You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Toxin, Toxin Target Database.
Record Information
Version2.0
Creation Date2009-07-03 22:19:12 UTC
Update Date2014-12-24 20:25:39 UTC
Accession NumberT3D2528
Identification
Common NameHistrionicotoxin
ClassSmall Molecule
DescriptionHistrionicotoxin is a toxin found in poison dart frogs (genus Dendrobates). It is a potent non-competitive antagonist of nicotinic acetylcholine receptors. (1)
Compound Type
  • Amine
  • Animal Toxin
  • Frog/Toad Toxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
Synonyms
Synonym
HTX
Chemical FormulaC19H25NO
Average Molecular Mass283.408 g/mol
Monoisotopic Mass283.194 g/mol
CAS Registry Number34272-51-0
IUPAC Name7-(but-1-en-3-yn-1-yl)-2-(pent-2-en-4-yn-1-yl)-1-azaspiro[5.5]undecan-8-ol
Traditional Name7-(but-1-en-3-yn-1-yl)-2-(pent-2-en-4-yn-1-yl)-1-azaspiro[5.5]undecan-8-ol
SMILESOC1CCCC2(CCCC(CC=CC#C)N2)C1C=CC#C
InChI IdentifierInChI=1S/C19H25NO/c1-3-5-7-10-16-11-8-14-19(20-16)15-9-13-18(21)17(19)12-6-4-2/h1-2,5-7,12,16-18,20-21H,8-11,13-15H2/b7-5+,12-6+
InChI KeyInChIKey=JBRYWENFVHQBGY-YTEPGLGFSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as histrionicotoxins. These are frog toxins structurally characterized by the presence of a dodecahydropyrrolo[1,2-a]quinolin-1-yl}ethanol moiety or a 2,7-disubstituted 1-azaspiro[5.5]undecan-8-ol moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassAlkaloids and derivatives
Sub ClassHistrionicotoxins
Direct ParentHistrionicotoxins
Alternative Parents
Substituents
  • Histrionicotoxin skeleton
  • Azaspirodecane
  • Piperidine
  • Cyclic alcohol
  • Secondary alcohol
  • Acetylide
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
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 Solubility0.00898 mg/mLALOGPS
logP3.2ALOGPS
logP2.67ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)14.84ChemAxon
pKa (Strongest Basic)10.52ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area32.26 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity89.49 m3·mol-1ChemAxon
Polarizability33.24 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Toxicity Profile
Route of ExposureInjection (sting/bite) (2) ; inhalation (smoking) (3)
Mechanism of ToxicityHistrionicotoxin is a potent non-competitive antagonist of nicotinic acetylcholine receptors. (1)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesHistrionicotoxin is a toxin found in poison dart frogs (genus Dendrobates). (1)
Minimum Risk LevelNot Available
Health EffectsHistrionicotoxin is neurotoxic. (1)
SymptomsHistrionicotoxin is neurotoxic. (1)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID6437364
ChEMBL IDNot Available
ChemSpider IDNot Available
KEGG IDC13683
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDC007948
Stitch IDHistrionicotoxin
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Wikipedia. Histrionicotoxin. Last Updated 23 January 2009. [Link]
  2. Wikipedia. Insect toxins. Last Updated 19 February 2009. [Link]
  3. Wikipedia. Frog. Last Updated 10 August 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNA1
Uniprot ID:
P02708
Molecular Weight:
54545.235 Da
References
  1. Wikipedia. Histrionicotoxin. Last Updated 23 January 2009. [Link]
General Function:
Ligand-gated ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNB1
Uniprot ID:
P11230
Molecular Weight:
56697.9 Da
References
  1. Wikipedia. Histrionicotoxin. Last Updated 23 January 2009. [Link]
General Function:
Acetylcholine-activated cation-selective channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRND
Uniprot ID:
Q07001
Molecular Weight:
58894.55 Da
References
  1. Wikipedia. Histrionicotoxin. Last Updated 23 January 2009. [Link]
General Function:
Cation transmembrane transporter activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNE
Uniprot ID:
Q04844
Molecular Weight:
54696.54 Da
References
  1. Wikipedia. Histrionicotoxin. Last Updated 23 January 2009. [Link]
General Function:
Channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNG
Uniprot ID:
P07510
Molecular Weight:
57882.8 Da
References
  1. Wikipedia. Histrionicotoxin. Last Updated 23 January 2009. [Link]
General Function:
Receptor binding
Specific Function:
Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding may induce an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane. In the ear, this may lead to a reduction in basilar membrane motion, altering the activity of auditory nerve fibers and reducing the range of dynamic hearing. This may protect against acoustic trauma.
