<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2628</id>
  <title>T3D2587</title>
  <common-name>Maitotoxin</common-name>
  <description>Maitotoxin (MTX) is an extremely potent toxin produced by a species of dinoflagellates (Gambierdiscus toxicus). It activates calcium permeable, non-selective cation channels, leading to an increase in levels of cytosolic calcium ions. Ultimately, a cell death cascade is activated, resulting in membrane blebbing and eventually cell lysis. (L1114)</description>
  <cas>59392-53-9</cas>
  <pubchem-id>71460273</pubchem-id>
  <chemical-formula>C164H256Na2O68S2</chemical-formula>
  <weight>3425.8741</weight>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility></solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Injection (sting/bite) (L1815)</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Maitotoxin activates calcium permeable, non-selective cation channels, leading to an increase in levels of cytosolic calcium ions. It is thought that maitotoxin leads to the formation of pores on these ion channels. Ultimately, a cell death cascade is activated, resulting in membrane blebbing and eventually cell lysis. Maitotoxin is also known to activate cytosolic calcium-activated proteases calpain-1 and calpain-2, contributing to necrosis. (L1114)</mechanism-of-toxicity>
  <metabolism nil="true"/>
  <toxicity>LD50: 50 ug/kg (Mouse) (L1114)</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Maitotoxin is an extremely potent toxin produced by a species of dinoflagellates (Gambierdiscus toxicus). (L1114)</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Maitotoxin is a potent cytotoxin. (L1114)</health-effects>
  <symptoms>Toxin from Gambierdiscus toxicus can cause a type of food poisoning called ciguatera. Hallmark symptoms of ciguatera include gastrointestinal and neurological effects. Gastrointestinal symptoms include nausea, vomiting, and diarrhea usually followed by neurological symptoms such as headaches, muscle aches, paresthesia, numbness, ataxia, and hallucinations. Severe cases of ciguatera can also result in cold allodynia. (L995)</symptoms>
  <treatment>Ciguatera poisoning is treated with supportive care. Some medications such as the use of Amitriptyline may reduce some symptoms of ciguatera, such as fatigue and paresthesia, although benefit does not occur in every case. Also used are steroids and vitamin supplements, but these merely support the body's recovery rather than directly reducing the toxic effects. (L995)</treatment>
  <created-at type="dateTime">2009-07-05T17:25:24Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:25:44Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>http://en.wikipedia.org/wiki/Maitotoxin</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id></chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id>C020394</ctd-id>
  <stitch-id>Maitotoxin</stitch-id>
