Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA000214
PROPERTIES
| NPAID | NPA000214 |
|---|---|
| CLUSTER ID | 180 |
| NODE ID | 168 |
| NAME | Spirotryprostatin A |
| FORMULA | C22H25N3O4 |
| MOLECULAR WEIGHT (Da) | 395.4590 |
| ACCURATE MASS (Da) | 395.1845 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Aspergillus |
| ORIGIN SPECIES | fumigatus |
| InChIKey | MQJKGSIAJNXSCM-ORGXJRBJSA-N |
| InChI | InChI=1S/C22H25N3O4/c1-12(2)9-18-22(14-7-6-13(29-3)10-15(14)23-21(22)28)11-17-19(26)24-8-4-5-16(24)20(27)25(17)18/h6-7,9-10,16-18H,4-5,8,11H2,1-3H3,(H,23,28)/t16-,17-,18-,22-/m0/s1 |
| SMILES | CC(=C[C@H]1[C@]2(C[C@@H]3N1C(=O)[C@@H]4CCCN4C3=O)C5=C(C=C(C=C5)OC)NC2=O)C |
ORIGINAL ISOLATION REFERENCE
| CITATION | Cui, Cheng-Bin; Kakeya, Hideaki; Osada, Hiroyuki Novel mammalian cell cycle inhibitors, spirotryprostatins A and B, produced by Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase Tetrahedron 1996 52 (39) 12651-12666. | ||
|---|---|---|---|
| DOI | 10.1016/0040-4020(96)00737-5 | PMID | - |
SYNTHESES
| CITATION 1 | Onishi T; Sebahar PR; Williams RM Concise, asymmetric total synthesis of spirotryprostatin A. Organic Letters 2003 5 (17) 3135-7. DOI: 10.1021/ol0351910 PMID: 12917000 | ||
|---|---|---|---|
| CITATION 2 | Cheng MN; Wang H; Gong LZ Asymmetic organocatalytic 1,3-dipolar cycloaddition of azomethine ylide to methyl 2-(2-nitrophenyl)acrylate for the synthesis of diastereoisomers of spirotryprostatin A. Organic Letters 2011 13 (9) 2418-21. DOI: 10.1021/ol200652j PMID: 21486026 | ||
| CITATION 3 | Edmondson SD; Danishefsky SJ The Total Synthesis of Spirotryprostatin A. Angewandte Chemie International Edition 1998 37 (8) 1138-1140. DOI: 10.1002/(SICI)1521-3773(19980504)37:8<1138::AID-ANIE1138>3.0.CO;2-N PMID: 29711010 | ||
