Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA009778
PROPERTIES
| NPAID | NPA009778 |
|---|---|
| CLUSTER ID | 92 |
| NODE ID | 87 |
| NAME | Epothilone A |
| FORMULA | C26H39NO6S |
| MOLECULAR WEIGHT (Da) | 493.6660 |
| ACCURATE MASS (Da) | 493.2498 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Sorangium |
| ORIGIN SPECIES | cellulosum |
| InChIKey | HESCAJZNRMSMJG-KKQRBIROSA-N |
| InChI | InChI=1S/C26H39NO6S/c1-14-8-7-9-19-21(32-19)11-20(15(2)10-18-13-34-17(4)27-18)33-23(29)12-22(28)26(5,6)25(31)16(3)24(14)30/h10,13-14,16,19-22,24,28,30H,7-9,11-12H2,1-6H3/b15-10+/t14-,16+,19+,20-,21-,22-,24-/m0/s1 |
| SMILES | C[C@H]1CCC[C@@H]2[C@@H](O2)C[C@H](OC(=O)C[C@@H](C(C(=O)[C@@H]([C@H]1O)C)(C)C)O)/C(=C/C3=CSC(=N3)C)/C |
ORIGINAL ISOLATION REFERENCE
| CITATION | Höfle, Gerhard; Bedorf, Norbert; Steinmetz, Heinrich; Schomburg, Dietmar; Gerth, Klaus; Reichenbach, Hans Epothilone A and B-Novel 16-Membered Macrolides with Cytotoxic Activity: Isolation, Crystal Structure, and Conformation in Solution Angewandte Chemie International Edition 1996 35 (13-14) 1567-1569. | ||
|---|---|---|---|
| DOI | 10.1002/anie.199615671 | PMID | 25855820 |
SYNTHESES
| CITATION 1 | Liu ZY; Chen ZC; Yu CZ; Wang RF; Zhang RZ; Huang CS; Yan Z; Cao DR; Sun JB; Li G Total synthesis of epothilone a through stereospecific epoxidation of the p-methoxybenzyl ether of epothilone C. Chemistry - A European Journal 2002 8 (16) 3747-3756. DOI: 10.1002/1521-3765(20020816)8:16<3747::AID-CHEM3747>3.0.CO;2-A PMID: 12203301 | ||
|---|---|---|---|
| CITATION 2 | Sawada D; Shibasaki M Enantioselective Total Synthesis of Epothilone A Using Multifunctional Asymmetric Catalyses. Angewandte Chemie International Edition 2000 39 (1) 209-213. DOI: 10.1002/(sici)1521-3773(20000103)39:1<209::aid-anie209>3.0.co;2-f PMID: 10649378 | ||
| CITATION 3 | Zhu B; Panek JS Total synthesis of epothilone A. Organic Letters 2000 2 (17) 2575-2578. DOI: 10.1021/ol006104w PMID: 10990400 | ||
| CITATION 4 | Fürstner A; Mathes C; Lehmann CW Alkyne metathesis: development of a novel molybdenum-based catalyst system and its application to the total synthesis of epothilone A and C. Chemistry - A European Journal 2001 7 (24) 5299-5317. DOI: 10.1002/1521-3765(20011217)7:24<5299::aid-chem5299>3.0.co;2-x PMID: 11822430 | ||
| CITATION 5 | Cachoux F; Isarno T; Wartmann M; Altmann KH Total synthesis and biological assessment of benzimidazole-based analogues of epothilone A: ambivalent effects on cancer cell growth inhibition. ChemBioChem 2006 7 (1) 54-7. DOI: 10.1002/cbic.200500351 PMID: 16345113 | ||
