Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA019282
PROPERTIES
| NPAID | NPA019282 |
|---|---|
| CLUSTER ID | 26 |
| NODE ID | 25 |
| NAME | Nocardioazine B |
| FORMULA | C28H30N4O2 |
| MOLECULAR WEIGHT (Da) | 454.5740 |
| ACCURATE MASS (Da) | 454.2369 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Nocardiopsis |
| ORIGIN SPECIES | sp. CMB-M0232 |
| InChIKey | UWHKKMQINZUOFY-GYFBIRQUSA-N |
| InChI | InChI=1S/C28H30N4O2/c1-16(2)12-13-28-15-23-26(34)31-22(14-18-17-8-4-6-10-20(17)29-24(18)31)25(33)32(23)27(28)30(3)21-11-7-5-9-19(21)28/h4-12,18,22-24,27,29H,13-15H2,1-3H3/t18-,22+,23+,24-,27+,28+/m0/s1 |
| SMILES | CC(C)=CC[C@]12C[C@@H]3C(=O)N4[C@H](C[C@H]5C6=CC=CC=C6N[C@H]54)C(=O)N3[C@H]1N(C)C1=CC=CC=C12 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Raju, Ritesh; Piggott, Andrew M; Huang, Xiao-Cong; Capon, Robert J Nocardioazines: a novel bridged diketopiperazine scaffold from a marine-derived bacterium inhibits P-glycoprotein Organic Letters 2011 13 (10) 2770-2773. | ||
|---|---|---|---|
| DOI | 10.1021/ol200904v | PMID | 21513295 |
SYNTHESES
| CITATION 1 | Wang M; Feng X; Cai L; Xu Z; Ye T Total synthesis and absolute configuration of nocardioazine B. Chemical Communications 2012 48 (36) 4344-4346. DOI: 10.1039/c2cc31025b PMID: 22447070 | ||
|---|---|---|---|
| CITATION 2 | Shen X; Zhao J; Xi Y; Chen W; Zhou Y; Yang X; Zhang H Enantioselective Total Synthesis of (+)-Nocardioazine B. Journal of Organic Chemistry 2018 83 (23) 14507-14517. DOI: 10.1021/acs.joc.8b02329 PMID: 30387357 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | CC(=CC[C@@]12C[C@H]3C(=O)N4[C@@H](C[C@]5([C@@H]4NC6=CC=CC=C65)C)C(=O)N3[C@@H]1N(C7=CC=CC=C27)C)C | Raju, Ritesh; Piggott, Andrew M; Huang, Xiao-Cong; Capon, Robert J Nocardioazines: a novel bridged diketopiperazine scaffold from a marine-derived bacterium inhibits P-glycoprotein Organic Letters 2011 13 (10) 2770-2773. DOI: 10.1021/ol200904v PMID: 21513295 | ||
| 2 | CC(C)=CC[C@]12C[C@@H]3C(=O)N4[C@H](C[C@H]5C6=CC=CC=C6N[C@H]54)C(=O)N3[C@H]1N(C)C1=CC=CC=C12 | Wang M; Feng X; Cai L; Xu Z; Ye T Total synthesis and absolute configuration of nocardioazine B. Chemical Communications 2012 48 (36) 4344-4346. DOI: 10.1039/c2cc31025b PMID: 22447070 | ||
