T3DB: Grayanotoxin II

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

Targets (14)

Record Information

Version

2.0

Creation Date

2009-07-23 18:26:12 UTC

Update Date

2014-12-24 20:25:58 UTC

Accession Number

T3D3091

Identification

Common Name

Grayanotoxin II

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)

Compound Type

Natural Compound
Organic Compound
Plant Toxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
(3beta,6beta,14R)-Grayanotox-10(20)-ene-3,5,6,14,16-pentol
Deacetylanhydroandromedotoxin
G-II

Chemical Formula

C₂₀H₃₂O₅

Average Molecular Mass

352.465 g/mol

Monoisotopic Mass

352.225 g/mol

CAS Registry Number

4678-44-8

IUPAC Name

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

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

InChIKey=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
LogP	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	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-0009000000-080300d45f1240cae267	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014r-0029000000-733b9050dac66f653dd3	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0529000000-ed7f5acdb7c10290d3ed	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-8998f938266edcd3d88c	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f89-0009000000-bd48f2bd4675ef569be1	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004j-3963000000-0f57561692cad584d7a8	2016-08-03	View 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)

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

PubChem Compound ID

107976

ChEMBL ID

Not Available

ChemSpider ID

Not Available

KEGG ID

Not Available

UniProt ID

Not Available

OMIM ID

ChEBI ID

Not Available

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Grayanotoxin II

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Wikipedia. Grayanotoxin. Last Updated 13 September 2009. [Link]
Wikipedia. Phytotoxin. Last Updated 7 August 2009. [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Sodium channel protein type 1 subunit alpha

General Function:: Voltage-gated sodium channel activity
Specific Function:: Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient.
Gene Name:: SCN1A
Uniprot ID:: P35498
Molecular Weight:: 228969.49 Da

References

Target Details

2. Sodium channel protein type 10 subunit alpha

General Function:: Voltage-gated sodium channel activity
Specific Function:: Tetrodotoxin-resistant channel that mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. Plays a role in neuropathic pain mechanisms.
Gene Name:: SCN10A
Uniprot ID:: Q9Y5Y9
Molecular Weight:: 220623.605 Da

References

Target Details

3. Sodium channel protein type 11 subunit alpha

General Function:: Voltage-gated sodium channel activity
Specific Function:: This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant sodium channel isoform. Also involved, with the contribution of the receptor tyrosine kinase NTRK2, in rapid BDNF-evoked neuronal depolarization.
Gene Name:: SCN11A
Uniprot ID:: Q9UI33
Molecular Weight:: 204919.66 Da

References

Target Details

4. Sodium channel protein type 2 subunit alpha

General Function:: Voltage-gated sodium channel activity
Specific Function:: Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient.
Gene Name:: SCN2A
Uniprot ID:: Q99250
Molecular Weight:: 227972.64 Da

References

Target Details

5. Sodium channel protein type 3 subunit alpha

General Function:: Voltage-gated sodium channel activity
Specific Function:: Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient.
Gene Name:: SCN3A
Uniprot ID:: Q9NY46
Molecular Weight:: 226291.905 Da

References

Target Details

6. Sodium channel protein type 4 subunit alpha

General Function:: Voltage-gated sodium channel activity
Specific Function:: This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. This sodium channel may be present in both denervated and innervated skeletal muscle.
Gene Name:: SCN4A
Uniprot ID:: P35499
Molecular Weight:: 208059.175 Da

References

Target Details

7. Sodium channel protein type 5 subunit alpha

General Function:: Voltage-gated sodium channel activity involved in sa node cell action potential
Specific Function:: This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential. Channel inactivation is regulated by intracellular calcium levels.
Gene Name:: SCN5A
Uniprot ID:: Q14524
Molecular Weight:: 226937.475 Da

References

Target Details

8. Sodium channel protein type 7 subunit alpha

General Function:: Voltage-gated sodium channel activity
Specific Function:: Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient.
Gene Name:: SCN7A
Uniprot ID:: Q01118
Molecular Weight:: 193491.605 Da

References

Target Details

9. Sodium channel protein type 8 subunit alpha

General Function:: Voltage-gated sodium channel activity
Specific Function:: Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. In macrophages and melanoma cells, isoform 5 may participate in the control of podosome and invadopodia formation.
Gene Name:: SCN8A
Uniprot ID:: Q9UQD0
Molecular Weight:: 225278.005 Da

References

Target Details

10. Sodium channel protein type 9 subunit alpha

General Function:: Voltage-gated sodium channel activity
Specific Function:: Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-sensitive Na(+) channel isoform. Plays a role in pain mechanisms, especially in the development of inflammatory pain (By similarity).
Gene Name:: SCN9A
Uniprot ID:: Q15858
Molecular Weight:: 226370.175 Da

References

Target Details

11. Sodium channel subunit beta-1

General Function:: Voltage-gated sodium channel activity involved in purkinje myocyte action potential
Specific Function:: Crucial in the assembly, expression, and functional modulation of the heterotrimeric complex of the sodium channel. The subunit beta-1 can modulate multiple alpha subunit isoforms from brain, skeletal muscle, and heart. Its association with neurofascin may target the sodium channels to the nodes of Ranvier of developing axons and retain these channels at the nodes in mature myelinated axons.Isoform 2: Cell adhesion molecule that plays a critical role in neuronal migration and pathfinding during brain development. Stimulates neurite outgrowth.
Gene Name:: SCN1B
Uniprot ID:: Q07699
Molecular Weight:: 24706.955 Da

References

Target Details

12. Sodium channel subunit beta-2

General Function:: Voltage-gated sodium channel activity involved in cardiac muscle cell action potential
Specific Function:: Crucial in the assembly, expression, and functional modulation of the heterotrimeric complex of the sodium channel. The subunit beta-2 causes an increase in the plasma membrane surface area and in its folding into microvilli. Interacts with TNR may play a crucial role in clustering and regulation of activity of sodium channels at nodes of Ranvier (By similarity).
Gene Name:: SCN2B
Uniprot ID:: O60939
Molecular Weight:: 24325.69 Da

References

Target Details

13. Sodium channel subunit beta-3

General Function:: Voltage-gated sodium channel activity involved in cardiac muscle cell action potential
Specific Function:: Modulates channel gating kinetics. Causes unique persistent sodium currents. Inactivates the sodium channel opening more slowly than the subunit beta-1. Its association with neurofascin may target the sodium channels to the nodes of Ranvier of developing axons and retain these channels at the nodes in mature myelinated axons (By similarity).
Gene Name:: SCN3B
Uniprot ID:: Q9NY72
Molecular Weight:: 24702.08 Da

References

Target Details

14. Sodium channel subunit beta-4

General Function:: Voltage-gated sodium channel activity involved in cardiac muscle cell action potential
Specific Function:: Modulates channel gating kinetics. Causes negative shifts in the voltage dependence of activation of certain alpha sodium channels, but does not affect the voltage dependence of inactivation. Modulates the suceptibility of the sodium channel to inhibition by toxic peptides from spider, scorpion, wasp and sea anemone venom.
Gene Name:: SCN4B
Uniprot ID:: Q8IWT1
Molecular Weight:: 24968.755 Da

References

Grayanotoxin II (T3D3091)

Structure for T3D3091: Grayanotoxin II

Targets

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