Grayanotoxin I
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Basic Info
| Common Name | Grayanotoxin I(F04803) |
| 2D Structure | |
| 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. (L1251) |
| FRCD ID | F04803 |
| CAS Number | 4720-09-6 |
| PubChem CID | 19604097 |
| Formula | C54H27N3O18P3+3 |
| IUPAC Name | None |
| InChI Key | GHNOMWWHLPYWND-OCRXAWBASA-Q |
| InChI | InChI=1S/C54H24N3O18P3/c58-49(59)40-21-28-1-11-33(12-2-28)70-48-39-26-44(53(66)67)57-73-45(27-38(39)40)47(48)41(50(60)61)22-29-7-17-36(18-8-29)74-77(57)55(42(51(62)63)23-30-3-13-34(71-55)14-4-30)76-46(54(68)69)25-32-9-19-37(20-10-32)75-78(57)56(76)43(52(64)65)24-31-5-15-35(72-56)16-6-31/h1-3,5,7-9,11-13,15,17-19,21-27H,(H3-3,58,59,60,61,62,63,64,65,66,67,68,69)/p+3/b40-21+,41-22+,42-23-,43-24-,44-26-,46-25+ |
| Canonical SMILES | C1=CC2=CC=C1C=C(C3=CC4=C5C(=CC6=CC=C(C=C6)OP7[N+]8(C(=CC9=C=C=C(O8)C=C9)C(=O)O)P1C(=CC6=C=C=C(C=C6)OP([N+]11C(=CC6=C=C=C(O1)C=C6)C(=O)O)[N+]7(O4)C(=CC3=C5O2)C(=O)O)C(=O)O)C(=O)O)C(=O)O |
| Isomeric SMILES | C1=CC2=CC=C1/C=C(\C3=CC4=C5/C(=C\C6=CC=C(C=C6)OP7[N+]8(/C(=C\C9=C=C=C(O8)C=C9)/C(=O)O)P1/C(=C/C6=C=C=C(C=C6)OP([N+]11/C(=C\C6=C=C=C(O1)C=C6)/C(=O)O)[N+]7(O4)/C(=C\C3=C5O2)/C(=O)O)/C(=O)O)/C(=O)O)/C(=O)O |
| Classifies |
Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 1098.734 |
| Hydrogen Bond Donor Count | 6 |
| Hydrogen Bond Acceptor Count | 18 |
| Rotatable Bond Count | 6 |
| Complexity | 2770 |
| Monoisotopic Mass | 1098.05 |
| Exact Mass | 1098.05 |
| XLogP | 4.6 |
| Formal Charge | 3 |
| Heavy Atom Count | 78 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 6 |
| Defined Bond Stereocenter Count | 6 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Determination of Grayanotoxins from Rhododendron brachycarpum in Dietary Supplements and Homemade Wine by Liquid Chromatography-Quadrupole Time-of-Flight-Mass Spectrometry and Liquid Chromatography-Tandem Mass Spectrometry. | J Agric Food Chem | 2018 Feb 28 | 29433311 |
| Labrador tea--the aromatic beverage and spice: a review of origin, processing and safety. | J Sci Food Agric | 2015 Jun | 25156477 |
| A case of human poisoning by grayanotoxins following honey ingestion: elucidation of the toxin profile by mass spectrometry. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2015 | 25906176 |
| Determination of grayanotoxins in honey by liquid chromatography tandem mass spectrometry using dilute-and-shoot sample preparation approach. | J Agric Food Chem | 2014 Jun 18 | 24882375 |
| Toxic compounds in honey. | J Appl Toxicol | 2014 Jul | 24214851 |
| Grayanotoxin poisoning: 'mad honey disease' and beyond. | Cardiovasc Toxicol | 2012 Sep | 22528814 |
| Cardiac effects of "mad honey": a case series. | Clin Toxicol (Phila) | 2010 Jul | 20575670 |
| An unusual presentation of mad honey poisoning: acute myocardial infarction. | Int J Cardiol | 2008 Sep 26 | 17889382 |
| Grayanotoxin poisoning from Rhododendron simsii in an infant. | Hong Kong Med J | 2008 Oct | 18840915 |
| Clinical review of grayanotoxin/mad honey poisoning past and present. | Clin Toxicol (Phila) | 2008 Jun | 18568799 |
| Cardiac problems in mad-honey intoxication. | Circ J | 2008 Jul | 18577838 |
| Hypotension, bradycardia and syncope caused by honey poisoning. | Resuscitation | 2006 Mar | 16457936 |
| A rare cause of atrioventricular block: Mad Honey intoxication. | Int J Cardiol | 2005 Mar 18 | 15749202 |
| Determination of grayanotoxins in biological samples by LC-MS/MS. | J Agric Food Chem | 2001 Mar | 11312909 |
| Grayanotoxin poisoning in three goats. | J Am Vet Med Assoc | 2001 Feb 15 | 11229512 |
| Effects of grayanotoxin-I on threshold intensity and compound action potential of frog sciatic nerve. | J Physiol Pharmacol | 1996 Jun | 8807561 |
| [Acute life-threatening bradycardia: food poisoning by Turkish wild honey]. | Dtsch Med Wochenschr | 1996 Jul 26 | 8765701 |
| Poisoning by toxic honey in Turkey. | Arch Toxicol | 1993 | 8481104 |
| [Honey-induced poisoning]. | Schweiz Rundsch Med Prax | 1992 Apr 21 | 1579779 |
| Site of action of grayanotoxins in mad honey in rats. | J Appl Toxicol | 1991 Jun | 1918794 |
Targets
- 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
- Mechanism of Action:
- Grayanotoxins bind to specific sodium ion channels in cell membranes. The grayanotoxins prevent inactivation, leaving excitable cells depolarized.
