Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA003701
PROPERTIES
| NPAID | NPA003701 |
|---|---|
| CLUSTER ID | 2013 |
| NODE ID | 1614 |
| NAME | Scyphostatin |
| FORMULA | C29H43NO5 |
| MOLECULAR WEIGHT (Da) | 485.6650 |
| ACCURATE MASS (Da) | 485.3141 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Trichopeziza |
| ORIGIN SPECIES | mollissima SANK 13892 |
| InChIKey | KSIWZCYBCSQXTA-JPOQAJQISA-N |
| InChI | InChI=1S/C29H43NO5/c1-6-20(2)15-22(4)17-23(5)16-21(3)11-9-7-8-10-12-27(33)30-24(19-31)18-29(34)26(32)14-13-25-28(29)35-25/h7-15,20-21,23-25,28,31,34H,6,16-19H2,1-5H3,(H,30,33)/b8-7+,11-9+,12-10+,22-15+/t20-,21+,23+,24+,25+,28+,29-/m1/s1 |
| SMILES | CC[C@@H](C)/C=C(\C)C[C@@H](C)C[C@@H](C)/C=C/C=C/C=C/C(=O)N[C@H](CO)C[C@@]1(O)C(=O)C=C[C@@H]2O[C@@H]21 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Nara, Futoshi; Tanaka, Masahiro; Hosoya, Tsuyoshi; Suzuki-Konagai, Keiko; Ogita, Takeshi Scyphostatin, a neutral sphingomyelinase inhibitor from a discomycete, Trichopeziza mollissima: Taxonomy of the producing organism, fermentation, isolation, and physico-chemical properties Journal of Antibiotics 1999 52 (6) 525-530. | ||
|---|---|---|---|
| DOI | 10.7164/antibiotics.52.525 | PMID | 10470675 |
SYNTHESES
| CITATION 1 | Pitsinos E; Athinaios N; Xu Z; Wang G; Negishi E Total synthesis of (+)-scyphostatin featuring an enantioselective and highly efficient route to the side-chain via Zr-catalyzed asymmetric carboalumination of alkenes (ZACA). Chemical Communications 2010 46 (13) 2200-2202. DOI: 10.1039/b920261g PMID: 20234905 | ||
|---|---|---|---|
| CITATION 2 | Fujioka H; Sawama Y; Kotoku N; Ohnaka T; Okitsu T; Murata N; Kubo O; Li R; Kita Y Concise asymmetric total synthesis of scyphostatin, a potent inhibitor of neutral sphingomyelinase. Chemistry - A European Journal 2007 13 (36) 10225-10238. DOI: 10.1002/chem.200700871 PMID: 17907134 | ||
| CITATION 3 | Inoue M; Yokota W; Murugesh MG; Izuhara T; Katoh T Total synthesis of (+)-scyphostatin, a potent and specific inhibitor of neutral sphingomyelinase. Angewandte Chemie International Edition 2004 43 (32) 4207-4209. DOI: 10.1002/anie.200454192 PMID: 15307088 | ||
| CITATION 4 | Takagi R; Miyanaga W; Tojo K; Tsuyumine S; Ohkata K Stereoselective total synthesis of (+)-Scyphostatin via a pi-facially selective Diels-Alder reaction. Journal of Organic Chemistry 2007 72 (11) 4117-4125. DOI: 10.1021/jo070337k PMID: 17477576 | ||
| CITATION 5 | Izuhara T; Katoh T Studies toward the total synthesis of scyphostatin: first entry to the highly functionalized cyclohexenone segment. Organic Letters 2001 3 (11) 1653-1656. DOI: 10.1021/ol015873s PMID: 11405678 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | CCC(C)/C=C(\C)/CC(C)CC(C)/C=C/C=C/C=C/C(=O)N[C@@H](C[C@@]1([C@@H]2[C@@H](O2)C=CC1=O)O)CO | Nara, Futoshi; Tanaka, Masahiro; Hosoya, Tsuyoshi; Suzuki-Konagai, Keiko; Ogita, Takeshi Scyphostatin, a neutral sphingomyelinase inhibitor from a discomycete, Trichopeziza mollissima: Taxonomy of the producing organism, fermentation, isolation, and physico-chemical properties Journal of Antibiotics 1999 52 (6) 525-530. DOI: 10.7164/antibiotics.52.525 PMID: 10470675 | ||
| 2 | CC[C@@H](C)/C=C(\C)C[C@@H](C)C[C@@H](C)/C=C/C=C/C=C/C(=O)N[C@H](CO)C[C@@]1(O)C(=O)C=C[C@@H]2O[C@@H]21 | Takagi R; Miyanaga W; Tojo K; Tsuyumine S; Ohkata K Stereoselective total synthesis of (+)-Scyphostatin via a pi-facially selective Diels-Alder reaction. Journal of Organic Chemistry 2007 72 (11) 4117-4125. DOI: 10.1021/jo070337k PMID: 17477576 | ||
