ContaminantDB: Grayanotoxin I

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (14)XML

Record Information

Version

1.0

Creation Date

2009-07-23 18:26:11 UTC

Update Date

2016-11-09 01:08:46 UTC

Accession Number

CHEM002426

Identification

Common Name

Grayanotoxin I

Class

Small Molecule

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)

Contaminant Sources

T3DB toxins

Contaminant Type

Ester
Ether
Natural Compound
Organic Compound
Plant Toxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Acetylandromedol	MeSH
Andromedotoxin	MeSH

Chemical Formula

C₂₂H₃₆O₇

Average Molecular Mass

412.517 g/mol

Monoisotopic Mass

412.246 g/mol

CAS Registry Number

4720-09-6

IUPAC Name

3,4,6,9,14-pentahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl acetate

Traditional Name

3,4,6,9,14-pentahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl acetate

SMILES

CC(=O)OC1C2CCC3C1(CC2(C)O)CC(O)C1(O)C(CC(O)C1(C)C)C3(C)O

InChI Identifier

InChI=1S/C22H36O7/c1-11(23)29-17-12-6-7-13-20(5,27)14-8-15(24)18(2,3)22(14,28)16(25)9-21(13,17)10-19(12,4)26/h12-17,24-28H,6-10H2,1-5H3

InChI Key

NXCYBYJXCJWMRY-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as leucothol and grayanotoxane diterpenoids. These are diterpenoids with a structure based either on the leucothol or the grayanotoxane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Leucothol and grayanotoxane diterpenoids

Alternative Parents

Substituents

Grayanotoxane diterpenoid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	28.1 mg/mL at 12°C [SEIDELL,A (1941)]

Predicted Properties

Property	Value	Source
Water Solubility	4.06 g/L	ALOGPS
logP	0.66	ALOGPS
logP	-0.77	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	13.06	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.45 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	104.1 m³·mol⁻¹	ChemAxon
Polarizability	44.06 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	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	splash10-01bd-3309000000-1fa8eb7e1da3343f09df	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	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	splash10-004j-0009100000-5ddf7d9c194fa15b4bbe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fba-0009000000-b9fda3cf49e8fd4e3ed9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ufr-0009000000-8da669856576af22490a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03dl-1009500000-01c0f615981e0767c5b2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6x-2009100000-43ce097ad4faf4e8b7df	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fb9-4509000000-c6f0b485a9a5c03398eb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0008900000-e4c9c1a68bd32f0602cb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0009200000-3ebeb6d15944444a471a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-054o-4928100000-86cb846976a7a9f60f45	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-2000900000-64262917c7823f9be5ee	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bt9-9006500000-3f3a2de14a2eb410f35a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000100000-9cbe2a357d4800479f4b	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
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	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	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	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

231125

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 I (CHEM002426)

Structure for CHEM002426: Grayanotoxin I