Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA015948
PROPERTIES
| NPAID | NPA015948 |
|---|---|
| CLUSTER ID | 3563 |
| NODE ID | 2683 |
| NAME | Cruentaren A |
| FORMULA | C33H51NO8 |
| MOLECULAR WEIGHT (Da) | 589.7700 |
| ACCURATE MASS (Da) | 589.3615 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Byssovorax |
| ORIGIN SPECIES | cruenta |
| InChIKey | UXPPKIOUXFFKDI-QGMVIAOPSA-N |
| InChI | InChI=1S/C33H51NO8/c1-7-12-26(35)22(4)32(39)34-16-11-10-14-21(3)31(38)23(5)29-15-9-8-13-20(2)27(36)18-24-17-25(41-6)19-28(37)30(24)33(40)42-29/h8-11,17,19-23,26-27,29,31,35-38H,7,12-16,18H2,1-6H3,(H,34,39)/b9-8-,11-10-/t20-,21+,22+,23+,26-,27+,29-,31+/m0/s1 |
| SMILES | CCC[C@H](O)[C@@H](C)C(=O)NC/C=C\C[C@@H](C)[C@@H](O)[C@H](C)[C@@H]1C/C=C\C[C@H](C)[C@H](O)CC2=C(C(=O)O1)C(O)=CC(OC)=C2 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Kunze, Brigitte; Steinmetz, Heinrich; Hoefle, Gerhard; Huss, Markus; Wieczorek, Helmut; Reichenbach, Hans Cruentaren, a new antifungal salicylate-type macrolide from Byssovorax cruenta (Myxobacteria) with inhibitory effect on mitochondrial ATPase activity: Fermentation and biological properties Journal of Antibiotics 2006 59 (10) 664-668. | ||
|---|---|---|---|
| DOI | 10.1038/ja.2006.89 | PMID | 17191683 |
SYNTHESES
| CITATION 1 | Kusuma BR; Brandt GE; Blagg BS Synthesis of cruentaren A. Organic Letters 2012 14 (24) 6242-6245. DOI: 10.1021/ol302999v PMID: 23205851 | ||
|---|---|---|---|
| CITATION 2 | Fürstner A; Bindl M; Jean L Concise total synthesis of cruentaren A. Angewandte Chemie International Edition 2007 46 (48) 9275-9278. DOI: 10.1002/anie.200703839 PMID: 17973287 | ||
| CITATION 3 | Vintonyak VV; Maier ME Total synthesis of cruentaren A. Angewandte Chemie International Edition 2007 46 (27) 5209-5211. DOI: 10.1002/anie.200701423 PMID: 17523207 | ||
| CITATION 4 | Fouché M; Rooney L; Barrett AG Biomimetic total synthesis of cruentaren A via aromatization of diketodioxinones. Journal of Organic Chemistry 2012 77 (7) 3060-3070. DOI: 10.1021/jo300225z PMID: 22401367 | ||
| CITATION 5 | Bindl M; Jean L; Herrmann J; Müller R; Fürstner A Preparation, modification, and evaluation of cruentaren A and analogues. Chemistry - A European Journal 2009 15 (45) 12310-12319. DOI: 10.1002/chem.200901817 PMID: 19821471 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | CCCC(C(C)C(=O)NC/C=C\CC(C)C(C(C)C1C/C=C\CC(C(CC2=CC(=CC(=C2C(=O)O1)O)OC)O)C)O)O | Kunze, Brigitte; Steinmetz, Heinrich; Hoefle, Gerhard; Huss, Markus; Wieczorek, Helmut; Reichenbach, Hans Cruentaren, a new antifungal salicylate-type macrolide from Byssovorax cruenta (Myxobacteria) with inhibitory effect on mitochondrial ATPase activity: Fermentation and biological properties Journal of Antibiotics 2006 59 (10) 664-668. DOI: 10.1038/ja.2006.89 PMID: 17191683 | ||
| 2 | CCC[C@H](O)[C@@H](C)C(=O)NC/C=C\C[C@@H](C)[C@@H](O)[C@H](C)[C@@H]1C/C=C\C[C@H](C)[C@H](O)CC2=C(C(=O)O1)C(O)=CC(OC)=C2 | Kusuma BR; Brandt GE; Blagg BS Synthesis of cruentaren A. Organic Letters 2012 14 (24) 6242-6245. DOI: 10.1021/ol302999v PMID: 23205851 | ||
