<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2513</id>
  <title>T3D2472</title>
  <common-name>Phallacin</common-name>
  <description>Phallacin is a solid compound with the formula C37H50N8O12S. Phallacin belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. With an average molecular weight of 830.90 g/mol, Phallacin is a heavy molecule. It is an exogenous substance and is one of a group of toxins known as phallotoxins isolated from the death cap (Amanita phalloides). The phallotoxins consist of at least seven compounds, all of which have seven similar peptide rings.

Phallacin targets four specific proteins: ACTB (Actin, cytoplasmic 1), ACTG1 (Actin, cytoplasmic 2), ACTA1 (Actin, alpha skeletal muscle), and ACTA2 (Actin, aortic smooth muscle). Phallotoxins bind specifically at the interface between F-actin subunits, locking adjacent subunits together and preventing depolymerization. This interaction leads to a decrease in the rate constant for the dissociation of actin subunits from filament ends, which essentially stabilizes actin filaments. Furthermore, phallotoxins inhibit the ATP hydrolysis activity of F-actin, ultimately poisoning the cell.</description>
  <cas>53568-40-4</cas>
  <pubchem-id>171277</pubchem-id>
  <chemical-formula>C37H50N8O12S</chemical-formula>
  <weight>830.9043</weight>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility></solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>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)</mechanism-of-toxicity>
  <metabolism nil="true"/>
  <toxicity>LD50: 1.5 mg/kg (Mouse) (T258)</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Phallacidin is one of a group of toxins from the death cap (Amanita phalloides) known as phallotoxins. (L996)</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Liver lesions, tachycardia, hypoglycemia, hypotension and electrolyte imbalance with acid- base disturbance (L1160).</health-effects>
  <symptoms>Hypovolemic 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 (L1160).</symptoms>
  <treatment>Consider gastric lavage and activated charcoal. (A678)</treatment>
  <created-at type="dateTime">2009-07-03T21:46:57Z</created-at>
  <updated-at type="dateTime">2026-08-31T21:59:11Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia nil="true"/>
  <uniprot-id nil="true"/>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id></chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Phallacin</stitch-id>
  <drugbank-id nil="true"/>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CC(C)C1N=C(O)C(CC(C)(C)O)N=C(O)C2CC3=C(NC4=CC=CC=C34)SCC(N=C(O)C(N=C1O)C(O)C(O)=O)C(=O)N1CC(O)CC1C(O)=NC(C)C(O)=N2</moldb-smiles>
  <moldb-formula>C37H50N8O12S</moldb-formula>
  <moldb-inchi>InChI=1S/C37H50N8O12S/c1-15(2)25-32(52)44-26(27(47)36(55)56)33(53)41-23-14-58-34-19(18-8-6-7-9-20(18)42-34)11-21(29(49)40-22(30(50)43-25)12-37(4,5)57)39-28(48)16(3)38-31(51)24-10-17(46)13-45(24)35(23)54/h6-9,15-17,21-27,42,46-47,57H,10-14H2,1-5H3,(H,38,51)(H,39,48)(H,40,49)(H,41,53)(H,43,50)(H,44,52)(H,55,56)</moldb-inchi>
  <moldb-inchikey>LAVFLHFIXHMDLZ-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">830.904</moldb-average-mass>
  <moldb-mono-mass type="decimal">830.326889794</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>-0.5</logp>
  <hmdb-id nil="true"/>
  <chembl-id nil="true"/>
  <chemspider-id>149740</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002057</chemdb-id>
  <dsstox-id nil="true"/>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00123066</susdat-id>
  <iupac>2-hydroxy-2-[18-hydroxy-28-(2-hydroxy-2-methylpropyl)-23-methyl-15,21,24,26,29,32,35-heptaoxo-31-propan-2-yl-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-tetraen-34-yl]acetic acid</iupac>
  <moldb-polar-surface-area>329.62999999999994</moldb-polar-surface-area>
  <moldb-refractivity>206.25760000000008</moldb-refractivity>
  <moldb-polarizability>82.56185117963525</moldb-polarizability>
  <moldb-rotatable-bond-count>5</moldb-rotatable-bond-count>
  <moldb-acceptor-count>18</moldb-acceptor-count>
  <moldb-donor-count>11</moldb-donor-count>
  <moldb-pka-strongest-acidic>2.3269348559850003</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>5.446897046969477</moldb-pka-strongest-basic>
  <moldb-physiological-charge>-1</moldb-physiological-charge>
  <moldb-number-of-rings>5</moldb-number-of-rings>
  <moldb-alogps-logp>0.68</moldb-alogps-logp>
  <moldb-alogps-logs>-3.75</moldb-alogps-logs>
  <moldb-alogps-solubility>1.48e-01 g/l</moldb-alogps-solubility>
  <kingdom>Organic compounds</kingdom>
  <superklass>Organic acids and derivatives</superklass>
  <klass>Carboxylic acids and derivatives</klass>
  <subklass>Amino acids, peptides, and analogues</subklass>
  <paper-count type="integer">1</paper-count>
  <sync-id>CED0035781</sync-id>
  <structure-inchikey>LAVFLHFIXHMDLZ-UHFFFAOYSA-N</structure-inchikey>
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</structure-pickle>
  <structure-indexed-at type="dateTime">2026-09-19T04:00:28Z</structure-indexed-at>
</compound>
