T3DB: Phalloidin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (6)XML

Targets (6)

Record Information

Version

2.0

Creation Date

2009-07-03 21:46:55 UTC

Update Date

2014-12-24 20:25:33 UTC

Accession Number

T3D2467

Identification

Common Name

Phalloidin

Class

Protein

Description

Phalloidin is one of a group of toxins from the death cap (Amanita phalloides) known as phallotoxins. The phallotoxins consist of at least seven compounds, all of which have seven similar peptide rings, isolated from the death cap (Amanita phalloides). Though highly toxic to liver cells, it has since been found to have little input into the death cap's toxicity as it is not absorbed through the gut. Furthermore, it is also found in the edible (and sought after) Blusher (Amanita rubescens). (7)

Compound Type

Amide
Amine
Fungal Toxin
Mycotoxin
Natural Compound
Organic Compound
Phallotoxin
Protein

Protein Structure

Synonyms

Synonym
Phalloidine

Chemical Formula

Not Available

Average Molecular Mass

3301.700 g/mol

CAS Registry Number

17466-45-4

Sequence

Not Available

Chemical Taxonomy

Description

Not Available

Kingdom

Organic Compounds

Super Class

Organic Acids

Class

Carboxylic Acids and Derivatives

Sub Class

Amino Acids, Peptides, and Analogues

Direct Parent

Peptides

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Not Available

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Acrosome
Actin Cytoskeleton
Actin Filament
Apical Membrane
Axoneme
Basolateral Membrane
Caveolae
Cell junction
Cell projection
Cell surface
Centrosome
Clathrin Coated Vesicle
Cytoplasmic vesicle
Cytoskeleton
Cytosol
Endocytic Vesicle
Endoplasmic reticulum
Endosome
Extracellular
Extracellular matrix
Focal adhesion
Golgi apparatus
Intermediate Filament
Intracellular Vesicle
Kinetochore
Lysosome
Membrane Fraction
Microsome
Microtubule
Mitochondrial Membrane
Mitochondrion
Nerve Fiber
Nuclear Matrix
Nuclear Membrane
Nucleolus
Nucleoplasm
Perinuclear region
Plasma Membrane
Ribosome
Sarcoplasmic Reticulum
Secretory Granule
Secretory vesicle
Soluble Fraction
Synaptic Vesicle
Tubulin
Zymogen Granule

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Apoptosis	Not Available	map04210
Endocytosis	Not Available	map04144
Cell cycle	Not Available	map04110
Bile secretion	Not Available	map04976
Phagosome	Not Available	map04145
Insulin secretion	Not Available	map04911
Aminoglycosides	Not Available	Not Available
Salivary secretion	Not Available	map04970
Regulation of actin cytoskeleton	Not Available	map04810
Long-term potentiation	Not Available	map04720
Tetracyclines	Not Available	Not Available
Synaptic vesicle cycle	Not Available	map04721
Oxidative phosphorylation	Not Available	map00190
Homologous recombination	Not Available	map03440
Glutamatergic synapse	Not Available	map04724
Dna replication	Not Available	map03030
Arachidonic Acid Metabolism	SMP00075	map00590

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Clear solution.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	5 mg/mL at 0°C [MERCK INDEX (1996)]
LogP	Not Available

Predicted Properties

Not Available

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_10) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_11) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uk9-0000000900-ebd478c5bd9c63b08193	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0000001900-8fee6566492247b5d131	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-1000001900-5413b2ebe3f0f32820ba	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00li-0000003900-d39aaa3924f5eb66149c	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00lu-0000005900-5b17208fe0f1aa6b0f0a	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ox-5000004900-94f47194e23cca657f71	2019-02-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-10-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-10-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-10-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-10-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-10-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-10-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-10-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-10-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-10-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-10-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-10-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-10-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-10-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-10-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-10-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-10-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-10-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-10-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-10-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-10-25	View Spectrum

Toxicity Profile

Route of Exposure

Oral, dermal, inhalation, and parenteral (contaminated drugs). (1)

Mechanism of Toxicity

It binds actin, preventing its depolymerization and poisoning the cell. Phalloidin binds specifically at the interface between F-actin subunits, locking adjacent subunits together. Phalloidin, a bicyclic heptapeptide, binds to actin filaments much more tightly than to actin monomers, leading to a decrease in the rate constant for the dissociation of actin subunits from filament ends, which essentially stabilizes actin filaments through the prevention of filament depolymerization. Moreover, phalloidin is found to inhibit the ATP hydrolysis activity of F-actin (9).

Metabolism

Phalloidin was suggested to undergo bioactivation in the liver (2). Free toxin may be removed by opsonization via the reticuloendothelial system (primarily the liver and kidneys) or it may be degraded through cellular internalization via the lysosomes. Lysosomes are membrane-enclosed organelles that contain an array of digestive enzymes, including several proteases.

Toxicity Values

LD50: 2 mg/kg (Mouse) (6)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity (not listed by IARC). (10)

Uses/Sources

The property of phalloidin is a useful tool for investigating the distribution of F-actin in cells by labeling phalloidin with fluorescent analogs and using them to stain actin filaments for light microscopy (7).

