<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3639</id>
  <title>T3D3589</title>
  <common-name>Amanullinic acid</common-name>
  <description>Amanullinic acid is an exogenous organic compound that exists as a solid at room temperature. It is characterized by the chemical formula C39H53N9O13S. With an average molecular weight of 887.96 g/mol, Amanullinic acid is a heavy molecule. Amanullinic acid belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds.

The compound 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. Regarding its biological activity, the major toxic mechanism of amatoxins is the inhibition of RNA polymerase II, which is a vital enzyme in the synthesis of messenger RNA (mRNA), microRNA, and small nuclear RNA (snRNA). The resulting lack of mRNA prevents essential protein synthesis and cell metabolism, causing the cell to die.</description>
  <cas>54532-45-5</cas>
  <pubchem-id>171349</pubchem-id>
  <chemical-formula>C39H53N9O13S</chemical-formula>
  <weight>888</weight>
  <appearance>White powder.</appearance>
  <melting-point nil="true"/>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility nil="true"/>
  <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>The 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. (L1774)</mechanism-of-toxicity>
  <metabolism nil="true"/>
  <toxicity>LD50: &gt;20 mg/kg (Mouse) (T258)</toxicity>
  <lethaldose>0.1 mg/kg for an adult human. (L1774)</lethaldose>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Amatoxins 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. (L1774)</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Amatoxins 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. (L1774)</health-effects>
  <symptoms>Diarrhea and cramps are the first symptoms. (L993)</symptoms>
  <treatment>Treatment 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. (L1774)</treatment>
  <created-at type="dateTime">2009-08-12T21:34:06Z</created-at>
  <updated-at type="dateTime">2026-08-31T23:08:58Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>http://en.wikipedia.org/wiki/Amanullinic_acid</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id nil="true"/>
  <omim-id nil="true"/>
  <chebi-id nil="true"/>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id>Amanullinic acid</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>CCC(C)C1NC(=O)CNC(=O)C2CC3=C(NC4=CC(O)=CC=C34)S(=O)CC(NC(=O)CNC1=O)C(=O)NC(CC(O)=O)C(=O)N1CC(O)CC1C(=O)NC(C(C)CC)C(=O)N2</moldb-smiles>
  <moldb-formula>C39H53N9O13S</moldb-formula>
  <moldb-inchi>InChI=1S/C39H53N9O13S/c1-5-17(3)31-36(58)41-13-28(51)42-26-16-62(61)38-22(21-8-7-19(49)9-23(21)45-38)11-24(33(55)40-14-29(52)46-31)43-37(59)32(18(4)6-2)47-35(57)27-10-20(50)15-48(27)39(60)25(12-30(53)54)44-34(26)56/h7-9,17-18,20,24-27,31-32,45,49-50H,5-6,10-16H2,1-4H3,(H,40,55)(H,41,58)(H,42,51)(H,43,59)(H,44,56)(H,46,52)(H,47,57)(H,53,54)</moldb-inchi>
  <moldb-inchikey>HFENEIQMWRYNGK-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">887.956</moldb-average-mass>
  <moldb-mono-mass type="decimal">887.348353517</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>-1.6</logp>
  <hmdb-id nil="true"/>
  <chembl-id nil="true"/>
  <chemspider-id>149798</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>CHEM002568</chemdb-id>
  <dsstox-id nil="true"/>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00121894</susdat-id>
  <iupac>2-[13,34-di(butan-2-yl)-8,22-dihydroxy-2,5,11,14,27,30,33,36,39-nonaoxo-27lambda4-thia-3,6,12,15,25,29,32,35,38-nonazapentacyclo[14.12.11.06,10.018,26.019,24]nonatriaconta-18(26),19(24),20,22-tetraen-4-yl]acetic acid</iupac>
  <moldb-polar-surface-area>334.62999999999994</moldb-polar-surface-area>
  <moldb-refractivity>216.29330000000016</moldb-refractivity>
  <moldb-polarizability>87.72003616402505</moldb-polarizability>
  <moldb-rotatable-bond-count>6</moldb-rotatable-bond-count>
  <moldb-acceptor-count>13</moldb-acceptor-count>
  <moldb-donor-count>11</moldb-donor-count>
  <moldb-pka-strongest-acidic>3.646986074183188</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-5.529577316852756</moldb-pka-strongest-basic>
  <moldb-physiological-charge>-1</moldb-physiological-charge>
  <moldb-number-of-rings>5</moldb-number-of-rings>
  <moldb-alogps-logp>-0.55</moldb-alogps-logp>
  <moldb-alogps-logs>-2.38</moldb-alogps-logs>
  <moldb-alogps-solubility>3.74e+00 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">3796327</paper-count>
  <sync-id>CED0034443</sync-id>
  <structure-inchikey>HFENEIQMWRYNGK-UHFFFAOYSA-N</structure-inchikey>
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  <structure-indexed-at type="dateTime">2026-09-19T04:00:49Z</structure-indexed-at>
</compound>