References
- Wikipedia. Grayanotoxin. Last Updated 13 September 2009. : http://en.wikipedia.org/wiki/Grayanotoxin
- 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
- Mechanism of Action:
- Grayanotoxins bind to specific sodium ion channels in cell membranes. The grayanotoxins prevent inactivation, leaving excitable cells depolarized.
References
- Wikipedia. Grayanotoxin. Last Updated 13 September 2009. : http://en.wikipedia.org/wiki/Grayanotoxin
- 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
- Mechanism of Action:
- Grayanotoxins bind to specific sodium ion channels in cell membranes. The grayanotoxins prevent inactivation, leaving excitable cells depolarized.
References
- Wikipedia. Grayanotoxin. Last Updated 13 September 2009. : http://en.wikipedia.org/wiki/Grayanotoxin
- 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
- Mechanism of Action:
- Grayanotoxins bind to specific sodium ion channels in cell membranes. The grayanotoxins prevent inactivation, leaving excitable cells depolarized.
References
- Wikipedia. Grayanotoxin. Last Updated 13 September 2009. : http://en.wikipedia.org/wiki/Grayanotoxin
- 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
- Mechanism of Action:
- Grayanotoxins bind to specific sodium ion channels in cell membranes. The grayanotoxins prevent inactivation, leaving excitable cells depolarized.
References
- Wikipedia. Grayanotoxin. Last Updated 13 September 2009. : http://en.wikipedia.org/wiki/Grayanotoxin
- 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
- Mechanism of Action:
- Grayanotoxins bind to specific sodium ion channels in cell membranes. The grayanotoxins prevent inactivation, leaving excitable cells depolarized.
References
- Wikipedia. Grayanotoxin. Last Updated 13 September 2009. : http://en.wikipedia.org/wiki/Grayanotoxin
- 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
- Mechanism of Action:
- Grayanotoxins bind to specific sodium ion channels in cell membranes. The grayanotoxins prevent inactivation, leaving excitable cells depolarized.
References
- Wikipedia. Grayanotoxin. Last Updated 13 September 2009. : http://en.wikipedia.org/wiki/Grayanotoxin
- 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
- Mechanism of Action:
- Grayanotoxins bind to specific sodium ion channels in cell membranes. The grayanotoxins prevent inactivation, leaving excitable cells depolarized.
References
- Wikipedia. Grayanotoxin. Last Updated 13 September 2009. : http://en.wikipedia.org/wiki/Grayanotoxin
- 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
- Mechanism of Action:
- Grayanotoxins bind to specific sodium ion channels in cell membranes. The grayanotoxins prevent inactivation, leaving excitable cells depolarized.
References
- Wikipedia. Grayanotoxin. Last Updated 13 September 2009. : http://en.wikipedia.org/wiki/Grayanotoxin
- 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
- Mechanism of Action:
- Grayanotoxins bind to specific sodium ion channels in cell membranes. The grayanotoxins prevent inactivation, leaving excitable cells depolarized.
References
- Wikipedia. Grayanotoxin. Last Updated 13 September 2009. : http://en.wikipedia.org/wiki/Grayanotoxin
- 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
- Mechanism of Action:
- Grayanotoxins bind to specific sodium ion channels in cell membranes. The grayanotoxins prevent inactivation, leaving excitable cells depolarized.
References
- Wikipedia. Grayanotoxin. Last Updated 13 September 2009. : http://en.wikipedia.org/wiki/Grayanotoxin
- 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
- Mechanism of Action:
- Grayanotoxins bind to specific sodium ion channels in cell membranes. The grayanotoxins prevent inactivation, leaving excitable cells depolarized.
References
- Wikipedia. Grayanotoxin. Last Updated 13 September 2009. : http://en.wikipedia.org/wiki/Grayanotoxin
- 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
- Mechanism of Action:
- Grayanotoxins bind to specific sodium ion channels in cell membranes. The grayanotoxins prevent inactivation, leaving excitable cells depolarized.
References
- Wikipedia. Grayanotoxin. Last Updated 13 September 2009. : http://en.wikipedia.org/wiki/Grayanotoxin
- 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
- Mechanism of Action:
- Grayanotoxins bind to specific sodium ion channels in cell membranes. The grayanotoxins prevent inactivation, leaving excitable cells depolarized.
References
- Wikipedia. Grayanotoxin. Last Updated 13 September 2009. : http://en.wikipedia.org/wiki/Grayanotoxin