<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3638</id>
  <title>T3D3588</title>
  <common-name>Amanullin</common-name>
  <description>Amanullin is an exogenous compound that exists as a solid at room temperature. It has the chemical formula C39H54N10O12S. Amanullin 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 886.97 g/mol, Amanullin is a heavy molecule.

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). When mRNA is absent, cell metabolism and essential protein synthesis grind to a halt, resulting in cell death.</description>
  <cas>21803-57-6</cas>
  <pubchem-id>114856</pubchem-id>
  <chemical-formula>C39H54N10O12S</chemical-formula>
  <weight>887</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">2009-08-12T21:34:05Z</created-at>
  <updated-at type="dateTime">2026-08-31T23:09:15Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>http://en.wikipedia.org/wiki/Amanullin</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>Amanullin</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(N)=O)C(=O)N1CC(O)CC1C(=O)NC(C(C)CC)C(=O)N2</moldb-smiles>
  <moldb-formula>C39H54N10O12S</moldb-formula>
  <moldb-inchi>InChI=1S/C39H54N10O12S/c1-5-17(3)31-36(58)42-13-29(53)43-26-16-62(61)38-22(21-8-7-19(50)9-23(21)46-38)11-24(33(55)41-14-30(54)47-31)44-37(59)32(18(4)6-2)48-35(57)27-10-20(51)15-49(27)39(60)25(12-28(40)52)45-34(26)56/h7-9,17-18,20,24-27,31-32,46,50-51H,5-6,10-16H2,1-4H3,(H2,40,52)(H,41,55)(H,42,58)(H,43,53)(H,44,59)(H,45,56)(H,47,54)(H,48,57)</moldb-inchi>
  <moldb-inchikey>QQLVIKWYAVVKKF-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">886.971</moldb-average-mass>
  <moldb-mono-mass type="decimal">886.364337932</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>-2.2</logp>
  <hmdb-id nil="true"/>
  <chembl-id nil="true"/>
  <chemspider-id>102814</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>CHEM002567</chemdb-id>
  <dsstox-id nil="true"/>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00124752</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]acetamide</iupac>
  <moldb-polar-surface-area>340.41999999999996</moldb-polar-surface-area>
  <moldb-refractivity>218.11550000000014</moldb-refractivity>
  <moldb-polarizability>88.07029780740064</moldb-polarizability>
  <moldb-rotatable-bond-count>6</moldb-rotatable-bond-count>
  <moldb-acceptor-count>12</moldb-acceptor-count>
  <moldb-donor-count>11</moldb-donor-count>
  <moldb-pka-strongest-acidic>9.385735943676053</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-5.529577316852756</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>5</moldb-number-of-rings>
  <moldb-alogps-logp>-0.77</moldb-alogps-logp>
  <moldb-alogps-logs>-2.31</moldb-alogps-logs>
  <moldb-alogps-solubility>4.38e+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">1</paper-count>
  <sync-id>CED0030195</sync-id>
  <structure-inchikey>QQLVIKWYAVVKKF-UHFFFAOYSA-N</structure-inchikey>
  <structure-fingerprint>440010040020000000008000000411002008000000000000200000000100000000000010020400280000000000400004000000000000008000000000000081000000000000000000000300000000000000200000000800008010000010400000000000000100000000830008101000400000000201000000000060000208001002200008c000000040000020000000000000100000000000000000000040000200080000c020000000040000080000000000000080000000000000002008000801800000010000002000080108404000000000440000000004004200000000000000000200000000002044000020000500000000008000200000000000000000</structure-fingerprint>
  <structure-pattern-fingerprint>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</structure-pattern-fingerprint>
  <structure-pickle type="binary" encoding="base64">776t3gAAAAAQAAAAAwAAAAAAAAA+AAAAQgAAAIABBgBgAAAAAQMGAGAAAAAC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</structure-pickle>
  <structure-indexed-at type="dateTime">2026-09-19T04:00:49Z</structure-indexed-at>
</compound>
