Basic information
- CAS
28227-92-1- Standard SMILES
CC1NC(=O)C(CC(C)(C)O)NC(=O)C2Cc3c([nH]c4ccccc34)SCC(NC(=O)C(C(C)O)NC1=O)C(=O)N1CC(O)CC1C(=O)NC(C)C(=O)N2- InChIKey
VVAHMTWEOWYEHQ-UHFFFAOYSA-N- Molecular formula
- C35H48N8O10S
- Average molar mass
- 772.9 g/mol
- Monoisotopic mass
- 772.32141074
Overview
phalloin has been reported in Amanita phalloides, Amanita bisporigera, and other organisms with data available.
Names & identifiers
- Preferred name
- Phalloin
- IUPAC
- 18-hydroxy-34-(1-hydroxyethyl)-28-(2-hydroxy-2-methylpropyl)-23,31-dimethyl-12-thia-10,16,22,25,27,30,33,36-octazapentacyclo[12.11.11.03,11.04,9.016,20]hexatriaconta-3(11),4,6,8-tetraene-15,21,24,26,29,32,35-heptone
- English name
- phalloin
- Molecular formula
- C35H48N8O10S
- Molecular weight
- 772.87
Names & synonyms
PHALLOIN28227-92-1DTXSID40104631818-hydroxy-34-(1-hydroxyethyl)-28-(2-hydroxy-2-methylpropyl)-23,31-dimethyl-12-thia-10,16,22,25,27,30,33,36-octazapentacyclo[12.11.11.03,11.04,9.016,20]hexatriaconta-3(11),4,6,8-tetraene-15,21,24,26,29,32,35-heptone18-hydroxy-34-(1-hydroxyethyl)-28-(2-hydroxy-2-methylpropyl)-23,31-dimethyl-12-thia-10,16,22,25,27,30,33,36-octazapentacyclo(12.11.11.03,11.04,9.016,20)hexatriaconta-3(11),4,6,8-tetraene-15,21,24,26,29,32,35-heptoneRefChem:860501DTXCID70152814718,21,24,26,29,32,35-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-onePhalloineHSDB 3525Phalloidin, 7-(4-hydroxy-L-leucine)-SCHEMBL30682996
Show more names
Phalloin (6CI,7CI,8CI,9CI)Cyclo(L-Ala-D-Thr-L-Cys(1)-L-c4Hyp-L-Ala-L-Trp2(1)-4-hydroxy-L-Leu-)
NS00126146Q9257868
Properties
Computed structural properties
- XLogP
- -0.6
- Topological polar surface area
- 297 Ų
- Hydrogen bond donors
- 10
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 3
- Heavy atoms
- 54
- Formal charge
- 0
- Complexity
- 1,480
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Mushroom Toxins
Physicochemical properties
- Boiling point
- 1314.6 · 1314.6±65.0 °C(Predicted)
- Density
- 1.1492 · 1.1492 (rough estimate)
- refractive index
- 1.74 · 1.7400 (estimate)
- pka
- 13.04 · 13.04±0.70(Predicted)
- EWG's Food Scores
- 1 · 1
- Hazardous Substances Data
- 28227 · 28227-92-1(Hazardous Substances Data)
- Toxicity
- 50 ipr-mus: · LD50 ipr-mus: 1 mg/kg NEJMAG 269,223,63
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Hazards Summary
Phalloin and gamma-amanitin were detected within the 1st day and phalloidin within the 2nd day in the urine of rats after the administration of amanita phalloides extracts. [HSDB] Intraperitoneal LD50 (mouse) = 1 mg/kg; [RTECS] See Phalloidin.
Special Reports
THE HISTORY OF TOXIC COMPONENTS MAY BE DIVIDED INTO 2 PERIODS. THE 1ST STUDIES BEGAN IN THE LATE 18TH CENTURY AND RESULTED IN DISTINGUISHING BETWEEN NON-TOXIC HEMOLYSIN OR PHALLINE, AND A POORLY DEFINED TOXIC COMPOUND. THE 2ND PERIOD BEGAN WITH THE ISOLATION OF PHALLOIDINE IN 1937, FOLLOWED BY ISOLATION OF ALPHA, BETA AND GAMMA AMANITINE AND PHALLOINE. CLASSIFICATION, STRUCTURE, CONCENTRATIONS, TOXICITY IN ANIMALS AND STRUCTURE-ACTIVITY RELATIONSHIPS ARE DISCUSSED FOR THESE. ALSO REVIEWED ARE DATA ON SYNTHESIS OF TOXIN CONSTITUENTS, RESEARCH ON THE ANTITOXIN, ANTAMANIDE.[THEVENIN M ET AL; AMANITA PHALLOIDES AND ITS TOXINS: I. REVIEW OF RESEARCH ON THE IDENTITY OF THE TOXIC COMPONENTS; EUR J TOXICOL ENVIRON HYG 9(4) 197 (1976)]
Toxicology
TreatmentConsider gastric lavage and activated charcoal. (A678)
Health EffectsLiver lesions, tachycardia, hypoglycemia, hypotension and electrolyte imbalance with acid- base disturbance (L1160).
Adverse EffectsNeurotoxin - Other CNS neurotoxin
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary
Phallotoxins 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. (L1183, A2465)
Chemistry & industry
Pharmacology
Metabolism/MetabolitesPHALLOIN AND GAMMA-AMANITIN WERE DETECTED WITHIN THE 1ST DAY AND PHALLOIDIN WITHIN THE 2ND DAY IN THE URINE OF RATS AFTER THE ADMINISTRATION OF AMANITA PHALLOIDES EXTRACTS.
Uses & manufacturing
Uses
Oligopeptide similar to phalloidin. [ChemIDplus]
Prophalloin is one of a group of toxins from the death cap (Amanita phalloides) known as phallotoxins. (L996)
Methods of Manufacturing
COUPLING OF THE S-CHLORIDE OF BOC TERT-BUTYLOXYCARBONYL-ALANYL-D-THREONYL-CYSTEINYL-ALLO-HYDROXYPROLINE WITH ALANYL-TRYPTOPHYL-GAMMA-HYDROXYLEUCINE LACTONE GAVE A THIOETHER, WHICH ON CYCLIZATION YIELDED BOC-SECOPHALLOIN LACTONE. REMOVAL OF THE BOC RESIDUE, OPENING OF THE LACTONE RING AND A 2ND CYCLIZATION LED TO PHALLOIN, WHICH PROVED IDENTICAL WITH THE NATURAL TOXIN IN PHYSICAL AND TOXICOLOGICAL RESPECTS.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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