ContaminantDB: Histrionicotoxin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (16)XML

Record Information

Version

1.0

Creation Date

2009-07-03 22:19:12 UTC

Update Date

2026-04-05 15:24:42 UTC

Accession Number

CHEM002070

Identification

Common Name

Histrionicotoxin

Class

Small Molecule

Description

Histrionicotoxin is a toxin found in poison dart frogs (genus Dendrobates). It is a potent non-competitive antagonist of nicotinic acetylcholine receptors. (1)

Contaminant Sources

T3DB toxins

Contaminant Type

Amine
Animal Toxin
Frog/Toad Toxin
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₁₉H₂₅NO

Average Molecular Mass

283.415 g/mol

Monoisotopic Mass

283.194 g/mol

CAS Registry Number

34272-51-0

IUPAC Name

7-[(1E)-but-1-en-3-yn-1-yl]-2-[(2E)-pent-2-en-4-yn-1-yl]-1-azaspiro[5.5]undecan-8-ol

Traditional Name

7-[(1E)-but-1-en-3-yn-1-yl]-2-[(2E)-pent-2-en-4-yn-1-yl]-1-azaspiro[5.5]undecan-8-ol

SMILES

[H]\C(CC1CCCC2(CCCC(O)C2\C([H])=C(/[H])C#C)N1)=C(\[H])C#C

InChI Identifier

InChI=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 Key

JBRYWENFVHQBGY-YTEPGLGFSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds 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.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Histrionicotoxins

Sub Class

Not Available

Direct Parent

Histrionicotoxins

Alternative Parents

Substituents

Histrionicotoxin skeleton
Azaspirodecane
Piperidine
Cyclic alcohol
Secondary alcohol
Acetylide
Azacycle
Organoheterocyclic compound
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

metabolite

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

Predicted Properties

Property	Value	Source
Water Solubility	0.009 g/L	ALOGPS
logP	3.2	ALOGPS
logP	2.67	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	14.84	ChemAxon
pKa (Strongest Basic)	10.52	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	32.26 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	89.49 m³·mol⁻¹	ChemAxon
Polarizability	33.49 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0090000000-64706804cb43fb4f58d9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0333-0390000000-92f8e5e48d998d002c98	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ik9-5890000000-11b23ff54c2ee4711a33	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-cc56b475fb47297af3ce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0090000000-d1357f3e3dff82db9cec	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02t9-0490000000-0400a22d45510fe155b0	Spectrum

Toxicity Profile

Route of Exposure

Injection (sting/bite) (2) ; inhalation (smoking) (3)

Mechanism of Toxicity

Histrionicotoxin is a potent non-competitive antagonist of nicotinic acetylcholine receptors. (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

Histrionicotoxin is a toxin found in poison dart frogs (genus Dendrobates). (1)

Minimum Risk Level

Not Available

Health Effects

Histrionicotoxin is neurotoxic. (1)

Symptoms

Histrionicotoxin is neurotoxic. (1)

Treatment

Not Available

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

14134870

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

Histrionicotoxin (CHEM002070)

Structure for CHEM002070: Histrionicotoxin