yessotoxin

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.

In the Vinony graph

Within Vinony's link graph, yessotoxin is referenced by 9 other articles, and connects out to toxin, fluorescence and Pectinidae.

It is catalogued under topics including Alkene derivatives, Chembox image size set and Marine neurotoxins.

Its subject is documented across 8 Wikipedia language editions.

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 Å²
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 sections

Contents

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

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.