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Record Information
Version2.0
Creation Date2009-07-05 17:25:24 UTC
Update Date2014-12-24 20:25:44 UTC
Accession NumberT3D2587
Identification
Common NameMaitotoxin
ClassSmall Molecule
DescriptionMaitotoxin (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. (2)
Compound Type
  • Animal Toxin
  • Ester
  • Ether
  • Marine Toxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
Synonyms
Synonym
MTX
Chemical FormulaC164H256Na2O68S2
Average Molecular Mass3425.856 g/mol
Monoisotopic Mass3423.581 g/mol
CAS Registry Number59392-53-9
IUPAC Namedisodium (2S,3R,4R,4aS,5aR,6aS,7aS,8R,9R,10R,11aR,12R,12aR,13aS,14aR)-10-[(2R,3R,4R,4aS,6S,7R,8aS)-6-[(1R,3R)-4-[(2S,3R,4R,4aS,6R,7R,8aS)-6-[(1R,3S,5R,7S,9R,10R,12R,13S,14S,16R,19S,21R,23S,25S,28R,30S)-25-[(1S,3R,5S,7R,9S,11S,14R,16S,18R,20S,21Z,24R,26S,28R,30S,32R,34R,35R,37S,39R,42S,44R)-11-[(1S,2R,4R,5S)-1,2-dihydroxy-4,5-dimethyloct-7-en-1-yl]-35-hydroxy-14,16,18,32,34,39,42,44-octamethyl-2,6,10,15,19,25,29,33,38,43-decaoxadecacyclo[22.21.0.0³,²⁰.0⁵,¹⁸.0⁷,¹⁶.0⁹,¹⁴.0²⁶,⁴⁴.0²⁸,⁴².0³⁰,³⁹.0³²,³⁷]pentatetracont-21-en-34-yl]-9,13-dihydroxy-3,7,14,19,30-pentamethyl-2,6,11,15,20,24,29-heptaoxaheptacyclo[17.12.0.0³,¹⁶.0⁵,¹⁴.0⁷,¹².0²¹,³⁰.0²³,²⁸]hentriacontan-10-yl]-3,4,7-trihydroxy-octahydropyrano[3,2-b]pyran-2-yl]-1,3-dihydroxybutyl]-3,4,7-trihydroxy-octahydropyrano[3,2-b]pyran-2-yl]-2-[(2S,3R)-2,3-dihydroxy-3-[(1S,3R,5S,6S,7R,8S,10R,11R,13S,15R,17S,19R,21R,22S,24S,25S,26R)-6,7,11,21,25-pentahydroxy-13,17-dimethyl-8-[(2R,3R,4R,7S,8R,9R,11R,13E)-3,8,11,15-tetrahydroxy-4,9,13-trimethyl-12-methylidene-7-(sulfonatooxy)pentadec-13-en-2-yl]-4,9,14,18,23,27-hexaoxahexacyclo[13.12.0.0³,¹³.0⁵,¹⁰.0¹⁷,²⁶.0¹⁹,²⁴]heptacosan-22-yl]propyl]-4,8,9,12-tetrahydroxy-hexadecahydro-2H-1,5,7,11,13-pentaoxapentacen-3-yl sulfate
Traditional Namedisodium (2S,3R,4R,4aS,5aR,6aS,7aS,8R,9R,10R,11aR,12R,12aR,13aS,14aR)-10-[(2R,3R,4R,4aS,6S,7R,8aS)-6-[(1R,3R)-4-[(2S,3R,4R,4aS,6R,7R,8aS)-6-[(1R,3S,5R,7S,9R,10R,12R,13S,14S,16R,19S,21R,23S,25S,28R,30S)-25-[(1S,3R,5S,7R,9S,11S,14R,16S,18R,20S,21Z,24R,26S,28R,30S,32R,34R,35R,37S,39R,42S,44R)-11-[(1S,2R,4R,5S)-1,2-dihydroxy-4,5-dimethyloct-7-en-1-yl]-35-hydroxy-14,16,18,32,34,39,42,44-octamethyl-2,6,10,15,19,25,29,33,38,43-decaoxadecacyclo[22.21.0.0³,²⁰.0⁵,¹⁸.0⁷,¹⁶.0⁹,¹⁴.0²⁶,⁴⁴.0²⁸,⁴².0³⁰,³⁹.0³²,³⁷]pentatetracont-21-en-34-yl]-9,13-dihydroxy-3,7,14,19,30-pentamethyl-2,6,11,15,20,24,29-heptaoxaheptacyclo[17.12.0.0³,¹⁶.0⁵,¹⁴.0⁷,¹².0²¹,³⁰.0²³,²⁸]hentriacontan-10-yl]-3,4,7-trihydroxy-octahydropyrano[3,2-b]pyran-2-yl]-1,3-dihydroxybutyl]-3,4,7-trihydroxy-octahydropyrano[3,2-b]pyran-2-yl]-2-[(2S,3R)-2,3-dihydroxy-3-[(1S,3R,5S,6S,7R,8S,10R,11R,13S,15R,17S,19R,21R,22S,24S,25S,26R)-6,7,11,21,25-pentahydroxy-13,17-dimethyl-8-[(2R,3R,4R,7S,8R,9R,11R,13E)-3,8,11,15-tetrahydroxy-4,9,13-trimethyl-12-methylidene-7-(sulfonatooxy)pentadec-13-en-2-yl]-4,9,14,18,23,27-hexaoxahexacyclo[13.12.0.0³,¹³.0⁵,¹⁰.0¹⁷,²⁶.0¹⁹,²⁴]heptacosan-22-yl]propyl]-4,8,9,12-tetrahydroxy-hexadecahydro-2H-1,5,7,11,13-pentaoxapentacen-3-yl sulfate
