Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA020387
PROPERTIES
| NPAID | NPA020387 |
|---|---|
| CLUSTER ID | 83 |
| NODE ID | 78 |
| NAME | Acetylaranotin |
| FORMULA | C22H20N2O8S2 |
| MOLECULAR WEIGHT (Da) | 504.5420 |
| ACCURATE MASS (Da) | 504.0661 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Aspergillus |
| ORIGIN SPECIES | terreus |
| InChIKey | OHTZNUUGYPDWEB-NEEVBFIGSA-N |
| InChI | InChI=1S/C22H20N2O8S2/c1-11(25)31-15-3-5-29-9-13-7-21-20(28)24-18-14(10-30-6-4-16(18)32-12(2)26)8-22(24,34-33-21)19(27)23(21)17(13)15/h3-6,9-10,15-18H,7-8H2,1-2H3/t15-,16-,17-,18-,21+,22+/m0/s1 |
| SMILES | CC(=O)O[C@H]1C=COC=C2C[C@@]34SS[C@]5(CC6=COC=C[C@H](OC(C)=O)[C@H]6N5C3=O)C(=O)N4[C@@H]21 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Kamata; S; Sakai, H; Hirota, A Isolation of Acetylaranotin, Bisdethiodi(methylthio)- acetylaranotin and Terrein as Plant Growth Inhibitors from a Strain of Aspergillus terreus Agricultural and Biological Chemistry 1983 47 (11) 2637-2638. | ||
|---|---|---|---|
| DOI | 10.1271/bbb1961.47.2637 | PMID | - |
SYNTHESES
| CITATION 1 | Codelli JA; Puchlopek AL; Reisman SE Enantioselective total synthesis of (-)-acetylaranotin, a dihydrooxepine epidithiodiketopiperazine. Journal of the American Chemical Society 2012 134 (4) 1930-3. DOI: 10.1021/ja209354e PMID: 22023250 | ||
|---|---|---|---|
| CITATION 2 | Fujiwara H; Kurogi T; Okaya S; Okano K; Tokuyama H Total synthesis of (-)-acetylaranotin. Angewandte Chemie International Edition 2012 51 (52) 13062-5. DOI: 10.1002/anie.201207307 PMID: 23161829 | ||
| CITATION 3 | Belov DS; Ratmanova NK; Andreev IA; Kurkin AV Synthesis of bicyclic proline derivatives by the aza-Cope-Mannich reaction: formal synthesis of (±)-acetylaranotin. Chemistry - A European Journal 2015 21 (10) 4141-7. DOI: 10.1002/chem.201405811 PMID: 25631763 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | CC(=O)OC1C=COC=C2C1N3C(=O)C45CC6=COC=CC(C6N4C(=O)C3(C2)SS5)OC(=O)C | Kamata; S; Sakai, H; Hirota, A Isolation of Acetylaranotin, Bisdethiodi(methylthio)- acetylaranotin and Terrein as Plant Growth Inhibitors from a Strain of Aspergillus terreus Agricultural and Biological Chemistry 1983 47 (11) 2637-2638. DOI: 10.1271/bbb1961.47.2637 | ||
| 2 | CC(=O)O[C@H]1C=COC=C2C[C@@]34SS[C@]5(CC6=COC=C[C@H](OC(C)=O)[C@H]6N5C3=O)C(=O)N4[C@@H]21 | Fujiwara H; Kurogi T; Okaya S; Okano K; Tokuyama H Total synthesis of (-)-acetylaranotin. Angewandte Chemie International Edition 2012 51 (52) 13062-5. DOI: 10.1002/anie.201207307 PMID: 23161829 | ||
