| Record Information |
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| Version | 1.0 |
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| Creation Date | 2009-07-03 22:19:12 UTC |
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| Update Date | 2016-11-09 01:08:40 UTC |
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| Accession Number | CHEM002070 |
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| Identification |
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| Common Name | Histrionicotoxin |
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| Class | Small Molecule |
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| Description | Histrionicotoxin is a toxin found in poison dart frogs (genus Dendrobates). It is a potent non-competitive antagonist of nicotinic acetylcholine receptors. (1) |
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| Contaminant Sources | |
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| Contaminant Type | - Amine
- Animal Toxin
- Frog/Toad Toxin
- Natural Compound
- Organic Compound
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| Chemical Structure | |
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| Synonyms | Not Available |
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| Chemical Formula | C19H25NO |
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| Average Molecular Mass | 283.415 g/mol |
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| Monoisotopic Mass | 283.194 g/mol |
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| CAS Registry Number | 34272-51-0 |
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| IUPAC Name | 7-[(1E)-but-1-en-3-yn-1-yl]-2-[(2E)-pent-2-en-4-yn-1-yl]-1-azaspiro[5.5]undecan-8-ol |
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| Traditional Name | 7-[(1E)-but-1-en-3-yn-1-yl]-2-[(2E)-pent-2-en-4-yn-1-yl]-1-azaspiro[5.5]undecan-8-ol |
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| SMILES | [H]\C(CC1CCCC2(CCCC(O)C2\C([H])=C(/[H])C#C)N1)=C(\[H])C#C |
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| InChI Identifier | InChI=1S/C19H25NO/c1-3-5-7-10-16-11-8-14-19(20-16)15-9-13-18(21)17(19)12-6-4-2/h1-2,5-7,12,16-18,20-21H,8-11,13-15H2/b7-5+,12-6+ |
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| InChI Key | JBRYWENFVHQBGY-YTEPGLGFSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as histrionicotoxins. These are frog toxins structurally characterized by the presence of a dodecahydropyrrolo[1,2-a]quinolin-1-yl}ethanol moiety or a 2,7-disubstituted 1-azaspiro[5.5]undecan-8-ol moiety. |
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| Kingdom | Organic compounds |
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| Super Class | Alkaloids and derivatives |
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| Class | Histrionicotoxins |
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| Sub Class | Not Available |
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| Direct Parent | Histrionicotoxins |
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| Alternative Parents | |
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| Substituents | - Histrionicotoxin skeleton
- Azaspirodecane
- Piperidine
- Cyclic alcohol
- Secondary alcohol
- Acetylide
- Azacycle
- Organoheterocyclic compound
- Secondary amine
- Secondary aliphatic amine
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Amine
- Alcohol
- Aliphatic heteropolycyclic compound
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| Molecular Framework | Aliphatic 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 | |
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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 | splash10-0159-0090000000-64706804cb43fb4f58d9 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0333-0390000000-92f8e5e48d998d002c98 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ik9-5890000000-11b23ff54c2ee4711a33 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0090000000-cc56b475fb47297af3ce | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0090000000-d1357f3e3dff82db9cec | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-02t9-0490000000-0400a22d45510fe155b0 | Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Injection (sting/bite) (2) ; inhalation (smoking) (3) |
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| Mechanism of Toxicity | Histrionicotoxin is a potent non-competitive antagonist of nicotinic acetylcholine receptors. (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 | Histrionicotoxin is a toxin found in poison dart frogs (genus Dendrobates). (1) |
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| Minimum Risk Level | Not Available |
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| Health Effects | Histrionicotoxin is neurotoxic. (1) |
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| Symptoms | Histrionicotoxin is neurotoxic. (1) |
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| Treatment | Not Available |
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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 | 14134870 |
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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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