Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA012289
PROPERTIES
| NPAID | NPA012289 |
|---|---|
| CLUSTER ID | 2835 |
| NODE ID | 130 |
| NAME | Metacycloprodigiosin |
| FORMULA | C25H33N3O |
| MOLECULAR WEIGHT (Da) | 391.5590 |
| ACCURATE MASS (Da) | 391.2624 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Streptomyces |
| ORIGIN SPECIES | longisporus ruber |
| InChIKey | XEPVVPTUOMXJRW-JLPGSUDCSA-N |
| InChI | InChI=1S/C25H33N3O/c1-3-18-11-8-6-4-5-7-9-12-19-15-20(18)22(27-19)16-24-25(29-2)17-23(28-24)21-13-10-14-26-21/h10,13-18,26-27H,3-9,11-12H2,1-2H3/b24-16- |
| SMILES | CCC1CCCCCCCCC2=CC1=C(N2)/C=C\3/C(=CC(=N3)C4=CC=CN4)OC |
ORIGINAL ISOLATION REFERENCE
| CITATION | Wasserman, H H; Rodgers, G C; Keith, D D Metacycloprodigiosin, a tripyrrole pigment from Streptomyces longisporus ruber Journal of the American Chemical Society 1969 91 (5) 1263-1264. | ||
|---|---|---|---|
| DOI | 10.1021/ja01033a065 | PMID | 5780510 |
SYNTHESES
| CITATION 1 | Clift MD; Thomson RJ Development of a merged conjugate addition/oxidative coupling sequence. Application to the enantioselective total synthesis of metacycloprodigiosin and prodigiosin R1. Journal of the American Chemical Society 2009 131 (40) 14579-14583. DOI: 10.1021/ja906122g PMID: 19754115 | ||
|---|---|---|---|
| CITATION 2 | Vega MM; Crain DM; Konkol LC; Thomson RJ Enantioselective synthesis of metacycloprodigiosin via the "Wasserman pyrrole". Tetrahedron Letters 2015 56 (23) 3228-3230. DOI: 10.1016/j.tetlet.2014.12.075 PMID: 26120213 | ||
