| Record Information |
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| Version | 1.0 |
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| Creation Date | 2009-07-06 21:35:29 UTC |
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| Update Date | 2016-11-09 01:08:41 UTC |
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| Accession Number | CHEM002107 |
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| Identification |
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| Common Name | alpha-Agatoxin |
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| Class | Small Molecule |
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| Description | Agatoxins are a class of chemically diverse polyamine and peptide toxins which are isolated from the venom of various spiders, in particular the North American funnel-web spider (Agelenopsis aperta), after which agatoxins are named. alpha-Agatoxins are composed of polyamines which are attached to an aromatic moiety. They block the glutamate-activated receptor channels in the neuronal postsynaptic terminals of insects and mammals. (1) |
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| Contaminant Sources | |
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| Contaminant Type | - Amide
- Amine
- Animal Toxin
- Natural Compound
- Organic Compound
- Spider Toxin
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| Chemical Structure | |
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| Synonyms | | Value | Source |
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| a-Agatoxin | Generator | | Α-agatoxin | Generator | | Agatoxin 489 | MeSH | | Agatoxin-489 | MeSH |
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| Chemical Formula | C26H47N7O2 |
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| Average Molecular Mass | 489.697 g/mol |
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| Monoisotopic Mass | 489.379 g/mol |
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| CAS Registry Number | 128549-96-2 |
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| IUPAC Name | N-[3-(17-amino-1-hydroxy-1,5,9,14-tetraazaheptadecan-1-yl)propyl]-2-(1H-indol-3-yl)acetamide |
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| Traditional Name | N-[3-(17-amino-1-hydroxy-1,5,9,14-tetraazaheptadecan-1-yl)propyl]-2-(1H-indol-3-yl)acetamide |
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| SMILES | NCCCNCCCCNCCCNCCCN(O)CCCNC(=O)CC1=CNC2=CC=CC=C12 |
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| InChI Identifier | InChI=1S/C26H47N7O2/c27-11-5-14-28-12-3-4-13-29-15-6-16-30-17-7-19-33(35)20-8-18-31-26(34)21-23-22-32-25-10-2-1-9-24(23)25/h1-2,9-10,22,28-30,32,35H,3-8,11-21,27H2,(H,31,34) |
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| InChI Key | LIURIBSBVUMOJS-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Indoles and derivatives |
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| Sub Class | Indoles |
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| Direct Parent | 3-alkylindoles |
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| Alternative Parents | |
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| Substituents | - 3-alkylindole
- Substituted pyrrole
- Benzenoid
- Pyrrole
- Heteroaromatic compound
- Amino acid or derivatives
- Carboxamide group
- Secondary carboxylic acid amide
- Carboxylic acid derivative
- Secondary aliphatic amine
- Secondary amine
- Azacycle
- N-organohydroxylamine
- Organopnictogen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Organic nitrogen compound
- Amine
- Organic oxide
- Hydrocarbon derivative
- Carbonyl group
- Organic oxygen compound
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Exogenous |
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| Cellular Locations | |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Solid |
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| Appearance | White powder. |
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| Experimental Properties | | Property | Value |
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| Melting Point | Not Available | | Boiling Point | Not Available | | Solubility | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-008c-1549700000-501119752a578c927008 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-06sl-4944000000-75339ff8fec08d60e067 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-056c-3930000000-8d15f6829defd32f5195 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0241900000-5cbf1504e4ef06035b22 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-3893400000-381e821411fe14a6dfa7 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00xu-6920000000-bb3ae0dbaf92d949a39f | Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Injection (sting/bite) (3) |
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| Mechanism of Toxicity | alpha-Agatoxins block the glutamate-activated receptor channels in the neuronal postsynaptic terminals of insects and mammals, preventing excitory junction potential from developing. (1) |
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| Metabolism | Not Available |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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| Uses/Sources | Agatoxins are a class of chemically diverse polyamine and peptide toxins which are isolated from the venom of various spiders, in particular the North American funnel-web spider (Agelenopsis aperta). (1) |
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| Minimum Risk Level | Not Available |
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| Health Effects | alpha-Agatoxin causes a rapid reversible paralysis. Death can result from progressive hypotension or possibly raised intracranial pressure resulting from cerebral oedema. (1, 2) |
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| Symptoms | The bites of funnel-web spiders may cause tingling around the mouth and tongue, facial muscle twitching, nausea, vomiting, profuse sweating, salivation, and shortness of breath. Patients may also rapidly develop agitation, confusion and coma associated with hypertension, metabolic acidosis, dilation of the pupils, generalised muscle twitching and pulmonary oedema. (2) |
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| Treatment | First aid for funnel-web bites consists of applying a pressure immobilization bandage to slow venom movement. Further supportive care may be necessary, but the mainstay of treatment is antivenom. (2) |
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| Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | Not Available |
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| HMDB ID | Not Available |
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| FooDB ID | Not Available |
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| Phenol Explorer ID | Not Available |
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| KNApSAcK ID | Not Available |
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| BiGG ID | Not Available |
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| BioCyc ID | Not Available |
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| METLIN ID | Not Available |
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| PDB ID | Not Available |
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| Wikipedia Link | Not Available |
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| Chemspider ID | Not Available |
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| ChEBI ID | Not Available |
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| PubChem Compound ID | 131007 |
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| Kegg Compound ID | Not Available |
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| YMDB ID | Not Available |
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| ECMDB ID | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | Not Available |
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| General References | Not Available |
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