ContaminantDB: Gonyautoxin II

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-08-29 04:54:37 UTC

Update Date

2026-04-15 16:34:56 UTC

Accession Number

CHEM002999

Identification

Common Name

Gonyautoxin II

Class

Small Molecule

Description

Gonyautoxin II is a neurotoxin that is a sodium channel blocker.

Contaminant Sources

FooDB Chemicals
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Amide
Amine
Animal Toxin
Ester
Ether
Food Toxin
Marine Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Gonyautoxin III	MeSH, HMDB
Gonyautoxin II, 9-alpha-isomer	MeSH, HMDB
{[10,10-dihydroxy-2,6-diimino-9-(sulfooxy)-decahydropyrrolo[1,2-c]purin-4-yl]methoxy}carboximidate	Generator, HMDB
{[10,10-dihydroxy-2,6-diimino-9-(sulphooxy)-decahydropyrrolo[1,2-c]purin-4-yl]methoxy}carboximidate	Generator, HMDB
{[10,10-dihydroxy-2,6-diimino-9-(sulphooxy)-decahydropyrrolo[1,2-c]purin-4-yl]methoxy}carboximidic acid	Generator, HMDB
Gonyautoxin II	MeSH

Chemical Formula

C₁₀H₁₇N₇O₈S

Average Molecular Mass

395.349 g/mol

Monoisotopic Mass

395.086 g/mol

CAS Registry Number

60508-89-6

IUPAC Name

{4-[(carbamoyloxy)methyl]-10,10-dihydroxy-2,6-diimino-decahydropyrrolo[1,2-c]purin-9-yl}oxidanesulfonic acid

Traditional Name

{4-[(carbamoyloxy)methyl]-10,10-dihydroxy-2,6-diimino-hexahydro-1H-pyrrolo[1,2-c]purin-9-yl}oxidanesulfonic acid

SMILES

NC(=O)OCC1NC(=N)N2CC(OS(O)(=O)=O)C(O)(O)C22NC(=N)NC12

InChI Identifier

InChI=1S/C10H17N7O8S/c11-6-15-5-3(2-24-8(13)18)14-7(12)17-1-4(25-26(21,22)23)10(19,20)9(5,17)16-6/h3-5,19-20H,1-2H2,(H2,12,14)(H2,13,18)(H3,11,15,16)(H,21,22,23)

InChI Key

ARSXTTJGWGCRRR-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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Saxitoxins, gonyautoxins, and derivatives

Sub Class

Not Available

Direct Parent

Saxitoxins, gonyautoxins, and derivatives

Alternative Parents

Substituents

Saxitoxin-gonyautoxin skeleton
Imidazopyrimidine
Alkaloid or derivatives
1,3-diazinane
Sulfuric acid monoester
Sulfate-ester
Alkyl sulfate
Sulfuric acid ester
Imidazolidine
Organic sulfuric acid or derivatives
Pyrrolidine
Guanidine
Azacycle
Carboximidic acid derivative
Carboximidamide
Carbonyl hydrate
Organoheterocyclic compound
Hydrocarbon derivative
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Imine
Organic oxygen compound
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane
Microsome

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	3.22 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-4.2	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	-1.9	ChemAxon
pKa (Strongest Basic)	10.32	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	243.41 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	99.92 m³·mol⁻¹	ChemAxon
Polarizability	34.13 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fdo-6829000000-ee8ac99bf17208348f99	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00fu-9310700000-af6c7dff52137ef3e170	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-1029000000-40176d25bf90d6552449	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052s-2097000000-978b906350958f395ab0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0005-9150000000-9f5cb22b07d49b3c4331	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9003000000-ba990f1d035bed2f8a2e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9001000000-b4701b38c91768b28d3c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9110000000-851e696f0dddcb991cc1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f6x-0009000000-5537e1aaadefc2ffd501	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01oy-9004000000-05191795541a87ed2cde	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9132000000-122ca155d4853030474e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0009000000-c092305201217902f987	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0019000000-8d15d1916ec2ca63b083	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zfr-0091000000-0f225befa2a44b3ccb25	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

The 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)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Gonyautoxin II is a neurotoxin that is a sodium channel blocker.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0252915

FooDB ID

FDB011560

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

26502445

ChEBI ID

Not Available

PubChem Compound ID

53461849

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Gonyautoxin II (CHEM002999)

Structure for CHEM002999: Gonyautoxin II