Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA006699
PROPERTIES
| NPAID | NPA006699 |
|---|---|
| CLUSTER ID | 1242 |
| NODE ID | 1052 |
| NAME | Cyclizidine |
| FORMULA | C17H25NO3 |
| MOLECULAR WEIGHT (Da) | 291.3910 |
| ACCURATE MASS (Da) | 291.1834 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Streptomyces |
| ORIGIN SPECIES | sp. NCIB 1 1649 |
| InChIKey | WGALLPIJABPILU-VLZDLOPHSA-N |
| InChI | InChI=1S/C17H25NO3/c1-10(3-4-11-5-6-11)9-12-16(19)17(2,20)15-14-13(21-14)7-8-18(12)15/h3-4,9,11-16,19-20H,5-8H2,1-2H3/b4-3+,10-9+/t12-,13+,14+,15?,16-,17-/m0/s1 |
| SMILES | CC(/C=C/C1CC1)=C\[C@H]1[C@H](O)[C@@](C)(O)C2[C@@H]3O[C@@H]3CCN21 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Freer, Andrew A; Gardner, Donald; Greatbanks, David; Poyser, J Philip; Sim, George A Structure of cyclizidine (antibiotic M146791): X-ray crystal structure of an indolizidinediol metabolite bearing a unique cyclopropyl side-chain Journal of the Chemical Society, Chemical Communications 1982 (20) 1160-1162. | ||
|---|---|---|---|
| DOI | 10.1039/c39820001160 | PMID | - |
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | C/C(=C\[C@H]1[C@@H]([C@@]([C@@H]2N1CC[C@@H]3[C@H]2O3)(C)O)O)/C=C/C4CC4 | Freer, Andrew A; Gardner, Donald; Greatbanks, David; Poyser, J Philip; Sim, George A Structure of cyclizidine (antibiotic M146791): X-ray crystal structure of an indolizidinediol metabolite bearing a unique cyclopropyl side-chain Journal of the Chemical Society, Chemical Communications 1982 (20) 1160-1162. DOI: 10.1039/c39820001160 | ||
| 2 | CC(/C=C/C1CC1)=C\[C@H]1[C@H](O)[C@@](C)(O)C2[C@@H]3O[C@@H]3CCN21 | Hanessian, Stephen; Soma, Udaykumar; Dorich, Stéphane; Deschênes-Simard, Benoît Total synthesis of (+)-ent-cyclizidine: absolute configurational confirmation of antibiotic M146791. Organic Letters 2011 13 (5) 1048-51. DOI: 10.1021/ol103094j PMID: 21271743 | ||