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
InChI IdentifierInChI=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
InChI KeyInChIKey=NWQUHAJRFNRIIU-DVGFTKJRSA-L
Chemical Taxonomy
ClassificationNot classified
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Acrosome
  • Actin Cytoskeleton
  • Actin Filament
  • Cell surface
  • Cytoskeleton
  • Cytosol
  • Endoplasmic reticulum
  • Extracellular
  • Membrane
  • Microtubule
  • Mitochondrion
  • Nuclear Matrix
  • Plasma Membrane
  • Secretory Granule
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Cell cycleNot Availablemap04110
ApoptosisNot Availablemap04210
Insulin secretionNot Availablemap04911
Oxidative phosphorylationNot Availablemap00190
Inositol Phosphate MetabolismSMP00462 map00562
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
logP-9.4ChemAxon
pKa (Strongest Acidic)-2ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count66ChemAxon
Hydrogen Donor Count28ChemAxon
Polar Surface Area994.66 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity800.11 m³·mol⁻¹ChemAxon
Polarizability369.16 ųChemAxon
Number of Rings32ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-7ef155cf949e833ed523JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0000900000-7ef155cf949e833ed523JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0000900000-7ef155cf949e833ed523JSpectraViewer
Toxicity Profile
Route of ExposureInjection (sting/bite) (3)
Mechanism of ToxicityMaitotoxin 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. (2)
MetabolismNot Available
Toxicity ValuesLD50: 50 ug/kg (Mouse) (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesMaitotoxin is an extremely potent toxin produced by a species of dinoflagellates (Gambierdiscus toxicus). (2)
Minimum Risk LevelNot Available
Health EffectsMaitotoxin is a potent cytotoxin. (2)
SymptomsToxin 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. (1)
TreatmentCiguatera 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. (1)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID71460273
ChEMBL IDCHEMBL2152261
ChemSpider ID10477103
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDC020394
Stitch IDMaitotoxin
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkMaitotoxin
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Wikipedia. Ciguatera. Last Updated 3 August 2009. [Link]
  2. Wikipedia. Maitotoxin. Last Updated 10 June 2009. [Link]
  3. Wikipedia. Mollusca. Last Updated 5 August 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available