T3DB: Gonyautoxin I

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

Record Information

Version

2.0

Creation Date

2014-08-29 04:54:13 UTC

Update Date

2014-12-24 20:26:36 UTC

Accession Number

T3D4038

Identification

Common Name

Gonyautoxin I

Class

Small Molecule

Description

Gonyautoxin 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym
Gonyautoxin 1
Gonyautoxin-I
GTX I
GTX1
Toxin GTX1

Chemical Formula

C₁₀H₁₇N₇O₉S

Average Molecular Mass

411.348 g/mol

Monoisotopic Mass

411.081 g/mol

CAS Registry Number

60748-39-2

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

SMILES

ON1C(COC(O)=N)C2NC(=N)NC22N(CC(OS(O)(=O)=O)C2(O)O)C1=N

InChI Identifier

InChI=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 Key

InChIKey=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.

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
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 Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

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
LogP	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	3.05 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-3.7	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	-1.9	ChemAxon
pKa (Strongest Basic)	10.13	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	254.85 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	101.69 m³·mol⁻¹	ChemAxon
Polarizability	35.01 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-007o-7619000000-ed68b555eab6772d72b9	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00fu-9210710000-dd21a56151783c5d669b	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-2009600000-5bd70d0c7323125dc4a8	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0w93-1049000000-32fd5080f106be27748c	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01oy-9030000000-e35b154cd167754ef1c8	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9002100000-2e600e9ec3735e4b8979	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9002000000-fb621e4e590b8e9d6d65	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9120000000-5823afe405114b8d148d	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000900000-7325e0beea21a1d7d553	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ik9-0019500000-b90a75fcb47e1061a710	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udj-0091000000-6f88df41cc8bd598701e	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-02ta-0009400000-7feadb65706cff02f029	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03xv-9004100000-7fe00f4d9626977ccda9	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9154000000-b86a4c99b2c7fb3017eb	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-25	View 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

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB33506

PubChem Compound ID

46173840

ChEMBL ID

Not Available

ChemSpider ID

30791735

KEGG ID

C16855

UniProt ID

Not Available

OMIM ID

ChEBI ID

Not Available

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Not Available

MSDS

T3D4038.pdf

General References

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 ]
Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Gonyautoxin I (T3D4038)

Structure for T3D4038: Gonyautoxin I