Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA002699
PROPERTIES
| NPAID | NPA002699 |
|---|---|
| CLUSTER ID | 1581 |
| NODE ID | 1297 |
| NAME | Apicularen A |
| FORMULA | C25H31NO6 |
| MOLECULAR WEIGHT (Da) | 441.5240 |
| ACCURATE MASS (Da) | 441.2151 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Chondromyces |
| ORIGIN SPECIES | robustus |
| InChIKey | MVOORUCGKRDJFW-ZZBSXQHZSA-N |
| InChI | InChI=1S/C25H31NO6/c1-2-3-4-5-11-23(29)26-12-7-9-19-16-21-15-18(27)14-20(31-21)13-17-8-6-10-22(28)24(17)25(30)32-19/h3-8,10-12,18-21,27-28H,2,9,13-16H2,1H3,(H,26,29)/b4-3-,11-5-,12-7+/t18-,19+,20+,21-/m1/s1 |
| SMILES | CC/C=C\C=C/C(=O)N/C=C/C[C@H]1C[C@H]2C[C@H](O)C[C@H](CC3=C(C(=O)O1)C(O)=CC=C3)O2 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Kunze, Brigitte; JANSEN, ROLF; Sasse, Florenz; Höfle, Gerhard; Reichenbach, Hans Apicularens A and B, New Cytostatic Macrolides from Chondromyces Species (Myxobacteria) Journal of Antibiotics 1998 51 (12) 1075-1080. | ||
|---|---|---|---|
| DOI | 10.7164/antibiotics.51.1075 | PMID | 10048565 |
SYNTHESES
| CITATION 1 | Nicolaou KC; Kim DW; Baati R Stereocontrolled total synthesis of apicularen A and its delta(17,18) Z isomer. Angewandte Chemie International Edition 2002 41 (19) 3701-4; 3523. DOI: 10.1002/1521-3773(20021004)41:19<3701::AID-ANIE3701>3.0.CO;2-4 PMID: 12370936 | ||
|---|---|---|---|
| CITATION 2 | Palimkar SS; Uenishi J; Ii H Total synthesis and biological evaluation of (-)-apicularen A and its analogues. Journal of Organic Chemistry 2012 77 (1) 388-399. DOI: 10.1021/jo2019762 PMID: 22118352 | ||
| CITATION 3 | Nicolaou KC; Kim DW; Baati R; O'Brate A; Giannakakou P Total synthesis and biological evaluation of (-)apicularen A and analogues thereof. Chemistry - A European Journal 2003 9 (24) 6177-6191. DOI: 10.1002/chem.200305230 PMID: 14679529 | ||
| CITATION 4 | Petri AF; Bayer A; Maier ME Total synthesis of apicularen A through transannular pyran formation. Angewandte Chemie International Edition 2004 43 (43) 5821-5823. DOI: 10.1002/anie.200460760 PMID: 15523724 | ||
| CITATION 5 | Hilli F; White JM; Rizzacasa MA Formal total synthesis of (-)-apicularen A via transannular conjugate addition. Organic Letters 2004 6 (8) 1289-1292. DOI: 10.1021/ol0497943 PMID: 15070319 | ||
| CITATION 6 | Lewis A; Stefanuti I; Swain SA; Smith SA; Taylor RJ A formal total synthesis of (+)-apicularen A: base-induced conversion of apicularen-derived intermediates into salicylihalamide-like products. Organic & Biomolecular Chemistry 2003 1 (1) 104-116. DOI: 10.1039/b209637b PMID: 12929396 | ||
| CITATION 7 | Palimkar SS; Uenishi J Total synthesis of (-)-apicularen A. Organic Letters 2010 12 (18) 4160-4163. DOI: 10.1021/ol101753y PMID: 20707358 | ||
| CITATION 8 | Li M; O'Doherty GA De novo formal synthesis of (-)-apicularen A via an iterative asymmetric hydration sequence. Organic Letters 2006 8 (26) 6087-6090. DOI: 10.1021/ol062595u PMID: 17165936 | ||
| CITATION 9 | Su Q; Panek JS Total synthesis of (-)-apicularen A. Journal of the American Chemical Society 2004 126 (8) 2425-2430. DOI: 10.1021/ja037957x PMID: 14982450 | ||
| CITATION 10 | Jung YH; Kim YJ; Lee J; Tae J Formal total synthesis of (-)-apicularen a by a strategy based on ring-closing metathesis and transannular cyclization. Chemistry – An Asian Journal 2007 2 (5) 656-661. DOI: 10.1002/asia.200700024 PMID: 17465410 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | CC/C=C\C=C/C(=O)N/C=C/CC1CC2CC(CC(O2)CC3=C(C(=CC=C3)O)C(=O)O1)O | Kunze, Brigitte; JANSEN, ROLF; Sasse, Florenz; Höfle, Gerhard; Reichenbach, Hans Apicularens A and B, New Cytostatic Macrolides from Chondromyces Species (Myxobacteria) Journal of Antibiotics 1998 51 (12) 1075-1080. DOI: 10.7164/antibiotics.51.1075 PMID: 10048565 | ||
| 2 | CC/C=C\C=C/C(=O)N/C=C/C[C@H]1C[C@H]2C[C@H](O)C[C@H](CC3=C(C(=O)O1)C(O)=CC=C3)O2 | Palimkar SS; Uenishi J Total synthesis of (-)-apicularen A. Organic Letters 2010 12 (18) 4160-4163. DOI: 10.1021/ol101753y PMID: 20707358 | ||
