Yessotoxin

"YTX" redirects here. For the defunct airport in British Columbia, see Telegraph Creek Airport.
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
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • 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
  • 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
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).

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.