| NODE ID | 191 |
| NAME | Guanacastepene |
| FORMULA | C22H30O5 |
| MOLECULAR WEIGHT (Da) | 374.4770 |
| ACCURATE MASS (Da) | 374.2093 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Unknown-fungus |
| ORIGIN SPECIES | sp. CR115 |
| InChIKey | KCPNSIPCHJTGHJ-MYHSIESUSA-N |
| InChI | InChI=1S/C22H30O5/c1-12(2)18-20(27-13(3)24)19(26)16-10-15-14(11-23)17(25)6-7-21(15,4)8-9-22(16,18)5/h10-12,17-18,20,25H,6-9H2,1-5H3/t17-,18-,20+,21-,22-/m0/s1 |
| SMILES | CC(C)[C@H]1[C@H](C(=O)C2=CC3=C([C@H](CC[C@]3(CC[C@]12C)C)O)C=O)OC(=O)C |
ORIGINAL ISOLATION REFERENCE
| CITATION | SINGH, M. P.; JANSO, J. E.; LUCKMAN, S. W.; BRADY, S. F.; CLARDY, J.; GREENSTEIN, M.; MAIESE, W. M. Biological Activity of Guanacastepene, a Novel Diterpenoid Antibiotic Produced by an Unidentified Fungus CR115 Journal of Antibiotics 2000 53 (3) 256-261. | ||
|---|---|---|---|
| DOI | 10.7164/antibiotics.53.256 | PMID | 10819296 |
SYNTHESES
| CITATION 1 | Boyer FD; Hanna I; Ricard L Formal synthesis of (+/-)-guanacastepene A: a tandem ring-closing metathesis approach. Organic Letters 2004 6 (11) 1817-20. DOI: 10.1021/ol049452x PMID: 15151422 | ||
|---|---|---|---|
| CITATION 2 | Mandal M; Yun H; Dudley GB; Lin S; Tan DS; Danishefsky SJ Total synthesis of guanacastepene a: a route to enantiomeric control. Journal of Organic Chemistry 2005 70 (26) 10619-37. DOI: 10.1021/jo051470k PMID: 16355979 | ||
