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Record Information
Version2.0
Creation Date2009-07-03 22:19:21 UTC
Update Date2014-12-24 20:25:41 UTC
Accession NumberT3D2551
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).
Compound Type
  • Amide
  • Amine
  • Animal Toxin
  • Bacterial Toxin
  • Ester
  • Ether
  • Food Toxin
  • Marine Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
Synonyms
Synonym
Gonyaulax catenella poison
Mytilus californianus poison
Saxidomus giganteus poison
Saxitoxin (8ci)
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=1/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 KeyInChIKey=RPQXVSUAYFXFJA-UHFFFAOYNA-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
LogPNot 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-2097000000-3814af84eec46bf93e43JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1090000000-ce1fb02a6f246a7e3403JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9120000000-7105c7189bbd1aa881edJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9040000000-5dc55665b8d155cb69b5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9010000000-4619f97d0750a0c8188bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-9b2ea3145ece3a9f9f0cJSpectraViewer
Toxicity Profile
Route of ExposureInjection (sting/bite) (5)
Mechanism of ToxicitySaxitoxin blocks voltage-gated sodium channels of nerve cells. (3)
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). (3)
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. (3)
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. (3, 4)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB29368
PubChem Compound ID37165
ChEMBL IDNot Available
ChemSpider ID34106
KEGG IDC13757
UniProt IDNot Available
OMIM ID
ChEBI ID610951
BioCyc IDNot Available
CTD IDD012530
Stitch IDSaxitoxin
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkSaxitoxin
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Holstege CP, Bechtel LK, Reilly TH, Wispelwey BP, Dobmeier SG: Unusual but potential agents of terrorists. Emerg Med Clin North Am. 2007 May;25(2):549-66; abstract xi. [17482032 ]
  2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  3. Wikipedia. Saxitoxin. Last Updated 29 April 2009. [Link]
  4. Wikipedia. Paralytic shellfish poisoning. Last Updated 19 March 2009. [Link]
  5. Wikipedia. Mollusca. Last Updated 5 August 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Voltage-gated sodium channel activity
Specific Function:
Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient.
Gene Name:
SCN1A
Uniprot ID:
P35498
Molecular Weight:
228969.49 Da
References
  1. Wikipedia. Saxitoxin. Last Updated 29 April 2009. [Link]
General Function:
Voltage-gated sodium channel activity
Specific Function:
Tetrodotoxin-resistant channel that mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. Plays a role in neuropathic pain mechanisms.
Gene Name:
SCN10A
Uniprot ID:
Q9Y5Y9
Molecular Weight:
220623.605 Da
References
  1. Wikipedia. Saxitoxin. Last Updated 29 April 2009. [Link]
General Function:
Voltage-gated sodium channel activity
Specific Function:
This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant sodium channel isoform. Also involved, with the contribution of the receptor tyrosine kinase NTRK2, in rapid BDNF-evoked neuronal depolarization.
Gene Name:
SCN11A
Uniprot ID:
Q9UI33
Molecular Weight:
204919.66 Da
References
  1. Wikipedia. Saxitoxin. Last Updated 29 April 2009. [Link]
General Function:
Voltage-gated sodium channel activity
Specific Function:
Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient.
Gene Name:
SCN2A
Uniprot ID:
Q99250
Molecular Weight:
227972.64 Da
References
  1. Wikipedia. Saxitoxin. Last Updated 29 April 2009. [Link]
General Function:
Voltage-gated sodium channel activity
Specific Function:
Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient.
Gene Name:
SCN3A
Uniprot ID:
Q9NY46
Molecular Weight:
226291.905 Da
References
  1. Wikipedia. Saxitoxin. Last Updated 29 April 2009. [Link]
General Function:
Voltage-gated sodium channel activity
Specific Function:
This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. This sodium channel may be present in both denervated and innervated skeletal muscle.
Gene Name:
SCN4A
Uniprot ID:
P35499
Molecular Weight:
208059.175 Da
References
  1. Wikipedia. Saxitoxin. Last Updated 29 April 2009. [Link]
General Function:
Voltage-gated sodium channel activity involved in sa node cell action potential
Specific Function:
This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential. Channel inactivation is regulated by intracellular calcium levels.
