Compounds
| ID | Spectrum Quality | Annotated Name |
|---|---|---|
| CCMSLIB00000478581 | Gold | 1 |
COMPOUND NPA006085
PROPERTIES
| NPAID | NPA006085 |
|---|---|
| CLUSTER ID | 92 |
| NODE ID | 87 |
| NAME | Epothilone B |
| FORMULA | C27H41NO6S |
| MOLECULAR WEIGHT (Da) | 507.6930 |
| ACCURATE MASS (Da) | 507.2655 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Sorangium |
| ORIGIN SPECIES | cellulosum |
| InChIKey | QXRSDHAAWVKZLJ-PVYNADRNSA-N |
| InChI | InChI=1S/C27H41NO6S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)33-23(30)13-21(29)26(5,6)25(32)17(3)24(15)31/h11,14-15,17,20-22,24,29,31H,8-10,12-13H2,1-7H3/b16-11+/t15-,17+,20-,21-,22-,24-,27+/m0/s1 |
| SMILES | C[C@H]1CCC[C@@]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)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 | Wang J; Sun BF; Cui K; Lin GQ An efficient total synthesis of (-)-epothilone B. Organic Letters 2012 14 (24) 6354-6357. DOI: 10.1021/ol303148g PMID: 23214997 | ||
|---|---|---|---|
| CITATION 2 | 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 3 | Balog A; Harris C; Savin K; Zhang XG; Chou TC; Danishefsky SJ A Novel Aldol Condensation with 2-Methyl-4-pentenal and Its Application to an Improved Total Synthesis of Epothilone B. Angewandte Chemie International Edition 1998 37 (19) 2675-2678. DOI: 10.1002/(SICI)1521-3773(19981016)37:19<2675::AID-ANIE2675>3.0.CO;2-O PMID: 29711598 | ||
| CITATION 4 | Valluri M; Hindupur RM; Bijoy P; Labadie G; Jung JC; Avery MA Total synthesis of epothilone B. Organic Letters 2001 3 (23) 3607-3609. DOI: 10.1021/ol016173q PMID: 11700093 | ||
| CITATION 5 | Martin HJ; Pojarliev P; Kählig H; Mulzer J The 12,13-diol cyclization approach for a truly stereocontrolled total synthesis of epothilone B and the synthesis of a conformationally restrained analogue. Chemistry - A European Journal 2001 7 (10) 2261-2271. DOI: 10.1002/1521-3765(20010518)7:10<2261::aid-chem2261>3.0.co;2-f PMID: 11411998 | ||
| CITATION 6 | White JD; Sundermann KF; Carter RG Improved synthesis of epothilone B employing alkylation of an alkyne for assembly of subunits. Organic Letters 1999 1 (9) 1431-1434. DOI: 10.1021/ol990248x PMID: 10825989 | ||
