Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA014651
PROPERTIES
| NPAID | NPA014651 |
|---|---|
| CLUSTER ID | 92 |
| NODE ID | 87 |
| NAME | Epothilone D |
| FORMULA | C27H41NO5S |
| MOLECULAR WEIGHT (Da) | 491.6940 |
| ACCURATE MASS (Da) | 491.2705 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Sorangium |
| ORIGIN SPECIES | cellulosum |
| InChIKey | XOZIUKBZLSUILX-GIQCAXHBSA-N |
| InChI | InChI=1S/C27H41NO5S/c1-16-9-8-10-17(2)25(31)19(4)26(32)27(6,7)23(29)14-24(30)33-22(12-11-16)18(3)13-21-15-34-20(5)28-21/h11,13,15,17,19,22-23,25,29,31H,8-10,12,14H2,1-7H3/b16-11-,18-13+/t17-,19+,22-,23-,25-/m0/s1 |
| SMILES | C[C@H]1CCC/C(=C\C[C@H](OC(=O)C[C@@H](C(C(=O)[C@@H]([C@H]1O)C)(C)C)O)/C(=C/C2=CSC(=N2)C)/C)/C |
ORIGINAL ISOLATION REFERENCE
| CITATION | Hardt; Steinmetz; Gerth; Sasse; Reichenbach; Hoefle New natural epothilones from Sorangium cellulosum, strains So ce90/B2 and So ce90/D13: Isolation, structure elucidation, and SAR studies Journal of Natural Products 2001 64 (7) 847-856. | ||
|---|---|---|---|
| DOI | 10.1021/np000629f | PMID | 11473410 |
SYNTHESES
| CITATION 1 | White JD; Carter RG; Sundermann KF; Wartmann M Total synthesis of epothilone B, epothilone D, and cis- and trans-9,10-dehydroepothilone D. Journal of the American Chemical Society 2001 123 (23) 5407-5413. DOI: 10.1021/ja010454b PMID: 11389619 | ||
|---|---|---|---|
| CITATION 2 | Wessjohann LA; Scheid GO; Eichelberger U; Umbreen S Total synthesis of epothilone D: the nerol/macroaldolization approach. Journal of Organic Chemistry 2013 78 (21) 10588-10595. DOI: 10.1021/jo401355r PMID: 24079664 | ||
| CITATION 3 | Sang F; Feng P; Chen J; Ding Y; Duan X; Zhai J; Ma X; Zhang B; Zhang Q; Lin J; Chen Y Epothilone D and its 9-Methyl analogues: combinatorial syntheses, conformation, and biological activities. European Journal of Medicinal Chemistry 2013 68 321-332. DOI: 10.1016/j.ejmech.2013.08.003 PMID: 23994325 | ||
| CITATION 4 | Prantz K; Mulzer J Synthesis of (Z)-trisubstituted olefins by decarboxylative grob-type fragmentations: epothilone D, discodermolide, and peloruside A. Chemistry - A European Journal 2010 16 (2) 485-506. DOI: 10.1002/chem.200901567 PMID: 19943284 | ||
| CITATION 5 | Broadrup RL; Sundar HM; Swindell CS Total synthesis of 12,13-desoxyepothilone B (Epothilone D). Bioorganic Chemistry 2005 33 (2) 116-133. DOI: 10.1016/j.bioorg.2004.11.002 PMID: 15788167 | ||
