Record Information
Version1.0
Creation date2010-04-08 22:04:34 UTC
Update date2018-05-29 00:29:02 UTC
Primary IDFDB000437
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSaxitoxin
DescriptionParalytic poison from Alaska butter clams (Saxidomus giganteus), toxic mussels (Mytilus californianus), the plankton Gonyaulax cantenella and Protogonyaulax tamarensis. Causal agent of paralytic shellfish poisoning Saxitoxin (STX) is a neurotoxin naturally produced by certain species of marine dinoflagellates (Alexandrium species, Gymnodinium species, Pyrodinium species) and cyanobacteria (Anabaena species, some Aphanizomenon subspecies, Cylindrospermopsis species, Lyngbya species, Planktothrix species). Ingestion of saxitoxin (usually through shellfish contaminated by toxic algal blooms) is responsible for the human illness known as paralytic shellfish poisoning (PSP).
CAS Number35523-89-8
Structure
Thumb
Synonyms
SynonymSource
Gonyaulax catenella poisonHMDB
Mytilus californianus poisonHMDB
Saxidomus giganteus poisonHMDB
Saxitoxin (8ci)HMDB
Gonyaulax toxinMeSH
MitilotoxinMeSH
Toxin, gonyaulaxMeSH
SaxitoninMeSH
Predicted Properties
PropertyValueSource
Water Solubility4.12 g/LALOGPS
logP-2.7ALOGPS
logP-2.8ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)10.74ChemAxon
pKa (Strongest Basic)9.89ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area182.31 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity78.13 m³·mol⁻¹ChemAxon
Polarizability28.07 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H17N7O4
IUPAC name[(4R,10aS,10bS)-2-amino-10,10-dihydroxy-6-imino-3H,4H,5H,6H,8H,9H,10H,10bH-pyrrolo[1,2-c]purin-4-yl]methyl carbamate
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)/t4-,5-,10-/m0/s1
InChI KeyRPQXVSUAYFXFJA-HGRQIUPRSA-N
Isomeric SMILESNC(=O)OC[C@@H]1NC(=N)N2CCC(O)(O)[C@@]22N=C(N)N[C@@H]12
Average Molecular Weight299.2865
Monoisotopic Molecular Weight299.134202067
Classification
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
  • 1,3-diazinane
  • Imidazolidine
  • Pyrrolidine
  • Guanidine
  • Organoheterocyclic compound
  • Carboximidamide
  • Carbonyl hydrate
  • Carboximidic acid derivative
  • Azacycle
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Industrial application:

Indirect biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 40.13%; H 5.73%; N 32.76%; O 21.38%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +130DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00bc-9150000000-c7788a08720613df04ddView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-5294100000-915e52718988f6d4be56View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-1097000000-1045553e7245622b4f08View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1090000000-621ed7cec113c38d0486View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9120000000-1eb9eb2878c62a2b539eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9030000000-ebf5f0a9cd0e1074d70aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-efd2b04051c5353e8364View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-b7b1dbf14e0d49a40002View in MoNA
ChemSpider ID34106
ChEMBL IDCHEMBL501134
KEGG Compound IDC13757
Pubchem Compound ID37165
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB29368
CRC / DFC (Dictionary of Food Compounds) IDBCC32-R:BCC32-R
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDSaxitoxin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference