Tetrodotoxin (CHEM002066)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (14)XML
Record Information
Version1.0
Creation Date2009-07-03 22:09:29 UTC
Update Date2016-11-09 01:08:40 UTC
Accession NumberCHEM002066
Identification
Common NameTetrodotoxin
ClassSmall Molecule
DescriptionAn aminoperhydroquinazoline poison found mainly in the liver and ovaries of fishes in the order tetraodontiformes, which are eaten. Tetrodotoxin is a potent neurotoxin that is produced by bacteria (genus Pseudoalteromonas, Pseudomonas, Vibrio) and found in certain species of Tetraodontiformes (puffer fish, porcupine fish, ocean sunfish, triggerfish), from which its name is derived. It acts on the voltage-gated sodium channels of nerve cells. (1) The toxin causes paresthesia and paralysis through interference with neuromuscular conduction. Tetrodotoxin is being investigated by Wex Pharmaceuticals for the treatment of chronic and breakthrough pain in advanced cancer patients as well as for the treatment of opioid dependence.
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Animal Toxin
  • Ether
  • Marine Toxin
  • Natural Compound
  • Organic Compound
  • Sodium Channel Blocker
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
TTXKegg
Chemical FormulaC11H17N3O8
Average Molecular Mass319.268 g/mol
Monoisotopic Mass319.102 g/mol
CAS Registry Number4368-28-9
IUPAC Name(11S,13S)-3-amino-5,12,13,14-tetrahydroxy-14-(hydroxymethyl)-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradec-3-en-4-ium-9-olate
Traditional Nametetrodotoxin
SMILES[H][C@]12OC3([O-])OC(C4C(O)[NH+]=C(N)NC4(C1O)[C@@H]3O)C2(O)CO
InChI IdentifierInChI=1S/C11H16N3O8/c12-8-13-6(17)2-4-9(19,1-15)5-3(16)10(2,14-8)7(18)11(20,21-4)22-5/h2-7,15-19H,1H2,(H3,12,13,14)/q-1/p+1/t2?,3?,4?,5-,6?,7-,9?,10?,11?/m0/s1
InChI KeySLBCPBUVHCASIJ-UFHSVNPDSA-O
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetrodotoxins. Tetrodotoxins are compounds structurally characterized by the presence of the tetrodotoxin skeleton, which is based on 5,7-(epoxymethanooxy)quinazolin-10-olate moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazanaphthalenes
Sub ClassBenzodiazines
Direct ParentTetrodotoxins
Alternative Parents
Substituents
  • Tetrodotoxin-skeleton
  • Meta-dioxane
  • Hydropyrimidine
  • 1,4,5,6-tetrahydropyrimidine
  • Monosaccharide
  • Oxane
  • Cyclic alcohol
  • Tertiary alcohol
  • Guanidine
  • Orthocarboxylic acid derivative
  • Secondary alcohol
  • Carboximidamide
  • Organic 1,3-dipolar compound
  • Azacycle
  • Propargyl-type 1,3-dipolar organic compound
  • Alkanolamine
  • Polyol
  • Oxacycle
  • Organic zwitterion
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Primary alcohol
  • Alkoxide
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceColorless Solid (2).
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility117 g/LALOGPS
logP0.42ALOGPS
logP-4.8ChemAxon
logS-0.5ALOGPS
pKa (Strongest Acidic)10.4ChemAxon
pKa (Strongest Basic)9.62ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area194.69 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity86.74 m³·mol⁻¹ChemAxon
Polarizability27.83 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-b7ce9130a531ed988be9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-0098000000-4cc9d0d4fc807afd209bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-3091000000-da2933642dbc3ad9bc9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uxr-0059000000-7c5f6a917cfd35b2ed23Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0v03-5096000000-9c701d5e323a195da9b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-5090000000-3e75d9ff468628c782c0Spectrum
Toxicity Profile
Route of ExposureOral (1) ; injection (sting/bite) (1)
Mechanism of ToxicityTetrodotoxin binds to what is known as site 1 of the fast voltage-gated sodium channel. Site 1 is located at the extracellular pore opening of the ion channel. The binding of any molecules to this site will temporarily disable the function of the ion channel. Saxitoxin and several of the conotoxins also bind the same site.
MetabolismThe metabolic source of tetrodotoxin is uncertain. No algal source has been identified, and until recently tetrodotoxin was assumed to be a metabolic product of the host. However, recent reports of the production of tetrodotoxin/anhydrotetrodotoxin by several bacterial species, including strains of the family Vibrionaceae, Pseudomonas sp., and Photobacterium phosphoreum, point toward a bacterial origin of this family of toxins (3).
Toxicity ValuesLD50: 334 ug/kg (Oral, Mouse) (1)
Lethal Dose25 mg for an adult human. (1)
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of chronic and breakthrough pain in advanced cancer patients as well as for the treatment of opioid dependence. Tetrodotoxin is produced by bacteria (genus Pseudoalteromonas, Pseudomonas, Vibrio) and found in certain species of Tetraodontiformes (puffer fish, porcupine fish, ocean sunfish, triggerfish), from which its name is derived. (1)
Minimum Risk LevelNot Available
Health EffectsTetrodoxin is a potent neurotoxin and produces paralysis, which may be followed by death due to respiratory failure. (1)
SymptomsSymptoms of tetrodoxin poisoning typically occur within 30 minutes of exposure and include paresthesias of the lips and tongue, sialorrhea, sweating, headache, weakness, lethargy, ataxia, uncoordination, tremor, paralysis, cyanosis, aphonia, dysphagia, seizures, dyspnoea, bronchorrhea, bronchospasm, respiratory failure, coma, and hypotension. Gastroenteric symptoms are often severe and include nausea, vomiting, diarrhoea, and abdominal pain. Cardiac arrhythmias may precede complete respiratory failure and cardiovascular collapse. (1)
TreatmentTreatment of tetrodoxin poisoning is supportive and symptomatic, with aggressive early airway management. In cases of ingestion gastric lavage and/or the administration of active charcoal may be performed. Alpha adrenergic agonists are recommended in addition to intravenous fluids to combat hypotension. (1)
Concentrations
Not Available
DrugBank IDDB05232
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTetrodotoxin
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID443368
Kegg Compound IDC11692
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available