Gene Name:
SCN5A
Uniprot ID:
Q14524
Molecular Weight:
226937.475 Da
References
  1. Wikipedia. Saxitoxin. Last Updated 29 April 2009. [Link]
General Function:
Voltage-gated sodium channel activity
Specific Function:
Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient.
Gene Name:
SCN7A
Uniprot ID:
Q01118
Molecular Weight:
193491.605 Da
References
  1. Wikipedia. Saxitoxin. Last Updated 29 April 2009. [Link]
General Function:
Voltage-gated sodium channel activity
Specific Function:
Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. In macrophages and melanoma cells, isoform 5 may participate in the control of podosome and invadopodia formation.
Gene Name:
SCN8A
Uniprot ID:
Q9UQD0
Molecular Weight:
225278.005 Da
References
  1. Wikipedia. Saxitoxin. Last Updated 29 April 2009. [Link]
General Function:
Voltage-gated sodium channel activity
Specific Function:
Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-sensitive Na(+) channel isoform. Plays a role in pain mechanisms, especially in the development of inflammatory pain (By similarity).
Gene Name:
SCN9A
Uniprot ID:
Q15858
Molecular Weight:
226370.175 Da
References
  1. Wikipedia. Saxitoxin. Last Updated 29 April 2009. [Link]
General Function:
Voltage-gated sodium channel activity involved in purkinje myocyte action potential
Specific Function:
Crucial in the assembly, expression, and functional modulation of the heterotrimeric complex of the sodium channel. The subunit beta-1 can modulate multiple alpha subunit isoforms from brain, skeletal muscle, and heart. Its association with neurofascin may target the sodium channels to the nodes of Ranvier of developing axons and retain these channels at the nodes in mature myelinated axons.Isoform 2: Cell adhesion molecule that plays a critical role in neuronal migration and pathfinding during brain development. Stimulates neurite outgrowth.
Gene Name:
SCN1B
Uniprot ID:
Q07699
Molecular Weight:
24706.955 Da
References
  1. Wikipedia. Saxitoxin. Last Updated 29 April 2009. [Link]
General Function:
Voltage-gated sodium channel activity involved in cardiac muscle cell action potential
Specific Function:
Crucial in the assembly, expression, and functional modulation of the heterotrimeric complex of the sodium channel. The subunit beta-2 causes an increase in the plasma membrane surface area and in its folding into microvilli. Interacts with TNR may play a crucial role in clustering and regulation of activity of sodium channels at nodes of Ranvier (By similarity).
Gene Name:
SCN2B
Uniprot ID:
O60939
Molecular Weight:
24325.69 Da
References
  1. Wikipedia. Saxitoxin. Last Updated 29 April 2009. [Link]
General Function:
Voltage-gated sodium channel activity involved in cardiac muscle cell action potential
Specific Function:
Modulates channel gating kinetics. Causes unique persistent sodium currents. Inactivates the sodium channel opening more slowly than the subunit beta-1. Its association with neurofascin may target the sodium channels to the nodes of Ranvier of developing axons and retain these channels at the nodes in mature myelinated axons (By similarity).
Gene Name:
SCN3B
Uniprot ID:
Q9NY72
Molecular Weight:
24702.08 Da
References
  1. Wikipedia. Saxitoxin. Last Updated 29 April 2009. [Link]
General Function:
Voltage-gated sodium channel activity involved in cardiac muscle cell action potential
Specific Function:
Modulates channel gating kinetics. Causes negative shifts in the voltage dependence of activation of certain alpha sodium channels, but does not affect the voltage dependence of inactivation. Modulates the suceptibility of the sodium channel to inhibition by toxic peptides from spider, scorpion, wasp and sea anemone venom.
Gene Name:
SCN4B
Uniprot ID:
Q8IWT1
Molecular Weight:
24968.755 Da
References
  1. Wikipedia. Saxitoxin. Last Updated 29 April 2009. [Link]