Record Information
Version1.0
Creation Date2009-07-03 21:46:55 UTC
Update Date2026-04-06 13:28:57 UTC
Accession NumberCHEM002055
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). (4)
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Ether
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
  • Phallotoxin
Chemical Structure
Thumb
SynonymsNot Available
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=1S/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 KeyVVAHMTWEOWYEHQ-UHFFFAOYSA-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
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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0000000900-5d7ddc891f10b353ad87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000001900-bb0be11923dfa92629deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ul0-3914211100-e84b69bad2ec1effa7a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fk9-0000001900-72a0082999e5eea4fbd8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-1100004900-0463b104a7cf333b95bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-8900101000-91f434d99446ab370b55Spectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (3)
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. (6, 2)
MetabolismNot Available
Toxicity ValuesLD50: 1.5 mg/kg (Mouse) (9)
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. (4)
Minimum Risk LevelNot Available
Health EffectsLiver lesions, tachycardia, hypoglycemia, hypotension and electrolyte imbalance with acid- base disturbance (5).
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 (5).
TreatmentConsider gastric lavage and activated charcoal. (1)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID34183
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available