| Record Information |
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| Version | 1.0 |
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| Creation Date | 2009-07-23 18:26:12 UTC |
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| Update Date | 2016-11-09 01:08:46 UTC |
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| Accession Number | CHEM002427 |
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| Identification |
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| Common Name | Grayanotoxin II |
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| Class | Small Molecule |
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| Description | Grayanotoxins are toxins found in rhododendrons and other plants of the family Ericaceae. It can be found in honey made from their nectar and cause a very rare poisonous reaction called grayanotoxin poisoning, honey intoxication, or rhododendron poisoning. (1) |
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| Contaminant Sources | |
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| Contaminant Type | - Natural Compound
- Organic Compound
- Plant Toxin
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| Chemical Structure | |
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| Synonyms | Not Available |
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| Chemical Formula | C20H32O5 |
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| Average Molecular Mass | 352.465 g/mol |
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| Monoisotopic Mass | 352.225 g/mol |
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| CAS Registry Number | 4678-44-8 |
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| IUPAC Name | 5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecane-3,4,6,14,16-pentol |
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| Traditional Name | 5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecane-3,4,6,14,16-pentol |
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| SMILES | CC1(O)CC23CC(O)C4(O)C(CC(O)C4(C)C)C(=C)C2CCC1C3O |
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| InChI Identifier | InChI=1S/C20H32O5/c1-10-11-5-6-12-16(23)19(11,9-18(12,4)24)8-15(22)20(25)13(10)7-14(21)17(20,2)3/h11-16,21-25H,1,5-9H2,2-4H3 |
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| InChI Key | KEOQZUCOGXIEQR-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). |
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| Kingdom | Organic compounds |
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| Super Class | Organic oxygen compounds |
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| Class | Organooxygen compounds |
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| Sub Class | Alcohols and polyols |
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| Direct Parent | Tertiary alcohols |
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| Alternative Parents | |
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| Substituents | - Tertiary alcohol
- Cyclic alcohol
- Secondary alcohol
- Polyol
- Hydrocarbon derivative
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic 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 | splash10-00kr-0009000000-080300d45f1240cae267 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014r-0029000000-733b9050dac66f653dd3 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-014i-0529000000-ed7f5acdb7c10290d3ed | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0009000000-8998f938266edcd3d88c | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0f89-0009000000-bd48f2bd4675ef569be1 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004j-3963000000-0f57561692cad584d7a8 | Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Oral (ingestion) (2) ; dermal (2) |
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| Mechanism of Toxicity | Grayanotoxins bind to specific sodium ion channels in cell membranes. The grayanotoxins prevent inactivation, leaving excitable cells depolarized. (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 | Grayanotoxins are toxins found in rhododendrons and other plants of the family Ericaceae. (1) |
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| Minimum Risk Level | Not Available |
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| Health Effects | Grayanotoxins affect the nervous system but are not usually fatal. (1) |
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| Symptoms | Initial symptoms include excessive salivation, perspiration, vomiting, dizziness, weakness and paresthesia in the extremities and around the mouth, low blood pressure and sinus bradycardia. In higher doses symptoms can include loss of coordination, severe and progressive muscular weakness, bradycardia (and, paradoxically, ventricular tachycardia), and nodal rhythm or Wolff-Parkinson-White syndrome. (1) |
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| Treatment | Medical treatment is not often needed but sometimes atropine therapy, vasopressors and other agents are used to mitigate symptoms. (1) |
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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 | 14060929 |
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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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