Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA004016
PROPERTIES
| NPAID | NPA004016 |
|---|---|
| CLUSTER ID | 105 |
| NODE ID | 100 |
| NAME | Zaragozic acid C |
| FORMULA | C40H50O14 |
| MOLECULAR WEIGHT (Da) | 754.8260 |
| ACCURATE MASS (Da) | 754.3201 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Leptodontium |
| ORIGIN SPECIES | elatius |
| InChIKey | KQMNJFMTGHRJHM-OSXSUEQMSA-N |
| InChI | InChI=1S/C40H50O14/c1-25(15-12-20-28-16-6-4-7-17-28)14-10-11-22-31(42)52-33-32(43)38(53-34(35(44)45)39(50,36(46)47)40(33,54-38)37(48)49)23-13-21-30(51-27(3)41)26(2)24-29-18-8-5-9-19-29/h4-10,14,16-19,25-26,30,32-34,43,50H,11-13,15,20-24H2,1-3H3,(H,44,45)(H,46,47)(H,48,49)/b14-10+/t25-,26+,30+,32+,33+,34?,38?,39?,40?/m0/s1 |
| SMILES | C[C@H](CCCC1=CC=CC=C1)/C=C/CCC(=O)O[C@@H]2[C@H](C3(OC(C(C2(O3)C(=O)O)(C(=O)O)O)C(=O)O)CCC[C@H]([C@H](C)CC4=CC=CC=C4)OC(=O)C)O |
ORIGINAL ISOLATION REFERENCE
| CITATION | Dufresne, Claude; Wilson, Kenneth E.; Zink, Deborah; Smith, Jack; Bergstrom, James D.; Kurtz, Marc; Rew, Deborah; Nallin, Mary; Jenkins, Rosalind; Bartizal, Ken; Trainor, Charlotte; Bills, Gerald; Meinz, Maria; Huang, Leeyuan; Onishi, Janet; Milligan, James; Mojena, Marina; Pelaez, Fernando The isolation and structure elucidation of zaragozic acid C, a novel potent squalene synthase inhibitor Tetrahedron 1992 48 (47) 10221-10226. | ||
|---|---|---|---|
| DOI | 10.1016/s0040-4020(01)88327-7 | PMID | - |
SYNTHESES
| CITATION 1 | Armstrong A; Barsanti PA; Jones LH; Ahmed G Total synthesis of (+)-zaragozic acid C. Journal of Organic Chemistry 2000 65 (21) 7020-32. DOI: 10.1021/jo000700m PMID: 11031024 | ||
|---|---|---|---|
| CITATION 2 | Nakamura S; Hirata Y; Kurosaki T; Anada M; Kataoka O; Kitagaki S; Hashimoto S Total synthesis of the squalene synthase inhibitor zaragozic acid C by a carbonyl ylide cycloaddition strategy. Angewandte Chemie International Edition 2003 42 (43) 5351-5. DOI: 10.1002/anie.200352629 PMID: 14613174 | ||
| CITATION 3 | Nakamura S Total synthesis of the squalene synthase inhibitor zaragozic acid C. Chemical and Pharmaceutical Bulletin 2005 53 (1) 1-10. DOI: 10.1248/cpb.53.1 PMID: 15635219 | ||
| CITATION 4 | Bunte JO; Cuzzupe AN; Daly AM; Rizzacasa MA Formal total synthesis of (+)-zaragozic acid C through an Ireland-Claisen rearrangement. Angewandte Chemie International Edition 2006 45 (38) 6376-80. DOI: 10.1002/anie.200602507 PMID: 16941713 | ||
| CITATION 5 | Kawamata T; Nagatomo M; Inoue M Total Synthesis of Zaragozic Acid C: Implementation of Photochemical C(sp Journal of the American Chemical Society 2017 139 (5) 1814-1817. DOI: 10.1021/jacs.6b13263 PMID: 28092952 | ||
