ContaminantDB: Pumiliotoxin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (25)XML

Record Information

Version

1.0

Creation Date

2009-07-03 22:19:12 UTC

Update Date

2026-04-06 12:35:08 UTC

Accession Number

CHEM002071

Identification

Common Name

Pumiliotoxin

Class

Small Molecule

Description

Pumiliotoxin is a toxin found in poison dart frogs (genus Dendrobates and Phyllobates). It affects the calcium channels, interfering with muscle contraction in the heart and skeletal muscle. (3)

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

C₁₆H₂₉NO

Average Molecular Mass

251.414 g/mol

Monoisotopic Mass

251.225 g/mol

CAS Registry Number

73376-35-9

IUPAC Name

(6E)-8-methyl-6-(2-methylhexylidene)-octahydroindolizin-8-ol

Traditional Name

(6E)-8-methyl-6-(2-methylhexylidene)-hexahydroindolizin-8-ol

SMILES

[H]\C(C(C)CCCC)=C1/CN2CCCC2C(C)(O)C1

InChI Identifier

InChI=1S/C16H29NO/c1-4-5-7-13(2)10-14-11-16(3,18)15-8-6-9-17(15)12-14/h10,13,15,18H,4-9,11-12H2,1-3H3/b14-10+

InChI Key

OKTQTXDNHCOLHT-GXDHUFHOSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pumiliotoxins, homopumiliotoxins, and allopumiliotoxins. These are neurotoxic alkaloids, containing a 8-methyl-octahydroindolizin-8-ol or 1-methyl-octahydro-1H-quinolizin-1-ol moiety.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Pumiliotoxins, homopumiliotoxins, and allopumiliotoxins

Sub Class

Not Available

Direct Parent

Pumiliotoxins, homopumiliotoxins, and allopumiliotoxins

Alternative Parents

Substituents

Pumiliotoxin-skeleton
Indolizidine
Piperidine
N-alkylpyrrolidine
Pyrrolidine
Tertiary alcohol
1,2-aminoalcohol
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
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

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

Predicted Properties

Property	Value	Source
Water Solubility	0.27 g/L	ALOGPS
logP	3.38	ALOGPS
logP	3.26	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	14.36	ChemAxon
pKa (Strongest Basic)	10.15	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	23.47 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	78.14 m³·mol⁻¹	ChemAxon
Polarizability	31.02 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	splash10-0f89-1190000000-3b8d3c7cf1952252d985	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001m-9570000000-6bbfe07fa23f594c5de9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9300000000-e9387f922cd5ec217999	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-2274e849217f6b1a7c32	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ue9-0190000000-840f36a35a7b1d0b279d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0083-6950000000-198c11cdc2efa43d3e3b	Spectrum

Toxicity Profile

Route of Exposure

Injection (sting/bite) (6) ; inhalation (smoking) (5)

Mechanism of Toxicity

Pumiliotoxin affects voltage-gated calcium channels, interfering with muscle contraction in the heart and skeletal muscle. They also may block sodium and potassium channels in cells and inhibit calcium-dependent ATPase. (3, 4, 1, 2)

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

Pumiliotoxin is a toxin found in poison dart frogs (genus Dendrobates and Phyllobates). (3)

Minimum Risk Level

Not Available

Health Effects

Pumiliotoxin interferes with muscle contraction in the heart and skeletal muscle. (3)

Symptoms

Some of the symptoms of pumiliotoxins are partial paralysis, having difficulty moving, being hyperactive and in some cases death. (3)

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

Not Available

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

Pumiliotoxin (CHEM002071)

Structure for CHEM002071: Pumiliotoxin