Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA008563
PROPERTIES
| NPAID | NPA008563 |
|---|---|
| CLUSTER ID | 3649 |
| NODE ID | 2742 |
| NAME | Etnangien |
| FORMULA | C49H76O11 |
| MOLECULAR WEIGHT (Da) | 841.1360 |
| ACCURATE MASS (Da) | 840.5388 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Sorangium |
| ORIGIN SPECIES | cellulosum strain So ce750 |
| InChIKey | VHPBIOVAVQXSJO-DLGDGFEOSA-N |
| InChI | InChI=1S/C49H76O11/c1-34(22-17-13-11-9-8-10-12-14-19-24-40(50)30-35(2)28-29-46(54)55)31-43(52)37(4)45-32-41(51)25-21-27-42(59-7)26-20-16-15-18-23-36(3)48(57)39(6)49(58)38(5)44(53)33-47(56)60-45/h8-20,22,30-31,36-45,48-53,57-58H,21,23-29,32-33H2,1-7H3,(H,54,55)/b9-8+,12-10+,13-11+,18-15+,19-14+,20-16-,22-17+,34-31+,35-30+/t36-,37+,38+,39-,40-,41+,42+,43+,44+,45-,48+,49-/m0/s1 |
| SMILES | CO[C@@H]1C/C=C\C=C\C[C@H](C)[C@@H](O)[C@H](C)[C@@H](O)[C@H](C)[C@H](O)CC(=O)O[C@H]([C@H](C)[C@H](O)/C=C(C)/C=C/C=C/C=C/C=C/C=C/C[C@H](O)/C=C(\C)CCC(=O)O)C[C@H](O)CCC1 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Irschik, Herbert; Schummer, Dietmar; Hoefle, Gerhard; Reichenbach, Hans; Steinmetz, Heinrich; Jansen, Rolf Etnangien, a macrolide-polyene antibiotic from Sorangium cellulosum that inhibits nucleic acid polymerases Journal of Natural Products 2007 70 (6) 1060-1063. | ||
|---|---|---|---|
| DOI | 10.1021/np070115h | PMID | 17547459 |
SYNTHESES
| CITATION 1 | Li P; Li J; Arikan F; Ahlbrecht W; Dieckmann M; Menche D Total synthesis of etnangien. Journal of the American Chemical Society 2009 131 (33) 11678-11679. DOI: 10.1021/ja9056163 PMID: 19645468 | ||
|---|---|---|---|
| CITATION 2 | Li P; Li J; Arikan F; Ahlbrecht W; Dieckmann M; Menche D Stereoselective total synthesis of etnangien and etnangien methyl ester. Journal of Organic Chemistry 2010 75 (8) 2429-2444. DOI: 10.1021/jo100201f PMID: 20334428 | ||
| CITATION 3 | Menche D; Li P; Irschik H Design, synthesis and biological evaluation of simplified analogues of the RNA polymerase inhibitor etnangien. Bioorganic and Medicinal Chemistry Letters 2010 20 (3) 939-41. DOI: 10.1016/j.bmcl.2009.12.066 PMID: 20045639 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | CC1C/C=C/C=C\CC(CCCC(CC(OC(=O)CC(C(C(C(C1O)C)O)C)O)C(C)C(/C=C(\C)/C=C/C=C/C=C/C=C/C=C/CC(/C=C(\C)/CCC(=O)O)O)O)O)OC | Irschik, Herbert; Schummer, Dietmar; Hoefle, Gerhard; Reichenbach, Hans; Steinmetz, Heinrich; Jansen, Rolf Etnangien, a macrolide-polyene antibiotic from Sorangium cellulosum that inhibits nucleic acid polymerases Journal of Natural Products 2007 70 (6) 1060-1063. DOI: 10.1021/np070115h PMID: 17547459 | ||
| 2 | CO[C@@H]1C/C=C\C=C\C[C@H](C)[C@@H](O)[C@H](C)[C@@H](O)[C@H](C)[C@H](O)CC(=O)O[C@H]([C@H](C)[C@H](O)/C=C(C)/C=C/C=C/C=C/C=C/C=C/C[C@H](O)/C=C(\C)CCC(=O)O)C[C@H](O)CCC1 | Menche, Dirk; Arikan, Fatih; Perlova, Olena; Horstmann, Nicole; Ahlbrecht, Wiebke; Wenzel, Silke C.; Jansen, Rolf; Irschik, Herbert; Mueller, Rolf Stereochemical determination and complex biosynthetic assembly of etnangien, a highly potent RNA polymerase inhibitor from the myxobacterium Sorangium cellulosum Journal of the American Chemical Society 2008 130 (43) 14234-14243. DOI: 10.1021/ja804194c PMID: 18826315 | ||
