Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA001691
PROPERTIES
| NPAID | NPA001691 |
|---|---|
| CLUSTER ID | 1084 |
| NODE ID | 933 |
| NAME | 7-Epicylindrospermopsin |
| FORMULA | C15H21N5O7S |
| MOLECULAR WEIGHT (Da) | 415.4280 |
| ACCURATE MASS (Da) | 415.1162 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Aphanizomenon |
| ORIGIN SPECIES | ovalisporum |
| InChIKey | KDNLTVRXCBZFNF-YUQKHPEDSA-N |
| InChI | InChI=1S/C15H21N5O7S/c1-6-10-5-16-14-17-8(13(22)9-4-12(21)19-15(23)18-9)2-7(20(10)14)3-11(6)27-28(24,25)26/h4,6-8,10-11,13,22H,2-3,5H2,1H3,(H4,16,17,18,19,21,23,24,25,26)/t6-,7+,8-,10-,11+,13+/m1/s1 |
| SMILES | C[C@H]1[C@@H](OS(=O)(=O)[O-])C[C@@H]2C[C@H]([C@H](O)C3=CC(=O)NC(=O)N3)NC3=[N+]2[C@@H]1CN3 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Banker, Ronny; Teltsch, Benjamin; Sukenik, Assaf; Carmeli, Shmuel 7-Epicylindrospermopsin, a Toxic Minor Metabolite of the Cyanobacterium Aphanizomen onovalisporum from Lake Kinneret, Israel Journal of Natural Products 2000 63 (3) 387-389. | ||
|---|---|---|---|
| DOI | 10.1021/np990498m | PMID | - |
SYNTHESES
| CITATION 1 | Heintzelman GR; Fang WK; Keen SP; Wallace GA; Weinreb SM Stereoselective total synthesis of the cyanobacterial hepatotoxin 7-epicylindrospermopsin: revision of the stereochemistry of cylindrospermopsin. Journal of the American Chemical Society 2001 123 (36) 8851-3. DOI: 10.1021/ja011291u PMID: 11535093 | ||
|---|---|---|---|
| CITATION 2 | Heintzelman GR; Fang WK; Keen SP; Wallace GA; Weinreb SM Stereoselective total syntheses and reassignment of stereochemistry of the freshwater cyanobacterial hepatotoxins cylindrospermopsin and 7-epicylindrospermopsin. Journal of the American Chemical Society 2002 124 (15) 3939-45. DOI: 10.1021/ja020032h PMID: 11942831 | ||
| CITATION 3 | White JD; Hansen JD Total synthesis of (-)-7-epicylindrospermopsin, a toxic metabolite of the freshwater cyanobacterium aphanizomenonovalisporum, and assignment of its absolute configuration. Journal of Organic Chemistry 2005 70 (6) 1963-77. DOI: 10.1021/jo0486387 PMID: 15760174 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | C[C@H]1[C@H](C[C@@H]2C[C@@H](NC3=NC[C@H]1N23)[C@H](C4=CC(=O)NC(=O)N4)O)S(=O)(=O)O | Banker, Ronny; Teltsch, Benjamin; Sukenik, Assaf; Carmeli, Shmuel 7-Epicylindrospermopsin, a Toxic Minor Metabolite of the Cyanobacterium Aphanizomen onovalisporum from Lake Kinneret, Israel Journal of Natural Products 2000 63 (3) 387-389. DOI: 10.1021/np990498m | ||
| 2 | C[C@H]1[C@@H](OS(=O)(=O)[O-])C[C@@H]2C[C@H]([C@H](O)C3=CC(=O)NC(=O)N3)NC3=[N+]2[C@@H]1CN3 | Heintzelman GR; Fang WK; Keen SP; Wallace GA; Weinreb SM Stereoselective total syntheses and reassignment of stereochemistry of the freshwater cyanobacterial hepatotoxins cylindrospermopsin and 7-epicylindrospermopsin. Journal of the American Chemical Society 2002 124 (15) 3939-45. DOI: 10.1021/ja020032h PMID: 11942831 | ||
