Compounds
| ID | Spectrum Quality | Annotated Name |
|---|---|---|
| CCMSLIB00000851777 | Gold | 1 |
| CCMSLIB00012130980 | Gold | 4 |
| CCMSLIB00012130981 | Gold | 4 |
| CCMSLIB00009970777 | Gold | 4 |
| CCMSLIB00009970778 | Gold | 4 |
COMPOUND NPA003590
PROPERTIES
| NPAID | NPA003590 |
|---|---|
| CLUSTER ID | 193 |
| NODE ID | 181 |
| NAME | Paraherquamide |
| FORMULA | C28H35N3O5 |
| MOLECULAR WEIGHT (Da) | 493.6040 |
| ACCURATE MASS (Da) | 493.2577 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Penicillium |
| ORIGIN SPECIES | paraherquei |
| InChIKey | UVZZDDLIOJPDKX-ITKQZBBDSA-N |
| InChI | InChI=1S/C28H35N3O5/c1-23(2)10-12-35-20-17(36-23)8-7-16-19(20)29-21(32)27(16)14-26-15-31-11-9-25(5,34)28(31,22(33)30(26)6)13-18(26)24(27,3)4/h7-8,10,12,18,34H,9,11,13-15H2,1-6H3,(H,29,32)/t18-,25+,26+,27+,28-/m0/s1 |
| SMILES | C[C@]1(CCN2[C@]13C[C@@H]4[C@](C2)(C[C@@]5(C4(C)C)C6=C(C7=C(C=C6)OC(C=CO7)(C)C)NC5=O)N(C3=O)C)O |
ORIGINAL ISOLATION REFERENCE
| CITATION | Yamazaki; Okuyama; Kobayashi; Inoue The structure of paraherquamide, a toxic metabolite from Penicillium paraherquei Tetrahedron Letters 1981 22 (2) 135-136. | ||
|---|---|---|---|
| DOI | 10.1016/0040-4039(81)80168-2 | PMID | - |
SYNTHESES
| CITATION 1 | Williams RM; Cao J; Tsujishima H Asymmetric, Stereocontrolled Total Synthesis of Paraherquamide A This work was supported by the NIH (Grant CA 70375). The Japanese Society for the Promotion of Science (JSPS) is acknowledged for providing support to H.T. Mass spectra were obtained on instruments supported by the NIH Shared Instrumentation Grant (GM 49631). We also wish to thank Dr. Timothy Blizzard (Merck & Co.) for providing an authentic sample of natural paraherquamide A. We also wish to acknowledge Dr. Byung H. Lee (Pharmacia-Upjohn Co.) for providing NMR spectra and an authentic specimen of 14-oxoparaherquamide B. We also wish to thank Dr. Alfredo Vazquez for assistance with purification and characterization of synthetic paraherquamide A. Angewandte Chemie International Edition 2000 39 (14) 2540-2544. DOI: 10.1002/1521-3773(20000717)39:14<2540::aid-anie2540>3.0.co;2-r PMID: 10941129 | ||
|---|---|---|---|
| CITATION 2 | Williams RM; Cao J; Tsujishima H; Cox RJ Asymmetric, stereocontrolled total synthesis of paraherquamide A. Journal of the American Chemical Society 2003 125 (40) 12172-12178. DOI: 10.1021/ja036713+ PMID: 14519003 | ||
