Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA006425
PROPERTIES
| NPAID | NPA006425 |
|---|---|
| CLUSTER ID | 2987 |
| NODE ID | 2286 |
| NAME | Herboxidiene |
| FORMULA | C25H42O6 |
| MOLECULAR WEIGHT (Da) | 438.6050 |
| ACCURATE MASS (Da) | 438.2981 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Streptomyces |
| ORIGIN SPECIES | sp. A7847 (ATCC 49982) |
| InChIKey | ISZXEMUWHQLLTC-GZSUCXPKSA-N |
| InChI | InChI=1S/C25H42O6/c1-15(14-25(6)24(31-25)18(4)23(29-7)19(5)26)9-8-10-16(2)22-17(3)11-12-20(30-22)13-21(27)28/h8-10,15,17-20,22-24,26H,11-14H2,1-7H3,(H,27,28)/b9-8+,16-10+/t15?,17-,18?,19?,20?,22+,23?,24?,25?/m1/s1 |
| SMILES | C[C@@H]1CCC(O[C@H]1/C(=C/C=C/C(C)CC2(C(O2)C(C)C(C(C)O)OC)C)/C)CC(=O)O |
ORIGINAL ISOLATION REFERENCE
| CITATION | Isaac, Barbara G.; Ayer, Stephen W.; Elliott, Robert C.; Stonard, Richard J. Herboxidiene: A Potent Phytotoxic Polyketide from Streptomyces sp. A7847 Journal of Organic Chemistry 1992 57 (28) 7220-7226. | ||
|---|---|---|---|
| DOI | 10.1021/jo00052a042 | PMID | - |
SYNTHESES
| CITATION 1 | Lagisetti C; Yermolina MV; Sharma LK; Palacios G; Prigaro BJ; Webb TR Pre-mRNA splicing-modulatory pharmacophores: the total synthesis of herboxidiene, a pladienolide-herboxidiene hybrid analog and related derivatives. ACS Chemical Biology 2014 9 (3) 643-648. DOI: 10.1021/cb400695j PMID: 24377313 | ||
|---|---|---|---|
| CITATION 2 | Rohrs TM; Qin Q; Floreancig PE Re Angewandte Chemie International Edition 2017 56 (36) 10900-10904. DOI: 10.1002/anie.201705924 PMID: 28686815 | ||
| CITATION 3 | Pellicena M; Krämer K; Romea P; Urpí F Total synthesis of (+)-herboxidiene from two chiral lactate-derived ketones. Organic Letters 2011 13 (19) 5350-5353. DOI: 10.1021/ol202210k PMID: 21913648 | ||
| CITATION 4 | Gómez-Palomino A; Pellicena M; Krämer K; Romea P; Urpí F; Aullón G; Padrón JM Total synthesis of (+)-herboxidiene/GEX 1A. Organic & Biomolecular Chemistry 2017 15 (8) 1842-1862. DOI: 10.1039/c7ob00072c PMID: 28155959 | ||
| CITATION 5 | Zhang Y; Panek JS Total synthesis of herboxidiene/GEX 1A. Organic Letters 2007 9 (16) 3141-3143. DOI: 10.1021/ol701427k PMID: 17629295 | ||
| CITATION 6 | Thirupathi B; Mohapatra DK Gold-catalyzed Hosomi-Sakurai type reaction for the total synthesis of herboxidiene. Organic & Biomolecular Chemistry 2016 14 (26) 6212-6224. DOI: 10.1039/c6ob00321d PMID: 27193332 | ||
