Batrachotoxin (T3D2527)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (14)XML
Targets (14)
Record Information
Version2.0
Creation Date2009-07-03 22:19:11 UTC
Update Date2014-12-24 20:25:39 UTC
Accession NumberT3D2527
Identification
Common NameBatrachotoxin
ClassSmall Molecule
DescriptionBatrachotoxins (BTX) are extremely potent cardiotoxic and neurotoxic steroidal alkaloids found in poison dart frogs (genus Dendrobates and Phyllobates), Melyridae beetles, and certain birds (genus Pitohui and Ifrita). They act directly on sodium channels. (1). It is the most potent non-peptidal neurotoxin known.
Compound Type
  • Amide
  • Amine
  • Animal Toxin
  • Ester
  • Ether
  • Frog/Toad Toxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
BTX
Chemical FormulaC31H42N2O6
Average Molecular Mass538.675 g/mol
Monoisotopic Mass538.304 g/mol
CAS Registry Number23509-16-2
IUPAC Name1-{9,12-dihydroxy-6,16-dimethyl-10,19-dioxa-16-azahexacyclo[12.5.3.1⁵,⁹.0¹,¹⁴.0²,¹¹.0⁶,¹¹]tricosa-2,21-dien-22-yl}ethyl 2,4-dimethyl-1H-pyrrole-3-carboxylate
Traditional Name1-{9,12-dihydroxy-6,16-dimethyl-10,19-dioxa-16-azahexacyclo[12.5.3.1⁵,⁹.0¹,¹⁴.0²,¹¹.0⁶,¹¹]tricosa-2,21-dien-22-yl}ethyl 2,4-dimethyl-1H-pyrrole-3-carboxylate
SMILESCC(OC(=O)C1=C(C)NC=C1C)C1=CCC23OCCN(C)CC12CC(O)C12OC4(O)CCC1(C)C(CC=C32)C4
InChI IdentifierInChI=1/C31H42N2O6/c1-18-16-32-19(2)25(18)26(35)38-20(3)22-8-9-30-23-7-6-21-14-29(36)11-10-27(21,4)31(23,39-29)24(34)15-28(22,30)17-33(5)12-13-37-30/h7-8,16,20-21,24,32,34,36H,6,9-15,17H2,1-5H3
InChI KeyInChIKey=ISNYUQWBWALXEY-UHFFFAOYNA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrrole carboxylic acids and derivatives. These are heterocyclic compounds containing a pyrrole ring bearing a carboxyl group (or a derivative thereof).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrroles
Sub ClassPyrrole carboxylic acids and derivatives
Direct ParentPyrrole carboxylic acids and derivatives
Alternative Parents
Substituents
  • Pyrrole-3-carboxylic acid or derivatives
  • Para-oxazepine
  • Oxane
  • Substituted pyrrole
  • Cyclic alcohol
  • Vinylogous amide
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary aliphatic amine
  • Tertiary amine
  • Hemiacetal
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Amine
  • Organic nitrogen compound
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cell surface
  • Extracellular
  • Membrane
  • Membrane Fraction
  • Mitochondrion
  • Nerve Fiber
  • Plasma Membrane
  • Sarcoplasmic Reticulum
  • Synaptic Vesicle
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
AnticonvulsantsNot AvailableNot Available
Vascular smooth muscle contractionNot Availablemap04270
EndocytosisNot Availablemap04144
Antiarrhythmic DrugsNot AvailableNot Available
Cell cycleNot Availablemap04110
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP3.14ALOGPS
logP2.67ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)12.02ChemAxon
pKa (Strongest Basic)8.61ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.25 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity148.9 m³·mol⁻¹ChemAxon
Polarizability58.67 ųChemAxon
Number of Rings7ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0302390000-95806a83933e485bad912016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-3715930000-1cd3a85e8d3d3496a7a72016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-7912000000-4c69959424f897dadfaa2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-2001490000-ee586b0996e270ee7a952016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-8302390000-0573bafbdf0b177deece2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006y-9328200000-a55a34ac2784a1dc5fda2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0001690000-3d0d8bddf60c524a93352021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fkm-6802960000-6039b235411c5d81c9eb2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6y-9007610000-ac37901672847fa49e192021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1503090000-d614010212f7e16b1ecc2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-3402980000-b2e73f3e645c34c639952021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9102200000-c875103e3d7279857eee2021-10-12View Spectrum
Toxicity Profile
Route of ExposureInjestion or inhalation (smoking). L1810
Mechanism of ToxicityBatrachotoxins act on sodium channels by modifying both their ion selectivity and voltage sensitivity. By increasing the permeability of the cell membrane, the cell is depolarized by the influx of sodium. Sodium channels become persistently active at the resting membrane potential and nerve signal transmission to the muscles is blocked. Batrachotoxin also induces a massive release of acetylcholine in nerves and muscles and destroys of synaptic vesicles. (1)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesBatrachotoxins are found in poison dart frogs (genus Dendrobates and Phyllobates), Melyridae beetles, and certain birds (genus Pitohui and Ifrita). (1)
Minimum Risk LevelNot Available
Health EffectsBatrachotoxins affect the peripheral nervous system and heart muscles. (1)
SymptomsBatrachotoxins interfere with heart conduction, causing arrhythmias, extrasystoles, ventricular fibrillation and other changes which lead to cardiac arrest. (1)
TreatmentWhile it is not an antidote to batrachotocins, the membrane depolarization can be prevented or reversed by either tetrodotoxin, which is a non-competitive inhibitor, or saxitoxin. These both have effects antagonistic to those of batrachotoxin on sodium flux. Certain anaesthetics may act as receptor antagonists to the action of this alkaloid poison, while other local anaesthetics block its action altogether by acting as competitive antagonists. (1)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID31958
ChEMBL IDNot Available
ChemSpider IDNot Available
KEGG IDC13750
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDBatrachotoxin
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkBatrachotoxin
References
Synthesis ReferenceNot Available
MSDST3D2527.pdf
General References
  1. Wikipedia. Batrachotoxin. Last Updated 8 April 2008. [Link]
  2. Wikipedia. Frog. Last Updated 10 August 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot 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
  1. Wikipedia. Batrachotoxin. Last Updated 8 April 2008. [Link]
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
  1. Wikipedia. Batrachotoxin. Last Updated 8 April 2008. [Link]
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
  1. Wikipedia. Batrachotoxin. Last Updated 8 April 2008. [Link]
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
  1. Wikipedia. Batrachotoxin. Last Updated 8 April 2008. [Link]
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
  1. Wikipedia. Batrachotoxin. Last Updated 8 April 2008. [Link]
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
  1. Wikipedia. Batrachotoxin. Last Updated 8 April 2008. [Link]
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
  1. Wikipedia. Batrachotoxin. Last Updated 8 April 2008. [Link]
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
  1. Wikipedia. Batrachotoxin. Last Updated 8 April 2008. [Link]
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
  1. Wikipedia. Batrachotoxin. Last Updated 8 April 2008. [Link]
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
  1. Wikipedia. Batrachotoxin. Last Updated 8 April 2008. [Link]
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
  1. Wikipedia. Batrachotoxin. Last Updated 8 April 2008. [Link]
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
  1. Wikipedia. Batrachotoxin. Last Updated 8 April 2008. [Link]
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
  1. Wikipedia. Batrachotoxin. Last Updated 8 April 2008. [Link]
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
  1. Wikipedia. Batrachotoxin. Last Updated 8 April 2008. [Link]