ContaminantDB: Grayanotoxin II

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (39)XML

Record Information

Version

1.0

Creation Date

2009-07-23 18:26:12 UTC

Update Date

2026-04-05 15:21:11 UTC

Accession Number

CHEM002427

Identification

Common Name

Grayanotoxin II

Class

Small Molecule

Description

Grayanotoxin II is an exogenous organic compound with the formula C20H32O5 and an average molecular weight of 352.47 g/mol. It exists as a solid at room temperature. Grayanotoxin II belongs to the alcohols and polyols, a subclass of organooxygen compounds within the organic compounds. This compound is found in or released from 13 recorded sources across several sectors. These include electrical and electronic equipment such as batteries, capacitors, printed circuit boards, cell phones, and wires and cables; textiles, leather and furnishings including carpets, rugs, and synthetic textiles; food packaging within the food, food processing and cookware sector; medical devices in healthcare, pharmaceuticals and veterinary products; and lubricants used in energy, oil and gas as well as industrial manufacturing and chemical processing. Recorded exposure routes for the compound include oral, inhalation, and touch. Grayanotoxin II interacts with 13 recorded protein targets, including sodium channel protein type 1 subunit alpha (SCN1A), sodium channel protein type 2 subunit alpha (SCN2A), sodium channel protein type 10 subunit alpha (SCN10A), sodium channel protein type 11 subunit alpha (SCN11A), and nine other proteins. Grayanotoxins bind to specific sodium ion channels in cell membranes, which prevents inactivation and leaves excitable cells depolarized.

Contaminant Sources

T3DB toxins

Contaminant Type

Human Neurotoxin
Natural Compound
Organic Compound
PFAS
Phytotoxin
Plant Toxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂O₅

Average Molecular Mass

352.465 g/mol

Monoisotopic Mass

352.225 g/mol

CAS Registry Number

4678-44-8

IUPAC Name

Not Available

Traditional Name

5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecane-3,4,6,14,16-pentol

SMILES

CC1(O)CC23CC(O)C4(O)C(CC(O)C4(C)C)C(=C)C2CCC1C3O

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

InChI Key

KEOQZUCOGXIEQR-UHFFFAOYSA-N

Chemical Taxonomy

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 ).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Tertiary alcohols

Alternative Parents

Substituents

Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Polyol
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

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

Predicted Properties

Property	Value	Source
Water Solubility	7.76 g/L	ALOGPS
logP	0.58	ALOGPS
logP	-0.29	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	13.06	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	101.15 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	93.15 m³·mol⁻¹	ChemAxon
Polarizability	38.43 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
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

Toxicity Profile

Route of Exposure

Oral (ingestion) (2) ; dermal (2)

Mechanism of Toxicity

Grayanotoxins bind to specific sodium ion channels in cell membranes. The grayanotoxins prevent inactivation, leaving excitable cells depolarized. (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

Grayanotoxins are toxins found in rhododendrons and other plants of the family Ericaceae. (1)

Minimum Risk Level

Not Available

Health Effects

Grayanotoxins affect the nervous system but are not usually fatal. (1)

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)

Treatment

Medical treatment is not often needed but sometimes atropine therapy, vasopressors and other agents are used to mitigate symptoms. (1)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

14060929

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Grayanotoxin II (CHEM002427)

Structure for CHEM002427: Grayanotoxin II