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Record Information
Version2.0
Creation Date2014-08-29 04:54:13 UTC
Update Date2014-12-24 20:26:36 UTC
Accession NumberT3D4038
Identification
Common NameGonyautoxin I
ClassSmall Molecule
DescriptionGonyautoxin I is found in mollusks. Gonyautoxin I is produced by Gonyaulax and Protogonyaulax species and isolated from shellfish. It is a neurotoxin and the causal agent, with Saxitoxin, of shellfish poisoning.
Compound Type
  • Amide
  • Amine
  • Animal Toxin
  • Ester
  • Ether
  • Food Toxin
  • Marine Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
Synonyms
Synonym
Gonyautoxin 1
Gonyautoxin-I
GTX I
GTX1
Toxin GTX1
Chemical FormulaC10H17N7O9S
Average Molecular Mass411.348 g/mol
Monoisotopic Mass411.081 g/mol
CAS Registry Number60748-39-2
IUPAC Name{4-[(carbamoyloxy)methyl]-5,10,10-trihydroxy-2,6-diimino-decahydropyrrolo[1,2-c]purin-9-yl}oxidanesulfonic acid
Traditional Name{4-[(carbamoyloxy)methyl]-5,10,10-trihydroxy-2,6-diimino-hexahydropyrrolo[1,2-c]purin-9-yl}oxidanesulfonic acid
SMILESON1C(COC(O)=N)C2NC(=N)NC22N(CC(OS(O)(=O)=O)C2(O)O)C1=N
InChI IdentifierInChI=1/C10H17N7O9S/c11-6-14-5-3(2-25-8(13)18)17(21)7(12)16-1-4(26-27(22,23)24)10(19,20)9(5,16)15-6/h3-5,12,19-21H,1-2H2,(H2,13,18)(H3,11,14,15)(H,22,23,24)
InChI KeyInChIKey=CETRDCWBMBILAL-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
  • 1,3-diazinane
  • Sulfuric acid monoester
  • Sulfate-ester
  • Sulfuric acid ester
  • Alkyl sulfate
  • N-hydroxyguanidine
  • 2-imidazoline
  • Organic sulfuric acid or derivatives
  • Pyrrolidine
  • Carbamic acid ester
  • Guanidine
  • Carbonic acid derivative
  • Organic 1,3-dipolar compound
  • Organoheterocyclic compound
  • Azacycle
  • Carboximidamide
  • Polyol
  • Propargyl-type 1,3-dipolar organic compound
  • Carbonyl hydrate
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Imine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
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 Solubility3.05 g/LALOGPS
logP-2.3ALOGPS
logP-3.7ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)-1.9ChemAxon
pKa (Strongest Basic)10.13ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area254.85 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity101.69 m³·mol⁻¹ChemAxon
Polarizability35.01 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007o-7619000000-ed68b555eab6772d72b92017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00fu-9210710000-dd21a56151783c5d669b2017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2009600000-5bd70d0c7323125dc4a82016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w93-1049000000-32fd5080f106be27748c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01oy-9030000000-e35b154cd167754ef1c82016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9002100000-2e600e9ec3735e4b89792016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9002000000-fb621e4e590b8e9d6d652016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9120000000-5823afe405114b8d148d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000900000-7325e0beea21a1d7d5532021-09-21View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ik9-0019500000-b90a75fcb47e1061a7102021-09-21View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udj-0091000000-6f88df41cc8bd598701e2021-09-21View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02ta-0009400000-7feadb65706cff02f0292021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xv-9004100000-7fe00f4d9626977ccda92021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9154000000-b86a4c99b2c7fb3017eb2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityThe gonyautoxin toxicity is caused by the reversibly binding to its receptor site on the voltage-gated sodium channel on excitable cells, thus blocking the influx of Na+ ions and preventing nerve and muscle cells from producing action potentials, therefore, blocking neuronal transmission, which results in a temporary paralysis of muscles. Gonyautoxin paralyzes the injected sphincter reducing anal tone, leaving the other muscles unaffected. The paretic effect lasts for more than one week. Its effect is dose-dependent and the binding to its receptor site is only regulated by affinity.(1)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB33506
PubChem Compound ID46173840
ChEMBL IDNot Available
ChemSpider ID30791735
KEGG IDC16855
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D4038.pdf
General References
  1. Garrido R, Lagos N, Lattes K, Abedrapo M, Bocic G, Cuneo A, Chiong H, Jensen C, Azolas R, Henriquez A, Garcia C: Gonyautoxin: new treatment for healing acute and chronic anal fissures. Dis Colon Rectum. 2005 Feb;48(2):335-40; discussion 340-3. [15812585 ]
  2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available