Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA013937
PROPERTIES
| NPAID | NPA013937 |
|---|---|
| CLUSTER ID | 5043 |
| NODE ID | 3614 |
| NAME | Penifulvin A |
| FORMULA | C18H26O4 |
| MOLECULAR WEIGHT (Da) | 306.4020 |
| ACCURATE MASS (Da) | 306.1831 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Penicillium |
| ORIGIN SPECIES | griseofulvum |
| InChIKey | DROISJUYARPXHO-ATIWLJMLSA-N |
| InChI | InChI=1S/C18H26O4/c1-13(2)10-14(3)9-11(19)21-17(6)18(14)15(4,12(20)22-17)7-8-16(13,18)5/h7-10H2,1-6H3/t14-,15-,16-,17-,18-/m0/s1 |
| SMILES | CC1(C)C[C@]2(C)CC(=O)O[C@@]3(C)OC(=O)[C@]4(C)CC[C@]1(C)[C@@]234 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Shim, Sang Hee; Swenson, Dale C; Gloer, James B; Dowd, Patrick F; Wicklow, Donald T Penifulvin A: a sesquiterpenoid-derived metabolite containing a novel dioxa[5,5,5,6]fenestrane ring system from a fungicolous isolate of Penicillium griseofulvum Organic Letters 2006 8 (6) 1225-1228. | ||
|---|---|---|---|
| DOI | 10.1021/ol060107c | PMID | 16524309 |
SYNTHESES
| CITATION 1 | Gaich T; Mulzer J Total synthesis of (-)-Penifulvin A, an insecticide with a dioxafenestrane skeleton. Journal of the American Chemical Society 2009 131 (2) 452-3. DOI: 10.1021/ja8083048 PMID: 19140787 | ||
|---|---|---|---|
| CITATION 2 | Das D; Kant R; Chakraborty TK An approach to a bislactone skeleton: a scalable total synthesis of (±)-penifulvin A. Organic Letters 2014 16 (10) 2618-21. DOI: 10.1021/ol500768w PMID: 24804798 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | C[C@@]12CC(=O)O[C@@H]3[C@@]14[C@@H](CC[C@H]4C(C2)(C)C)C(=O)O3 | Shim, Sang Hee; Swenson, Dale C; Gloer, James B; Dowd, Patrick F; Wicklow, Donald T Penifulvin A: a sesquiterpenoid-derived metabolite containing a novel dioxa[5,5,5,6]fenestrane ring system from a fungicolous isolate of Penicillium griseofulvum Organic Letters 2006 8 (6) 1225-1228. DOI: 10.1021/ol060107c PMID: 16524309 | ||
| 2 | CC1(C)C[C@]2(C)CC(=O)O[C@@]3(C)OC(=O)[C@]4(C)CC[C@]1(C)[C@@]234 | Gaich T; Mulzer J Total synthesis of (-)-Penifulvin A, an insecticide with a dioxafenestrane skeleton. Journal of the American Chemical Society 2009 131 (2) 452-3. DOI: 10.1021/ja8083048 PMID: 19140787 | ||
