Record Information
Version1.0
Creation Date2009-07-03 21:46:56 UTC
Update Date2026-04-06 13:07:55 UTC
Accession NumberCHEM002056
Identification
Common NamePhallisin
ClassSmall Molecule
DescriptionPhallisin 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 FormulaC35H48N8O12S
Average Molecular Mass804.867 g/mol
Monoisotopic Mass804.311 g/mol
CAS Registry Number19774-69-7
IUPAC Name28-[2,3-dihydroxy-2-(hydroxymethyl)propyl]-18,21,24,26,29,32,35-heptahydroxy-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 Name28-[2,3-dihydroxy-2-(hydroxymethyl)propyl]-18,21,24,26,29,32,35-heptahydroxy-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(O)(CO)CO)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/C35H48N8O12S/c1-15-27(48)38-22-9-20-19-6-4-5-7-21(19)41-33(20)56-12-24(34(54)43-11-18(47)8-25(43)31(52)37-15)40-32(53)26(17(3)46)42-28(49)16(2)36-30(51)23(39-29(22)50)10-35(55,13-44)14-45/h4-7,15-18,22-26,41,44-47,55H,8-14H2,1-3H3,(H,36,51)(H,37,52)(H,38,48)(H,39,50)(H,40,53)(H,42,49)
InChI KeySRDQDZSLNAKOIT-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
  • Heteroaromatic compound
  • Pyrrole
  • Pyrrolidine
  • Tertiary alcohol
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Lactam
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Azacycle
  • Organoheterocyclic compound
  • Thioether
  • Primary alcohol
  • 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 Solubility0.15 g/LALOGPS
logP-0.14ALOGPS
logP-6ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)-6.6ChemAxon
pKa (Strongest Basic)15ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area332.79 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity198.94 m³·mol⁻¹ChemAxon
Polarizability78.09 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, Positivesplash10-014r-0000000900-8105d239fd133b6e73ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000002900-0935a47522edc1690bb5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0089-4915120300-8a3798a4563ee580c216Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f79-2000005930-b9970002fa0934e032a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001u-2000009800-478c9deee10e5ae0e0e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-8900001000-4131a990fa6dc9f7e38fSpectrum
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: 2 mg/kg (Mouse) (9)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesPhalloin 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 ID115286
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available