  <drugbank-id nil="true"/>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>[Na+].[Na+].[H]\C(CO)=C(\C)C(=C)[C@]([H])(O)C[C@@]([H])(C)[C@@]([H])(O)[C@]([H])(CC[C@@]([H])(C)[C@@]([H])(O)[C@@]([H])(C)[C@]1([H])O[C@@]2([H])[C@@]([H])(O[C@]3([H])C[C@]4([H])O[C@]5([H])[C@@]([H])(O)[C@]6([H])O[C@]([H])([C@]([H])(O)[C@@]([H])(O)C[C@]7([H])O[C@]8([H])C[C@]9([H])O[C@@]%10([H])[C@]([H])(C[C@@]9([H])O[C@@]8([H])[C@@]([H])(O)[C@@]7([H])OS([O-])(=O)=O)O[C@@]7([H])[C@]([H])(O)[C@@]([H])(O)[C@@]([H])(O[C@]7([H])[C@]%10([H])O)[C@]7([H])O[C@@]8([H])C[C@@]([H])(O)[C@@]([H])(O[C@@]8([H])[C@]([H])(O)[C@@]7([H])O)[C@]([H])(O)C[C@@]([H])(O)C[C@]7([H])O[C@@]8([H])C[C@@]([H])(O)[C@@]([H])(O[C@@]8([H])[C@]([H])(O)[C@@]7([H])O)[C@]7([H])O[C@]8([H])[C@]([H])(O)[C@]9(C)O[C@]%10([H])CC[C@]%11(C)O[C@]%12([H])C[C@]%13([H])O[C@@]([H])(CC[C@@]%13([H])O[C@@]%12(C)C[C@@]%11([H])O[C@@]%10(C)C[C@@]9([H])O[C@@]8(C)C[C@@]7([H])O)[C@]7(C)O[C@]8(C)C[C@]9([H])O[C@]%10([H])C[C@]%11([H])O[C@]%12([H])C\C([H])=C([H])/[C@]%13([H])O[C@]%14(C)C[C@]%15(C)O[C@]%16(C)CC[C@]([H])(O[C@@]%16([H])C[C@@]%15([H])O[C@@]%14([H])C[C@@]%13([H])O[C@@]%12([H])C[C@@]%11(C)O[C@@]%10(C)CC[C@@]9(C)O[C@@]8([H])C[C@@]7([H])O)[C@@]([H])(O)[C@]([H])(O)C[C@@]([H])(C)[C@@]([H])(C)CC=C)[C@]([H])(O)C[C@@]6([H])O[C@@]5(C)C[C@@]4([H])O[C@@]3(C)C[C@@]2([H])O)[C@@]([H])(O)[C@@]1([H])O)OS([O-])(=O)=O</moldb-smiles>
  <moldb-formula>C164H256Na2O68S2</moldb-formula>
  <moldb-inchi>InChI=1S/C164H258O68S2.2Na/c1-24-26-65(2)68(5)41-74(168)117(179)85-33-36-152(11)106(203-85)55-109-162(21,231-152)64-161(20)105(210-109)51-89-83(220-161)28-25-27-82-99(199-89)59-157(16)108(202-82)56-107-153(12,230-157)39-38-151(10)112(211-107)61-158(17)111(224-151)54-101(176)163(22,232-158)103-32-31-84-90(204-103)53-110-156(15,219-84)62-113-150(9,223-110)37-34-102-155(14,225-113)63-114-164(23,227-102)147(192)149-159(18,226-114)58-81(175)134(218-149)133-79(173)47-93-136(216-133)120(182)119(181)92(200-93)44-72(166)43-76(170)131-77(171)46-94-137(214-131)122(184)124(186)143(207-94)145-126(188)125(187)144-146(217-145)128(190)139-97(208-144)50-88-87(206-139)49-96-138(205-88)127(189)141(229-234(196,197)198)95(201-96)45-75(169)118(180)132-78(172)48-98-140(215-132)129(191)148-160(19,221-98)60-100-91(209-148)52-104-154(13,222-100)57-80(174)135-142(212-104)123(185)121(183)130(213-135)71(8)115(177)67(4)29-30-86(228-233(193,194)195)116(178)69(6)42-73(167)70(7)66(3)35-40-165;;/h24-25,28,35,65,67-69,71-149,165-192H,1,7,26-27,29-34,36-64H2,2-6,8-23H3,(H,193,194,195)(H,196,197,198);;/q;2*+1/p-2/b28-25-,66-35+;;/t65-,67+,68+,69+,71+,72+,73+,74+,75-,76+,77+,78+,79+,80+,81+,82+,83-,84+,85-,86-,87-,88+,89+,90-,91-,92-,93-,94-,95-,96+,97-,98+,99-,100+,101+,102+,103-,104+,105-,106-,107+,108-,109+,110+,111-,112-,113+,114+,115+,116+,117-,118+,119-,120+,121+,122+,123-,124+,125+,126+,127+,128+,129-,130-,131-,132-,133+,134+,135+,136+,137+,138+,139-,140+,141-,142-,143+,144-,145+,146+,147-,148+,149+,150-,151+,152+,153-,154-,155-,156-,157+,158+,159-,160-,161+,162-,163+,164+;;/m0../s1</moldb-inchi>
  <moldb-inchikey>InChIKey=NWQUHAJRFNRIIU-DVGFTKJRSA-L</moldb-inchikey>
  <moldb-average-mass type="decimal">3425.856</moldb-average-mass>
  <moldb-mono-mass type="decimal">3423.581083218</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id nil="true"/>
  <chembl-id>CHEMBL2152261</chembl-id>
  <chemspider-id>10477103</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
