Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA011935
PROPERTIES
| NPAID | NPA011935 |
|---|---|
| CLUSTER ID | 807 |
| NODE ID | 700 |
| NAME | Cyrneine A |
| FORMULA | C20H28O3 |
| MOLECULAR WEIGHT (Da) | 316.4410 |
| ACCURATE MASS (Da) | 316.2038 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Sarcodon |
| ORIGIN SPECIES | cyrneus |
| InChIKey | IXBCZHOTZLYJDA-CUDHKJQZSA-N |
| InChI | InChI=1S/C20H28O3/c1-12(2)14-10-17(23)20(4)8-7-19(3)15(18(14)20)6-5-13(11-21)9-16(19)22/h5-6,11-12,16-17,22-23H,7-10H2,1-4H3/t16-,17+,19+,20-/m0/s1 |
| SMILES | CC(C)C1=C2C3=CC=C(C[C@@H]([C@@]3(CC[C@]2([C@@H](C1)O)C)C)O)C=O |
ORIGINAL ISOLATION REFERENCE
| CITATION | Marcotullio, Maria; Pagiott, Rita; Maltese, Federica; Obara, Yutaro; Hoshino, Tomohiro; Nakahata, Norimichi; Curini, Massimo Neurite Outgrowth Activity of Cyathane Diterpenes from Sarcodon cyrneus, Cyrneines A and B Planta Medica 2006 72 (9) 819-823. | ||
|---|---|---|---|
| DOI | 10.1055/s-2006-946681 | PMID | 16881016 |
SYNTHESES
| CITATION 1 | Elamparuthi E; Fellay C; Neuburger M; Gademann K Total synthesis of cyrneine A. Angewandte Chemie International Edition 2012 51 (17) 4071-3. DOI: 10.1002/anie.201200515 PMID: 22431475 | ||
|---|---|---|---|
| CITATION 2 | Wu GJ; Zhang YH; Tan DX; Han FS Total synthesis of cyrneines A-B and glaucopine C. Nature Communications 2018 9 (1) 2148. DOI: 10.1038/s41467-018-04480-6 PMID: 29858575 | ||
| CITATION 3 | Wu GJ; Zhang YH; Tan DX; He L; Cao BC; He YP; Han FS Synthetic Studies on Enantioselective Total Synthesis of Cyathane Diterpenoids: Cyrneines A and B, Glaucopine C, and (+)-Allocyathin B Journal of Organic Chemistry 2019 84 (6) 3223-3238. DOI: 10.1021/acs.joc.8b03138 PMID: 30793912 | ||
