Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA001934
PROPERTIES
| NPAID | NPA001934 |
|---|---|
| CLUSTER ID | 1211 |
| NODE ID | 1030 |
| NAME | Ustiloxin |
| FORMULA | C28H43N5O12S |
| MOLECULAR WEIGHT (Da) | 673.7420 |
| ACCURATE MASS (Da) | 673.2629 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Ustilaginoidea |
| ORIGIN SPECIES | virens |
| InChIKey | QRLBQXQEGMBXFM-IARZYCKVSA-N |
| InChI | InChI=1S/C28H43N5O12S/c1-6-28(4)23(26(41)31-10-19(36)37)33-24(39)20(12(2)3)32-25(40)21(30-5)22(38)14-8-17(45-28)16(35)9-18(14)46(44)11-13(34)7-15(29)27(42)43/h8-9,12-13,15,20-23,30,34-35,38H,6-7,10-11,29H2,1-5H3,(H,31,41)(H,32,40)(H,33,39)(H,36,37)(H,42,43)/t13-,15-,20-,21-,22+,23+,28+,46-/m0/s1 |
| SMILES | CC[C@@]1([C@H](NC(=O)[C@@H](NC(=O)[C@H]([C@@H](C2=CC(=C(C=C2[S@@](=O)C[C@H](C[C@@H](C(=O)O)N)O)O)O1)O)NC)C(C)C)C(=O)NCC(=O)O)C |
ORIGINAL ISOLATION REFERENCE
| CITATION | Koiso, Yukiko; Natori, Mika; Iwasaki, Shigeo; Sato, Sadao; Sonoda, Ryoichi; Fujita, Yoshikatsu; Yaegashi, Hiroshi; Sato, Zenji Ustiloxin: A phytotoxin and a mycotoxin from false smuth balls on rice panicles Tetrahedron Letters 1992 33 (29) 4157-4160. | ||
|---|---|---|---|
| DOI | 10.1016/s0040-4039(00)74677-6 | PMID | - |
SYNTHESES
| CITATION 1 | Li P; Evans CD; Forbeck EM; Park H; Bai R; Hamel E; Joullié MM Total synthesis and biological evaluation of ustiloxin natural products and two analogs. Bioorganic and Medicinal Chemistry Letters 2006 16 (18) 4804-4807. DOI: 10.1016/j.bmcl.2006.06.071 PMID: 16837194 | ||
|---|---|---|---|
| CITATION 2 | Cao B; Park H; Joullié MM Total synthesis of ustiloxin D. Journal of the American Chemical Society 2002 124 (4) 520-521. DOI: 10.1021/ja017277z PMID: 11804473 | ||
| CITATION 3 | Tanaka H; Sawayama AM; Wandless TJ Enantioselective total synthesis of ustiloxin D. Journal of the American Chemical Society 2003 125 (23) 6864-6865. DOI: 10.1021/ja035429f PMID: 12783528 | ||
| CITATION 4 | Brown AL; Churches QI; Hutton CA Total Synthesis of Ustiloxin D Utilizing an Ammonia-Ugi Reaction. Journal of Organic Chemistry 2015 80 (20) 9831-9837. DOI: 10.1021/acs.joc.5b01519 PMID: 26394038 | ||
| CITATION 5 | Li P; Evans CD; Joullié MM A convergent total synthesis of ustiloxin D via an unprecedented copper-catalyzed ethynyl aziridine ring-opening by phenol derivatives. Organic Letters 2005 7 (23) 5325-5327. DOI: 10.1021/ol052287g PMID: 16268569 | ||
| CITATION 6 | Sawayama AM; Tanaka H; Wandless TJ Total synthesis of ustiloxin D and considerations on the origin of selectivity of the asymmetric allylic alkylation. Journal of Organic Chemistry 2004 69 (25) 8810-8820. DOI: 10.1021/jo048854f PMID: 15575762 | ||