Gene Name:
CHRNA10
Uniprot ID:
Q9GZZ6
Molecular Weight:
49704.295 Da
References
  1. Wikipedia. Histrionicotoxin. Last Updated 23 January 2009. [Link]
General Function:
Drug binding
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNA2
Uniprot ID:
Q15822
Molecular Weight:
59764.82 Da
References
  1. Wikipedia. Histrionicotoxin. Last Updated 23 January 2009. [Link]
General Function:
Ligand-gated ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNA3
Uniprot ID:
P32297
Molecular Weight:
57479.54 Da
References
  1. Wikipedia. Histrionicotoxin. Last Updated 23 January 2009. [Link]
General Function:
Ligand-gated ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeable to sodium ions.
Gene Name:
CHRNA4
Uniprot ID:
P43681
Molecular Weight:
69956.47 Da
References
  1. Wikipedia. Histrionicotoxin. Last Updated 23 January 2009. [Link]
General Function:
Ligand-gated ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNA5
Uniprot ID:
P30532
Molecular Weight:
53053.965 Da
References
  1. Wikipedia. Histrionicotoxin. Last Updated 23 January 2009. [Link]
General Function:
Acetylcholine-activated cation-selective channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNA6
Uniprot ID:
Q15825
Molecular Weight:
56897.745 Da
References
  1. Wikipedia. Histrionicotoxin. Last Updated 23 January 2009. [Link]
General Function:
Toxic substance binding
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is blocked by alpha-bungarotoxin.
Gene Name:
CHRNA7
Uniprot ID:
P36544
Molecular Weight:
56448.925 Da
References
  1. Wikipedia. Histrionicotoxin. Last Updated 23 January 2009. [Link]
General Function:
Calcium channel activity
Specific Function:
Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding induces a conformation change that leads to the opening of an ion-conducting channel across the plasma membrane (PubMed:11752216, PubMed:25282151). The channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane (PubMed:11752216, PubMed:25282151). In the ear, this may lead to a reduction in basilar membrane motion, altering the activity of auditory nerve fibers and reducing the range of dynamic hearing. This may protect against acoustic trauma. May also regulate keratinocyte adhesion (PubMed:11021840).
Gene Name:
CHRNA9
Uniprot ID:
Q9UGM1
Molecular Weight:
54806.63 Da
References
  1. Wikipedia. Histrionicotoxin. Last Updated 23 January 2009. [Link]
General Function:
Ligand-gated ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeable to sodiun ions.
Gene Name:
CHRNB2
Uniprot ID:
P17787
Molecular Weight:
57018.575 Da
References
  1. Wikipedia. Histrionicotoxin. Last Updated 23 January 2009. [Link]
General Function:
Drug binding
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNB3
Uniprot ID:
Q05901
Molecular Weight:
52728.215 Da
References
  1. Wikipedia. Histrionicotoxin. Last Updated 23 January 2009. [Link]
General Function:
Ligand-gated ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNB4
Uniprot ID:
P30926
Molecular Weight:
56378.985 Da
References
  1. Wikipedia. Histrionicotoxin. Last Updated 23 January 2009. [Link]