Compounds
| ID | Spectrum Quality | Annotated Name |
|---|---|---|
| CCMSLIB00005436470 | Gold | 3 |
COMPOUND NPA004201
PROPERTIES
| NPAID | NPA004201 |
|---|---|
| CLUSTER ID | 2213 |
| NODE ID | 1760 |
| NAME | Phormidolide |
| FORMULA | C59H97BrO12 |
| MOLECULAR WEIGHT (Da) | 1078.3170 |
| ACCURATE MASS (Da) | 1076.6163 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Phormidium |
| ORIGIN SPECIES | sp. |
| InChIKey | ZQZINNIFSWTJMU-OPUVCDAMSA-N |
| InChI | InChI=1S/C59H97BrO12/c1-12-13-14-15-16-17-18-19-20-21-22-23-24-28-56(67)70-47(35-44(6)51(39-60)69-11)36-49(62)45(7)50(63)38-53(65)58(8,9)52(64)32-43(5)33-54(66)59(10)55-37-48(72-59)31-42(4)29-41(3)30-46(61)27-25-26-40(2)34-57(68)71-55/h25-26,29,33-34,39,45-50,52-55,61-66H,3,6,12-24,27-28,30-32,35-38H2,1-2,4-5,7-11H3/b26-25+,40-34+,42-29+,43-33+,51-39+/t45-,46-,47+,48+,49+,50-,52-,53+,54+,55-,59-/m1/s1 |
| SMILES | C=C1/C=C(\C)C[C@H]2C[C@@H](OC(=O)/C=C(C)/C=C/C[C@@H](O)C1)[C@@](C)([C@@H](O)/C=C(\C)C[C@@H](O)C(C)(C)[C@@H](O)C[C@@H](O)[C@H](C)[C@@H](O)C[C@H](CC(=C)/C(=C\Br)OC)OC(=O)CCCCCCCCCCCCCCC)O2 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Williamson, R Thomas; Boulanger, Anna; Vulpanovici, Alexandra; Roberts, Mary A; Gerwick, William H Structure and absolute stereochemistry of phormidolide, a new toxic metabolite from the marine cyanobacterium Phormidium sp. Journal of Organic Chemistry 2002 67 (23) 7927-7936. | ||
|---|---|---|---|
| DOI | 10.1021/jo020240s | PMID | 12423120 |
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | CCCCCCCCCCCCCCCC(=O)O[C@H](C[C@H]1[C@H]([C@H](OC(O1)(C)C)C[C@H]2C([C@H](OC(O2)(C)C)C/C(=C/[C@@H]([C@@]3([C@H]4C[C@@H](O3)C/C(=C/C(=C)C[C@@H](C/C=C/C(=C/C(=O)O4)/C)O)/C)C)O)/C)(C)C)C)CC(=C)/C(=C\Br)/OC | Williamson, R Thomas; Boulanger, Anna; Vulpanovici, Alexandra; Roberts, Mary A; Gerwick, William H Structure and absolute stereochemistry of phormidolide, a new toxic metabolite from the marine cyanobacterium Phormidium sp. Journal of Organic Chemistry 2002 67 (23) 7927-7936. DOI: 10.1021/jo020240s PMID: 12423120 | ||
| 2 | C=C1/C=C(\C)C[C@H]2C[C@@H](OC(=O)/C=C(C)/C=C/C[C@@H](O)C1)[C@@](C)([C@@H](O)/C=C(\C)C[C@@H](O)C(C)(C)[C@@H](O)C[C@@H](O)[C@H](C)[C@@H](O)C[C@H](CC(=C)/C(=C\Br)OC)OC(=O)CCCCCCCCCCCCCCC)O2 | Lam, Nelson Y S; Muir, Garrett; Challa, Venugopal Rao; Britton, Robert; Paterson, Ian A counterintuitive stereochemical outcome from a chelation-controlled vinylmetal aldehyde addition leads to the configurational reassignment of phormidolide A. Chemical Communications 2019 55 (65) 9717-9720. DOI: 10.1039/c9cc05067a PMID: 31353378 | ||
