Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA013146
PROPERTIES
| NPAID | NPA013146 |
|---|---|
| CLUSTER ID | 2629 |
| NODE ID | 2046 |
| NAME | Apoptolidin |
| FORMULA | C58H96O21 |
| MOLECULAR WEIGHT (Da) | 1129.3850 |
| ACCURATE MASS (Da) | 1128.6444 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Nocardiopsis |
| ORIGIN SPECIES | sp. |
| InChIKey | WILMROCKORZEMQ-AIUMZUNXSA-N |
| InChI | InChI=1S/C58H96O21/c1-29-17-16-18-40(59)43(69-13)25-45(76-55(65)33(5)23-31(3)21-30(2)22-32(4)41(20-19-29)77-56-51(63)50(62)52(71-15)37(9)74-56)53(64)58(67)35(7)48(60)34(6)42(79-58)24-39(28-68-12)75-47-27-57(11,66)54(38(10)73-47)78-46-26-44(70-14)49(61)36(8)72-46/h17,19-23,32,34-54,56,59-64,66-67H,16,18,24-28H2,1-15H3/b20-19+,29-17+,30-22+,31-21+,33-23+/t32-,34+,35-,36-,37+,38+,39-,40+,41-,42-,43+,44-,45+,46+,47+,48+,49-,50+,51+,52+,53-,54+,56+,57+,58-/m1/s1 |
| SMILES | C[C@@H]1/C=C(/C=C(/C=C(/C(=O)O[C@@H](C[C@@H]([C@H](CC/C=C(/C=C/[C@H]1O[C@H]2[C@H]([C@@H]([C@H]([C@@H](O2)C)OC)O)O)\C)O)OC)[C@H]([C@]3([C@@H]([C@H]([C@H]([C@H](O3)C[C@H](COC)O[C@H]4C[C@]([C@H]([C@@H](O4)C)O[C@H]5C[C@H]([C@@H]([C@H](O5)C)O)OC)(C)O)C)O)C)O)O)\C)\C)\C |
ORIGINAL ISOLATION REFERENCE
| CITATION | Kim, J W; Adachi, H; Shin-ya, K; Hayakawa, Y; Seto, H Apoptolidin, a new apoptosis inducer in transformed cells from Nocardiopsis sp Journal of Antibiotics 1997 50 (7) 628-630. | ||
|---|---|---|---|
| DOI | 10.7164/antibiotics.50.628 | PMID | 9711255 |
SYNTHESES
| CITATION 1 | Nicolaou KC; Li Y; Sugita K; Monenschein H; Guntupalli P; Mitchell HJ; Fylaktakidou KC; Vourloumis D; Giannakakou P; O'Brate A Total synthesis of apoptolidin: completion of the synthesis and analogue synthesis and evaluation. Journal of the American Chemical Society 2003 125 (50) 15443-15454. DOI: 10.1021/ja030496v PMID: 14664590 | ||
|---|---|---|---|
| CITATION 2 | Wehlan H; Dauber M; Fernaud MT; Schuppan J; Keiper S; Mahrwald R; Garcia ME; Koert U Apoptolidin A: total synthesis and partially glycosylated analogues. Chemistry - A European Journal 2006 12 (28) 7378-7397. DOI: 10.1002/chem.200600462 PMID: 16865757 | ||
| CITATION 3 | Crimmins MT; Christie HS; Long A; Chaudhary K Total synthesis of apoptolidin A. Organic Letters 2009 11 (4) 831-834. DOI: 10.1021/ol802829n PMID: 19199767 | ||
| CITATION 4 | Nicolaou KC; Li Y; Fylaktakidou KC; Mitchell HJ; Sugita K Total Synthesis of Apoptolidin: Part 2. Coupling of Key Building Blocks and Completion of the Synthesis. Angewandte Chemie International Edition 2001 40 (20) 3854-3857. DOI: 10.1002/1521-3773(20011015)40:20<3854::AID-ANIE3854>3.0.CO;2-D PMID: 29712136 | ||
| CITATION 5 | Wehlan H; Dauber M; Mujica Fernaud MT; Schuppan J; Mahrwald R; Ziemer B; Juarez Garcia ME; Koert U Total synthesis of apoptolidin. Angewandte Chemie International Edition 2004 43 (35) 4597-4601. DOI: 10.1002/anie.200460172 PMID: 15352185 | ||
| CITATION 6 | Nicolaou KC; Fylaktakidou KC; Monenschein H; Li Y; Weyershausen B; Mitchell HJ; Wei HX; Guntupalli P; Hepworth D; Sugita K Total synthesis of apoptolidin: construction of enantiomerically pure fragments. Journal of the American Chemical Society 2003 125 (50) 15433-42. DOI: 10.1021/ja0304953 PMID: 14664589 | ||
