Compounds
| ID | Spectrum Quality | Annotated Name |
|---|---|---|
| CCMSLIB00010111745 | Gold | 3 |
| CCMSLIB00010111746 | Gold | 3 |
| CCMSLIB00010111747 | Gold | 3 |
| CCMSLIB00010111748 | Gold | 3 |
| CCMSLIB00010123079 | Gold | 3 |
| CCMSLIB00010123080 | Gold | 3 |
| CCMSLIB00010123081 | Gold | 3 |
| CCMSLIB00010123082 | Gold | 3 |
COMPOUND NPA002378
PROPERTIES
| NPAID | NPA002378 |
|---|---|
| CLUSTER ID | 1424 |
| NODE ID | 1184 |
| NAME | Streptonigrin |
| FORMULA | C25H22N4O8 |
| MOLECULAR WEIGHT (Da) | 506.4710 |
| ACCURATE MASS (Da) | 506.1438 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Streptomyces |
| ORIGIN SPECIES | flocculus |
| InChIKey | PVYJZLYGTZKPJE-UHFFFAOYSA-N |
| InChI | InChI=1S/C25H22N4O8/c1-9-14(10-6-8-13(35-2)23(36-3)20(10)30)15(26)19(29-17(9)25(33)34)12-7-5-11-18(28-12)22(32)16(27)24(37-4)21(11)31/h5-8,30H,26-27H2,1-4H3,(H,33,34) |
| SMILES | CC1=C(C(=C(N=C1C(=O)O)C2=NC3=C(C=C2)C(=O)C(=C(C3=O)N)OC)N)C4=C(C(=C(C=C4)OC)OC)O |
ORIGINAL ISOLATION REFERENCE
| CITATION | Rao, Koppaka V; Biemann, K; Woodward, RB The structure of streptonigrin Journal of the American Chemical Society 1963 85 (16) 2532-2533. | ||
|---|---|---|---|
| DOI | 10.1021/ja00899a051 | PMID | - |
SYNTHESES
| CITATION 1 | Donohoe TJ; Jones CR; Barbosa LC Total synthesis of (±)-streptonigrin: de novo construction of a pentasubstituted pyridine using ring-closing metathesis. Journal of the American Chemical Society 2011 133 (41) 16418-16421. DOI: 10.1021/ja207835w PMID: 21942896 | ||
|---|---|---|---|
| CITATION 2 | Donohoe TJ; Jones CR; Kornahrens AF; Barbosa LC; Walport LJ; Tatton MR; O'Hagan M; Rathi AH; Baker DB Total synthesis of the antitumor antibiotic (±)-streptonigrin: first- and second-generation routes for de novo pyridine formation using ring-closing metathesis. Journal of Organic Chemistry 2013 78 (24) 12338-12350. DOI: 10.1021/jo402388f PMID: 24328139 | ||