Minimum Risk Level

Not Available

Health Effects

Liver lesions, tachycardia, hypoglycemia, hypotension and electrolyte imbalance with acid- base disturbance (8).

Symptoms

Hypovolemic shock; Gastrointestinal symptoms occur after a latent period and include abdominal pain, vomiting, and watery diarrhea. Neurologic symptoms are related to hepatic failure and may include encephalopathy, somnolence, confusion, coma and seizures (8).

Treatment

Consider gastric lavage and activated charcoal. (3)

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

UniProt ID

OMIM ID

ChEBI ID

8040

BioCyc ID

Not Available

CTD ID

D010590

Stitch ID

Phalloidin

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Phalloidin

References

Synthesis Reference

Not Available

MSDS

T3D2467.pdf

General References

Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
Oliveira VX Jr, Fazio MA, Miranda MT, da Silva JM, Bittencourt JC, Elias CF, Miranda A: Leptin fragments induce Fos immunoreactivity in rat hypothalamus. Regul Pept. 2005 Apr 15;127(1-3):123-32. [15680478 ]
Uusi-Oukari M, Korpi ER: Specific alterations in the cerebellar GABA(A) receptors of an alcohol-sensitive ANT rat line. Alcohol Clin Exp Res. 1991 Mar;15(2):241-8. [1647706 ]
The Chemical Society (1972). Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society.
Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 142, edition expires Nov, 2009.
Deshpande SS (2002). Handbook of food toxicology. New York, NY: Marcel Dekker Inc.
Wikipedia. Phallotoxin. Last Updated 5 July 2009. [Link]
Wikipedia. Tramadol. Last Updated 8 August 2009. [Link]
Wikipedia. Phalloidin. Last Updated 17 July 2009. [Link]
International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Actin, alpha cardiac muscle 1

General Function:: Myosin binding
Specific Function:: Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells.
Gene Name:: ACTC1
Uniprot ID:: P68032
Molecular Weight:: 42018.6 Da

References

Huang ZJ, Haugland RP, You WM, Haugland RP: Phallotoxin and actin binding assay by fluorescence enhancement. Anal Biochem. 1992 Jan;200(1):199-204. [1595896 ]
Wikipedia. Phalloidin. Last Updated 17 July 2009. [Link]

Target Details

2. Actin, alpha skeletal muscle

General Function:: Structural constituent of cytoskeleton
Specific Function:: Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells.
Gene Name:: ACTA1
Uniprot ID:: P68133
Molecular Weight:: 42050.67 Da

References

Huang ZJ, Haugland RP, You WM, Haugland RP: Phallotoxin and actin binding assay by fluorescence enhancement. Anal Biochem. 1992 Jan;200(1):199-204. [1595896 ]
Wikipedia. Phalloidin. Last Updated 17 July 2009. [Link]

Target Details

3. Actin, aortic smooth muscle

General Function:: Protein kinase binding
Specific Function:: Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells.
Gene Name:: ACTA2
Uniprot ID:: P62736
Molecular Weight:: 42008.57 Da

References

Huang ZJ, Haugland RP, You WM, Haugland RP: Phallotoxin and actin binding assay by fluorescence enhancement. Anal Biochem. 1992 Jan;200(1):199-204. [1595896 ]
Wikipedia. Phalloidin. Last Updated 17 July 2009. [Link]

Target Details

4. Actin, cytoplasmic 1

General Function:: Tat protein binding
Specific Function:: Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells.
Gene Name:: ACTB
Uniprot ID:: P60709
Molecular Weight:: 41736.37 Da

References

Huang ZJ, Haugland RP, You WM, Haugland RP: Phallotoxin and actin binding assay by fluorescence enhancement. Anal Biochem. 1992 Jan;200(1):199-204. [1595896 ]
Wikipedia. Phalloidin. Last Updated 17 July 2009. [Link]

Target Details

5. Actin, cytoplasmic 2

General Function:: Ubiquitin protein ligase binding
Specific Function:: Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells.
Gene Name:: ACTG1
Uniprot ID:: P63261
Molecular Weight:: 41792.48 Da

References

Huang ZJ, Haugland RP, You WM, Haugland RP: Phallotoxin and actin binding assay by fluorescence enhancement. Anal Biochem. 1992 Jan;200(1):199-204. [1595896 ]
Wikipedia. Phalloidin. Last Updated 17 July 2009. [Link]

Target Details

6. Actin, gamma-enteric smooth muscle

General Function:: Atp binding
Specific Function:: Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells.
Gene Name:: ACTG2
Uniprot ID:: P63267
Molecular Weight:: 41876.495 Da

References

Huang ZJ, Haugland RP, You WM, Haugland RP: Phallotoxin and actin binding assay by fluorescence enhancement. Anal Biochem. 1992 Jan;200(1):199-204. [1595896 ]
Wikipedia. Phalloidin. Last Updated 17 July 2009. [Link]

Phalloidin (T3D2467)

Targets

References

References

References

References

References

References