Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA007540
PROPERTIES
| NPAID | NPA007540 |
|---|---|
| CLUSTER ID | 1035 |
| NODE ID | 892 |
| NAME | Aureothin |
| FORMULA | C22H23NO6 |
| MOLECULAR WEIGHT (Da) | 397.4270 |
| ACCURATE MASS (Da) | 397.1525 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Streptomyces |
| ORIGIN SPECIES | thioluteus |
| InChIKey | OGUMLESFFBGVOO-VJDLAWOBSA-N |
| InChI | InChI=1S/C22H23NO6/c1-13(11-16-5-7-17(8-6-16)23(25)26)12-18-9-10-19(28-18)21-14(2)20(24)15(3)22(27-4)29-21/h5-8,11-12,19H,9-10H2,1-4H3/b13-11+,18-12-/t19-/m1/s1 |
| SMILES | CC1=C(OC(=C(C1=O)C)OC)[C@H]2CC/C(=C/C(=C/C3=CC=C(C=C3)[N+](=O)[O-])/C)/O2 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Hirata, Yoshimasa; Nakata, Hisao; Yamada, Kiyoyuki; Okuhara, Kunio; Naito, Takayuki The structure of aureothin, a nitro compound obtained from Streptomyces thioluteus Tetrahedron 1961 14 (3-4) 252-274. | ||
|---|---|---|---|
| DOI | 10.1016/s0040-4020(01)92175-1 | PMID | - |
SYNTHESES
| CITATION 1 | Jacobsen MF; Moses JE; Adlington RM; Baldwin JE A short total synthesis of aureothin and N-acetylaureothamine. Organic Letters 2005 7 (4) 641-644. DOI: 10.1021/ol047594l PMID: 15704914 | ||
|---|---|---|---|
| CITATION 2 | Werneburg M; Hertweck C Chemoenzymatic total synthesis of the antiproliferative polyketide (+)-(R)-aureothin. ChemBioChem 2008 9 (13) 2064-6. DOI: 10.1002/cbic.200800301 PMID: 18690656 | ||
| CITATION 3 | Henrot M; Jean A; Peixoto PA; Maddaluno J; De Paolis M Flexible Total Synthesis of (±)-Aureothin, a Potent Antiproliferative Agent. Journal of Organic Chemistry 2016 81 (12) 5190-201. DOI: 10.1021/acs.joc.6b00878 PMID: 27213834 | ||
