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Record Information
Version2.0
Creation Date2009-07-03 21:46:55 UTC
Update Date2014-12-24 20:25:33 UTC
Accession NumberT3D2469
Identification
Common NamePhalloin
ClassSmall Molecule
DescriptionPhalloin 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). (6)
Compound Type
  • Amide
  • Amine
  • Ether
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
  • Phallotoxin
Chemical Structure
Thumb
Synonyms
Synonym
Phalloidin, 7-(4-hydroxy-L-leucine)- (9CI)
Phalloine
Chemical FormulaC35H48N8O10S
Average Molecular Mass772.868 g/mol
Monoisotopic Mass772.321 g/mol
CAS Registry Number28227-92-1
IUPAC Name18,21,24,26,29,32,35-heptahydroxy-28-(2-hydroxy-2-methylpropyl)-34-(1-hydroxyethyl)-23,31-dimethyl-12-thia-10,16,22,25,27,30,33,36-octaazapentacyclo[12.11.11.0³,¹¹.0⁴,⁹.0¹⁶,²⁰]hexatriaconta-3(11),4,6,8,21,24,26,29,32,35-decaen-15-one
Traditional Name18,21,24,26,29,32,35-heptahydroxy-28-(2-hydroxy-2-methylpropyl)-34-(1-hydroxyethyl)-23,31-dimethyl-12-thia-10,16,22,25,27,30,33,36-octaazapentacyclo[12.11.11.0³,¹¹.0⁴,⁹.0¹⁶,²⁰]hexatriaconta-3(11),4,6,8,21,24,26,29,32,35-decaen-15-one
SMILESCC(O)C1N=C(O)C(C)N=C(O)C(CC(C)(C)O)N=C(O)C2CC3=C(NC4=CC=CC=C34)SCC(N=C1O)C(=O)N1CC(O)CC1C(O)=NC(C)C(O)=N2
InChI IdentifierInChI=1/C35H48N8O10S/c1-15-27(46)38-22-11-20-19-8-6-7-9-21(19)41-33(20)54-14-24(34(52)43-13-18(45)10-25(43)31(50)37-15)40-32(51)26(17(3)44)42-28(47)16(2)36-30(49)23(39-29(22)48)12-35(4,5)53/h6-9,15-18,22-26,41,44-45,53H,10-14H2,1-5H3,(H,36,49)(H,37,50)(H,38,46)(H,39,48)(H,40,51)(H,42,47)
InChI KeyInChIKey=VVAHMTWEOWYEHQ-UHFFFAOYNA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Cyclic alpha peptide
  • Macrolactam
  • Alpha-amino acid or derivatives
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Aryl thioether
  • Alkylarylthioether
  • Benzenoid
  • Pyrrole
  • Pyrrolidine
  • Tertiary alcohol
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Lactam
  • Organoheterocyclic compound
  • Azacycle
  • Thioether
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Actin Filament
  • Cytoskeleton
  • Membrane
  • Microtubule
  • Nucleoplasm
  • Plasma Membrane
  • Tubulin
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
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 Solubility0.16 g/LALOGPS
logP0.69ALOGPS
logP-3.7ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)-6.5ChemAxon
pKa (Strongest Basic)14.96ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area292.33 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity195.85 m³·mol⁻¹ChemAxon
Polarizability76.35 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0000000900-5d7ddc891f10b353ad87JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000001900-bb0be11923dfa92629deJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ul0-3914211100-e84b69bad2ec1effa7a2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fk9-0000001900-72a0082999e5eea4fbd8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-1100004900-0463b104a7cf333b95bfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-8900101000-91f434d99446ab370b55JSpectraViewer
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (2)
Mechanism of ToxicityPhallotoxins bind actin, preventing its depolymerization and poisoning the cell. They bind specifically at the interface between F-actin subunits, locking adjacent subunits together. This leads 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, they inhibit the ATP hydrolysis activity of F-actin. (8, 1)
MetabolismNot Available
Toxicity ValuesLD50: 1.5 mg/kg (Mouse) (5)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesProphalloin is one of a group of toxins from the death cap (Amanita phalloides) known as phallotoxins. (6)
Minimum Risk LevelNot Available
Health EffectsLiver lesions, tachycardia, hypoglycemia, hypotension and electrolyte imbalance with acid- base disturbance (7).
SymptomsHypovolemic 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 (7).
TreatmentConsider gastric lavage and activated charcoal. (3)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID34183
ChEMBL IDNot Available
ChemSpider ID31503
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDC024287
Stitch IDPhalloin
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. 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 ]
  2. Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
  3. 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 ]
  4. Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 142, edition expires Nov, 2009.
  5. Deshpande SS (2002). Handbook of food toxicology. New York, NY: Marcel Dekker Inc.
  6. Wikipedia. Phallotoxin. Last Updated 5 July 2009. [Link]
  7. Wikipedia. Tramadol. Last Updated 8 August 2009. [Link]
  8. Wikipedia. Phalloidin. Last Updated 17 July 2009. [Link]
  9. Wikipedia. Mushroom poisoning. Last Updated 10 August 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

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
  1. 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 ]
  2. Wikipedia. Phalloidin. Last Updated 17 July 2009. [Link]
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
  1. 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 ]
  2. Wikipedia. Phalloidin. Last Updated 17 July 2009. [Link]
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
  1. 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 ]
  2. Wikipedia. Phalloidin. Last Updated 17 July 2009. [Link]
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
  1. 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 ]
  2. Wikipedia. Phalloidin. Last Updated 17 July 2009. [Link]
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
  1. 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 ]
  2. Wikipedia. Phalloidin. Last Updated 17 July 2009. [Link]
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
  1. 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 ]
  2. Wikipedia. Phalloidin. Last Updated 17 July 2009. [Link]