Compounds
COMPOUND NPA000438
PROPERTIES
| NPAID | NPA000438 |
|---|---|
| CLUSTER ID | 341 |
| NODE ID | 308 |
| NAME | Huperzine A |
| FORMULA | C15H18N2O |
| MOLECULAR WEIGHT (Da) | 242.3220 |
| ACCURATE MASS (Da) | 242.1419 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Paecilomyces |
| ORIGIN SPECIES | tenuis YS-13 |
| InChIKey | ZRJBHWIHUMBLCN-GENIYJEYSA-N |
| InChI | InChI=1S/C15H18N2O/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10/h3-6,10H,7-8,16H2,1-2H3,(H,17,18)/t10?,15-/m1/s1 |
| SMILES | CC=C1C2C=C(C)C[C@]1(N)C1=C(C2)NC(=O)C=C1 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Su, Jingqian; Yang, Minhe Huperzine A production by Paecilomyces tenuis YS-13, an endophytic fungus isolated from Huperzia serrata Natural Product Research 2015 29 (11) 1035-1041. | ||
|---|---|---|---|
| DOI | 10.1080/14786419.2014.980245 | PMID | 25427833 |
SYNTHESES
| CITATION 1 | Lucey C; Kelly SA; Mann J A concise and convergent (formal) total synthesis of huperzine A. Organic & Biomolecular Chemistry 2007 5 (2) 301-6. DOI: 10.1039/b615059d PMID: 17205173 | ||
|---|---|---|---|
| CITATION 2 | Koshiba T; Yokoshima S; Fukuyama T Total synthesis of (-)-huperzine A. Organic Letters 2009 11 (22) 5354-6. DOI: 10.1021/ol9022408 PMID: 19873983 | ||
| CITATION 3 | Ding R; Sun BF; Lin GQ An efficient total synthesis of (-)-huperzine A. Organic Letters 2012 14 (17) 4446-9. DOI: 10.1021/ol301951r PMID: 22900755 | ||
| CITATION 4 | Ding R; Fu JG; Xu GQ; Sun BF; Lin GQ Divergent total synthesis of the Lycopodium alkaloids huperzine A, huperzine B, and huperzine U. Journal of Organic Chemistry 2014 79 (1) 240-50. DOI: 10.1021/jo402419h PMID: 24299147 | ||
| CITATION 5 | White JD; Li Y; Kim J; Terinek M Cyclobutane Synthesis and Fragmentation. A Cascade Route to the Lycopodium Alkaloid (-)-Huperzine A. Journal of Organic Chemistry 2015 80 (23) 11806-17. DOI: 10.1021/acs.joc.5b01619 PMID: 26355759 | ||
