Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA007258
PROPERTIES
| NPAID | NPA007258 |
|---|---|
| CLUSTER ID | 3077 |
| NODE ID | 2350 |
| NAME | FD-891 |
| FORMULA | C33H54O8 |
| MOLECULAR WEIGHT (Da) | 578.7870 |
| ACCURATE MASS (Da) | 578.3819 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Streptomyces |
| ORIGIN SPECIES | graminofaciens A-8890 |
| InChIKey | VOLRALTUADVHPT-ICYGPOAYSA-N |
| InChI | InChI=1S/C33H54O8/c1-19-17-21(3)29(36)32-31(41-32)27(35)13-11-9-10-12-14-28(40-33(38)22(4)18-19)20(2)15-16-26(34)24(6)30(37)23(5)25(7)39-8/h9-12,17-18,20-21,23-32,34-37H,13-16H2,1-8H3/b11-9+,12-10+,19-17+,22-18+/t20-,21-,23+,24+,25+,26-,27-,28+,29-,30-,31-,32+/m0/s1 |
| SMILES | CO[C@H](C)[C@@H](C)[C@H](O)[C@H](C)[C@@H](O)CC[C@H](C)[C@H]1C/C=C/C=C/C[C@H](O)[C@@H]2O[C@@H]2[C@@H](O)[C@@H](C)/C=C(C)/C=C(\C)C(=O)O1 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Sekie-Asano; Okazaki; Yamagishi; Sakai; Hanada; Mizoue Isolation and charecterization of new 18-membered macrolides FD-891 AND FD-892 Journal of Antibiotics 1994 47 (11) 1226-1233. | ||
|---|---|---|---|
| DOI | 10.7164/antibiotics.47.1226 | PMID | 8002384 |
SYNTHESES
| CITATION 1 | Kanoh N; Kawamata A; Itagaki T; Miyazaki Y; Yahata K; Kwon E; Iwabuchi Y A concise and unified strategy for synthesis of the C1-C18 macrolactone fragments of FD-891, FD-892 and their analogues: formal total synthesis of FD-891. Organic Letters 2014 16 (19) 5216-5219. DOI: 10.1021/ol502633j PMID: 25247478 | ||
|---|---|---|---|
| CITATION 2 | Yadav JS; Das SK; Sabitha G Stereoselective total synthesis of FD-891. Journal of Organic Chemistry 2012 77 (24) 11109-11118. DOI: 10.1021/jo302205t PMID: 23140482 | ||
| CITATION 3 | García-Fortanet J; Murga J; Carda M; Marco JA; Matesanz R; Díaz JF; Barasoain I The total synthesis and biological properties of the cytotoxic macrolide FD-891 and its non-natural (Z)-C12 isomer. Chemistry - A European Journal 2007 13 (18) 5060-5074. DOI: 10.1002/chem.200700342 PMID: 17516610 | ||
| CITATION 4 | García-Fortanet J; Murga J; Carda M; Marco JA Stereoselective synthesis of the cytotoxic macrolide FD-891. Organic Letters 2006 8 (13) 2695-2698. DOI: 10.1021/ol060669w PMID: 16774234 | ||
| CITATION 5 | Crimmins MT; Caussanel F Enantioselective total synthesis of FD-891. Journal of the American Chemical Society 2006 128 (10) 3128-3129. DOI: 10.1021/ja060018v PMID: 16522077 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | C[C@@H]1/C=C(/C=C(/C(=O)O[C@@H](C/C=C/C=C/C[C@H]([C@@H]2[C@@H]([C@@H]1O)O2)O)[C@@H](C)CCC(C(C)C(C(C)C(C)OC)O)O)\C)\C | Sekie-Asano; Okazaki; Yamagishi; Sakai; Hanada; Mizoue Isolation and charecterization of new 18-membered macrolides FD-891 AND FD-892 Journal of Antibiotics 1994 47 (11) 1226-1233. DOI: 10.7164/antibiotics.47.1226 PMID: 8002384 | ||
| 2 | CO[C@H](C)[C@@H](C)[C@H](O)[C@H](C)[C@@H](O)CC[C@H](C)[C@H]1C/C=C/C=C/C[C@H](O)[C@@H]2O[C@@H]2[C@@H](O)[C@@H](C)/C=C(C)/C=C(\C)C(=O)O1 | Eguchi, Tadashi; Yamamoto, Keita; Mizoue, Kazutoshi; Kakinuma, Katsumi Structure revision of FD-891, a 16-membered macrolide antibiotic. Journal of Antibiotics 2004 57 (2) 156-7. DOI: 10.7164/antibiotics.57.156 PMID: 15112965 | ||
