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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:00 UTC
Update Date2019-07-23 06:03:55 UTC
HMDB IDHMDB0029368
Secondary Accession Numbers
  • HMDB29368
Metabolite Identification
Common NameSaxitoxin
DescriptionSaxitoxin is a paralytic 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 sp., Gymnodinium sp., Pyrodinium sp.) and cyanobacteria (Anabaena sp., some Aphanizomenon species, Cylindrospermopsis sp., Lyngbya sp., Planktothrix sp.). Ingestion of saxitoxin (usually through shellfish contaminated by toxic algal blooms) is responsible for the human illness known as paralytic shellfish poisoning (PSP). (Wikipedia
Structure
Data?1563861835
Synonyms
ValueSource
Gonyaulax catenella poisonHMDB
Mytilus californianus poisonHMDB
Saxidomus giganteus poisonHMDB
Saxitoxin (8ci)HMDB
Chemical FormulaC10H17N7O4
Average Molecular Weight299.2865
Monoisotopic Molecular Weight299.134202067
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
Traditional Name[(4R,10aS,10bS)-2-amino-10,10-dihydroxy-6-imino-3H,4H,5H,8H,9H,10bH-pyrrolo[1,2-c]purin-4-yl]methyl carbamate
CAS Registry Number35523-89-8
SMILES
NC(=O)OC[C@@H]1NC(=N)N2CCC(O)(O)[C@@]22N=C(N)N[C@@H]12
InChI Identifier
InChI=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
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as saxitoxins, gonyautoxins, and derivatives. These 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
  • Alkaloid or derivatives
  • Imidazopyrimidine
  • 1,3-diazinane
  • Pyrrolidine
  • 2-imidazoline
  • Tertiary amine
  • Guanidine
  • Azacycle
  • Organoheterocyclic compound
  • 1,1-diol
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Monocarboxylic acid or derivatives
  • Carbonyl hydrate
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Amine
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Industrial application:

Indirect biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00bc-9150000000-c7788a08720613df04ddJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-5294100000-915e52718988f6d4be56JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-1097000000-1045553e7245622b4f08JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1090000000-621ed7cec113c38d0486JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9120000000-1eb9eb2878c62a2b539eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9030000000-ebf5f0a9cd0e1074d70aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-efd2b04051c5353e8364JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-b7b1dbf14e0d49a40002JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000437
KNApSAcK IDNot Available
Chemspider ID34106
KEGG Compound IDC13757
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSaxitoxin
METLIN IDNot Available
PubChem Compound37165
PDB IDNot Available
ChEBI ID610951
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:17482032 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .