ContaminantDB: Anatoxin a

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2014-08-29 05:21:37 UTC

Update Date

2026-04-05 15:24:22 UTC

Accession Number

CHEM003084

Identification

Common Name

Anatoxin a

Class

Small Molecule

Description

Anatoxin-a, also known as Very Fast Death Factor, is a secondary, bicyclic amine alkaloid and cyanotoxin with acute neurotoxicity. It was first discovered in the early 1960s in Canada, and was isolated in 1972. The toxin is produced by seven different genera of cyanobacteria and has been reported in North America, Europe, Africa, Asia, and New Zealand. Symptoms of anatoxin exposure include loss of coordination, muscular fasciculations, convulsions and death by respiratory paralysis. Its mode of action is through the nicotinic acetylcholine receptor (nAchR) where it acts as an agonist of acetylcholine. As such, anatoxin-a has been used for medicinal purposes to investigate diseases characterized by low acetylcholine levels. Due to its high toxicity and potential presence in drinking water, anatoxin-a poses a threat to humans and animals. While methods for detection and water treatment exist, scientists have called for more research to improve reliability and efficacy. Anatoxin-a is not to be confused with anatoxin-a(S), another potent cyanotoxin that has a similar mechanism of action to that of anatoxin-a and is produced by many of the same cyanobacteria genera, but is structurally unrelated.

Contaminant Sources

T3DB toxins

Contaminant Type

Amine
Bacterial Toxin
Ester
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-Anatoxin	ChEMBL
Anatoxin I	MeSH
Anatoxin-a	MeSH
ANTX-a	MeSH

Chemical Formula

C₁₀H₁₅NO

Average Molecular Mass

165.232 g/mol

Monoisotopic Mass

165.115 g/mol

CAS Registry Number

64285-06-9

IUPAC Name

1-{9-azabicyclo[4.2.1]non-2-en-2-yl}ethan-1-one

Traditional Name

anatoxin-a

SMILES

CC(=O)C1=CCCC2CCC1N2

InChI Identifier

InChI=1S/C10H15NO/c1-7(12)9-4-2-3-8-5-6-10(9)11-8/h4,8,10-11H,2-3,5-6H2,1H3

InChI Key

SGNXVBOIDPPRJJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as anatoxins. These are organic compounds containing or derived from anatoxin, homoanatoxin or other analogues. Anatoxins constitute a class of potent neurotoxic alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Anatoxins

Sub Class

Not Available

Direct Parent

Anatoxins

Alternative Parents

Substituents

Anatoxin skeleton
Azepine
Beta-aminoketone
Pyrrolidine
Ketone
Secondary aliphatic amine
Secondary amine
Organoheterocyclic compound
Azacycle
Organooxygen compound
Organonitrogen compound
Organic oxide
Carbonyl group
Organopnictogen compound
Hydrocarbon derivative
Amine
Organic nitrogen compound
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

tropane alkaloid (CHEBI:2706 )
Tropane alkaloids (C10841 )
Anatoxins (C10841 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Plasma Membrane
Sarcoplasmic Reticulum

Biofluid Locations

Not Available

Tissue Locations

Nerve Synapse

Pathways

Name	SMPDB Link	KEGG Link
Apoptosis	Not Available	map04210
Rna polymerase	Not Available	map03020
Metabolic Pathways	Not Available	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	5.57 g/L	ALOGPS
logP	1.25	ALOGPS
logP	1.19	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	19.12	ChemAxon
pKa (Strongest Basic)	10.21	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.1 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	48.83 m³·mol⁻¹	ChemAxon
Polarizability	18.59 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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	splash10-007c-5900000000-ba20b4a810e4d42d829b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-102ee8cf61f9a3fca40f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-1900000000-62ceaf7d188b3e837a0a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0frx-9100000000-86534e8472925e41161d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-61d9204215a77bd1ba8d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03k9-0900000000-0441fd550dfe2b4045ad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-7900000000-d66fc910a434d2965dae	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-a8baa4b5218fe504eb78	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-1900000000-1056846b3b1bb9f81930	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-4900000000-3a6f2ccf799ae8ef3163	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-5a67776f4d9f6897ce74	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-86ab77a5296b6cbb848b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03kd-4900000000-29dfc9ff3d3d7c9d9b9e	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	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	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C 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

Anatoxin-a is an agonist of both neuronal α4β2 and α4 nicotinic acetylcholine receptors present in the CNS as well as the α12βγδ muscle-type nAchRs that are present at the neuromuscular junction. Anatoxin-a has an affinity for these receptors that is about 20 times greater than that of acetylcholine. Anatoxin-a also shows much less potency in the CNS than in neuromuscular junctions. In hippocampal and brain stem neurons, a 5 to 10 times greater concentration of anatoxin-a was necessary to activate nAchRs than what was required in the PNS. Anatoxin-a binding is irreversible, and the anatoxin-a nAchR complex cannot be broken down by acetylcholinesterase. Thus, the nAchR is temporarily locked open and after a period of time becomes desensitized. In this desensitized state the nAchRs no longer let cations pass through, which ultimately leads to a blockage of neuromuscular transmission.

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

Anatoxin-a, also known as Very Fast Death Factor, is a secondary, bicyclic amine alkaloid and cyanotoxin with acute neurotoxicity. It was first discovered in the early 1960s in Canada, and was isolated in 1972. The toxin is produced by seven different genera of cyanobacteria and has been reported in North America, Europe, Africa, Asia, and New Zealand. Symptoms of anatoxin exposure include loss of coordination, muscular fasciculations, convulsions and death by respiratory paralysis. As such, anatoxin-a has been used for medicinal purposes to investigate diseases characterized by low acetylcholine levels. Due to its high toxicity and potential presence in drinking water, anatoxin-a poses a threat to humans and animals. While methods for detection and water treatment exist, scientists have called for more research to improve reliability and efficacy. Anatoxin-a is not to be confused with anatoxin-a(S), another potent cyanotoxin that has a similar mechanism of action to that of anatoxin-a and is produced by many of the same cyanobacteria genera, but is structurally unrelated. (Wikipedia)

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

HMDB0248385

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

C00002273

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

381822

ChEBI ID

Not Available

PubChem Compound ID

Not Available

Kegg Compound ID

C10841

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Anatoxin a (CHEM003084)

Structure for CHEM003084: Anatoxin a