Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA016301
PROPERTIES
| NPAID | NPA016301 |
|---|---|
| CLUSTER ID | 5584 |
| NODE ID | 3954 |
| NAME | Fusarisetin A |
| FORMULA | C22H31NO5 |
| MOLECULAR WEIGHT (Da) | 389.4920 |
| ACCURATE MASS (Da) | 389.2202 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Fusarium |
| ORIGIN SPECIES | sp. FN080326 |
| InChIKey | IIZSEOKGOHTBLK-KDLRZXEZSA-N |
| InChI | InChI=1S/C22H31NO5/c1-11-5-7-14-13(9-11)6-8-15-17-12(2)28-22(27)16(10-24)23(4)19(26)21(17,22)18(25)20(14,15)3/h6,8,11-17,24,27H,5,7,9-10H2,1-4H3/t11-,12+,13-,14-,15+,16+,17+,20+,21+,22+/m1/s1 |
| SMILES | C[C@@H]1CC[C@@H]2[C@H](C=C[C@H]3[C@@H]4[C@H](C)O[C@@]5(O)[C@H](CO)N(C)C(=O)[C@@]45C(=O)[C@@]23C)C1 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Jang, Jae-Hyuk; Asami, Yukihiro; Jang, Jun-Pil; Kim, Sun-Ok; Moon, Dong Oh; Shin, Kee-Sun; Hashizume, Daisuke; Muroi, Makoto; Saito, Tamio; Oh, Hyuncheol; Kim, Bo Yeon; Osada, Hiroyuki; Ahn, Jong Seog Fusarisetin A, an acinar morphogenesis inhibitor from a soil fungus, Fusarium sp. FN080326 Journal of the American Chemical Society 2011 133 (18) 6865-6867. | ||
|---|---|---|---|
| DOI | 10.1021/ja1110688 | PMID | 21500849 |
SYNTHESES
| CITATION 1 | Yin J; Kong L; Wang C; Shi Y; Cai S; Gao S Biomimetic synthesis of equisetin and (+)-fusarisetin A. Chemistry - A European Journal 2013 19 (39) 13040-13046. DOI: 10.1002/chem.201302163 PMID: 24038394 | ||
|---|---|---|---|
| CITATION 2 | Xu J; Caro-Diaz EJ; Lacoske MH; Hung CI; Jamora C; Theodorakis EA Fusarisetin A: Scalable Total Synthesis and Related Studies. Chemical Science 2012 3 (12) 3378-3386. DOI: 10.1039/C2SC21308G PMID: 23227303 | ||
| CITATION 3 | Liu C; Zeng Z; Chen R; Jiang X; Wang Y; Zhang Y Total Synthesis of (+)-Fusarisetin A Driven by a One-Pot Four-Reaction Process. Organic Letters 2016 18 (3) 624-627. DOI: 10.1021/acs.orglett.6b00036 PMID: 26812626 | ||
| CITATION 4 | Xu J; Caro-Diaz EJ; Trzoss L; Theodorakis EA Nature-inspired total synthesis of (-)-fusarisetin A. Journal of the American Chemical Society 2012 134 (11) 5072-5075. DOI: 10.1021/ja300807e PMID: 22390338 | ||
| CITATION 5 | Kong L; Rao M; Ou J; Yin J; Lu W; Liu M; Pang X; Gao S Total synthesis and biological studies of cryptocin and derivatives of equisetin and fusarisetin A. Organic & Biomolecular Chemistry 2014 12 (38) 7591-7597. DOI: 10.1039/c4ob01149j PMID: 25139438 | ||
| CITATION 6 | Deng J; Zhu B; Lu Z; Yu H; Li A Total synthesis of (-)-fusarisetin A and reassignment of the absolute configuration of its natural counterpart. Journal of the American Chemical Society 2012 134 (2) 920-923. DOI: 10.1021/ja211444m PMID: 22239597 | ||
| CITATION 7 | Huang J; Fang L; Long R; Shi LL; Shen HJ; Li CC; Yang Z Asymmetric total synthesis of (+)-fusarisetin A via the intramolecular Pauson-Khand reaction. Organic Letters 2013 15 (15) 4018-21. DOI: 10.1021/ol401831w PMID: 23869720 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | C[C@@H]1CC[C@@H]2[C@H](C=C[C@H]3[C@@H]4[C@@H](C)O[C@@]5(O)[C@H](CO)N(C)C(=O)[C@@]45C(=O)[C@]32C)C1 | Jang, Jae-Hyuk; Asami, Yukihiro; Jang, Jun-Pil; Kim, Sun-Ok; Moon, Dong Oh; Shin, Kee-Sun; Hashizume, Daisuke; Muroi, Makoto; Saito, Tamio; Oh, Hyuncheol; Kim, Bo Yeon; Osada, Hiroyuki; Ahn, Jong Seog Fusarisetin A, an acinar morphogenesis inhibitor from a soil fungus, Fusarium sp. FN080326 Journal of the American Chemical Society 2011 133 (18) 6865-6867. DOI: 10.1021/ja1110688 PMID: 21500849 | ||
| 2 | C[C@@H]1CC[C@@H]2[C@H](C=C[C@H]3[C@@H]4[C@H](C)O[C@@]5(O)[C@H](CO)N(C)C(=O)[C@@]45C(=O)[C@@]23C)C1 | Deng J; Zhu B; Lu Z; Yu H; Li A Total synthesis of (-)-fusarisetin A and reassignment of the absolute configuration of its natural counterpart. Journal of the American Chemical Society 2012 134 (2) 920-923. DOI: 10.1021/ja211444m PMID: 22239597 | ||
