Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA007302
PROPERTIES
| NPAID | NPA007302 |
|---|---|
| CLUSTER ID | 3273 |
| NODE ID | 2489 |
| NAME | Coronatine |
| FORMULA | C18H25NO4 |
| MOLECULAR WEIGHT (Da) | 319.4010 |
| ACCURATE MASS (Da) | 319.1784 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Pseudomonas |
| ORIGIN SPECIES | coronafacience var. atropurpurea |
| InChIKey | FMGBNISRFNDECK-CZSBRECXSA-N |
| InChI | InChI=1S/C18H25NO4/c1-3-10-7-13-12(5-6-15(13)20)14(8-10)16(21)19-18(17(22)23)9-11(18)4-2/h8,10-13H,3-7,9H2,1-2H3,(H,19,21)(H,22,23)/t10-,11+,12+,13+,18+/m1/s1 |
| SMILES | CC[C@H]1C=C(C(=O)N[C@@]2(C(=O)O)C[C@@H]2CC)[C@H]2CCC(=O)[C@H]2C1 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Ichihara, Akitami; Shiraishi, Kunio; Sato, Hiroji; Sakamura, Sadao; Nishiyama, Koji; Sakai, Ryutaro; Furusaki, Akio; Matsumoto, Takeshi The structure of coronatine Journal of the American Chemical Society 1977 99 (2) 636-637. | ||
|---|---|---|---|
| DOI | 10.1021/ja00444a067 | PMID | - |
SYNTHESES
| CITATION 1 | Littleson MM; Baker CM; Dalençon AJ; Frye EC; Jamieson C; Kennedy AR; Ling KB; McLachlan MM; Montgomery MG; Russell CJ; Watson AJB Scalable total synthesis and comprehensive structure-activity relationship studies of the phytotoxin coronatine. Nature Communications 2018 9 (1) 1105. DOI: 10.1038/s41467-018-03443-1 PMID: 29549326 | ||
|---|---|---|---|
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | CCC1CC2C(CCC2=O)C(=C1)C(=O)NC3(CC3CC)C(=O)O | Ichihara, Akitami; Shiraishi, Kunio; Sato, Hiroji; Sakamura, Sadao; Nishiyama, Koji; Sakai, Ryutaro; Furusaki, Akio; Matsumoto, Takeshi The structure of coronatine Journal of the American Chemical Society 1977 99 (2) 636-637. DOI: 10.1021/ja00444a067 | ||
| 2 | CC[C@H]1C=C(C(=O)N[C@@]2(C(=O)O)C[C@@H]2CC)[C@H]2CCC(=O)[C@H]2C1 | Tao, T; Parry, R J Determination by enantioselective synthesis of the absolute configuration of CPE, a potential intermediate in coronatine biosynthesis. Organic Letters 2001 3 (19) 3045-7. DOI: 10.1021/ol0165037 PMID: 11554839 | ||
