Saxitoxin (CHEM002079)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (14)XML
Record Information
Version1.0
Creation Date2009-07-03 22:19:21 UTC
Update Date2026-03-26 19:51:01 UTC
Accession NumberCHEM002079
Identification
Common NameSaxitoxin
ClassSmall Molecule
DescriptionSaxitoxin is a paralytic poison from Alaska butter clams (Saxidomus giganteus), toxic mussels (Mytilus californianus), the plankton Gonyaulax cantenella and Protogonyaulax tamarensis. Ingestion of saxitoxin (usually through shellfish contaminated by toxic algal blooms) is responsible for the human illness known as paralytic shellfish poisoning. Saxitoxin (STX) is a neurotoxin naturally produced by certain species of marine dinoflagellates (Alexandrium sp., Gymnodinium sp., Pyrodinium sp.) and cyanobacteria (Anabaena sp., some Aphanizomenon species, Cylindrospermopsis sp., Lyngbya sp., Planktothrix sp.). (Wikipedia) Saxitoxin has been shown to exhibit emetic function (1).
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Animal Toxin
  • Bacterial Toxin
  • Ester
  • Ether
  • Food Toxin
  • Marine Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC10H17N7O4
Average Molecular Mass299.287 g/mol
Monoisotopic Mass299.134 g/mol
CAS Registry Number35523-89-8
IUPAC Name({10,10-dihydroxy-2,6-diimino-decahydropyrrolo[1,2-c]purin-4-yl}methoxy)carboximidic acid
Traditional Name{10,10-dihydroxy-2,6-diimino-hexahydro-1H-pyrrolo[1,2-c]purin-4-yl}methoxycarboximidic acid
SMILESOC(=N)OCC1NC(=N)N2CCC(O)(O)C22NC(=N)NC12
InChI IdentifierInChI=1S/C10H17N7O4/c11-6-15-5-4(3-21-8(13)18)14-7(12)17-2-1-9(19,20)10(5,17)16-6/h4-5,19-20H,1-3H2,(H2,12,14)(H2,13,18)(H3,11,15,16)
InChI KeyRPQXVSUAYFXFJA-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as saxitoxins, gonyautoxins, and derivatives. Saxitoxins, gonyautoxins, and derivatives are compounds with a structure based on a 2,6-diamino-4-methyl-pyrrolo[1,2-c]purin-10-ol skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassSaxitoxins, gonyautoxins, and derivatives
Sub ClassNot Available
Direct ParentSaxitoxins, gonyautoxins, and derivatives
Alternative Parents
Substituents
  • Saxitoxin-gonyautoxin skeleton
  • Imidazopyrimidine
  • Alkaloid or derivatives
  • Hydropyrimidine
  • 1,4,5,6-tetrahydropyrimidine
  • 2-imidazoline
  • Pyrrolidine
  • Carbamic acid ester
  • Guanidine
  • Carbonic acid derivative
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Carbonyl hydrate
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Nerve Synapse
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.85 g/LALOGPS
logP-1.9ALOGPS
logP-4.4ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)-3.1ChemAxon
pKa (Strongest Basic)11.56ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area180.8 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity99.63 m³·mol⁻¹ChemAxon
Polarizability27.79 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
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, Positivesplash10-0ue9-2097000000-3814af84eec46bf93e43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1090000000-ce1fb02a6f246a7e3403Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9120000000-7105c7189bbd1aa881edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9040000000-5dc55665b8d155cb69b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9010000000-4619f97d0750a0c8188bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-9b2ea3145ece3a9f9f0cSpectrum
Toxicity Profile
Route of ExposureInjection (sting/bite) (4)
Mechanism of ToxicitySaxitoxin blocks voltage-gated sodium channels of nerve cells. (2)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesSaxitoxin is naturally produced by certain species of marine dinoflagellates (genus Alexandrium, Gymnodinium, Pyrodinium) and cyanobacteria (genus Anabaena, Aphanizomenon, Cylindrospermopsis, Lyngbya, Planktothrix). It is found in puffer fish and shellfish and is responsible for the human illness known as paralytic shellfish poisoning (PSP). (2)
Minimum Risk LevelNot Available
Health EffectsSaxitoxin is a neurotoxin. It causes a syndrome known as paralytic shellfish poisoning, which produces paralysis and may be fatal due to respiratory failure in extreme cases. (2)
SymptomsIngestion of shellfish containing saxitoxin causes a syndrome known as paralytic shellfish poisoning. Symptoms include nausea, vomiting, diarrhoea, abdominal pain, and tingling or burning lips, gums, tongue, face, neck, arms, legs, and toes. Shortness of breath, dry mouth, a choking feeling, confused or slurred speech, and lack of coordination are also possible. (2, 3)
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
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 LinkSaxitoxin
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID37173
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available