Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA013055
PROPERTIES
| NPAID | NPA013055 |
|---|---|
| CLUSTER ID | 4832 |
| NODE ID | 1607 |
| NAME | Neplanocin A |
| FORMULA | C11H13N5O3 |
| MOLECULAR WEIGHT (Da) | 263.2570 |
| ACCURATE MASS (Da) | 263.1018 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Ampullariella |
| ORIGIN SPECIES | regularis A11079 |
| InChIKey | XUGWUUDOWNZAGW-VDAHYXPESA-N |
| InChI | InChI=1S/C11H13N5O3/c12-10-7-11(14-3-13-10)16(4-15-7)6-1-5(2-17)8(18)9(6)19/h1,3-4,6,8-9,17-19H,2H2,(H2,12,13,14)/t6-,8-,9+/m1/s1 |
| SMILES | C1=C([C@H]([C@H]([C@@H]1N2C=NC3=C2N=CN=C3N)O)O)CO |
ORIGINAL ISOLATION REFERENCE
| CITATION | Yaginuma, S; Muto, N; Tsujino, M; Sudate, Y; Hayashi, M; Otani, M Studies on neplanocin A, new antitumor antibiotic. I. Producing organism, isolation and characterization Journal of Antibiotics 1981 34 (4) 359-366. | ||
|---|---|---|---|
| DOI | 10.7164/antibiotics.34.359 | PMID | 7275815 |
SYNTHESES
| CITATION 1 | Ono M; Nishimura K; Tsubouchi H; Nagaoka Y; Tomioka K Total synthesis of (-)-neplanocin a by using lithium thiolate-initiated Michael-aldol tandem cyclization reaction. Journal of Organic Chemistry 2001 66 (24) 8199-8203. DOI: 10.1021/jo016090n PMID: 11722225 | ||
|---|---|---|---|
| CITATION 2 | Khan FA; Rout B A formal total synthesis of (+/-)-neplanocin A. Journal of Organic Chemistry 2007 72 (18) 7011-7013. DOI: 10.1021/jo0710127 PMID: 17665958 | ||
| CITATION 3 | Gallos JK; Stathakis CI; Kotoulas SS; Koumbis AE An improved approach to chiral cyclopentenone building blocks. Total synthesis of pentenomycin I and neplanocin A. Journal of Organic Chemistry 2005 70 (17) 6884-6890. DOI: 10.1021/jo050987t PMID: 16095309 | ||
