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Yessotoxin information


Yessotoxin
Names
Preferred IUPAC name
(2S,4aS,5aR,6R,6aS,7aR,8S,10aS,11aR,13aS,14aR,15aS,16aR,18S,19R,20aS,21aR,22aS,23aR,24aS,25aR,26aS,27aR,28aS,29aR)-6-Hydroxy-2-[(2R,3E)-2-hydroxy-5-methylidene­octa-3,7-dien-2-yl]-5a,8,10a,11a,19-pentamethyl-3-methylidene-19-[2-(sulfooxy)ethyl]­octatriacontahydro­pyrano­[2,3:5,6]pyrano­[2,3:5,6]pyrano­[2,3:5,6]pyrano­[3,2-b]pyrano­[2,3:5,6]pyrano­[2,3:5,6]pyrano­[2,3:5,6]pyrano­[2,3:6,7]oxepino­[2,3:5,6]pyrano­[2,3-g]oxocin-18-yl hydrogen sulfate
Identifiers
CAS Number
  • 112514-54-2 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL1269577
ChemSpider
  • 4945067
PubChem CID
  • 6440821
UNII
  • P6M9FM2L2G checkY
CompTox Dashboard (EPA)
  • DTXSID20880023 Edit this at Wikidata
InChI
  • InChI=1S/C55H82O21S2/c1-10-11-28(2)12-15-51(5,57)50-30(4)20-39-38(71-50)26-46-55(9,74-39)49(56)48-42(70-46)24-41-47(72-48)29(3)13-16-53(7)44(69-41)27-43-54(8,76-53)17-14-31-32(68-43)21-34-33(65-31)22-35-36(66-34)23-40-37(67-35)25-45(75-78(61,62)63)52(6,73-40)18-19-64-77(58,59)60/h10,12,15,29,31-50,56-57H,1-2,4,11,13-14,16-27H2,3,5-9H3,(H,58,59,60)(H,61,62,63)/b15-12+/t29-,31-,32+,33+,34-,35-,36+,37+,38+,39-,40-,41-,42+,43-,44+,45-,46-,47+,48+,49+,50-,51+,52+,53-,54+,55-/m0/s1
    Key: HCYDZFJGUKMTQB-AVHIVUAZSA-N
  • InChI=1/C55H82O21S2/c1-10-11-28(2)12-15-51(5,57)50-30(4)20-39-38(71-50)26-46-55(9,74-39)49(56)48-42(70-46)24-41-47(72-48)29(3)13-16-53(7)44(69-41)27-43-54(8,76-53)17-14-31-32(68-43)21-34-33(65-31)22-35-36(66-34)23-40-37(67-35)25-45(75-78(61,62)63)52(6,73-40)18-19-64-77(58,59)60/h10,12,15,29,31-50,56-57H,1-2,4,11,13-14,16-27H2,3,5-9H3,(H,58,59,60)(H,61,62,63)/b15-12+/t29-,31-,32+,33+,34-,35-,36+,37+,38+,39-,40-,41-,42+,43-,44+,45-,46-,47+,48+,49+,50-,51+,52+,53-,54+,55-/m0/s1
    Key: HCYDZFJGUKMTQB-AVHIVUAZBJ
SMILES
  • O=S(=O)(O)O[C@H]4C[C@H]5O[C@H]6C[C@H]7O[C@H]8CC[C@]9(O[C@@]%10(C)CC[C@H](C)[C@H]%11O[C@@H]1[C@H](O[C@H]2C[C@H]3O[C@@H](C(=C)\C[C@@H]3O[C@]2(C)[C@@H]1O)[C@](O)(\C=C\C(=C)C\C=C)C)C[C@@H]%11O[C@@H]%10C[C@@H]9O[C@@H]8C[C@@H]7O[C@@H]6C[C@@H]5O[C@]4(C)CCOS(=O)(=O)O)C
Properties
Chemical formula
C55H82O21S2
Molar mass 1143.36 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Yessotoxins are a group of lipophilic, sulfur bearing polyether toxins that are related to ciguatoxins.[1] They are produced by a variety of dinoflagellates, most notably Lingulodinium polyedrum and Gonyaulax spinifera.[2]

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.[3]

  1. ^ A. Tubaro; V. Dell'Ovo; S. Sosa; C. Florio (2010). "Yessotoxins: A Toxicological Overview". Toxicon. 56 (2): 163–172. doi:10.1016/j.toxicon.2009.07.038. PMID 19660487.
  2. ^ M. D. A. Howard; M. Silver; R. M. Kudela (2008). "Yessotoxin detected in mussel (Mytilus californicus) and phytoplankton samples from the U.S. west coast". Harmful Algae. 7 (5): 646–652. doi:10.1016/j.hal.2008.01.003.
  3. ^ "Marine biotoxins in shellfish – Summary on regulated marine biotoxins" (pdf). Scientific opinion of the Panel on Contaminants in the Food Chain. European Food Safety Authority. 13 August 2009. Question No EFSA-Q-2009-00685.

and 13 Related for: Yessotoxin information

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Yessotoxin

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Yessotoxins are a group of lipophilic, sulfur bearing polyether toxins that are related to ciguatoxins. They are produced by a variety of dinoflagellates...

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Gonyaulax

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yesotoxins: for example, strains of Gonyaulax spinifera from New Zealand are yessotoxin producers. The plate formula in the genus Gonyaulax Diesing was redefined...

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Ciguatera fish poisoning

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ritual.[citation needed] Algal bloom Red tide Scombroid food poisoning Yessotoxin Friedman, MA; Fernandez, M; Backer, LC; Dickey, RW; Bernstein, J; Schrank...

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Mizuhopecten yessoensis

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refers to its being found north of Japan. Its tissues bioaccumulate algal yessotoxins and are studied extensively. The Yesso scallop (Mizuhopecten yessoensis)...

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Algal bloom

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major types of dinoflagellate toxins, in which the strains, Saxitoxin and Yessotoxin, are both bioluminescent and toxic. These two strains are found to have...

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Dinoflagellate

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scintillans (Noctiluciphyceae) Ciguatera Paralytic shellfish poisoning Yessotoxin Thin layers (oceanography) Parfrey LW, Lahr DJ, Knoll AH, Katz LA (August...

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Phycotoxin

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5) Chatonella marina, C. antiqua, C. cf. verruculosa Raphidophyceae Yessotoxins Protoceratium reticulatum, Lingulodinium polyedrum Dinophyceae Ladder-frame...

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Okadaic acid

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poisoning toxins, okadaic acid, dinophysistoxin-1, pectenotoxin-6 and yessotoxin in scallops Patinopecten yessoensis". Fisheries Science. 71 (4): 948–955...

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Lingulodinium polyedra

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variation. Lingulodinium polyedra has been related to production of yessotoxins (YTXs), a group of structurally related polyether toxins, which can accumulate...

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Dinotoxin

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lethal in concentrations of 411 micrograms per kilogram of body weight. Yessotoxins (YTXs) are potent cytotoxins which are made of disulfated polyether compounds...

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Canadian Reference Materials

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DTX, dinophysistoxin standards GYM, gymnodimine standards YTX and hYTX, yessotoxin standards PTX, pectenotoxin-2 standard SPX, 13-desmethyl spirolide C standard...

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Coolia

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blooms (HABs) that are of potential concern to human health. They produce yessotoxins. The species that are known to produce the toxins are Coolia tropicalis...

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Azaspiracid

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Florence; Savar, Véronique (2008). "First report on azaspiracid and yessotoxin groups detection in French shellfish". Toxicon. 52 (1): 39–48. doi:10...

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