Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA015043
PROPERTIES
| NPAID | NPA015043 |
|---|---|
| CLUSTER ID | 394 |
| NODE ID | 11 |
| NAME | Chaetominine |
| FORMULA | C22H18N4O4 |
| MOLECULAR WEIGHT (Da) | 402.4100 |
| ACCURATE MASS (Da) | 402.1328 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Chaetomium |
| ORIGIN SPECIES | sp. IFB-E015 |
| InChIKey | GEURDGODABUDHB-TYTLQBBQSA-N |
| InChI | InChI=1S/C22H18N4O4/c1-12-18(27)26-16-9-5-3-7-14(16)22(30)10-17(20(29)25(12)21(22)26)24-11-23-15-8-4-2-6-13(15)19(24)28/h2-9,11-12,17,21,30H,10H2,1H3/t12-,17+,21-,22-/m0/s1 |
| SMILES | C[C@H]1C(=O)N2[C@@H]3N1C(=O)[C@@H](C[C@@]3(C4=CC=CC=C42)O)N5C=NC6=CC=CC=C6C5=O |
ORIGINAL ISOLATION REFERENCE
| CITATION | Jiao, Rui H; Xu, Shu; Liu, Jun Y; Ge, Hui M; Ding, Hui; Xu, Chen; Zhu, Hai L; Tan, Ren X Chaetominine, a cytotoxic alkaloid produced by endophytic Chaetomium sp. IFB-E015 Organic Letters 2006 8 (25) 5709-5712. | ||
|---|---|---|---|
| DOI | 10.1021/ol062257t | PMID | 17134253 |
SYNTHESES
| CITATION 1 | Toumi M; Couty F; Marrot J; Evano G Total synthesis of chaetominine. Organic Letters 2008 10 (21) 5027-30. DOI: 10.1021/ol802155n PMID: 18847212 | ||
|---|---|---|---|
| CITATION 2 | Malgesini B; Forte B; Borghi D; Quartieri F; Gennari C; Papeo G A straightforward total synthesis of (-)-chaetominine. Chemistry - A European Journal 2009 15 (32) 7922-9. DOI: 10.1002/chem.200900793 PMID: 19562787 | ||
| CITATION 3 | Peng QL; Luo SP; Xia XE; Liu LX; Huang PQ The four-step total synthesis of (-)-chaetominine. Chemical Communications 2014 50 (16) 1986-8. DOI: 10.1039/c3cc48833k PMID: 24413776 | ||
| CITATION 4 | Geng H; Huang PQ Rapid Generation of Molecular Complexity by Chemical Synthesis: Highly Efficient Total Synthesis of Hexacyclic Alkaloid (-)-Chaetominine and Its Biosynthetic Implications. Chemical Record 2019 19 (2-3) 523-533. DOI: 10.1002/tcr.201800079 PMID: 30252197 | ||
