Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA010776
PROPERTIES
| NPAID | NPA010776 |
|---|---|
| CLUSTER ID | 1542 |
| NODE ID | 1266 |
| NAME | Lactimidomycin |
| FORMULA | C26H35NO6 |
| MOLECULAR WEIGHT (Da) | 457.5670 |
| ACCURATE MASS (Da) | 457.2464 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Streptomyces |
| ORIGIN SPECIES | amphibiosporus R310-104 |
| InChIKey | OYOKHBHOTQDIPM-UESXVERFSA-N |
| InChI | InChI=1S/C26H35NO6/c1-17-10-8-6-4-5-7-9-11-25(32)33-26(17)19(3)12-18(2)22(29)16-21(28)13-20-14-23(30)27-24(31)15-20/h4,6,8-12,17-18,20-21,26,28H,5,7,13-16H2,1-3H3,(H,27,30,31)/b6-4+,10-8-,11-9+,19-12+/t17-,18-,21+,26?/m0/s1 |
| SMILES | C[C@H]1/C=C\C=C\CC/C=C/C(=O)OC1/C(=C/[C@H](C)C(=O)C[C@@H](CC2CC(=O)NC(=O)C2)O)/C |
ORIGINAL ISOLATION REFERENCE
| CITATION | Sugawara, K; Nishiyama, Y; Toda, S; Komiyama, N; Hatori, M; Moriyama, T; Sawada, Y; Kamei, H; Konishi, M; Oki, T Lactimidomycin, a new glutarimide group antibiotic. Production, isolation, structure and biological activity Journal of Antibiotics 1992 45 (9) 1433-1441. | ||
|---|---|---|---|
| DOI | 10.7164/antibiotics.45.1433 | PMID | 1429229 |
SYNTHESES
| CITATION 1 | Gallenkamp D; Fürstner A Stereoselective synthesis of E,Z-configured 1,3-dienes by ring-closing metathesis. Application to the total synthesis of lactimidomycin. Journal of the American Chemical Society 2011 133 (24) 9232-9235. DOI: 10.1021/ja2031085 PMID: 21604689 | ||
|---|---|---|---|
| CITATION 2 | Li W; Georg GI A concise formal total synthesis of lactimidomycin. Chemical Communications 2015 51 (41) 8634-8636. DOI: 10.1039/c5cc02571k PMID: 25900419 | ||
| CITATION 3 | Nagasawa T; Kuwahara S Formal total synthesis of lactimidomycin. Organic Letters 2013 15 (12) 3002-3005. DOI: 10.1021/ol401214f PMID: 23731346 | ||
| CITATION 4 | Micoine K; Fürstner A Concise total synthesis of the potent translation and cell migration inhibitor lactimidomycin. Journal of the American Chemical Society 2010 132 (40) 14064-14066. DOI: 10.1021/ja107141p PMID: 20831202 | ||
| CITATION 5 | Larsen BJ; Sun Z; Lachacz E; Khomutnyk Y; Soellner MB; Nagorny P Synthesis and Biological Evaluation of Lactimidomycin and Its Analogues. Chemistry - A European Journal 2015 21 (52) 19159-19167. DOI: 10.1002/chem.201503527 PMID: 26577990 | ||
