<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3820</id>
  <title>T3D3766</title>
  <common-name>Janthitrem G</common-name>
  <description>Janthitrem G is an exogenous solid with the chemical formula C39H51NO6. Janthitrem G belongs to the naphthopyrans, a class of organoheterocyclic compounds within the organic compounds. With an average molecular weight of 629.83 g/mol, Janthitrem G is a heavy molecule.

This tremorgenic mycotoxin is produced by Penicillium janthinellum. It has 22 recorded protein targets, including mitochondrial 4-aminobutyrate aminotransferase (ABAT) and Gamma-aminobutyric acid receptor subunits alpha-1 (GABRA1), alpha-2 (GABRA2), and alpha-3 (GABRA3), among 18 other proteins. Tremorgenic mycotoxins are thought to inhibit gamma-aminobutyric acid (GABA) receptors, both pre- and postsynaptic, as well as inhibit transmitter breakdown at the GABA-T receptors. This mechanism would initially increase neurotransmitter levels, potentiating the GABA-induced chloride current, and subsequently lead to decreased levels of neurotransmitter in the synapse.</description>
  <cas>90986-51-9</cas>
  <pubchem-id>10394234</pubchem-id>
  <chemical-formula>C39H51NO6</chemical-formula>
  <weight>629.8</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>Tremorgenic mycotoxins exert their toxic effects by interfering with neurotransmitter release, possibly by causing degeneration of nerve terminals. They are thought to inhibit gamma-aminobutyric acid (GABA) receptors, both pre- and postsynaptic, as well as inhibit transmitter breakdown at the GABA-T receptors. This would initially increase neurotransmitter levels, potentiating the GABA-induced chloride current, then lead to decreased levels of neurotransmitter in the synapse. (A2976)</mechanism-of-toxicity>
  <metabolism nil="true"/>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Janthitrems are tremorgenic mycotoxins that have been found in the fungus Penicillium janthinellum. They may be found in contaminated cereal crops such as oats, barley, millet, corn and rice. (A2976, A3065)</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Tremorgenic mycotoxins affect central nervous system activity. They cause a neurological disease of cattle known as "staggers syndrome". (A2976)</health-effects>
  <symptoms>Tremorgenic mycotoxins affect central nervous system activity, inducing neurologic symptoms including mental confusion, paralysis, tremors, seizures, and death. They cause a neurological disease of cattle known as "staggers syndrome", which is characterized by muscle tremors, hyperexcitability, convulsions and ataxia. (A2976) </symptoms>
  <treatment>To control severe tremors caused by tremorgenic mycotoxins, methocarbamol should be administered. Generalized seizures may be treated with diazepam followed by methocarbamol or a barbiturate such as pentobarbital sodium. Gastric lavage should be performed and activated charcoal administered to limit further absorption of toxins. (A744)</treatment>
  <created-at type="dateTime">2010-05-20T15:21:17Z</created-at>
  <updated-at type="dateTime">2026-08-22T12:15:30Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia nil="true"/>
  <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 nil="true"/>
  <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)OC1C=C2C(CCC3(C)C4(C)C(CC5=C4NC4=C5C=C5CC6C(=CC(C)(C)OC6(C)C)C5=C4)CCC23O)OC1C(C)(C)O</moldb-smiles>
  <moldb-formula>C39H51NO6</moldb-formula>
  <moldb-inchi>InChI=1S/C39H51NO6/c1-20(41)44-31-18-28-30(45-33(31)35(4,5)42)11-12-37(8)38(9)22(10-13-39(28,37)43)16-25-24-14-21-15-27-26(19-34(2,3)46-36(27,6)7)23(21)17-29(24)40-32(25)38/h14,17-19,22,27,30-31,33,40,42-43H,10-13,15-16H2,1-9H3</moldb-inchi>
  <moldb-inchikey>PGYSJEQVCATFBQ-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">629.8253</moldb-average-mass>
  <moldb-mono-mass type="decimal">629.371638369</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>4.2</logp>
  <hmdb-id>HMDB30531</hmdb-id>
  <chembl-id nil="true"/>
  <chemspider-id>8569675</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 nil="true"/>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002733</chemdb-id>
  <dsstox-id nil="true"/>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00124342</susdat-id>
  <iupac>[12-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo[15.14.0.02,15.03,12.06,11.018,30.020,28.022,27]hentriaconta-1(17),10,18(30),19,26,28-hexaen-9-yl] acetate</iupac>
  <moldb-polar-surface-area>101.01000000000002</moldb-polar-surface-area>
  <moldb-refractivity>178.79439999999997</moldb-refractivity>
  <moldb-polarizability>74.82651436296125</moldb-polarizability>
  <moldb-rotatable-bond-count>3</moldb-rotatable-bond-count>
  <moldb-acceptor-count>5</moldb-acceptor-count>
  <moldb-donor-count>3</moldb-donor-count>
  <moldb-pka-strongest-acidic>13.611570040393485</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-3.1357150032455516</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>8</moldb-number-of-rings>
  <moldb-alogps-logp>6.16</moldb-alogps-logp>
  <moldb-alogps-logs>-6.40</moldb-alogps-logs>
  <moldb-alogps-solubility>2.48e-04 g/l</moldb-alogps-solubility>
  <kingdom>Organic compounds</kingdom>
  <superklass>Organoheterocyclic compounds</superklass>
  <klass>Naphthopyrans</klass>
  <subklass nil="true"/>
  <paper-count type="integer">4</paper-count>
  <sync-id>CED0022840</sync-id>
  <structure-inchikey>PGYSJEQVCATFBQ-UHFFFAOYSA-N</structure-inchikey>
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  <structure-pattern-fingerprint>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</structure-pattern-fingerprint>
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  <structure-indexed-at type="dateTime">2026-09-19T04:00:55Z</structure-indexed-at>
</compound>
