Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA008881
PROPERTIES
| NPAID | NPA008881 |
|---|---|
| CLUSTER ID | 1709 |
| NODE ID | 1394 |
| NAME | Pladienolide B |
| FORMULA | C30H48O8 |
| MOLECULAR WEIGHT (Da) | 536.7060 |
| ACCURATE MASS (Da) | 536.3349 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Streptomyces |
| ORIGIN SPECIES | platensis Mer-11107 |
| InChIKey | SDOUORKJIJYJNW-MYKOURMWSA-N |
| InChI | InChI=1S/C30H48O8/c1-8-24(33)21(5)29-25(37-29)16-18(2)10-9-11-19(3)28-20(4)12-13-26(36-22(6)31)30(7,35)15-14-23(32)17-27(34)38-28/h9-13,18,20-21,23-26,28-29,32-33,35H,8,14-17H2,1-7H3/b10-9+,13-12+,19-11+/t18-,20+,21-,23-,24+,25+,26+,28-,29-,30-/m1/s1 |
| SMILES | CC[C@H](O)[C@@H](C)[C@H]1O[C@H]1C[C@H](C)/C=C/C=C(\C)[C@H]1OC(=O)C[C@H](O)CC[C@@](C)(O)[C@@H](OC(C)=O)/C=C/[C@@H]1C |
ORIGINAL ISOLATION REFERENCE
| CITATION | Sakai, Takahashi; Sameshima, Tomohiro; Matsufuji, Motoko; Kawamura, Nato; Dobashi, Kazuyuki; Mizui, Yoshiharu Pladienolides, new substances from culture of Streptomyces platensis Mer-11107. I. taxonomy, fermentation, isolation and screening Journal of Antibiotics 2004 57 (3) 173-179. | ||
|---|---|---|---|
| DOI | 10.7164/antibiotics.57.173 | PMID | 15152802 |
SYNTHESES
| CITATION 1 | Kanada RM; Itoh D; Nagai M; Niijima J; Asai N; Mizui Y; Abe S; Kotake Y Total synthesis of the potent antitumor macrolides pladienolide B and D. Angewandte Chemie International Edition 2007 46 (23) 4350-4355. DOI: 10.1002/anie.200604997 PMID: 17437311 | ||
|---|---|---|---|
| CITATION 2 | Ghosh AK; Anderson DD Enantioselective total synthesis of pladienolide B: a potent spliceosome inhibitor. Organic Letters 2012 14 (18) 4730-4733. DOI: 10.1021/ol301886g PMID: 22954141 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | CCC(C(C)C1C(O1)CC(C)/C=C/C=C(\C)/C2C(/C=C/C(C(CCC(CC(=O)O2)O)(C)O)OC(=O)C)C)O | Sakai, Takahashi; Sameshima, Tomohiro; Matsufuji, Motoko; Kawamura, Nato; Dobashi, Kazuyuki; Mizui, Yoshiharu Pladienolides, new substances from culture of Streptomyces platensis Mer-11107. I. taxonomy, fermentation, isolation and screening Journal of Antibiotics 2004 57 (3) 173-179. DOI: 10.7164/antibiotics.57.173 PMID: 15152802 | ||
| 2 | CC[C@H](O)[C@@H](C)[C@H]1O[C@H]1C[C@H](C)/C=C/C=C(\C)[C@H]1OC(=O)C[C@H](O)CC[C@@](C)(O)[C@@H](OC(C)=O)/C=C/[C@@H]1C | Müller, Sarah; Sasse, Florenz; Maier, Martin E. Synthesis of Pladienolide B and Its 7‐Epimer with Insights into the Role of the Allylic Acetate. European Journal of Organic Chemistry 2014 2014 (5) 1025-1036. DOI: 10.1002/ejoc.201301468 | ||
