Compounds
| ID | Spectrum Quality | Annotated Name |
|---|---|---|
| CCMSLIB00000070246 | Gold | 2!CCMSLIB00000070247 |
| CCMSLIB00000001702 | Gold | 1 |
| CCMSLIB00000001774 | Gold | 1 |
| CCMSLIB00012105393 | Gold | 4 |
| CCMSLIB00012105394 | Gold | 4 |
| CCMSLIB00009945190 | Gold | 4 |
| CCMSLIB00009945191 | Gold | 4 |
COMPOUND NPA003734
PROPERTIES
| NPAID | NPA003734 |
|---|---|
| CLUSTER ID | 2027 |
| NODE ID | 1624 |
| NAME | Cyanolide A |
| FORMULA | C42H72O16 |
| MOLECULAR WEIGHT (Da) | 833.0220 |
| ACCURATE MASS (Da) | 832.4820 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Lyngbya |
| ORIGIN SPECIES | bouillonii |
| InChIKey | DLSUXMZHOIJLGM-MNCMQQDLSA-N |
| InChI | InChI=1S/C42H72O16/c1-13-23-15-25-17-29(57-39-37(49-11)35(47-9)27(45-7)21-51-39)41(3,4)32(53-25)20-34(44)56-24(14-2)16-26-18-30(42(5,6)31(54-26)19-33(43)55-23)58-40-38(50-12)36(48-10)28(46-8)22-52-40/h23-32,35-40H,13-22H2,1-12H3/t23-,24-,25-,26-,27-,28-,29+,30+,31+,32+,35+,36+,37-,38-,39+,40+/m1/s1 |
| SMILES | CC[C@@H]1C[C@@H]2C[C@@H](C([C@@H](O2)CC(=O)O[C@@H](C[C@@H]3C[C@@H](C([C@@H](O3)CC(=O)O1)(C)C)O[C@H]4[C@@H]([C@H]([C@@H](CO4)OC)OC)OC)CC)(C)C)O[C@H]5[C@@H]([C@H]([C@@H](CO5)OC)OC)OC |
ORIGINAL ISOLATION REFERENCE
| CITATION | Pereira, Alban R.; McCue, Christine F.; Gerwick, William H. Cyanolide A, a glycosidic macrolide with potent molluscicidal activity from the Papua new Guinea cyanobacterium lyngbya bouillonii Journal of Natural Products 2010 73 (2) 217-220. | ||
|---|---|---|---|
| DOI | 10.1021/np9008128 | PMID | 20131814 |
SYNTHESES
| CITATION 1 | Pabbaraja S; Satyanarayana K; Ganganna B; Yadav JS Formal total synthesis of cyanolide A. Journal of Organic Chemistry 2011 76 (6) 1922-1925. DOI: 10.1021/jo102401v PMID: 21280592 | ||
|---|---|---|---|
| CITATION 2 | Yang Z; Xie X; Jing P; Zhao G; Zheng J; Zhao C; She X Total synthesis of cyanolide A. Organic & Biomolecular Chemistry 2011 9 (4) 984-986. DOI: 10.1039/c0ob00971g PMID: 21152612 | ||
| CITATION 3 | Waldeck AR; Krische MJ Total synthesis of cyanolide A in the absence of protecting groups, chiral auxiliaries, or premetalated carbon nucleophiles. Angewandte Chemie International Edition 2013 52 (16) 4470-4473. DOI: 10.1002/anie.201300843 PMID: 23495211 | ||
| CITATION 4 | Tay GC; Gesinski MR; Rychnovsky SD Formation of highly substituted tetrahydropyranones: application to the total synthesis of cyanolide A. Organic Letters 2013 15 (17) 4536-4539. DOI: 10.1021/ol402095g PMID: 23962271 | ||
| CITATION 5 | Kim H; Hong J Total synthesis of cyanolide A and confirmation of its absolute configuration. Organic Letters 2010 12 (12) 2880-2883. DOI: 10.1021/ol101022z PMID: 20491466 | ||
