Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA004934
PROPERTIES
| NPAID | NPA004934 |
|---|---|
| CLUSTER ID | 2489 |
| NODE ID | 1953 |
| NAME | Berkeleyamide A |
| FORMULA | C18H25NO3 |
| MOLECULAR WEIGHT (Da) | 303.4020 |
| ACCURATE MASS (Da) | 303.1834 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Penicillium |
| ORIGIN SPECIES | rubrum |
| InChIKey | KACACYYTPVUKSL-BHYGNILZSA-N |
| InChI | InChI=1S/C18H25NO3/c1-12(2)8-14-10-16(18(22)19-14)17(21)11-15(20)9-13-6-4-3-5-7-13/h3-7,12,14,16-17,21H,8-11H2,1-2H3,(H,19,22)/t14-,16-,17+/m0/s1 |
| SMILES | CC(C)C[C@H]1C[C@@H]([C@H](O)CC(=O)CC2=CC=CC=C2)C(=O)N1 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Stierle, Andrea A.; Stierle, Donald B.; Patacini, Brianna The berkeleyamides, amides from the acid lake fungus Penicillum rubrum Journal of Natural Products 2008 71 (5) 856-860. | ||
|---|---|---|---|
| DOI | 10.1021/np0705054 | PMID | 18330993 |
SYNTHESES
| CITATION 1 | Kulkarni SJ; Pedduri Y; Chittiboyina AG; Avery MA Asymmetric total synthesis of the caspase-1 inhibitor (-)-berkeleyamide A. Journal of Organic Chemistry 2010 75 (9) 3113-3116. DOI: 10.1021/jo1001033 PMID: 20356061 | ||
|---|---|---|---|
| CITATION 2 | Sperry J; Harris EB; Brimble MA Total synthesis and absolute configuration of (-)-berkeleyamide A. Organic Letters 2010 12 (3) 420-423. DOI: 10.1021/ol902525k PMID: 20030315 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | CC(C)C[C@H]1C[C@@H](C(=O)N1)[C@H](CC(=O)CC2=CC=CC=C2)O | Stierle, Andrea A.; Stierle, Donald B.; Patacini, Brianna The berkeleyamides, amides from the acid lake fungus Penicillum rubrum Journal of Natural Products 2008 71 (5) 856-860. DOI: 10.1021/np0705054 PMID: 18330993 | ||
| 2 | CC(C)C[C@H]1C[C@@H]([C@H](O)CC(=O)CC2=CC=CC=C2)C(=O)N1 | Sperry J; Harris EB; Brimble MA Total synthesis and absolute configuration of (-)-berkeleyamide A. Organic Letters 2010 12 (3) 420-423. DOI: 10.1021/ol902525k PMID: 20030315 | ||
