Structure via PubChem · Public domain (PubChem)
yessotoxin
Sign in to saveYessotoxins are a group of lipophilic, sulfur bearing polyether toxins that are related to ciguatoxins. They are produced by a variety of dinoflagellates, most notably Lingulodinium polyedrum and Gonyaulax spinifera.
Chemical data
- Formula
- C55H82O21S2
- Molecular weight
- 1143.4 g/mol
- IUPAC name
- [(1R,3S,5R,7S,9R,11S,13R,14S,16R,18S,20R,22S,25R,27S,30S,31R,33S,34R,35R,37S,40S,42R,44S,46R,48S)-34-hydroxy-40-[(2R,3E)-2-hydroxy-5-methylideneocta-3,7-dien-2-yl]-13,25,27,30,35-pentamethyl-39-methylidene-13-(2-sulfooxyethyl)-4,8,12,17,21,26,32,36,41,45,49-undecaoxaundecacyclo[25.22.0.03,25.05,22.07,20.09,18.011,16.031,48.033,46.035,44.037,42]nonatetracontan-14-yl] hydrogen sulfate
- SMILES
- C[C@H]1CC[C@]2([C@@H](C[C@H]3[C@](O2)(CC[C@H]4[C@H](O3)C[C@H]5[C@H](O4)C[C@H]6[C@H](O5)C[C@H]7[C@H](O6)C[C@@H]([C@@](O7)(C)CCOS(=O)(=O)O)OS(=O)(=O)O)C)O[C@@H]8[C@@H]1O[C@@H]9[C@@H](C8)O[C@H]1C[C@@H]2[C@H](CC(=C)[C@H](O2)[C@@](C)(/C=C/C(=C)CC=C)O)O[C@@]1([C@@H]9O)C)C
- InChIKey
- HCYDZFJGUKMTQB-AVHIVUAZSA-N
- XLogP
- 3.4
- Polar surface area
- 286 Ų
- H-bond donors
- 4
- H-bond acceptors
- 21
- Formal charge
- 0
via PubChem
Research
367 papers- Yessotoxin, a Promising Therapeutic Tool.Marine drugs · 2016
- [Yessotoxin: risk assessment for public health. Justification of regulations of content in seafood].Voprosy pitaniia · 2018
- Yessotoxin as an apoptotic inducer.Toxicon : official journal of the International Society on Toxinology · 2011
- Yessotoxin as a tool to study induction of multiple cell death pathways.Toxins · 2012
- Yessotoxin triggers ribotoxic stress.Toxicology in vitro : an international journal published in association with BIBRA · 2014
via PubMed
Wikidata facts
- Mass
- 1142.479
Show 4 more facts
- canonical SMILES
- CC1CCC2(C(CC3C(O2)(CCC4C(O3)CC5C(O4)CC6C(O5)CC7C(O6)CC(C(O7)(C)CCOS(=O)(=O)O)OS(=O)(=O)O)C)OC8C1OC9C(C8)OC1CC2C(CC(=C)C(O2)C(C)(C=CC(=C)CC=C)O)OC1(C9O)C)C
- chemical formula
- C₅₅H₈₂O₂₁S₂
- isomeric SMILES
- C[C@H]1CC[C@]2([C@@H](C[C@H]3[C@](O2)(CC[C@H]4[C@H](O3)C[C@H]5[C@H](O4)C[C@H]6[C@H](O5)C[C@H]7[C@H](O6)C[C@@H]([C@@](O7)(C)CCOS(=O)(=O)O)OS(=O)(=O)O)C)O[C@@H]8[C@@H]1O[C@@H]9[C@@H](C8)O[C@H]1C[C@@H]2[C@H](CC(=C)[C@H](O2)[C@@](C)(/C=C/C(=C)CC=C)O)O[C@@]1([C@@H]9O)C)C
- subject has role
- toxin
Sources (2)
via Wikidata · CC0
~11 min read
Encyclopedic overview
14 sectionsContents
- History
- Toxicity
- Analysis
- Extraction methods
- Liquid–liquid or solvent extraction
- Solid phase extraction
- Analytical techniques
- Mouse bioassay
- Enzyme-linked immunosorbent assay
- Chromatographic methods
- Capillary electrophoresis
- See also
- References
- Sources
Yessotoxins are a group of lipophilic, sulfur bearing polyether toxins that are related to ciguatoxins. They are produced by a variety of dinoflagellates, most notably Lingulodinium polyedrum and Gonyaulax spinifera.
When the environmental conditions encourage the growth of YTX producing dinoflagellates, the toxin(s) bioaccumulate in edible tissues of bivalve molluscs, including mussels, scallops, and clams, thus allowing entry of YTX into the food chain.
Excerpted from Wikipedia’s “yessotoxin” article, available under the CC BY-SA 4.0 licence.