Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA018815
PROPERTIES
| NPAID | NPA018815 |
|---|---|
| CLUSTER ID | 1983 |
| NODE ID | 1017 |
| NAME | Nominine |
| FORMULA | C28H39NO |
| MOLECULAR WEIGHT (Da) | 405.6260 |
| ACCURATE MASS (Da) | 405.3032 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Aspergillus |
| ORIGIN SPECIES | nomius (NRRL 13137) |
| InChIKey | BSSPRCKKWJRAJZ-HBDSXALQSA-N |
| InChI | InChI=1S/C28H39NO/c1-19(2)9-8-15-28-24(17-22-18-29-25-11-7-6-10-23(22)25)20(3)14-16-27(28,5)21(4)12-13-26(28)30/h6-7,9-11,18,21,24,26,29-30H,3,8,12-17H2,1-2,4-5H3/t21-,24-,26+,27+,28-/m0/s1 |
| SMILES | C=C1CC[C@]2(C)[C@@H](C)CC[C@@H](O)[C@]2(CCC=C(C)C)[C@H]1CC1=CNC2=CC=CC=C12 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Gloer, James B.; Rinderknecht, Brad L.; Wicklow, Donald T.; Dowd, Patrick F. Nominine: A New Insecticidal Indole Diterpene from the Sclerotia of Aspergillus nomius Journal of Organic Chemistry 1989 54 (11) 2530-2532. | ||
|---|---|---|---|
| DOI | 10.1021/jo00272a012 | PMID | - |
SYNTHESES
| CITATION 1 | Peese KM; Gin DY Efficient synthetic access to the hetisine C20-diterpenoid alkaloids. A concise synthesis of nominine via oxidoisoquinolinium-1,3-dipolar and dienamine-Diels-Alder cycloadditions. Journal of the American Chemical Society 2006 128 (27) 8734-8735. DOI: 10.1021/ja0625430 PMID: 16819859 | ||
|---|---|---|---|
| CITATION 2 | Muratake H; Natsume M Total synthesis of (+/-)-nominine, a heptacyclic hetisine-type aconite alkaloid. Angewandte Chemie International Edition 2004 43 (35) 4646-4649. DOI: 10.1002/anie.200460332 PMID: 15352194 | ||
| CITATION 3 | Peese KM; Gin DY Asymmetric synthetic access to the hetisine alkaloids: total synthesis of (+)-nominine. Chemistry - A European Journal 2008 14 (5) 1654-1665. DOI: 10.1002/chem.200701290 PMID: 18046691 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | C[C@@H]1CC[C@@H]([C@@]2([C@]1(CCC(=C)[C@H]2CC3=CNC4=CC=CC=C43)C)CCC=C(C)C)O | Gloer, James B.; Rinderknecht, Brad L.; Wicklow, Donald T.; Dowd, Patrick F. Nominine: A New Insecticidal Indole Diterpene from the Sclerotia of Aspergillus nomius Journal of Organic Chemistry 1989 54 (11) 2530-2532. DOI: 10.1021/jo00272a012 | ||
| 2 | C=C1CC[C@]2(C)[C@@H](C)CC[C@@H](O)[C@]2(CCC=C(C)C)[C@H]1CC1=CNC2=CC=CC=C12 | Bradshaw, Ben; Etxebarria-Jardí, Gorka; Bonjoch, Josep Total synthesis of (-)-anominine. Journal of the American Chemical Society 2010 132 (17) 5966-7. DOI: 10.1021/ja101994q PMID: 20384301 | ||
