Record Information
Version1.0
Creation Date2009-07-03 21:46:55 UTC
Update Date2026-04-06 13:30:47 UTC
Accession NumberCHEM002054
Identification
Common NameProphalloin
ClassSmall Molecule
DescriptionProphalloin 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 FormulaC35H48N8O9S
Average Molecular Mass756.869 g/mol
Monoisotopic Mass756.326 g/mol
CAS Registry Number67739-84-8
IUPAC Name21,24,26,29,32,35-hexahydroxy-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 Name21,24,26,29,32,35-hexahydroxy-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)N1CCCC1C(O)=NC(C)C(O)=N2
InChI IdentifierInChI=1S/C35H48N8O9S/c1-16-27(45)38-22-13-20-19-9-6-7-10-21(19)41-33(20)53-15-24(34(51)43-12-8-11-25(43)31(49)37-16)40-32(50)26(18(3)44)42-28(46)17(2)36-30(48)23(39-29(22)47)14-35(4,5)52/h6-7,9-10,16-18,22-26,41,44,52H,8,11-15H2,1-5H3,(H,36,48)(H,37,49)(H,38,45)(H,39,47)(H,40,50)(H,42,46)
InChI KeyVXROMVCOGJAUJL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cyclic peptides. Cyclic peptides are compounds containing a cyclic moiety bearing a peptide backbone.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentCyclic peptides
Alternative Parents
Substituents
  • Cyclic alpha peptide
  • Macrolactam
  • Alpha-amino acid or derivatives
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Aryl thioether
  • Alkylarylthioether
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Pyrrolidine
  • Cyclic carboximidic acid
  • Tertiary alcohol
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Lactam
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Polyol
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Thioether
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
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 Solubility0.12 g/LALOGPS
logP1.17ALOGPS
logP-2.6ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)-6.5ChemAxon
pKa (Strongest Basic)14.96ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area272.1 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity194.53 m³·mol⁻¹ChemAxon
Polarizability77.82 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, Positivesplash10-0079-0000000900-95af5475abb02b9a03c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0100002900-77a9f738307d74b574cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-4915202000-7063de131db35fec4f08Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4r-0000003900-7a75a5f6555512b045daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-2100009600-4dfc130836cabe66ff2dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9800101000-8fa7f7afb326b805274cSpectrum
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: >20 mg/kg (Mouse) (9)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesPhalloidin 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 ID155035
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available