<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2509</id>
  <title>T3D2468</title>
  <common-name>Prophalloin</common-name>
  <description>Prophalloin is a solid compound of exogenous origin with the formula C35H48N8O9S. Prophalloin 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 756.87 g/mol, Prophalloin is a heavy molecule.

This compound targets four specific proteins: cytoplasmic 1 actin (ACTB), cytoplasmic 2 actin (ACTG1), alpha skeletal muscle actin (ACTA1), and aortic smooth muscle actin (ACTA2). 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 mechanism 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.</description>
  <cas>67739-84-8</cas>
  <pubchem-id>155035</pubchem-id>
  <chemical-formula>C35H48N8O9S</chemical-formula>
  <weight>756.86882</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: &gt;20 mg/kg (Mouse) (T258)</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Phalloidin 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">2009-07-03T21:46:55Z</created-at>
  <updated-at type="dateTime">2026-08-31T20:54:25Z</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>Prophalloin</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(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</moldb-smiles>
  <moldb-formula>C35H48N8O9S</moldb-formula>
  <moldb-inchi>InChI=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)</moldb-inchi>
  <moldb-inchikey>VXROMVCOGJAUJL-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">756.869</moldb-average-mass>
  <moldb-mono-mass type="decimal">756.326495864</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>0.4</logp>
  <hmdb-id nil="true"/>
  <chembl-id nil="true"/>
  <chemspider-id>136585</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>CHEM002054</chemdb-id>
  <dsstox-id nil="true"/>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00126184</susdat-id>
  <iupac>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</iupac>
  <moldb-polar-surface-area>272.09999999999997</moldb-polar-surface-area>
  <moldb-refractivity>194.53300000000002</moldb-refractivity>
  <moldb-polarizability>77.82412219279004</moldb-polarizability>
  <moldb-rotatable-bond-count>3</moldb-rotatable-bond-count>
  <moldb-acceptor-count>15</moldb-acceptor-count>
  <moldb-donor-count>9</moldb-donor-count>
  <moldb-pka-strongest-acidic>-6.511189875682057</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>14.96284177199049</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>5</moldb-number-of-rings>
  <moldb-alogps-logp>1.17</moldb-alogps-logp>
  <moldb-alogps-logs>-3.80</moldb-alogps-logs>
  <moldb-alogps-solubility>1.19e-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">0</paper-count>
  <sync-id>CED0042839</sync-id>
  <structure-inchikey>VXROMVCOGJAUJL-UHFFFAOYSA-N</structure-inchikey>
  <structure-fingerprint>44000000000000020000800000202100000000044000000000000000110000000002001080000020000010000040002000800000000000020000000800000004000000000000000000000000000000200220000010090000001000000010000000000000010000000080010000000000000008020100000000002000020000100800000040000080c00000200000000000000000000100000000000020000000000410048004400000040000081010000000000000000000018000000000001000000000040000002004090000200000002008000000000040004200000001000000000008000000000040000000080000000000000400400000200000000000</structure-fingerprint>
  <structure-pattern-fingerprint>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</structure-pattern-fingerprint>
  <structure-pickle type="binary" encoding="base64">776t3gAAAAAQAAAAAwAAAAAAAAA1AAAAOQAAAIABBgBgAAAAAQMGAGAAAAAD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</structure-pickle>
  <structure-indexed-at type="dateTime">2026-09-19T04:00:28Z</structure-indexed-at>
</compound>
