Record Information
Version1.0
Creation Date2009-08-12 21:34:08 UTC
Update Date2026-04-06 10:52:26 UTC
Accession NumberCHEM002571
Identification
Common NameProamanullin
ClassSmall Molecule
DescriptionProamanullin is one of a group of at least eight Amatoxins found in several genera of poisonous mushrooms, most notably Amanita phalloides and several other members of the genus Amanita, as well as some Conocybe, Galerina and Lepiota mushroom species. (5)
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
SynonymsNot Available
Chemical FormulaC39H54N10O11S
Average Molecular Mass870.971 g/mol
Monoisotopic Mass870.369 g/mol
CAS Registry Number54532-46-6
IUPAC Name2-[13,34-bis(butan-2-yl)-22-hydroxy-2,5,11,14,27,30,33,36,39-nonaoxo-27λ⁴-thia-3,6,12,15,25,29,32,35,38-nonaazapentacyclo[14.12.11.0⁶,¹⁰.0¹⁸,²⁶.0¹⁹,²⁴]nonatriaconta-18(26),19,21,23-tetraen-4-yl]acetamide
Traditional Nameproamanullin
SMILESCCC(C)C1NC(=O)CNC(=O)C2CC3=C(NC4=CC(O)=CC=C34)S(=O)CC(NC(=O)CNC1=O)C(=O)NC(CC(N)=O)C(=O)N1CCCC1C(=O)NC(C(C)CC)C(=O)N2
InChI IdentifierInChI=1S/C39H54N10O11S/c1-5-18(3)31-36(57)42-15-29(52)43-26-17-61(60)38-22(21-10-9-20(50)12-23(21)46-38)13-24(33(54)41-16-30(53)47-31)44-37(58)32(19(4)6-2)48-35(56)27-8-7-11-49(27)39(59)25(14-28(40)51)45-34(26)55/h9-10,12,18-19,24-27,31-32,46,50H,5-8,11,13-17H2,1-4H3,(H2,40,51)(H,41,54)(H,42,57)(H,43,52)(H,44,58)(H,45,55)(H,47,53)(H,48,56)
InChI KeyCTYHFRWAIRSHQT-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as amatoxins. These are cyclic peptides containing eight amino acid residues arranged in a macrobicyclic motif.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAmatoxins
Alternative Parents
Substituents
  • Amatoxin skeleton
  • Alpha-oligopeptide
  • Alpha-amino acid or derivatives
  • Hydroxyindole
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Pyrrole
  • Pyrrolidine
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Lactam
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Sulfoxide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Azacycle
  • Sulfinyl compound
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • 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 Solubility1.57 g/LALOGPS
logP-0.19ALOGPS
logP-4ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)9.39ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area320.19 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity216.8 m³·mol⁻¹ChemAxon
Polarizability86.75 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0000000090-ed1c4a26af1289056c74Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ufr-1100001090-4c2de226bb2edd605015Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0910-9500111100-32e21a53b9ce040f53a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gb9-0000000090-9f4cd0026980bc4a3c9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6x-6110000090-fe4e770717212bafe72eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-7942000100-21d5eb4501acb321df41Spectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (3)
Mechanism of ToxicityThe major toxic mechanism of amatoxins is the inhibition of RNA polymerase II, a vital enzyme in the synthesis of messenger RNA (mRNA), microRNA, and small nuclear RNA (snRNA). Without mRNA, essential protein synthesis, and hence cell metabolism, grind to a halt and the cell dies. (5)
MetabolismNot Available
Toxicity ValuesLD50: >20 mg/kg (Mouse) (1)
Lethal Dose0.1 mg/kg for an adult human. (5)
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesAmatoxins are a subgroup of at least eight toxic compounds found in several genera of poisonous mushrooms, most notably Amanita phalloides and several other members of the genus Amanita, as well as some Conocybe, Galerina and Lepiota mushroom species. (5)
Minimum Risk LevelNot Available
Health EffectsAmatoxins cause liver damage. They may also affect the kidneys. The most severe effects are toxic hepatitis with centrolobular necrosis and hepatic steatosis, as well as acute tubulointerstitial nephropathy, which altogether induce a severe hepatorenal syndrome. (5)
SymptomsDiarrhea and cramps are the first symptoms. (4)
TreatmentTreatment involves high dose penicillin as well as supportive care in cases of hepatic and renal injury. Cautious attention is given to maintaining hemodynamic stability, although if hepatorenal syndrome has developed the prognosis is guarded at best. (5)
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 LinkProamanullin
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID171350
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available