Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA004506
PROPERTIES
| NPAID | NPA004506 |
|---|---|
| CLUSTER ID | 1211 |
| NODE ID | 1030 |
| NAME | Ustiloxin D |
| FORMULA | C23H34N4O8 |
| MOLECULAR WEIGHT (Da) | 494.5450 |
| ACCURATE MASS (Da) | 494.2377 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Ustilaginoidea |
| ORIGIN SPECIES | virens |
| InChIKey | GDXLZSYACWZHOC-ZNRYNLAGSA-N |
| InChI | InChI=1S/C23H34N4O8/c1-6-23(4)19(22(34)25-10-15(29)30)27-20(32)16(11(2)3)26-21(33)17(24-5)18(31)12-7-8-13(28)14(9-12)35-23/h7-9,11,16-19,24,28,31H,6,10H2,1-5H3,(H,25,34)(H,26,33)(H,27,32)(H,29,30)/t16-,17-,18+,19+,23+/m0/s1 |
| SMILES | CC[C@@]1([C@H](NC(=O)[C@@H](NC(=O)[C@H]([C@@H](C2=CC(=C(C=C2)O)O1)O)NC)C(C)C)C(=O)NCC(=O)O)C |
ORIGINAL ISOLATION REFERENCE
| CITATION | Koiso; Li; Iwasaki; Hanaoka; Kobayashi; Sonoda; Fujita; Yaegashi; Sato Ustiloxins, antimitotic cyclic peptides from false smut balls on rice panicles caused by Ustilaginoidea virens Journal of Antibiotics 1994 47 (7) 765-773. | ||
|---|---|---|---|
| DOI | 10.7164/antibiotics.47.765 | PMID | 8071121 |
SYNTHESES
| CITATION 1 | 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 2 | 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 3 | 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 4 | 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 5 | 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 | ||
